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Review

A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp.

1
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, China
2
School of Basic Medical Sciences, Beijing University of Chinese Medicine, Beijing 100029, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2014, 19(11), 17478-17535; https://doi.org/10.3390/molecules191117478
Submission received: 11 July 2014 / Revised: 13 August 2014 / Accepted: 15 August 2014 / Published: 30 October 2014
(This article belongs to the Section Metabolites)

Abstract

:
Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, a traditional Chinese medicine, popularly used for complementary cancer therapy. GTs are lanostane-tetracyclic triterpenes. They have been reported to possess anti-tumor, anti-inflammation, antioxidant, antimicrobial and blood fat reducing effects. To date, 316 GTs have been found and their similar chemical structures have proved difficult to elucidate. This paper compiles 316 naturally occurring triterpenes from Ganoderma based on the literature published through January 2013 along with their structures, physiological activities and 13C-NMR spectral data.

Graphical Abstract

1. Introduction

Ganoderma lucidum (Leyss. ex Fr.) Karst, a medicinal fungus called “Lingzhi” in China, is one of the most highly regarded medicinal fungi in the world. It is ranked as rare and precious in the ancient Chinese medical encyclopedias “Shen Nong’s Ben Cao Jing” and “Ben Cao Gang Mu”. The main Lingzhi-producing regions are East China, Southwest China and the provinces of Hebei, and Guangxi. It can be used in the prevention and treatment of various types of disease, such as cancer, hepatopathy, arthritis, hypertension, neurasthenia, debility, etc. Its the most attractive characteristics are its immunomodulatory and antitumor activities [1,2,3,4,5,6,7,8]. Ganoderma contains many bioactive natural components, including triterpenes (GTs), polysaccharides, proteins, and unsaturated fatty acids. The triterpenes and polysaccharides are deemed to be the primary bioactive compounds of Ganoderma.
Kubota isolated ganoderic acid A and ganoderic acid B from Ganoderma lucidum (FR.) KARST in 1982 [9]. Since then, more than 316 triterpenes have been isolated from the fruiting bodies, spores, gills, and mycelia of many Ganoderma mushrooms. This total was derived from our investigation of the references. As reported, the majority of GTs exhibit a wide range of biological activities, including antitumor, anti-HIV-1, antihypertensive, antiangiogenic, immunomodulatory, antiandrogenic, antihepatitis B, antioxidant, anticomplement, and antimicrobial activities [10,11,12,13]. All GTs are tetracyclic triterpenes. Their chemical structures are more complex than those of other lanostanes, owing to their highly oxidized state. Generally, GTs contain 30 or 27 carbon atoms, and some have 24. The numbers of substituents as well as the positions increase the structural complexity. In this paper, all 316 triterpenes are listed. In accordance with the number of carbon atoms and their molecular features, they can be divided into different structural groups. The 13C-NMR data of those triterpenes, elucidation of the compounds’ structures and their bioactivities are discussed. We aim at providing a useful and fast way for identifying GTs. Finally, possible trends and perspectives for future investigation of these mushrooms are also included.

2. Ganoderma Triterpenes

Triterpenes are widely distributed in traditional Chinese medicines. Their structures are considered to be derived from the acyclic precursor squalene. More than 20,000 triterpenes have been isolated and identified from Nature, including squalene, lanostane, dammarane, lupine, oleanane, ursane, and hopane structure types [14,15]. The Ganoderma triterpenes belong to the lanostane triterpenes (Figure 1).
Figure 1. A prototypical lanostane triterpenoid skeleton.
Figure 1. A prototypical lanostane triterpenoid skeleton.
Molecules 19 17478 g001
Most of them contain 30 or 27 carbon atoms. A few have 24 carbon atoms. These compounds possesses the same skeleton, namely a trans configuration of rings A/B, B/C, C/D and and 10β, 13β, 14α, 17β substituents. Moreover, substituents are always found at the C-3, 7, 11, 12, 15, 22, 23, 24 and 25 positions of the parent nucleus.
On the basis of the substituent groups and double bonds in the same position, they are classified into different types. Compounds 1221 (Figure 2, Figure 3, Figure 4, Figure 5, Figure 6, Figure 7, Figure 8, Figure 9, Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16, Figure 17, Figure 18, Figure 19, Figure 20 and Figure 21) possess 30 carbon atoms. Among them, 137 (Figure 2) contain double bonds between C-8 and C-9, a keto group at C-23, and substituent groups at C-3, 7, 11, 12, 15, 25. In this figure, compounds 1, 3, 4, 7, 8, 1114, 17, 18, 20, 25, 26, 28, 31, 32, 34, and 35 possess β-hydroxy groups at C-3, and the others possess a keto group, except 3β-oxo-formyl-7β, 12β-dihydroxy-5α-lanost-11,15,23-trioxo-8-en(E)-26-oic acid (21) with a formyl located at the C-3 position. Compounds 2, 3, 917, 1923, 25, 27, 31, 3436 have hydroxy groups at C-7, and furthermore, 19, 20, 22 have α-configurations. What’s more, compounds 1, 4, 18, 24, 26, 2830, 32, 33, and 37 have a carbonyl at C-7. In this group, C-11 mainly has a carbonyl substituent except in ganoderic acid Df (27) with a β-hydroxyl at this position. The majority of these compounds do not have any substituents at C-12, while compounds 1, 4, 24, 25, 28, 29, 31 possess β-acetyloxy and compounds 21, 3537 possess β-hydroxyls. All of these compounds display carbonyls or β-hydroxyls at C-15. As to other configurations, both α- and β-C-21, 17β (compounds 516, 21, 2830, 35) and 20 α-configurations can be found in this group. Carboxyl, formyl, ethanoyl or butyryl moieties can be found at C-25, most commonly carboxyl. These compounds have extensive biological activities.
Compared with the compounds in Figure 2, compounds 3870 in Figure 3 possess double bonds between C-24 and C-25, and have a hydroxy or no substituent at C-23, instead of a carbonyl. Some other substituents are also found at C-3, 7, 11, 12, 15, 23, 25. In this group, lucialdehyde C (46) displays strong antitumor activity and ganoderic acid β (53) reveals great anti-HIV-1 protease activity. Compounds 7184 (Figure 4) get an acetate substituent at C-22 and no substituent at C-11. Meanwhile, compounds 8598 (Figure 5) have double bonds at C-20(22) and keto groups at C-11. From all the listed structures, we can clearly identify compounds 99105 in Figure 6 by the carboxymethyl substitution at C-25, carbonyl substituent at C-11, a keto group at C-23, and β-configuration of C-21. Compounds 106110 are assigned to the same group owing to the methyl at C-20, carbonyl substituent at C-11, and carboxyl at C-25. Lucidumol A (111), ganoderiol C-H (112115), and ganoderitriol M (116) differ from the others on account of the hydroxy at C-24 and C-25. As is shown in Figure 9, Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17, compounds 117123, 124126, 127130, 131133, 134135, 136139, 140141, 142145 and 146147 possess extremely similar skeletons. Because of their distinctive skeletons, 148155 are listed independently. There are no double bonds between C-8 and C-9 in compounds 156221, and two double bonds at C-7(8) and C-9(11), respectively. Among the compounds above, ganoderic acid Jc (187), ganoderiol F (190), and 15α,26-dihydroxy-5α-lanosta-7,9,24(E)-trien-3-one (212) showed remarkable antitumor activity. Significant anti-HIV-1 protease activity has been expressed in ganoderic acid S1 (159) and ganodermic acid T-Q (183). Compounds 156196 (Figure 19) have the same skeleton with substituents at C-3, 15, 16, 20, 22, 23, 25 and double bonds at C-24(25). In this group, 3α, 16α-dihydroxylanosta-7,9(11),24-trien-21-oic acid (157), 3α, 16α, 26-trihydroxylanosta-7,9(11), 24-trien-21-oic acid (158) and 16α-hydroxy-3-oxolanosta-7,9(11),24-trien-21-oic acid (196) possess a hydroxyl at C-16 and carboxyl at C-20. Compounds 197213 (Figure 20) have the same position of substituents. They possess an α- or β-configuration at C-21. The majority have double bonds between C-24 and C-25, except some with hydroxyl, acetoxyl or no substituents at C-24 and C-25. Compounds 214219 (Figure 21) have a hydroxy or acetoxyl at C-22, while epoxyganoderiol B (220) and C (221) (Figure 22) possess an epoxy at C-24(25). Compounds 222266 have the basic skeleton of 27 carbon atoms. Furthermore, they are also subdivided into different groups due to the difference of substituents and position of double bonds. The C-8(9) double bonds are the same in compounds 222260 (Figure 23). 4,4,14α-Trimethyl-5α-chol-7,9(11)-dien-3-oxo-24-oic acid (261) and ganoderic acid Jd (262) (Figure 24) get two double bonds at C-7(8) and C-9(11), respectively. Compared with the compounds in Figure 22, compounds 263266 in Figure 25 have hydroxy substituents at C-29. Compounds 267287 are divided into different groups on account of their characteristic skeletons. We list the structures of compounds 288307 successively, in consideration of the number of substituents and the substituents’ complicated positions. Fornicatin B(308), G(309), A(310), H(311) and australic acid (312) are 3,4-seco-trinorlanostane triterpenoids. In addition, compounds 313316 only have 24 carbon atoms. The names, corresponding plant resources and references of the compounds are compiled in Table 1, Table 2, Table 3, Table 4, Table 5, Table 6, Table 7, Table 8, Table 9, Table 10 and Table 11.
Table 1. Ganoderma triterpenes 137 in Figure 2.
Table 1. Ganoderma triterpenes 137 in Figure 2.
No.Compound NameSourceRef.
1n-Butyl ganoderate H (n-butyl 12β-acetoxy-3β-hydroxy-7,11,15,23-tetraoxo-5α-lanost-8-en-26-oate)G. lucidum (fruit bodies)[16]
2Butyl ganoderate AG. lucidum (fruit bodies)[17]
3Butyl ganoderate BG. lucidum (fruit bodies)[17]
4Ganoderic acid α (12β-acetoxy-3β, 15β-dihydroxy-7,11,23-trioxo-5α-lanosta-8-en-26-oic acid)G. lucidum (fruit bodies)[18]
5Ganolucidic acid AG. lucidum (gill surface)[19]
6Methyl ganolucidate A (methyl 15α-hydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate)G. lucidum (gill surface)[19,20]
7Ganolucidic acid BG. lucidum (gill surface)[19]
8Methyl ganolucidate BG. lucidum (gill surface)[19,20]
9Ganoderic acid A (7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oic acid)G. lucidum[9,21]
10Methyl ganoderate A (methyl 7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate)G. lucidum[21]
11Ganoderic acid B (3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oic acid)G. lucidum[21]
12Methyl ganoderate B (methyl 3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate)G. lucidum[9,21]
13Ganoderic acid C (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oic acid)G. lucidum[21]
14Methyl ganoderate CG. lucidum[21]
15Ganoderic acid D (7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oic acid)G. lucidum[21]
16Methyl ganoderate DG. lucidum[21]
17Methyl ganoderate C2 (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate)G. lucidum (gills)[22]
18Methyl ganoderate KG. lucidum (gills)[22,23]
19Compound B8G. lucidum (gills)[22]
20Compound B9G. lucidum (gills)[22]
213β-Oxo-formyl-7β, 12β-dihydroxy-5α-lanost-11,15,23-trioxo-8-en(E)-26-oic acidG. lucidum (fruit bodies)[24]
22Ganoderic acid B8G. lucidum (fruit bodies)[25]
23Ganoderic acid C1G. lucidum (fruit bodies)[25]
2412β-Acetoxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acid ethyl esterG. lucidum[26]
253β, 7β-Dihydroxy-12β-acetoxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid methyl esterG. lucidum[27]
263β-Hydroxy-7,11,12,15,23-pentaoxolanost-8-en-26-oic acidG. lucidum (fruit bodies)[28]
27Ganoderic acid Df (7β, 11β-dihydroxy-3,15,23-trioxo-5α-lanosta-8-en-26-oic acid)G. lucidum[29]
28Ganoderic acid HG. lucidum (gill surface)[30]
29Ganoderic acid F (12β-acetoxy-3,7,11,15-pentaoxo-5α-lanost-8-en-26-oic acid)G. lucidum (dried fruit bodies)[31]
30Ganoderic acid E (3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oic acid)G. lucidum (dried fruit bodies)[31]
31Ganoderic acid KG. lucidum (fruit bodies)[32]
32Ganoderic acid AM1G. lucidum (fruit bodies)[32]
33Ganoderic acid JG. lucidum (fruit bodies)[32]
34Ganoderic acid C2 (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanosta-8-en-26-oic acid)G. lucidum (gills)[22]
35Ganoderic acid G (3β, 7β, 15β-trihydroxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid)G. lucidum (dried fruit bodies)[31]
367β, 12β-Dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8-en-26-oic acidG. lucidum[26]
3712β-Hydroxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acidG. lucidum[26]
Table 2. Ganoderma triterpenes (3870) in Figure 3.
Table 2. Ganoderma triterpenes (3870) in Figure 3.
No.Compound NameSourceRef.
38Ganoderic acid GS-1 (7β-hydroxy-3,11,15-trioxolanosta-8,24(E)-dien-26-oic acid)G. sinense (fruit bodies)[33]
39Ganoderic acid GS-2 (7β, 15α-dihydroxy-3,11-dioxolanosta-8,24(E)-dien-26-oic acid)G. sinense (fruit bodies)[33]
40Ganoderic acid GS-3 (12β-acetoxy-3β, 7β-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid)G. sinense (fruit bodies)[33]
41Ganoderic acid AP2 (12β, 15α-diacetoxy-3β-hydroxy-11-oxolanost-8,24(E)-dien-26-oic acid)G. applanatum (fruit bodies)[34]
4223S-Hydroxy-3,7,11,15-tetraoxolanost-8,24E-diene-26-oic acidG. lucidum (fruit bodies)[32]
437-Oxoganoderic acid Z (3β-hydroxy-7-oxo-5α-lanosta-8,24(E)-dien-26-oic acid)G. lucidum (fruit bodies)[35]
44Ganoderic acid LM2 ((23S) 7β,-dihydroxy-3,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid)G. lucidum (fruit bodies)[36]
45Lucialdehyde B ((24E)-3,7-dioxo-5α-lanosta-8,24-dien-26-al)G. lucidum (fruit bodies)[25]
46Lucialdehyde C ((24E)-3β-hydroxy-7-oxo-5α-lanosta-8,24-dien-26-al)G. lucidum (fruit bodies)[25]
47Ganoderic acid γ ((23S)-7β, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
48Ganoderic acid δ ((23S)-7α, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
49Ganoderic acid ε ((23S)-3β, 7β, 23-trihydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
50Ganoderic acid ζ ((23S)-3β, 23-dihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
51Ganoderic acid η ((23S)-3β, 7β, 12β, 23-tetrahydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
52Ganoderic acid θ ((23S)-3β, 12β, 23-trihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid)G. lucidum (spores)[37]
53Ganoderic acid β (3β, 7β-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid)G. lucidum (spores)[38]
54Ganolucidic acid E (15α-hydroxy-3,11-dioxo-5α-lanosta-8,24E-dien-26-oic acid)G. lucidum (fruit bodies)[39]
55Ganoderal B (7α-hydroxy-3-oxo-5α-lanosta-8,24E-dien-26-al)G. lucidum[40]
56Ganoderic acid Ma (3α, 7α-diacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (fruit bodies)[41]
57Lucialdehyde D (3,7,11-trioxo-5α-lanosta-8,24-diene-26-al)G. pfeifferi (fruit bodies)[42]
58Ganoderone A (5α-lanosta-8,24-diene-26-hydroxy-3,7-dione)G. pfeifferi (fruit bodies)[42]
59ganoderic acid Mi (3α-acetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (mycelial mat)[43]
6011α-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acidG. lucidum[26]
6111β-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acidG. lucidum[26]
62Lucidadiol (5α-lanosta-8,24-dien-3β, 26-dihydroxy-7-one)G. lucidum[44]
63Lucidal (5α-lanosta-8,24E-dien-3β-hydroxy-7-on-26-al)G. lucidum[44]
64Ganoderic acid DM (3,7-dioxo-8,24(E)-dien-lanosta-26-oic acid)G. lucidum (cultured fruit bodies)[45]
65Ganoderic acid VG. orbiforme[46]
66Ganolucidic acid γa (3β, 7β, 15α, 23-tetrahydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid)G. sinense (fruit bodies)[47]
67Ganolucidate F (3β, 15α, 23-trihydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid)G. sinense (fruit bodies)[47]
68Lucialdehyde E (7β, 15α-dihydroxy-3,11-dioxo-5α-lanosta-8,24-dien-26-al)G. lucidum (spores)[48]
69Ganolucidic acid DG. lucidum (spores)[37]
70Ganoderic acid WG. lucidum (fruit bodies)[41]
Figure 2. Structures of compounds 137.
Figure 2. Structures of compounds 137.
Molecules 19 17478 g002

CpdR1R2R3R4R5R6R7
1β-OH=O=Oβ-O-Ac=Oα-CH3COOBu
2=Oβ-OH=OHα-OHα-CH3COOBu
3β-OHβ-OH=OH=Oα-CH3COOBu
4β-OH=O=Oβ-O-Acα-OHα-CH3COOH
5=OH=OHα-OHβ-CH3COOH
6=OH=OHα-OHβ-CH3COOCH3
7β-OHH=OHα-OHβ-CH3COOH
8β-OHH=OHα-OHβ-CH3COOCH3
9=Oβ-OH=OHα-OHβ-CH3COOH
10=Oβ-OH=OHα-OHβ-CH3COOCH3
11β-OHβ-OH=OH=Oβ-CH3COOH
12β-OHβ-OH=OH=Oβ-CH3COOCH3
13β-OHβ-OH=OHα-OHβ-CH3COOH
14β-OHβ-OH=OHα-OHβ-CH3COOCH3
15=Oβ-OH=OH=Oβ-CH3COOH
16=Oβ-OH=OH=Oβ-CH3COOCH3
17β-OHβ-OH=OHα-OHα-CH3COOCH3
18β-OH=O=OHα-OHα-CH3COOCH3
19=Oα-OH=OHα-OHα-CH3COOCH3
20β-OHα-OH=OHα-OHα-CH3COOCH3
21O-CHOβ-OH=Oβ-OH=Oβ-CH3COOH
22=Oα-OH=OHα-OHα-CH3COOH
23=Oβ-OH=OH=Oα-CH3COOH
24=O=O=Oβ-O-COCH3=Oα-CH3COOEt
25β-OHβ-OH=Oβ-O-COCH3=Oα-CH3COOCH3
26β-OH=O=O=O=Oα-CH3COOH
27=Oβ-OHβ-OHH=Oα-CH3COOH
28β-OH=O=Oβ-O-Ac=Oβ-CH3COOH
29=O=O=Oβ-O-Ac=Oβ-CH3COOH
30=O=O=OH=Oβ-CH3COOH
31β-OHβ-OH=Oβ-O-Ac=Oα-CH3COOH
32β-OH=O=OH=Oα-CH3COOH
33=O=O=OHα-OHα-CH3COOH
34β-OHβ-OH=OHα-OHα-CH3COOH
35β-OHβ-OH=Oβ-OH=Oβ-CH3COOH
36=Oβ-OH=Oβ-OH=Oα-CH3COOH
37=O=O=Oβ-OH=Oα-CH3COOH
Figure 3. Structures of compounds 3870.
Figure 3. Structures of compounds 3870.
Molecules 19 17478 g003

CpdR1R2R3R4R5R6R7R8
38=Oβ-OH=OH=Oα-CH3HCOOH
39=Oβ-OH=OHα-OHα-CH3HCOOH
40β-OHβ-OH=Oβ-O-Ac=Oα-CH3HCOOH
41β-OHH=Oβ-O-Acα-O-Acα-CH3HCOOH
42=O=O=OH=Oα-CH3β-OHCOOH
43β-OH=OHHHβ-CH3HCOOH
44=OOH=OH=Oα-CH3OHCOOH
45=O=OHHHα-CH3HCHO
46β-OH=OHHHα-CH3HCHO
47=Oβ-OH=OHα-OHα-CH3β-OHCOOH
48=Oα-OH=OHα-OHα-CH3β-OHCOOH
49β-OHβ-OH=OH=Oα-CH3β-OHCOOH
50β-OH=O=OH=Oα-CH3β-OHCOOH
51β-OHβ-OH=Oβ-OH=Oα-CH3β-OHCOOH
52β-OH=O=Oβ-OH=Oα-CH3β-OHCOOH
53β-OHβ-OH=OH=Oα-CH3HCOOH
54=OH=OHα-OHβ-CH3HCOOH
55=Oα-OHHHHβ-CH3HCHO
56α-O-Acα-O-AcHHα-OHβ-CH3HCOOH
57=O=O=OHHα-CH3HCHO
58=O=OHHHα-CH3HCH2OH
59α-O-Acα-O-CH3HHα-OHβ-CH3HCOOH
60=O=Oα-OHHHα-CH3HCOOH
61=O=Oβ-OHHHα-CH3HCOOH
62β-OH=OHHHα-CH3HCH2OH
63β-OH=OHHHα-CH3HCHO
64=O=OHHHα-CH3HCOOH
65=Oα-OHHHα-O-Acα-CH3HCOOH
66β-OHβ-OH=OHα-OHα-CH3β-OHCOOH
67β-OHH=OHα-OHα-CH3β-OHCOOH
68=Oβ-OH=OHα-OHα-CH3HCHO
69=OH=OHα-OHα-CH3β-OHCOOH
70α-O-Acα-OHHHα-O-Acβ-CH3HCOOH
Table 3. Ganoderma triterpenes 7198 in Figure 4 and Figure 5.
Table 3. Ganoderma triterpenes 7198 in Figure 4 and Figure 5.
No.Compound NameSourceRef.
71Ganoderic acid Mb (3α, 15α, 22-triacetoxy-7α-hydroxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (fruit bodies)[41]
72Ganoderic acid Mc (3α, 7α, 22-triacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (fruit bodies)[41]
73Ganoderic acid Md (3α, 22-diacetoxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (fruit bodies)[41]
74Ganoderic acid Mg (3α, 22-diacetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (mycelial mat)[43]
75Ganoderic acid Mh (3α, 22-diacetoxy-7α, 15α-dihydroxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (mycelial mat)[43]
76Ganoderic acid Mj (22-acetoxy-3α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid)G. lucidum (mycelial mat)[43]
773α, 22β-Diacetoxy-7α-hydroxyl-5α-lanost-8,24E-dien-26-oic acidG. lucidum (mycelial mat)[49]
78Ganorbiformin BG. orbiforme[46]
79Ganorbiformin CG. orbiforme[46]
80Ganorbiformin DG. orbiforme[46]
81Ganorbiformin EG. orbiforme[46]
82Ganorbiformin FG. orbiforme[46]
83Ganoderic acid O ((22S, 24E)-3α, l5α, 22-triacetoxy-7α-hydroxy-5α-lanosta-7,24-dien-26-oic acid)G. lucidum (cultured mycelium)[50]
847-O-Methylganoderic acid O ((22S, 24E)-3α, l5α, 22-triacetoxy-7α-methoxy-5α-lanosta-8,24-dien-26-oic acid)G. Lucidum (cultured mycelium)[50]
8512β-Acetoxy-3β-hydroxy-7,11,15,23-tetraoxo-lanost-8,20E-diene-26-oic acidG. lucidum (fruit bodies)[32]
8623-Dihydroganoderenic acid D (7β, 23ξ-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic acid)G. applanatum (fruit bodies)[51]
87Methyl ganoderenate D (7β-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic acid methyl ester)G. applanatum (fruit bodies)[51]
88Ganoderenic acid A ((20E)-7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8,20-dien-26-oic acid)G. lucidum (dried fruit bodies)[31]
89Ganoderenic acid B ((20E)-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8,20-dien-26-oic acid)G. lucidum (dried fruit bodies)[31]
90Ganoderenic acid C ((20E)-3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8,20-dien-26-oic acid)G. lucidum (dried fruit bodies)[31]
91Ganoderenic acid D ((20E)-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8,20-dien-26-oic acid)G. lucidum (dried fruit bodies)[31]
9212β-Acetoxy-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20-dien-26-oic acidG. lucidum[26]
93Ganoderenic acid F (3,7,11,15,23-pentaoxo-5α-lanosta-8,20E-dien-26-oic acid)G. applanatum (fruit bodies)[52]
94Ganoderenic acid G (15α-hydroxy-3,7,11,23-tetraoxo-5α-lanosta-8,20E-dien-26-oic acid)G. applanatum (fruit bodies)[52]
95Methy ganoderenate H (methyl 3β-hydroxy-7,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate)G. applanatum (fruit bodies)[52]
96Methyl ganoderenate I (3β, 15α-dihydroxy-7,11,23-trioxo-5α-lanosta-8,20E-dien-26-oate)G. applanatum (fruit bodies)[52]
97Ganoderenic acid HG. lucidum (fruit bodies)[32]
9812β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanosta-8,20-dien-26-oic acidG. lucidum[26]
Figure 4. Structures of compounds 7184.
Figure 4. Structures of compounds 7184.
Molecules 19 17478 g004

CpdR1R2R3R4R5
71α-O-Acα-OHα-O-Acβ-CH3ξ-O-Ac
72α-O-Acα-O-Acα-OHβ-CH3ξ-O-Ac
73α-O-Acα-O-CH3Hβ-CH3ξ-O-Ac
74α-O-Acα-O-CH3α-OHβ-CH3ξ-O-Ac
75α-O-Acα-OHα-OHβ-CH3ξ-O-Ac
76α-OHα-O-CH3Hβ-CH3ξ-O-Ac
77α-O-Acα-OHHα-CH3β-O-Ac
78β-O-Ac=OHα-CH3β-O-Ac
79β-OH=OHα-CH3β-O-Ac
80=Oα-OHα-O-Acα-CH3β-O-Ac
81=Oα-OHHα-CH3β-O-Ac
82=Oα-O-CH3Hα-CH3β-O-Ac
83α-O-Acα-OHα-O-Acα-CH3β-O-Ac
84α-O-Acα-O-CH3α-O-Acα-CH3β-O-Ac
Figure 5. Structures of compounds 8598.
Figure 5. Structures of compounds 8598.
Molecules 19 17478 g005

CpdR1R2R3R4R5R6R7
85β-OH=Oβ-O-Ac=Oβ-CH3=OCOOH
86=Oβ-OHH=Oβ-CH3ξ-OHξ-COOH
87=Oβ-OHH=Oβ-CH3=Oξ-COOCH3
88=Oβ-OHHα-OHβ-CH3=OCOOH
89β-OHβ-OHH=Oβ-CH3=OCOOH
90β-OHβ-OHHα-OHβ-CH3=OCOOH
91=Oβ-OHH=Oβ-CH3=OCOOH
92=Oβ-OHβ-O-Ac=Oβ-CH3=OCOOH
93=O=OH=Oβ-CH3=OCOOH
94=O=OHα-OHβ-CH3=OCOOH
95β-OH=OH=Oβ-CH3=OCOCH3
96β-OH=OHα-OHβ-CH3=OCOCH3
97β-OH=OH=Oβ-CH3=OCOOH
98β-OHβ-OHβ-O-Ac=Oα-CH3=OCOOH
Table 4. Ganoderma triterpenes 99123 in Figure 6, Figure 7, Figure 8 and Figure 9.
Table 4. Ganoderma triterpenes 99123 in Figure 6, Figure 7, Figure 8 and Figure 9.
No.Compound NameSourceRef.
99Methyl ganoderate D (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate)G. lucidum (fruit bodies)[53,54]
100Methyl ganoderate E (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate)G. lucidum (gills)[54,55]
101Methyl ganoderate F (methyl 12β-acetoxy-3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oate)G. lucidum (gills)[56]
102Methyl ganoderate H (methyl 3β-hydroxy-12β-acetoxy-7,11,15,23-tetraoxo-5α-lanost-8-en-26-oate)G. lucidum (gills)[30,56]
103Methyl ganoderate G (methyl 3β, 7β, 12β-trihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate)G. lucidum[20]
104Compound C5G. lucidum (gill surface)[30]
105Compound C6G. lucidum (gill surface)[30]
106Ganoderic acid AP3 (15α, 20ξ-dihydroxy-3,7,11,23-tetraoxolanost-8-en-26-oic acid)G. applanatum (fruit bodies)[34]
10723-Dihydroganoderic acid I (3β, 7β, 20,23ξ-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic acid)G. applanatum (fruit bodies)[51]
10823-Dihydroganoderic acid N (7β, 20,23ξ-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid)G. applanatum (fruit bodies)[51]
10920-Hydroxylganoderic acid GG. lucidum (fruit bodies)[57]
110Ganoderic acid IG. lucidum (gills)[22]
111Lucidumol A ((24S)-24,25-dihydroxylanost-8-ene-3,7-dione)G. lucidum (spores)[38]
112Ganoderiol C (7α-ethoxy-24,25,26-trihydroxy-5α-lanost-8-en-3-one)G. lucidum (fruit bodies)[39]
113Ganoderiol D (24,25,26-trihydroxy-5α-lanost-8-en-3,7-dione)G. lucidum (fruit bodies)[39]
114Ganoderiol G (24,25,26-trihydroxy-7α-methoxy-5α-lanost-8-en-3-one)G. lucidum (fruit bodies)[39]
115Ganoderiol H (3β, 24,25,26-tetrahydroxy-5α-lanost-8-en-7-one)G. lucidum (fruit bodies)[39]
116Ganoderitriol M ((24S)-lanosta-7-oxo-8-en-3β, 24,25-triol)G. lucidum (fruit bodies)[58]
117Sinensoic acid (3,26-dihydroxy-5-lanosta-8,24E-dien-21-oic acid)G. sinense (fruit bodies)[59]
118Tsugarioside B (3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-d-xyloside)G. tsugae (fruit bodies)[60]
119Tsugaric acid A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid)G. tsugae[61]
120Ganosinoside A (3-oxo-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside)G. sinense (fruit bodies)[47]
121Tsugarioside A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside)G. tsugae (fruit bodies)[60]
1223-Oxo-5α-lanosta-8,24-dien-21-oic acidG. resinaceum (fruit bodies)[62]
1233β-Hydroxy-5α-lanosta-8,24-dien-21-oic acidG. tsugae (fruit bodies)[60]
Figure 6. Structures of compounds 99105.
Figure 6. Structures of compounds 99105.
Molecules 19 17478 g006

CpdR1R2R3R4
99β-OHβ-OHHα-OH
100=O=OH=O
101=O=Oβ-O-Ac=O
102β-OH=Oβ-O-Ac=O
103β-OHβ-OHβ-OH=O
104=Oβ-OHOH=O
105β-OH=OOH=O
Figure 7. Structures of compounds 106110
Figure 7. Structures of compounds 106110
Molecules 19 17478 g007

CpdR1R2R3R4R5R6R7R8
106=O=OHα-OHβ-CH3ξ-OH=OCOOH
107β-OHβ-OHH=Oα-CH3β-OHξ-OHξ-COOH
108=Oβ-OHH=Oα-CH3β-OHξ-OHξ-COOH
109β-OHβ-OHβ-OH=Oβ-CH3β-OH=OCOOH
110β-OHβ-OH=O=Oα-CH3ξ-OH=OCOOH
Figure 8. Structures of compounds 111116
Figure 8. Structures of compounds 111116
Molecules 19 17478 g008

CpdR1R2R3R4R5
111=O=Oα-CH3α-OHCH3
112=Oα-O-Etβ-CH3ξ-OHCH2OH
113=O=Oβ-CH3ξ-OHCH2OH
114=Oα-O-CH3β-CH3ξ-OHCH2OH
115β-OH=Oβ-CH3ξ-OHCH2OH
116β-OH=Oα-CH3α-OHCH3
Figure 9. Structures of compounds 117123.
Figure 9. Structures of compounds 117123.
Molecules 19 17478 g009

CpdR1R2R3
117β-OHα-COOHCH2OH
118α-O-AcCH2O-β-D-xylosylCH3
119α-O-COCH3α-COOHCH3
120=Oα-COO-β-D-glucopyranosylCH3
121α-O-Acα-COOHCH3
122=Oα-COOHCH3
123β-OHα-COOHCH3
Table 5. Ganoderma triterpenes 124147 in Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17 and Ganoderma triterpenes 148155 in Figure 18.
Table 5. Ganoderma triterpenes 124147 in Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17 and Ganoderma triterpenes 148155 in Figure 18.
No.Compound NameSourceRef.
1243β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acidG. lucidum (fruit bodies)[63]
1253β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid methyl esterG. lucidum (fruit bodies)[63]
12612β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acidG. lucidum (fruit bodies)[63]
127Methyl ganoderate IG. lucidum[20,22]
128Methyl ganoderate AP (methyl 12β, l5α, 20-trihydroxy-3,7,11,23- tetraoxo-5α-lanost-8-en-26-oate)G. applanatum (fruit bodies)[52]
129Methyl ganoderate N (Methyl 7β, 20-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate)G. lucidum (fruit bodies)[64]
130Methyl ganoderate M (methyl 7β, 12α-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate)G. lucidum (fruit bodies)[64]
131Ganoderiol E (3β, 26,27-trihydroxy-5α-lanosta-8,24-dien-7-one)G. lucidum (fruit bodies)[39]
132Ganoderiol I (15α, 26,27-trihydroxy-5α-lanosta-8,24-dien-3-one)G. lucidum (fruit bodies)[39]
133Ganoderiol J (26,27-dihydroxy-5α-lanosta-8,24-dien-3,7-dione)G. sinense (fruit bodies)[47]
134Epoxyganoderiol A (24S, 25S-epoxy-7α, 26-dihydroxy-5α-lanost-8-en-3-one)G. lucidum[40]
135Ganoderone C (5α-lanosta-8-ene-24,25-epoxy-26-hydroxy-3,7-dione)G. pfeifferi (fruit bodies)[42]
1363-O-Acetylganoderic acid B (3β-acetoxy-7β-hydroxy-11,15,23-trioxolanost-8-en-26-oic acid)G. lucidum (mycelia)[65]
1373-O-Acetylganoderic acid K (3β-acetyloxy-15α-hydroxy-7,11,23-trioxolanost-8-en-26-oic acid)G. lucidum (mycelia)[65]
138Ethyl 3-O-acetylganoderate BG. lucidum (mycelia)[65]
139Ethyl ganoderate JG. lucidum (mycelia)[65]
140Applanoxidic acid G (15β, 20-dihydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid)G. applanatum[66]
141Applanoxidic acid H (3β, 12α, 20-trihydroxy-7α, 8α-epoxydioxo-5α-lanosta-9(11),16-dien-26-oic acid)G. applanatum[66]
1428β, 9α-Dihydroganoderic acid JG. lucidum (fruit bodies)[57]
143Methyl 8β, 9α-dihydroganoderate JG. lucidum (fruit bodies)[57]
144Ganosporeric acid A (3,7,11,12,15,23-hexaoxo-5α-lanosta-8-en-26-oic acid)G. lucidum (spores)[67]
14524ξ-Methyl-5α-lanosta-25-oneG. applanatum (fruit bodies)[68]
1463α-Carboxyacetoxy-24-methylene-23-oxolanost-8-en-26-oic acidG. applanatum (fruit bodies)[69]
1473α-Carboxyacetoxy-24-methyl-23-oxolanost-8-en-26-oic acidG. applanatum (fruit bodies)[69]
148Fornicatin C ((3β)-3-hydroxy-18(13→12β)-abeo-lanosta-13(17),24-dien-18-oic acid)G. fornicatum (fruit bodies)[70]
1493-Epipachymic acid (3α-acetoxy-16α-hydroxy-24-methylene-5α-lanost-8-en-21-oic acid)G. resinaceum (fruit bodies)[62]
1503β, 15α-Diacetoxylanosta-8,24-dien-26-oic acidG. lucidum (mycelia)[71]
151Tsugaric acid C ((24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid)G. tsugae (fruit bodies)[60]
152Ganoderic acid V1 ((24E)-3β, 20ξ-dihydroxy-7,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid)G. lucidum[72]
153Tsugaric acid B (3α-acetoxy-16α-hydroxy-24ξ-methyl-5α-lanosta-8,25-dien-21-oic acid)G. tsugae[61]
154Methyl ganoderenate E (7β, 12β-dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate)G. lucidum (fruit bodies)[64]
1558β, 9α-Dihydroganoderic acid CG. lucidum (mycelia)[65]
Figure 10. Structures of compounds 124126.
Figure 10. Structures of compounds 124126.
Molecules 19 17478 g010

CpdR1R2
124HCOOH
125HCOOCH3
126β-O-AcCOOH
Figure 11. Structures of compounds 127130.
Figure 11. Structures of compounds 127130.
Molecules 19 17478 g011

CpdR1R2R3R4
127β-OHβ-OHH=O
128=O=Oβ-OHα-OH
129=Oβ-OHH=O
130=Oβ-OHα-OH=O
Figure 12. Structures of compounds 131133.
Figure 12. Structures of compounds 131133.
Molecules 19 17478 g012

CpdR1R2R3R4
131β-OH=OHβ-CH3
132=Oβ-CH3α-OHβ-CH3
133=O=OHα-CH3
Figure 13. Structures of compounds 134 and 135.
Figure 13. Structures of compounds 134 and 135.
Molecules 19 17478 g013

CpdR1R2
134α-OHβ-CH3
135=Oα-CH3
Figure 14. Structures of compounds 136139.
Figure 14. Structures of compounds 136139.
Molecules 19 17478 g014

CpdR1R2R3R4
136β-O-Acβ-OH=OCOOH
137β-O-Ac=Oα-OHCOOH
138β-O-Acβ-OH=OCOOEt
139=O=Oα-OHCOOEt
Figure 15. Structures of compounds 140141.
Figure 15. Structures of compounds 140141.
Molecules 19 17478 g015

CpdR1R2R3
140=O=Oβ-OH
141β-OHα-OH=O
Figure 16. Structures of compounds 142145.
Figure 16. Structures of compounds 142145.
Molecules 19 17478 g016

CpdR1R2R3R4R5R6R7R8R9
142=O=O=OHα-OHβ-CH3=OHCOOH
143=O=O=OHα-OHβ-CH3=OHCOOCH3
144=O=O=O=O=Oβ-CH3=OHCOOH
145HHHHHα-CH3Hξ-CH3=O
Figure 17. Structures of compounds 146147.
Figure 17. Structures of compounds 146147.
Molecules 19 17478 g017

CpdR
146CH2
147α-CH3
Figure 18. Structures of compounds 148155.
Figure 18. Structures of compounds 148155.
Molecules 19 17478 g018

Table 6. Ganoderma triterpenes 156196 in Figure 19.
No.Compound NameSourceRef.
15615-Hydroxy-ganoderic acid S
(15α-hydroxy-3-oxo-5α-lanosta-7,9(11),24(E)-trien-26-oic acid)
G. lucidum (fruit bodies)[35]
1573α, 16α-Dihydroxylanosta-7,9(11),24-trien-21-oic acidG. applanatum (fruit bodies)[69]
1583α, 16α, 26-Trihydroxylanosta-7,9(11),24-trien-21-oic acidG. applanatum (fruit bodies)[69]
159Ganoderic acid S1G. lucidum (fruit bodies)[73]
160Ganoderic acid SZ
(3-oxo-lanosta-7,9(11),24(Z)-trien-26-oic acid)
G. lucidum (fruit bodies)[74]
1615α-Lanosta-7,9(11),24-triene-15α-26-dihydroxy-3-oneG. concinna[75]
162Ganoderic acid Me (3α, 15α-diacetoxy-5α-lanost-7,9(11),24E-trien-26-oic acid)G. lucidum (cultured mycelial mat)[41]
163Ganoderic acid Mf (3α-acetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid)G. lucidum (cultured mycelial mat)[41]
164Ganodermenonol (26-hydroxy-5α-lanosta-7,9(11),24-trien-3-one)G. lucidum (dried fruit bodies)[76]
165Ganodermadiol (5α-lanosta-7,9(11),24-triene-3β, 26-diol)G. lucidum (dried fruit bodies)[76]
166Ganodermatriol (5α-lanosta-7,9(11),24-triene-3β, 26,27-triol)G. lucidum (fruit bodies)[77]
167Ganodermic acid S (lanosta-7,9(11),24-trien-3β, 15α-diacetoxy-26-oic acid)G. lucidum[78]
168Carnosodione (26,27-dihydroxylanosta-7,9(11),24-trien-3,16-dione)G. carnosum (fruit bodies)[79]
169Canoderol B ((24E)-5α-lanosta-7,9(11),24-trien-3,26-diol)G. lucidum[23]
170Ganoderic acid Mk (3α, 22-diacetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid)G. lucidum (mycelia mat)[43]
171Ganoderiol B (15α, 26,27-trihydroxy-5α-lanosta-7,9(11),24-trien-3-one)G. lucidum (fruit bodies)[77]
172Ganoderic acid T ((22S, 24E)-3α, 15α, 22-triacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid)G. lucidum (cultured mycelia)[80]
173Ganoderic acid S ((22S, 24E)-22-acetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (cultured mycelia)[23,80]
174Ganoderic acid R ((22S, 24E)-3α, 22-diacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid)G. lucidum (cultured mycelia)[80]
175Ganorbiformin GG. orbiforme[46]
176Lanosta-7,9(11),24-trien-3β, 15α, 22β-triacetoxy-26-oic acidG. lucidum[81]
177Lanosta-7,9(11),24-trien-15α-acetoxy-3α-hydroxy-23-oxo-26-oic acidG. lucidum[81]
178Lanosta-7,9(11),24-trien-3α, l5α-diacetoxy-23-oxo-26-oic acidG. lucidum[81]
179Lanosta-7,9(11),24-trien-3α, 15α-hydroxy-23-oxo-26-oic acidG. lucidum[81]
180Lanosta-7,9(11),24-trien-3α-acetoxy-15α, 22β-dihydroxy-26-oic acidG. lucidum[81]
181Ganodermic acid T-N (3β-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (mycelia)[82]
182Ganodermic acid T-O (3β-acetoxy-15α-hydroxy-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (mycelia)[82]
183Ganodermic acid T-Q (3β-oxo-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (mycelia)[82]
184Compound 10G. orbiforme[46]
185Ganoderic acid P ((22S, 24E)-15α, 22-diacetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (cultured mycelium)[50]
186Ganoderic acid Q ((22S, 24E)-3α, 22-diacetoxy-15α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid)G. lucidum (cultured mycelium)[50]
187Ganoderic acid Jc (15α, 23-dihydroxy-3-oxo-5α-lanosta-7,9(11),24-trien-26-oic acid)G. sinense (fruit bodies)[47]
188Ganodermatetraol (3β, 15α, 26,27-tetrahydroxy-5α-lanosta-7,9(11),24-triene)G. sinense (fruit bodies)[47]
1895α-Lanosta-7,9(11),24-triene-3β-hydroxy-26-alG. concinna[75]
190Ganoderiol F (26,27-dihydroxy-5α-lanosta-7,9(11),24-trien-3-one)G. lucidum (fruit bodies)[39]
19126,27-Dihydroxy-5α-lanosta-7,9(11),24-triene-3,22-dioneG. lucidum (basidiocarp)[83]
19226-Hydroxy-5α-lanosta-7,9(11),24-triene-3,22-dioneG. lucidum (basidiocarp)[83]
193Ganodermic acid P1 (lanosta-7,9(11),24-trien-3α, 22β-diacetoxy-15α-hydroxy-26-oic acid)G. lucidum (mycelia)[84]
194Ganodermic acid P2 (lanosta-7,9(11),24-trien-15α, 22β-diacetoxy-3β-hydroxy-26-oic acid)G. lucidum (mycelia)[84]
195Lanosta-7,9(11),24-trien-3β, 15α, 22-triacetoxy-26-oic acidG. amboinense (fruit bodies)[85]
19616α-Hydroxy-3-oxolanosta-7,9(11),24-trien-21-oic acidG. applanatum (fruit bodies)[69]
Table 7. Ganoderma triterpenes (197213) in Figure 20.
Table 7. Ganoderma triterpenes (197213) in Figure 20.
No.Compound NameSourceRef.
197Lucialdehyde A ((24E)-3β-hydroxy-5α-lanosta-7,9(11),24-trien-26-al)G. lucidum (fruit bodies)[25]
198Ganoderiol a triacetate (3β, 24,26-triacetoxy-5α-lanosta-7, 9(11)-dien-25-ol)G. sinense (fruit bodies)[86]
199Ganoderal AG. lucidum[23]
200Ganoderol AG. lucidum[23]
201Lucidumol B ((24S)-lanosta-7,9(11)-diene-3β, 24,25-triol)G. lucidum (spores)[38]
202Ganodermanontiol (24,25,26-trihydroxy-5α-lanosta-7,9(11)-dien-3-one)G. lucidum (spores)[67]
203Ganoderiol A (5α-lanosta-7,9(11)-dien-3β, 24,25,26-tetraol)G. lucidum (fruit bodies)[77]
204GanodermanondiolG. lucidum (fruit bodies)[87]
205Ganoderic acid X (3α-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid)G. amboinense[88]
206Ganoderic acid TRG. lucidum[89]
207Ganodermic acid Ja (lanosta-7,9(11),24-trien-3α, 15α-dihydroxy-26-oic acid)G. lucidum (mycelia)[84]
208Ganodermic acid Jb (lanosta-7,9(11),24-trien-3β, 15α-dihydroxy-26-oic acid)G. lucidum (mycelia)[84]
209Ganodermic acid R (lanosta-7,9(11),24-trien-3α, 15α-diacetoxy-26-oic acid)G. lucidum[78]
21115α-Hydroxy-3-oxo-5α-lanosta-7,9,24(E)-triene-26-oic acidG. lucidum[26]
21215α, 26-Dihydroxy-5α-lanosta-7,9,24(E)-trien-3-oneG. lucidum[26]
2133β-Hydroxy-5α-lanosta-7,9,24(E)-trien-26-oic acidG. lucidum[26]
Figure 19. Structures of compounds 156196.
Figure 19. Structures of compounds 156196.
Molecules 19 17478 g019

CpdR1R2R3R4R5R6R7R8
156=Oα-OHHβ-CH3HHCOOHCH3
157α-OHHα-OHα-COOHHHCH3CH3
158α-OHHα-OHα-COOHHHCH2OHCH3
159=OHHα-CH3HHCOOHCH3
160=OHHβ-CH3HHCOOHCH3
161=Oα-OHHα-CH3HHCH2OHCH3
162α-O-Acα-O-AcHβ-CH3ξ-H2HCOOHCH3
163β-O-Acα-OHHβ-CH3ξ-H2HCOOHCH3
164=OHHα-CH3HHCH2OHCH3
165β-OHHHα-CH3HHCH2OHCH3
166β-OHHHα-CH3HHCH2OHCH2OH
167β-O-Acα-O-AcHβ-CH3HHCOOHCH3
168=OHOβ-CH3HHCH2OHCH2OH
169β-OHHHβ-CH3HHCH2OHCH3
170α-O-Acα-OHHβ-CH3ξ-O-AcHCOOHCH3
171=Oα-OHHα-CH3HHCH2OHCH2OH
172α-O-Acα-O-AcHα-CH3β-O-AcHCOOHCH3
173α-OHHHα-CH3β-O-AcHCOOHCH3
174α-O-AcHHα-CH3β-O-AcHCOOHCH3
175=OHHα-CH3β-O-AcHCOOHCH3
176β-O-Acα-O-AcHβ-CH3β-O-AcHCOOHCH3
177α-OHα-O-AcHβ-CH3H=OCOOHCH3
178α-O-Acα-O-AcHβ-CH3H=OCOOHCH3
179α-O-Acα-OHHβ-CH3H=OCOOHCH3
180α-O-Acα-OHHβ-CH3HHCOOHCH3
181β-OHα-O-AcHβ-CH3HHCOOHCH3
182β-O-Acα-OHHβ-CH3HHCOOHCH3
183=Oα-O-AcHβ-CH3HHCOOHCH3
184=Oα-O-AcHα-CH3β-O-AcHCOOHCH3
185α-OHα-O-AcHα-CH3β-O-AcHCOOHCH3
186α-O-Acα-OHHα-CH3β-O-AcHCOOHCH3
187=Oα-OHHα-CH3HOHCOOHCH3
188β-OHα-OHHα-CH3HHCH2OHCH2OH
189β-OHHHα-CH3HHCHOCH3
190=OHHβ-CH3HHCH2OHCH2OH
191=OHHα-CH3=OHCH2OHCH2OH
192=OHHα-CH3=OHCH2OHCH3
193α-O-Acα-OHHβ-CH3O-AcHCOOHCH3
194β-OHα-O-AcHβ-CH3O-AcHCOOHCH3
195β-O-Acα-O-AcHα-CH3β-O-AcHCOOHCH3
196=OHα-OHα-COOHHHCH3CH3
Figure 20. Structures of compounds 197213.
Figure 20. Structures of compounds 197213.
Molecules 19 17478 g020

CpdR1R2R3R4R5R6
197β-OHHα-CH324,2524,25CHO
198β-O-AcHα-CH3OAcOHCH2-O-Ac
199=OHβ-CH324,2524,25CHO
200=OHβ-CH324,2524,25CH2OH
201β-OHHα-CH3α-OHOHCH3
202=OHβ-CH3α-OHHCH2OH
203β-OHHα-CH3OHOHCH2OH
204=OHα-CH3OHOHCH3
205β-OHα-O-Acβ-CH3HHCOOH
206=Oα-OHα-CH324,2524,25COOH
207α-OHα-OHβ-CH324,2524,25COOH
208β-OHα-OHβ-CH324,2524,25COOH
209α-O-Acα-O-Acβ-CH324,2524,25COOH
210=OHα-CH3OHOHCH2OH
211=Oα-OHα-CH324,2524,25COOH
212=Oα-OHα-CH324,2524,25CH2OH
213β-OHHα-CH324,2524,25COOH
Table 8. Ganoderma triterpenes (214221) in Figure 21 and Figure 22.
Table 8. Ganoderma triterpenes (214221) in Figure 21 and Figure 22.
No.Compound NameSourceRef.
2143α, 15α, 22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
2153β, 15α, 22β-Trihydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
2163α, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
2173β, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
21822β-Acetoxy-3α, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
21922β-Acetoxy-3β, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acidG. lucidum (mycelia)[71]
220Epoxyganoderiol B (24S, 25S-epoxy-26-hydroxy-5α-lanosta-7,9(11)-diene-3-one)G. lucidum[40]
221Epoxyganoderiol C (24S, 25S-epoxy-5α-lanosta-7,9(11)-diene-3β, 26-diol)G. lucidum[40]
Figure 21. Structures of compounds 214219.
Figure 21. Structures of compounds 214219.
Molecules 19 17478 g021

CpdR1R2R3
214α-OHα-OHα-OH
215β-OHα-OHβ-OH
216α-O-Acα-O-Acα-OH
217β-O-Acα-O-Acα-OH
218α-OHα-OHβ-O-Ac
219β-OHα-OHβ-O-Ac
Figure 22. Structure of compounds 220221.
Figure 22. Structure of compounds 220221.
Molecules 19 17478 g022

CpdR1
220β-OH
221=O
Table 9. Ganoderma triterpenes (222260) in Figure 23.
Table 9. Ganoderma triterpenes (222260) in Figure 23.
No.Compound NameSourceRef.
222Butyl lucidenate NG. lucidum (fruit bodies)[17]
223Butyl lucidenate AG. lucidum (fruit bodies)[17]
22420(21)-Dehydrolucidenic acid N (3β, 7β-dihydroxy-11,15-dioxo-25,26,27- trinorlanosta-8,20-dien-24-oic acid)G. sinense (fruit bodies)[33]
22520-Hydroxylucidenic acid A (7β, 20ξ-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid)G. sinense (fruit bodies)[33]
226Methyl lucidenate D (methyl 12β-acetoxy-3,7,11,15-tetraoxo-5α-lanost-8-en-24-oate)G. lucidum (fruit bodies)[53,54]
22720(21)-Dehydrolucidenic acid A (7β-Hydroxy-3,11,15-trioxo-25,26,27-trisnorlanosta-8,20(21)-dien-24-oic acid)G. lucidum (fruit bodies)[90]
228Methyl 20(21)-dehydrolucidenate A (methyl 7β-hydroxy-3,11,15-trioxo-25,26,27-trisnorlanosta-8,20(21)-dien-24-oate)G. lucidum (fruit bodies)[90]
229Lucidenic acid N (3,7-dihydroxy-4,4,14-trimethyl-11,15-dioxo-5-chol-8-en-24-oic acid)G. lucidum (dried fruit bodies)[91,92]
230Lucidenic acid D (12β-acetoxy-4,4,14α-trimethyl-3,7,11,15-tetraoxo-5α-chol-8-en-24-oic acid)G. lucidum (dried fruit bodies)[31]
231Methyl lucidenate EG. lucidum (gills)[54]
232Methyl lucidenate FG. lucidum (gills)[23,54]
233Ethyl lucidenates A (ethyl 7β-hydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oate)G. lucidum (fruit bodies)[93]
2343β-Oxo-formyl-7β, 12β-dihydroxy-4,4,14α-trimethyl-5α-chol-11,15-dioxo-8-en(E)-24-oic acidG. lucidum[24]
235Lucidenic acid A (7β-hydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oic acid)G. lucidum (dried fruit bodies)[94]
236Lucidenic acid B (7β, 12-dihydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oic acid)G. lucidum (dried fruit bodies)[94]
237Lucidenic acid C (3β, 7β, 12-trihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oic acid)G. lucidum (dried fruit bodies)[94]
2384,4,14α-Trimethyl-3,7-dioxo-5α-chol-8-en-24-oic acidG. lucidum[26]
239Lucidenic acid P (3β, 7β-dihydroxy-12β-acetoxy-25,26,27-trinor-11,15-dioxo dioxolanost-8-en-24-oic acid)G. lucidum (fruit bodies)[95]
240Methyl lucidenate PG. lucidum (fruit bodies)[95]
241Methyl lucidenate Q (methyl-7β, 15α-dihydroxy-25,26,27-trinor-3,11-dioxolanost-8-en-24-oate)G. lucidum (fruit bodies)[95]
2423β-Hydroxy-4,4,14-trimethyl-7,11,15-trioxochol-8-en-24-oic acidG. lucidum (fruit bodies)[28]
243Methyl lucidenate D2G. lucidum (gill surface)[30]
244Methyl lucidenate E2G. lucidum (gill surface)[30]
248Methyl lucidenate N (methyl 3β, 7β-dihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oate)G. lucidum (fruit bodies)[96]
249t-Butyl lucidenate B (t-butyl 7β, 12β-dihydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oate)G.lucidum (fruit bodies)[96]
250Methyl lucidenate AG. lucidum (fruit bodies)[93]
251Lucidenic acid D2G. lucidum (fruit bodies)[95]
25220-Hydroxylucidenic acid D2 ((20ξ)-12β-acetoxy-20-hydroxy-3,7,11,15-tet-raoxo-25,26,27-trisnorlanost-8-en-24-oic acid)G. lucidum (fruit bodies)[90]
25320-Hydroxylucidenic acid F ((20ξ)-20-hydroxy-3,7,11,15-tetraoxo-25,26,27-trisnorlanost-8-en-24-oic acid)G. lucidum (fruit bodies)[90]
25420-Hydroxylucidenic acid E2 (12β-acetoxy-3β-hydroxy-7,11,15-trioxo-25,26,27-trisnorlanost-8-en-24-oic acid)G. lucidum (fruit bodies)[90]
25520-Hydroxylucidenic acid N ((20ξ)-3β, 7β, 20-trihydroxy-11,15-dioxo-25,26,27-trisnorlanost-8-en-24-oic acid)G. lucidum (fruit bodies)[90]
25620-Hydroxylucidenic acid P ((20ξ)-12β-acetoxy-3β, 7β, 20-trihydroxy-11,15-dioxo-25,26,27-trisnorlanost-8-en-24-oic acid)G. lucidum (fruit bodies)[90]
257Lucidenic acid FG. lucidum (gills)[22]
258Methyl lucidenate CG. lucidum[26]
259Lucidenic acid E2G. lucidum (fruit bodies)[95]
260Lucideric acid AG. lucidum[26]
Figure 23. Structures of compounds 222260.
Figure 23. Structures of compounds 222260.
Molecules 19 17478 g023

CpdR1R2R3R4R5R6R7R8
222β-OHβ-OH=OH=Oα-CH3HCOOBu
223=Oβ-OH=OH=Oα-CH3HCOOBu
224β-OHβ-OH=OH=OCH220,21COOH
225=Oβ-OH=OH=Oβ-CH3ξ-OHCOOH
226=O=O=Oβ-O-Ac=Oβ-CH3HCOOCH3
227=Oβ-OH=OH=OCH220,21COOH
228=Oβ-OH=OH=OCH220,21COOCH3
229β-OHβ-OH=OH=Oα-CH3HCOOH
230=O=O=Oβ-O-Ac=Oβ-CH3HCOOH
231β-OH=O=Oβ-O-Ac=Oβ-CH3HCOOCH3
232=O=O=OH=Oβ-CH3HCOOCH3
233=OOH=OH=Oα-CH3HCOOEt
234β-O-CHOβ-OH=OOH=Oβ-CH3HCOOH
235=Oβ-OH=OH=Oβ-CH3HCOOH
236=Oβ-OH=Oβ-OH=Oβ-CH3HCOOH
237β-OHβ-OH=Oβ-OH=Oβ-CH3HCOOH
238=O=OHHHα-CH3HCOOH
239β-OHβ-OH=Oβ-O-Ac=Oα-CH3HCOOH
240β-OHβ-OH=Oβ-O-Ac=Oα-CH3HCOOCH3
241=Oβ-OH=OHα-OHα-CH3HCOOCH3
242β-OH=O=OH=Oα-CH3HCOOH
243=O=O=OO-Ac=Oβ-CH3HCOOCH3
244β-OH=O=OO-Ac=Oβ-CH3HCOOCH3
245=O=O=Oα-OH=Oβ-CH3HCOOCH3
246β-OH=O=Oβ-OH=Oβ-CH3HCOOCH3
247β-OHα-OH=OHα-OHβ-CH3HCOOCH3
248β-OHβ-OH=OH=Oα-CH3HCOOCH3
249=Oβ-OH=Oβ-OH=Oα-CH3HCOOBu
250=Oβ-OH=OH=Oα-CH3HCOOCH3
251=O=O=Oβ-O-Ac=Oα-CH3HCOOH
252=O=O=Oβ-O-Ac=Oβ-CH3ξ-OHCOOH
253=O=O=OH=Oβ-CH3ξ-OHCOOH
254β-OH=O=Oβ-O-Ac=Oβ-CH3ξ-OHCOOH
255β-OHβ-OH=OH=Oβ-CH3ξ-OHCOOH
256β-OHβ-OH=Oβ-O-Ac=Oβ-CH3ξ-OHCOOH
257=O=O=OH=Oα-CH3HCOOH
258β-OHβ-OH=OH=Oα-CH3HCOOCH3
259β-OH=O=Oβ-O-Ac=Oα-CH3HCOOH
260=Oβ-OH=OH=Oα-CH3HCOOH
Table 10. Ganoderma triterpenes 261280 in Figure 24, Figure 25, Figure 26, Figure 27, Figure 28, Figure 29, Figure 30 and Figure 31.
Table 10. Ganoderma triterpenes 261280 in Figure 24, Figure 25, Figure 26, Figure 27, Figure 28, Figure 29, Figure 30 and Figure 31.
No.Compound NameSourceRef.
2614,4,14α-Trimethyl-5α-chol-7,9(11)-dien-3-oxo-24-oic acidG. lucidum (dried fruit bodies)[73]
262Ganoderic acid Jd (15α-hydroxy-3-oxo-5α-lano-sta-7,9(11)-dien-24-oic acid)G. sinense (fruit bodies)[47]
263Methyl lucidenate H (methyl 3β, 7β-dihydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-11,15-dioxo-5α-chol-8-en-24-oate)G. lucidum (fruit bodies)[64]
264Methyl lucidenate I (3β-hydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-7,11,15-trioxo-5α-chol-8-en-24-oate)G. lucidum (fruit bodies)[64]
265Methyl lucidenate J (3β, 12β-dihydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-7,11,15-trioxo-5α-chol-8-en-24-oate)G. lucidum (fruit bodies)[64]
266Methyl lucidenate HaG. sinense (fruit bodies)[47]
267Colossolactone I ((22S)-3-β-hydroxylanosta-8,24-dien-26,22-olide)G. colossum[97]
268Colossolactone II ((22S)-1,3-β-dihydroxylanosta-8,24-dien-26,22-olide)G. colossum[97]
269Colossolactone DG. colossum (fruit bodies)[98]
270Colossolactone EG. colossum (fruit bodies)[98]
271Colossolactone FG. colossum (fruit bodies)[98]
272Colossolactone GG. colossum (fruit bodies)[98]
273Ganosporelactone AG. lucidum (spores)[99]
274Ganosporelactone BG. lucidum (spores)[99]
275Ganosinensin B (ganodermanontriol 24-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)-2-oxo-ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9-dienate)G. sinense (fruit bodies)[100]
276Ganosinensin C (ganodermanontriol 24-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9- dien-ate)G. sinense (fruit bodies)[100]
277Ganodermacetal (methyl 7β, 15α-isopropylide-nedioxy-3β-hydroxy-11,23-dioxo-5α-lanost-8-en-26-oate)G. amboinense (fruit bodies)[85]
278Methyl ganoderate A acetonide (methyl 7β, 15α-isopropylidenedioxy-3,11,23-trioxo-5α-lanost-8-en-26-oate)G. lucidum (fruit bodies)[16]
279Applanoxidic acid A (15α-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid)G. applanatum[101]
280Applanoxidic acid B (3β-hydroxy-7α, 8α-epoxy-12,15,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid)G. applanatum[101]
Figure 24. Structures of compounds 261262.
Figure 24. Structures of compounds 261262.
Molecules 19 17478 g024

CpdR1R2
261=OH
262=Oα-OH
Figure 25. Structures of compounds 263266.
Figure 25. Structures of compounds 263266.
Molecules 19 17478 g025

CpdR1R2R3
263β-OHHβ-CH3
264=OHβ-CH3
265=Oβ-OHβ-CH3
266β-OHHα-CH3
Figure 26. Structures of compounds 267268.
Figure 26. Structures of compounds 267268.
Molecules 19 17478 g026

CpdR
267H
268β-OH
Figure 27. Structures of compounds 269272.
Figure 27. Structures of compounds 269272.
Molecules 19 17478 g027

CpdR1R2R3
269α-Hβ-Hβ-OH
270α-Hβ-Hβ-O-Ac
271α-Hβ-OHβ-O-Ac
272ξ-OHHβ-O-COCH3
Figure 28. Structures of compounds 273274.
Figure 28. Structures of compounds 273274.
Molecules 19 17478 g028

CpdR
273=O
274β-OH
Figure 29. Structures of compounds 275276.
Figure 29. Structures of compounds 275276.
Molecules 19 17478 g029

CpdR
275=O
276H
Figure 30. Structures of compounds 277278.
Figure 30. Structures of compounds 277278.
Molecules 19 17478 g030

CpdR1R2
277β-OHCOOH
278=OCOOCH3
Figure 31. Structures of compounds 279280.
Figure 31. Structures of compounds 279280.
Molecules 19 17478 g031

CpdR1R2
279=Oα-OH
280β-OH=O
Table 11. Ganoderma triterpenes 281287, 288307, 308311, 312, 313315, 316 in Figure 32, Figure 33, Figure 34, Figure 35, Figure 36, Figure 37, Figure 38, Figure 39 and Figure 40.
Table 11. Ganoderma triterpenes 281287, 288307, 308311, 312, 313315, 316 in Figure 32, Figure 33, Figure 34, Figure 35, Figure 36, Figure 37, Figure 38, Figure 39 and Figure 40.
No.Compound NameSourceRef.
281Applanoxidic acid C (20-hydroxy-7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),16-dien-26-oic acid)G. applanatum[101]
282Applanoxidic acid D (3β, 20-dihydroxy-7α, 8α-epoxy-12,15,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid)G. applanatum[101]
283Lanosta-7,9(11),24-trien-3-one15,26-dihydroxyG. zonatum Murill.[27]
284Lanosta-7,9(11),24-trien-26-oic,3-hydroxyG. zonatum Murill.[27]
285Ganoderic acid Y ((24E)-3-ol-5α-lanosta-7,9(11),24-trien-26-oic acid)G. zonatum Murill.[27]
286Applanoxidic acid E (15β-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid)G. applanatum[66]
287Applanoxidic acid F (7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),20E-dien-26-oic acid)G. applanatum[66]
288Ganosinensin A (ganodermanontriol 26-O-{(2Z, 5E, 9E)-2-[2-(2,5-dihydroxyphenyl)-2-oxo-ethylidene]-11-hydroxy-6,10-dimethylundeca-5,9-dienate})G. sinense (fruit bodies)[100]
289Colossolactone III ((22S)-3β, 19-epoxy-lanosta-8,24-dien-26,22-olide)G. colossum[97]
290Colossolactone IV ((22S)-A,B-dihomo-19-nor-4-oxalanosta-8,24-dien-26,22-olide)G. colossum[97]
291Colossolactone VIII ((22S, 23R)-A,B-dihomo-19-nor-15-β-acetoxy-23-hydroxy-4-oxa-3-oxolanosta-1,8,19,24-tetraen-26,22-olide)G. colossum[102]
292Austrolactone ((23S, 25S)-12α, 23-epoxy-3β, 15β, 20α-trihydroxy-7,11-dioxo-5α-lanosta-8,16-dien-23,26-olide)G. australe[103]
293Ganolactone B (3β, 7β-dihydroxy-11,15-dioxolanosta-8-en-24→20 lactone)G. sinense (fruit bodies)[86]
294Ganolactone (7β-hydroxy-3,11,15-trioxo-lanosta-8-en-24→20s lactone)G. lucidum (fruit bodies)[104]
295Colossolactone BG. colossum (fruit bodies)[98]
296Colossolactone C G. colossum (fruit bodies)[98]
2973α-(3-Hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5α-lanost-8-en-21-oic acidG. resinaceum (fruit bodies)[62]
298Colossolactone AG. colossum (fruit bodies)[98]
299Methyl ganosinensate AG. sinense (fruit bodies)[56]
300Ganosinensic acid AG. sinense (fruit bodies)[56]
301Ganosinensic acid BG. sinense (fruit bodies)[56]
302Tsugarioside C (3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside)G. tsugae (fruit bodies)[60]
303Ganorbiformin AG. colossum (fruit bodies)[46]
304Colossolactone V ((22R)-3,4-seco-19,22-diacetoxy-4-hydroxylanosta-8,24(Z)-dien-3,26-dioic acid 3-methyl-ester)G. colossum (fruit bodies)[102]
305Colossolactone VI ((22R)-3,4-seco-19,22-diacetoxy-4-hydroxylanosta-7,9(11),24(Z)-trien-3,26-dioic acid 3-methyl ester)G. colossum (fruit bodies)[102]
306Colossolactone VII ((22S)-3,4-seco-19-acetoxy-4-hydroxylanosta-8,24-dien-26,22-olide 3-methyl ester)G. colossum (fruit bodies)[102]
307Furanoganoderic acid (21,23-epoxy-15α-hydroxy-3,7,1l-trioxo-5α-lanosta-8,20(21),22-trien-26-oic acid)G. applanatum (fruit bodies)[52]
308Fornicatin B (7β-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-4(28),8-dien-3,24-dioic acid)G. fornicatum (fruit bodies)[105]
309Fornicatin G (7β-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-4(28),8-dien-24-oic-3-acetyl ester)G. cochlear (sporophore)[106]
310Fornicatin A (4, 7β-epoxy-28-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlanosta-8-en-3,24-dioic acid)G. fornicatum (fruit bodies)[105]
311Fornicatin H (4, 7β-epoxy-28-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlansta-8-en-3,24-diester)G. cochlear (sporophore)[106]
312Australic acid ((20Z, 23R, 25R)-15α-acetyl-7α, 8α-epoxy-12-oxo-3,4-seco-5α-lanosta-4(28),9,20(22)-trien-23,26-olid-3-oic acid)G. australe[103]
313Lucidone AG. tsugae[107]
314LucidenolG. tsugae[107]
315Ganosineniol AG. sinense (fruit bodies)[47]
3168α, 9α-Epoxy-4,4,14α-trimethyl-3,7,11,15,20-pentaoxo-5α-pregnaneG. concinna[75]
Figure 32. Structures of compounds 281282.
Figure 32. Structures of compounds 281282.
Molecules 19 17478 g032

CpdR
281=O
282β-OH
Figure 33. Structures of compounds 283285.
Figure 33. Structures of compounds 283285.
Molecules 19 17478 g033

CpdRR2
283α-OHCOOH
284=OCH2OH
285β-OHCOOH
Figure 34. Structures of compounds 286287.
Figure 34. Structures of compounds 286287.
Molecules 19 17478 g034

CpdR
286α-OH
287=O
Figure 35. Structures of compounds 288307.
Figure 35. Structures of compounds 288307.
Molecules 19 17478 g035aMolecules 19 17478 g035b
Figure 36. Structures of compounds 308309.
Figure 36. Structures of compounds 308309.
Molecules 19 17478 g036

CpdR
308COOH
309COOCH2CH3
Figure 37. Structure of compounds 310311.
Figure 37. Structure of compounds 310311.
Molecules 19 17478 g037

CpdR1R2
310COOHCOOH
311COOCH3COOCH3
Figure 38. Structure of compound 312.
Figure 38. Structure of compound 312.
Molecules 19 17478 g038
Figure 39. Structures of compounds 313315.
Figure 39. Structures of compounds 313315.
Molecules 19 17478 g039

CpdR1R2
313=O=O
314=OOH
315α-OHCH2OH
Figure 40. Structure of compound 316.
Figure 40. Structure of compound 316.
Molecules 19 17478 g040

3. 13C-NMR Data of Ganoderma Triterpenes

The reported GTs 13C-NMR data are shown in Table 12. For compounds 5, 7, 22, 23, 28, 3134, 36, 37, 54, 55, 59, 89, 95, 97, 98, 110, 112, 114, 121123, 130132, 146, 147, 154, 159, 169, 195, 199, 200, 206, 211213, 235237, 240, 245247, 250, 251, 257260, 265, 283285, 313 and 314 have no 13C-NMR data reported or cannot be researched.
As summarized above, a large number of triterpenes together with their potential pharmacological activities are described from Ganoderma. Being inclined to complement the prior reviews, we summarized the triterpenes from Ganoderma. They contain 30 or 27 carbon atoms, including some with 24 carbon atoms. The great majority of the triterpenes possess double bonds on the ring, at C-8 (9), with hydroxy and carbonyl substituted at C-3, C-7, C-11, and C-15 generally. For this type, the carbon atoms mentioned above are usually a characteristic for its structural determination. The 13C-NMR data of hydroxy substituted C-3 appear from 77–80 ppm, while the data of carbonyl substituted increase to 208–218 ppm. As to the double bonds, the resonance of C-8 arises at 131–165 ppm and the C-9 signal arises at 134–165 ppm, fluctuated for the neighbouring substituent groups.
In the other type, with double bonds located at C-7(8) and C-9(11), the resonance of C-7 appears from 119 ppm to 121 ppm, while the C-8 signal increases to 140–143 ppm. The C-9 signal appears at 144–147 ppm, while the C-11 signal moves to 115–118 ppm. C-23 tends to be oxidized to a carbonyl with 13C-NMR signals appearing at 206 ppm to 217 ppm, or to hydroxy with signals in the 65–67 ppm range. When double bonds appear between C-20 and C-22, the C-23 signal will move to 197–200 ppm. Moreover, C-24 and C-25 are sometimes linked by double bonds in some Ganoderma triterpenes. In this case, the 13C-NMR peaks of C-24 appear at 144–156 ppm and those of C-25 appear at 126–140 ppm. According to the compiled 13C-NMR data, this review should provide a useful and fast way for the identification of GTs.
Table 12. The 13C-NMR spectural data of compounds 1316 except those which have no reported 13C-NMR data.
Table 12. The 13C-NMR spectural data of compounds 1316 except those which have no reported 13C-NMR data.
NO.1b)2b)3b)4b)6b)8b)9b)10b)11b)12b)13b)14b)15b)16b)17b)18b)19b)20b)
C133.435.735.033.135.134.435.735.634.834.835.034.735.735.734.634.334.834.2
C227.534.527.927.234.228.034.434.427.628.328.028.234.334.327.827.734.127.3
C377.5217.178.577.3217.778.7208.4208.778.378.577.578.2217.5217.578.277.5217.878.5
C440.646.839.039.047.039.047.046.738.839.038.938.646.846.838.640.247.239.1
C551.549.049.351.251.751.849.248.849.245.749.549.149.049.049.149.845.247.7
C636.829.326.736.618.717.429.229.126.627.827.627.827.727.828.236.527.928.0
C7199.169.167.1199.029.630.469.168.966.967.069.569.566.466.369.5205.366.768.0
C8151.9159.1157.1145.6163.2162.9159.6159.5156.8155.0159.6158.0157.8157.8158.1154.6159.3158.8
C9145.9140.5142.9151.7138.6140.0140.6140.1142.7142.9142.2142.0141.3141.3141.9149.8140.0141.6
C1039.338.238.840.337.137.846.846.838.645.438.938.638.338.338.538.938.038.6
C11194.2199.6198.0193.9198.1198.3200.0199.7197.9200.0201.2199.8197.6197.6199.9201.3199.1199.4
C1279.351.950.579.151.752.151.951.850.351.052.352.050.250.251.952.351.852.2
C1348.147.045.547.946.847.238.238.045.438.847.447.145.045.047.148.046.446.1
C1458.754.159.658.553.653.554.254.159.458.554.454.059.459.454.052.853.453.5
C15205.972.7217.766.272.973.072.672.4217.5207.572.472.4216.6216.472.572.172.472.3
C1638.136.741.138.038.638.736.236.340.941.035.936.241.041.036.136.337.837.8
C1744.948.445.844.648.748.748.348.245.649.248.548.145.745.848.148.249.049.0
C1812.317.517.612.117.217.117.417.317.417.217.217.117.717.717.117.417.517.3
C1918.119.518.717.919.019.019.619.418.517.619.619.518.218.219.617.617.517.3
C2029.632.832.129.432.632.532.832.832.032.133.032.732.032.032.732.432.532.5
C2121.819.719.821.519.419.419.419.719.619.819.719.619.619.719.619.519.319.3
C2248.649.949.448.549.649.749.849.749.049.350.049.849.049.149.749.549.649.6
C23207.7208.6207.9206.1208.3208.3217.3217.4207.6215.9210.0208.5207.5207.6208.7208.2208.3208.3
C2446.846.946.846.646.846.846.746.846.646.946.946.746.646.846.746.846.946.9
C2534.935.035.135.134.734.634.834.834.634.935.034.734.534.734.634.734.734.7
C26175.9176.0175.9181.0176.2176.127.427.5180.326.8178.5176.2180.3176.1176.3176.1176.2176.4
C2717.317.317.317.117.117.1180.1176.316.9176.217.217.116.917.117.117.117.117.1
C2828.127.528.427.8----------------------------
C2915.720.915.615.5----------------------------
C3021.519.824.621.227.828.317.017.228.215.528.328.227.027.028.227.827.628.2
OCOCH3Bu1'Bu1'CH3COC31C31C31C31C31C31C31C31C31C31C31C31C31C31
170.464.864.8170.220.615.720.820.815.524.515.915.720.820.815.715.420.515.8
OCOCH3Bu 2'Bu 2'CH3COC32C32C32C32C32C32C32C32C32C32C32C32C32C32
21.030.930.920.918.818.819.819.724.418.719.519.424.724.719.420.321.121.1
N-BU1'Bu 3'Bu3' OCH3OCH3 COOCH3 COOCH3 COOCH3 COOCH3OCH3OCH3OCH3OCH3
64.819.319.3 51.951.8 52.0 51.7 51.9 51.951.951.951.951.9
NO.21b)24b)25b)26b)27c)29b)30b)35c)38b)39b)40b)41b)42d)43b)44a)45b)46b)47c)
C134.533.934.434.535.437.437.235.235.635.734.433.834.034.836.035.434.835.2
C224.033.627.428.434.734.134.627.634.434.527.427.533.527.434.534.328.833.9
C379.9215.178.278.4221.0214.9215.478.0216.8218.078.278.5215.578.0215.9214.678.0218.6
C438.046.838.640.747.246.947.039.146.247.038.538.838.739.047.047.239.846.4
C549.250.849.153.045.751.050.949.848.849.049.151.349.749.948.750.450.748.3
C626.637.436.737.828.133.733.827.427.629.226.617.336.836.628.837.136.728.1
C766.1198.666.2201.167.1198.6199.467.066.369.266.229.3199.6199.166.0198.0199.068.2
C8157.4149.8155.8151.9161.8149.9149.8157.3157.8159.2155.9161.5146.1138.9159.7139.8138.9160.4
C9141.6145.9142.9153.6140.2146.1146.8143.1141.2140.6142.0140.1149.0164.9140.9162.6164.7139.6
C1037.539.238.542.438.439.439.338.938.238.238.537.546.439.838.439.438.937.6
C11199.3194.1192.0195.072.0194.1199.4200.3197.7200.1192.1191.6199.823.7198.223.823.6200.3
C1277.978.979.5199.852.479.048.978.450.152.079.880.148.530.250.930.130.251.5
C1351.947.649.662.247.647.743.952.444.946.949.951.556.845.045.245.045.046.3
C1460.358.760.661.354.158.757.260.959.354.160.553.943.547.859.047.849.053.7
C15216.8205.6216.2207.5201.0205.5207.0217.8218.172.9216.474.6207.832.0217.028.727.571.6
C1638.337.837.940.835.337.839.838.641.236.737.333.639.928.842.031.832.035.6
C1745.744.345.240.749.544.544.346.646.748.746.148.644.449.046.849.049.948.5
C1812.012.012.013.517.812.116.012.317.717.413.412.315.415.817.815.915.316.6
C1918.818.718.618.617.918.718.619.118.219.618.619.018.418.418.217.918.418.9
C2028.729.428.233.833.229.532.129.135.536.235.534.132.936.233.936.236.333.1
C2121.321.621.920.419.521.619.821.818.218.520.819.719.718.619.818.618.619.0
C2248.348.447.950.250.048.448.848.734.534.833.133.742.834.843.834.734.842.9
C23208.1207.6207.4211.1210.7207.3207.6210.325.625.926.526.365.425.966.526.026.065.9
C2446.146.646.648.047.246.446.546.9144.1145.3143.2144.2144.4145.6145.0155.2155.3143.2
C2534.234.734.636.637.434.634.635.4127.0127.2127.1127.2126.9126.6128.8139.2139.2128.4
C26180.5175.6176.1180.7179.0180.8180.9178.8171.2172.0171.0172.7169.0172.4170.7195.3195.3170.2
C2716.917.117.118.017.416.916.917.312.112.312.112.012.712.013.49.29.212.3
C2827.927.628.028.727.8------24.719.724.128.227.025.027.025.427.527.0
C2916.420.315.416.620.7------26.927.628.115.719.927.520.821.415.820.1
C3023.020.724.024.921.427.627.628.420.720.915.419.820.015.325.124.925.019.0
C31CH3COCH3CO C31C31C31 CH3CO12-COCH3
161.0170.2170.4 20.420.315.8 170.1170.5
CH3COCH3CO C32C32C32 CH3CO12-COCH3
20.920.9 20.821.023.5 20.721.0
OCH2CH3OCH3 OCOCH3 15-COCH3
60.751.9 170.2 170.6
NO48c)49c)50c)51c)52c)53b)56b)57b)58b)60b)61b)62b)63b)64b)65b)66a)67a)68a)
C134.935.733.634.433.234.730.135.035.334.834.534.734.635.435.235.535.235.2
C234.328.026.927.126.727.623.334.134.334.634.427.327.334.434.329.028.934.1
C3219.578.777.278.076.878.377.3215.5214.6214.4214.977.877.8214.6217.277.677.9218.4
C446.639.739.038.440.038.836.246.947.247.547.438.838.847.246.639.339.745.9
C545.350.050.849.051.249.140.549.850.450.851.649.749.849.044.849.952.448.6
C627.727.636.226.536.426.626.137.137.137.537.236.536.537.228.428.830.928.8
C766.667.7199.966.2199.566.870.0201.3198.1199.4199.8199.0198.9198.066.269.417.968.6
C8160.9158.4148.6156.6146.2156.9131.1151.5139.6142.1139.7138.9138.8139.6134.8160.5164.8159.8
C9139.7143.9151.8142.0151.0142.7145.1149.8162.7158.7160.6164.8164.6162.8140.1141.3139.8140.3
C1037.939.440.438.138..838.638.338.839.440.139.739.739.739.438.139.138.337.5
C11200.1200.1200.1199.5201.4198.021.4201.823.865.867.223.623.523.820.8200.1198.6199.8
C1252.051.249.678.277.650.331.251.230.144.642.730.030.130.231.252.952.951.6
C1347.046.444.251.749.545.345.846.744.947.643.444.844.945.045.347.647.446.2
C1453.460.357.060.157.559.352.148.747.848.148.947.747.747.851.254.754.053.7
C1571.7218.5209.0217.4207.6217.972.431.931.932.631.931.931.928.776.472.472.172.1
C1637.542.045.636.836.741.139.727.4328.727.928.728.728.731.936.437.539.636.2
C1749.747.242.746.245.546.148.849.149.049.748.148.948.950.549.349.549.947.5
C1817.317.615.911.910.617.416.316.915.916.917.315.715.715.916.617.417.017.0
C1917.518.817.618.617.618.417.717.917.919.219.518.218.217.917.319.919.419.3
C2033.534.033.128.529.435.536.236.136.236.036.236.136.136.236.234.634.435.9
C2119.220.019.322.021.318.218.418.318.718.418.618.618.518.418.220.219.918.4
C2243.343.740.441.341.837.434.734.535.934.634.635.834.734.734.644.544.434.4
C2366.466.865.967.066.525.625.825.9224.525.825.824.425.925.925.967.066.926.0
C24142.4144.2142.8142.7142.2143.9145.2154.6126.8145.3145.3126.8155.1145.5144.9145.4145.4156.3
C25130.2129.6128.8129.3129.0127.5126.8139.4134.4126.8126.7134.3139.1126.5126.7128.7128.7138.6
C26172.0171.2170.8170.8175.0172.3172.4195.269.0172.7172.769.0195.3172.5171.2170.8170.8194.4
C2713.113.112.612.812.612.112.09.213.611.911.913.59.012.012.113.513.59.2
C2827.528.627.527.927.428.127.227.4425.425.125.124.924.925.026.528.828.920.8
C2920.516.115.315.215.215.422.720.321.421.621.827.327.325.921.216.716.727.5
C3021.024.921.622.920.124.417.925.8724.925.324.915.215.221.420.120.219.819.1
COCH3
171.9
COCH3
21.9
NO.69c)70b)71b)72b)73b)74b)75b)77b)78b)79b)80b)81b)82b)83h)84b)85b)86b)87b)
C134.930.330.330.130.230.330.330.334.534.835.235.335.331.330.033.335.935.6
C234.023.323.323.323.423.223.323.323.827.434.234.334.324.323.327.334.534.2
C3219.677.577.577.377.677.377.577.679.677.9217.2217.4217.477.777.277.4216.7216.4
C446.836.336.336.236.436.536.436.337.838.946.646.746.737.236.339.147.046.7
C551.340.140.040.540.440.140.540.249.949.844.745.045.040.839.651.249.248.8
C618.427.427.426.022.421.328.128.936.436.628.430.023.328.521.336.527.927.6
C729.366.566.569.976.576.366.867.0198.6198.966.166.776.167.175.9198.566.566.2
C8165.1133.9133.8131.1134.3132.8134.5135.6138.9138.8134.6136.4135.3141.7142.9145.8157.8157.3
C9137.9141.8141.8145.0141.3143.6141.7141.3164.4164.6140.1139.4139.5135.1132.7151.9141.4141.2
C1036.838.438.438.338.138.438.138.239.639.838.137.937.839.238.740.538.638.3
C11199.120.720.721.221.020.920.621.023.623.620.721.321.021.521.1193.5197.5196.8
C1251.631.231.231.231.131.431.731.030.130.131.231.031.132.130.778.549.248.9
C1346.445.545.345.645.046.245.745.044.944.945.145.044.946.045.657.845.945.9
C1453.351.251.352.150.052.852.449.747.847.851.249.749.952.451.748.758.858.6
C1572.076.576.072.230.272.072.429.831.931.975.929.930.176.075.2204.6217.3216.6
C1638.136.636.339.327.937.338.127.928.528.536.127.927.837.337.137.638.137.8
C1749.049.345.945.547.246.446.447.145.645.745.947.147.246.945.248.948.349.7
C1816.716.516.316.215.916.616.415.915.615.616.416.016.017.016.113.319.219.0
C1918.617.517.517.717.517.217.317.318.518.417.317.317.418.017.617.818.418.1
C2033.136.339.939.539.839.339.539.739.539.539.939.739.741.039.9154.7138.5153.3
C2118.818.212.712.912.913.012.912.813.113.112.612.812.813.612.721.118.321.0
C2242.934.774.474.674.874.974.774.774.874.874.374.774.774.874.3126.0126.9124.7
C2366.025.931.931.731.931.931.931.831.831.831.931.831.832.831.8197.874.5197.9
C24142.4145.0138.9139.1139.6139.1139.1139.4139.4139.4138.8139.6139.5140.0139.147.537.247.7
C25129.5126.8129.5129.3129.1129.3129.3129.2129.0129.0129.5129.2129.0130.2129.334.434.534.8
C26171.5172.2172.0171.7172.1172.0171.4172.4171.3171.2171.9172.0171.7172.9172.2180.2179.8176.3
C2712.712.012.312.312.312.312.412.312.312.312.312.312.313.112.317.016.017.2
C2827.527.427.427.227.327.327.427.427.427.426.526.526.5----27.927.327.0
C2920.221.922.021.922.222.021.922.016.315.321.221.321.3----15.521.020.8
C3018.720.220.218.025.618.519.226.325.125.026.126.125.428.227.321.324.824.7
OCOCH3COCH3COCH3COCH3COCH3COCH3CO3-OC-22-OC-15-OC-22-OC-7-OCH3C31C31C31 OCH3
170.9170.9171.9171.1170.9170.9170.9OCH3OCH3OCH3OCH355.822.622.2170.3 51.9
OCOCH3COCH3COCH3COCH3COCH3COCH3CO170.8170.6170.5170.7 C32C32C32
21.421.421.721.621.521.4170.7 21.119.020.5
NO.88c)89c)90b)91b)92b)93h)94h)96h)99b)100b)101b)102b)103b)104b)105b)106b)107b)108b)
C135.534.834.835.635.134.935.234.535.737.337.536.634.635.233.435.035.135.9
C234.327.727.834.234.134.733.927.934.334.734.127.327.634.327.433.928.034.5
C3217.478.378.1216.5215.9213.3213.077.0217.5217.2214.877.378.3216.877.5215.478.6216.8
C446.739.038.846.846.846.846.340.446.843.946.940.438.647.040.346.439.147.0
C548.849.250.048.949.248.549.050.149.050.951.051.449.249.551.549.049.449.2
C629.026.727.627.727.636.136.836.527.833.833.733.226.927.836.836.826.927.9
C768.966.969.466.365.8198.4204.5205.066.3199.3198.7198.766.265.8198.8204.667.166.5
C8159.1156.6158.8157.4156.7146.9150.3149.6157.8149.7149.9151.6157.4158.3150.5150.4156.9157.9
C9140.3142.8142.0141.4141.6149.5152.6154.6141.3146.8146.1145.7141.9140.5147.1152.3142.7141.3
C1038.138.738.838.438.239.539.238.838.339.439.339.138.437.939.239.138.938.5
C11199.1198.0200.0197.8191.8198.1199.8200.1197.6199.3194.1193.9199.3199.5201.6201.2198.0197.8
C1250.549.150.848.978.547.850.551.050.248.979.079.177.978.177.552.151.150.9
C1348.146.349.346.050.344.848.649.245.047.047.747.951.951.749.847.846.045.7
C1453.458.753.558.759.956.852.452.559.457.258.658.460.360.457.952.859.859.8
C1572.7216.472.5216.4215.1204.972.972.9216.4206.8205.4205.5216.8215.5206.071.8217.9218.0
C1631.837.731.637.938.437.132.332.541.039.837.837.838.438.537.930.236.236.4
C1752.249.752.449.750.150.852.052.145.844.544.544.745.845.845.350.950.250.4
C1819.018.818.819.014.417.516.715.517.716.112.112.112.012.110.918.919.119.4
C1919.918.419.718.118.118.417.417.318.218.618.717.918.818.318.117.518.618.4
C20157.0153.8157.3153.6154.1153.6155.6155.732.032.029.429.328.728.729.573.373.473.3
C2121.321.021.320.920.321.521.121.119.719.821.621.621.421.421.326.626.426.3
C22124.3124.7124.5124.7126.1124.6124.5124.649.149.148.548.448.448.548.952.548.548.5
C23198.6197.2199.6196.9197.8197.2197.4197.3207.6207.6207.4207.4208.1208.1208.1211.274.874.8
C2447.547.648.147.547.547.647.647.946.846.746.746.646.446.446.647.736.836.8
C2535.134.834.834.834.435.135.235.234.734.634.734.634.634.734.734.533.833.7
C26180.2180.0179.0180.6180.0181.2181.2175.9176.1176.1176.0176.0176.1176.1176.1177.8178.8178.8
C2717.117.117.317.017.017.017.017.317.117.117.117.017.117.117.117.016.116.1
C28--------26.627.227.027.7--------------27.228.427.2
C29--------21.020.320.318.7--------------20.215.721.0
C3027.528.228.227.024.020.920.720.727.027.627.627.928.126.328.020.625.125.3
C31C31C31C31CH3CO CO-C31C31C31C31C31C31C31
20.715.515.820.8170.6 OCH320.820.920.815.515.421.315.6
C32C32C32C32CH3CO 51.4C32C32C32C32C32C32C32
19.424.419.524.720.6 24.720.320.421.223.123.320.3
NO.109f)111b)113b)115a)116b)117a)118b)119b)120b)124b)125b)126b)127b)128h)129b)133a)134b)135b)
C135.935.335.435.234.935.930.230.436.134.634.634.234.934.535.735.235.535.4
C228.434.434.428.927.528.523.323.434.727.527.727.327.833.934.334.334.434.3
C379.2214.8214.677.178.077.878.178.0216.378.278.278.278.4208.9217.8214.9217.3214.6
C439.947.247.340.138.839.336.736.847.338.638.738.538.946.245.347.146.747.2
C550.550.349.149.649.950.745.345.351.349.349.349.249.249.149.450.250.750.4
C628.437.137.237.236.518.518.018.019.626.026.126.026.736.827.737.028.237.1
C767.7198.2198.1198.7198.826.626.026.026.567.167.166.666.9203.566.3198.266.8198.0
C8157.3139.5139.6138.9138.8134.1134.0133.8135.0158.0158.1158.3156.6151.1157.6139.4136.7139.5
C9144.2162.8162.8164.9164.6134.1134.6134.6133.9142.2142.1142.6142.3152.6141.0163.0139.6162.6
C1039.839.439.539.539.737.236.936.937.139.139.238.738.738.938.339.338.039.4
C11199.423.823.923.823.721.021.020.821.4197.4197.3192.2197.8200.9197.623.821.123.8
C1278.730.130.230.530.230.630.830.829.044.344.475.850.778.550.530.031.030.1
C1353.344.945.045.245.044.744.344.345.051.451.454.045.754.446.844.845.144.9
C1462.747.447.848.247.849.649.949.649.958.358.359.459.755.059.747.749.747.8
C15217.428.628.728.332.027.327.527.031.0210.9210.8209.9217.772.1216.831.830.031.9
C1638.631.831.932.728.729.229.729.027.3122.4122.3122.536.133.336.328.629.928.7
C1753.949.050.550.649.047.540.647.247.6187.6187.6187.149.355.349.048.845.149.0
C1813.815.916.016.115.916.116.116.016.530.930.926.319.013.119.315.816.215.9
C1919.524.917.918.318.419.219.018.918.618.518.518.418.417.318.117.817.217.9
C2073.836.636.637.336.748.944.947.548.528.628.629.173.072.972.936.036.436.2
C2128.318.918.919.319.0178.470.2182.0175.819.419.418.526.726.426.718.518.518.7
C2252.333.433.634.533.533.030.732.533.447.647.647.452.751.252.736.032.832.6
C23211.528.628.829.128.626.124.725.926.4205.8205.9206.1210.4208.9210.424.225.325.0
C2449.479.579.177.179.6124.0124.8123.6124.746.146.346.047.748.347.7131.460.660.3
C2536.273.273.974.873.2136.7131.4132.2131.934.434.634.234.535.034.5136.760.760.7
C26180.223.267.769.323.367.817.717.625.8179.9176.0180.3175.9176.3175.967.465.465.5
C2717.826.520.920.126.613.725.725.717.816.917.116.717.017.217.059.814.214.2
C2828.925.325.427.925.0--27.627.626.428.228.228.0--27.927.025.226.525.4
C2916.421.421.416.027.5--21.821.821.315.515.515.3--19.620.821.321.321.4
C3023.317.925.025.215.328.424.424.324.433.233.233.028.220.725.124.826.124.9
C31C1' Glc C31C31C31CO-CO-
16.2102.7 C1' 51.9170.715.5OCH3OCH3
C32C2' 95.8 C32C3251.452.0
24.371.9 20.724.8
NO.136b)137b)138b)139b)140141142c)143b)144b)145b)148a)149e)150b)151g)152b)153c)155b)
C134.734.834.734.735.935.637.236.337.239.234.131.135.230.533.730.535.9
C224.224.124.224.233.627.635.234.034.518.228.523.624.124.627.423.033.8
C380.279.380.280.2216.478.2217.5214.2214.541.378.377.880.878.877.678.2215.3
C437.837.937.737.846.041.649.047.847.438.339.437.037.838.140.536.547.7
C549.249.949.549.240.539.153.652.850.959.552.445.850.346.950.845.154.4
C626.737.026.726.723.122.240.940.033.422.319.118.326.319.436.217.740.3
C766.9202.866.966.962.462.6215.6212.8198.232.422.526.418.027.3199.325.8204.8
C8157.0154.7157.0157.063.662.855.054.0150.042.851.2134.7132.9135.6146.8133.946.2
C9142.8149.9142.8142.8167.7158.260.459.5149.553.144.9134.9135.4136.3151.4134.359.1
C1038.940.138.938.940.537.938.036.539.237.535.737.237.038.439.136.637.5
C11197.9199.5197.9197.5130.0128.7210.1207.6197.022.327.121.020.822.2199.821.0207.7
C1250.452.350.450.4203.678.153.752.6192.641.549.029.631.130.849.928.650.6
C1345.648.145.645.650.250.251.050.059.042.1145.246.244.745.844.945.646.2
C1459.653.059.659.664.864.451.349.761.059.547.948.851.051.057.249.354.7
C15217.672.3217.6217.678.4204.075.574.1203.835.633.843.676.028.3207.742.1210.4
C1641.136.541.141.1127.2127.239.038.438.930.531.376.636.528.735.076.640.2
C1745.748.345.845.7167.7168.949.047.738.353.1137.357.349.048.647.856.144.5
C1817.617.517.617.630.931.017.116.612.414.6179.217.816.117.017.817.015.8
C1918.718.018.718.724.725.713.713.118.518.619.719.019.120.017.821.413.0
C2032.232.632.232.272.272.233.532.032.236.035.448.736.249.073.947.932.1
C2119.919.619.919.928.628.720.019.423.317.918.6178.818.2178.126.5179.719.4
C2249.549.549.549.553.953.950.549.648.635.335.131.634.634.342.132.049.1
C23207.8208.5207.8207.8208.0208.7211.2208.3207.322.323.233.225.932.2(24R)23.424.9207.7
C2446.846.846.946.848.048.247.846.846.558.2125.6156.1145.276.5(24R)143.633.647.1
C2534.634.835.034.634.134.536.134.633.6213.2131.534.1126.7150.0(24R)127.6155.134.5
C26179.9179.3175.8179.9180.1179.6179.6176.2180.332.125.821.9172.6110.8(24R)173.0106.4176.2
C2717.117.117.417.116.816.917.817.116.831.817.721.912.018.7(24R)12.118.616.7
C2828.317.328.328.324.024.625.925.2--20.326.727.818.228.727.927.325.4
C2916.720.316.716.721.722.221.921.2--35.016.422.027.922.915.521.520.7
C3024.528.324.624.526.927.012.812.527.4 28.725.716.525.322.424.812.7
COCO OCH3C31 C31CH3COCOCH3
171.1170.9 51.920.3 107.0171.1171.3
CH3CH3 C32 CH3COCH3COCOCH3
21.521.4 19.3 21.1171.121.8
NO.156b)157d)158d)160b)161d)162b)163b)164165166167168b)170b)171172b)173b)174b)175b)
C136.629.829.736.635.830.930.736.635.835.435.336.430.636.930.829.830.536.6
C234.825.725.634.934.823.223.234.828.228.124.134.723.135.023.325.523.034.8
C3216.673.873.8216.9216.678.178.1217.079.080.880.6216.478.1215.278.276.078.0216.9
C447.437.237.047.547.336.636.647.438.738.037.447.436.547.536.837.136.447.5
C550.542.842.850.750.444.044.150.750.450.348.850.644.051.044.143.144.050.7
C623.622.622.623.723.622.922.823.623.124.322.723.622.823.922.727.527.523.7
C7121.2120.6120.6119.9121.0121.2121.3119.8120.3120.0120.9121.7121.6121.6121.6120.3120.2120.3
C8141.0142.0141.9142.9141.0140.3140.8142.8142.7142.6140.0139.9140.5142.1140.2142.2142.2142.5
C9144.8146.0145.9144.5144.7145.9146.2144.5145.9145.6145.5145.0146.2145.4146.2145.9145.8144.6
C1037.337.137.137.237.237.437.437.237.437.237.237.437.337.637.537.337.137.2
C11116.9115.1115.1117.3117.0115.7115.7117.2116.3116.5116.0116.8115.3117.3115.5115.5115.5116.9
C1238.535.335.337.838.538.038.537.837.937.837.936.638.438.938.137.637.637.8
C1344.443.943.943.844.344.244.543.743.843.843.944.344.344.644.143.643.643.7
C1452.048.548.450.351.951.552.150.349.249.351.242.952.152.651.650.350.350.3
C1574.643.443.331.574.677.574.727.928.027.977.247.074.573.777.431.231.331.4
C1640.075.175.027.940.137.040.131.431.531.536.8219.239.640.536.722.922.827.6
C1748.956.256.250.848.848.948.950.950.950.848.760.545.549.445.647.347.347.4
C1816.016.916.915.715.916.016.015.715.715.715.816.815.816.515.915.415.415.5
C1922.222.722.722.122.122.722.522.422.822.922.722.122.722.223.022.722.421.1
C2035.946.946.936.235.836.036.036.036.136.135.831.539.336.339.839.339.339.4
C2118.3177.2177.218.318.318.518.318.418.418.418.018.612.818.712.812.612.612.7
C2234.731.931.735.836.634.734.835.936.035.834.535.774.730.074.674.674.674.7
C2325.826.025.426.925.426.025.924.524.624.825.824.831.724.732.131.731.831.9
C24145.1124.3123.1147.1126.6144.9145.2126.9127.0128.6144.9131.2139.1127.6139.2139.5139.6139.5
C25126.8131.2135.7125.7134.6126.8126.8134.3134.3137.4126.7137.3129.4140.8129.4129.0129.0129.1
C26172.225.766.5172.169.0172.0172.169.069.166.8173.067.7172.265.5172.0172.2172.3171.9
C2712.017.713.620.613.512.112.113.613.759.811.860.512.358.612.412.212.212.3
C2817.028.728.725.416.927.827.825.325.625.618.222.427.825.7------25.3
C2925.422.822.825.325.422.522.725.427.828.228.025.322.522.4------22.5
C3022.526.226.122.522.118.217.222.015.817.016.825.717.318.027.928.127.725.5
COCH3COCH3 AcCH3 COCH3 C31C31C3122-O-COCH3
171.2170.8 21.1 170.8 22.622.522.5170.7
COCH3COCH3 AcCH3 COCH3 C32C32C3222-O-COCH3
21.421.3 21.2 21.3 18.625.725.621.1
NO.176b)177b)178b)179b)180b)181b)182b)183b)184b)185b)186b)187a)188a)189b)190b)191b)192b)193b)
C135.429.930.530.630.535.635.336.636.629.930.636.836.835.636.135.835.430.5
C224.225.523.023.123.127.624.137.534.825.523.135.029.227.834.936.536.523.1
C380.776.778.078.178.078.880.7216.6216.476.178.1215.378.478.8216.8216.5216.578.0
C437.637.336.436.536.438.537.447.447.437.036.547.539.838.647.547.647.636.4
C548.942.943.844.043.948.748.950.450.442.945.050.950.149.050.860.760.844.2
C622.823.022.722.822.722.922.623.623.723.022.823.823.922.923.723.823.822.7
C7121.3121.5121.3121.4121.2121.3121.0121.0121.3121.5121.6121.6122.5120.3120.0121.8121.8121.5
C8140.0140.0140.0140.6140.6140.0140.6140.4140.2140.0140.5142.0142.4142.4142.9140.1140.2140.4
C9145.8146.0145.8146.1146.1145.8145.7145.0144.7146.0146.2145.3147.4145.9144.6145.1145.1146.1
C1037.337.337.337.337.237.337.237.337.337.337.337.538.337.337.337.637.637.2
C11115.9115.5115.4115.5115.4115.8116.0116.9116.7115.3115.3117.2116.6116.0117.3117.0117.0115.2
C1238.037.937.838.338.337.938.338.038.037.938.438.839.237.737.936.836.838.4
C1343.944.144.144.544.344.044.244.143.943.944.244.545.043.743.844.544.543.9
C1451.351.751.452.252.051.251.851.351.451.452.052.653.050.250.443.143.152.0
C1577.077.077.274.674.577.374.577.276.776.974.573.674.231.427.934.934.974.4
C1636.637.237.140.140.236.939.837.036.636.739.840.941.027.731.525.025.339.6
C1745.448.748.648.849.248.748.748.945.545.445.050.149.850.750.931.631.745.4
C1815.716.015.916.015.715.915.816.015.815.815.816.316.815.715.817.017.115.7
C1922.822.622.522.722.522.722.722.422.122.722.622.123.622.622.522.322.322.6
C2039.632.832.833.033.435.835.835.939.639.639.334.436.836.036.150.850.839.2
C2112.619.419.319.619.418.118.118.212.712.712.820.319.018.218.418.718.812.7
C2274.451.551.551.967.034.534.734.674.474.474.644.737.334.636.7219.3219.074.5
C2331.9201.6201.4201.843.625.825.725.931.931.931.767.125.125.924.447.147.131.7
C24139.0133.8133.9134.1144.8144.9145.0144.5139.0139.1139.2145.5127.9155.4131.7131.4126.8139.2
C25129.2139.5139.4139.3128.3126.7126.8126.8129.2129.2129.4128.7141.3139.1136.8137.4134.8129.2
C26171.3171.2171.8171.0172.0172.9172.9172.1171.3171.6172.0170.365.8195.367.760.269.3172.1
C2712.314.113.914.112.611.911.912.012.312.312.313.558.89.060.267.913.812.2
C2818.418.518.317.217.118.317.018.225.4----25.629.325.425.525.525.517.2
C2928.128.227.727.827.728.128.025.422.4----22.317.128.022.122.622.627.6
C3016.922.622.322.522.315.716.822.118.328.227.718.018.615.525.425.825.822.4
AcCOAcCOAcCOAcCOAcCOAcCOAcCOAcCO15-O-C31C31 C1'
171.1171.0171.1170.9170.7171.1170.9171.2COCH322.822.5 170.8
AcCOAcCH3AcCOAcCH3AcCH3AcCOAcCOAcCO171.1C32C32 C2'
170.621.4170.721.321.221.321.221.4 18.517.3 170.5
AcCH3AcCH3 C3'
21.021.6 21.2
NO.194b)196d)197b)198b)201b)202b)203204b)205b)207b)208b)209210b)214b)215b)216b)217b)218b)
C135.636.135.735.435.736.636.636.529.930.035.530.536.729.835.630.635.429.9
C227.734.428.022.827.934.828.734.925.625.627.023.034.825.427.423.124.225.6
C378.8215.378.980.878.9216.778.1216.976.176.378.378.0217.075.878.678.080.776.1
C438.646.938.737.638.747.439.447.537.337.338.336.447.537.238.536.537.637.4
C548.750.549.149.349.150.749.850.342.943.148.543.850.342.949.043.949.043.0
C622.923.223.024.323.023.623.523.723.023.022.622.723.622.822.822.822.922.9
C7121.6120.1120.4120.0120.2119.9121.0119.9121.3121.4121.0121.0119.9121.2121.2121.2121.2121.7
C8139.9142.1142.5142.7142.6142.8143.0142.8140.2140.9140.5140.1142.8140.6140.7140.1140.2140.5
C9146.0144.2146.0146.7145.9144.5146.6144.5146.0146.3145.9145.4144.4146.1146.0145.9145.7146.3
C1037.437.037.437.837.337.237.837.837.337.337.137.237.837.237.337.337.337.4
C11115.5116.7116.1116.5116.2117.2116.6117.2115.6115.7115.5115.5117.2115.4115.8115.5116.1115.3
C1237.935.337.837.237.837.838.137.238.038.538.237.937.238.338.437.938.038.5
C1343.943.843.843.743.743.744.143.844.144.444.044.043.744.244.144.144.144.2
C1451.348.350.350.350.350.350.750.751.452.251.651.350.751.951.951.451.452.1
C1576.943.331.526.031.527.628.127.977.474.873.977.327.974.274.377.377.174.6
C1636.675.027.831.527.828.831.928.737.040.039.236.928.839.838.737.237.239.8
C1745.456.250.950.850.951.051.550.948.948.848.748.851.049.245.049.449.445.4
C1815.716.915.716.915.715.716.615.716.015.915.515.915.315.715.715.915.915.8
C1922.721.822.722.822.722.423.122.522.722.722.422.522.422.622.722.622.922.7
C2039.546.936.236.536.536.537.136.636.035.935.635.936.633.340.733.633.639.3
C2112.6177.218.318.618.618.619.018.618.218.317.918.118.619.312.419.319.312.8
C2274.431.834.732.633.531.434.431.534.734.834.534.531.566.572.167.267.274.6
C2331.826.026.127.828.733.528.933.525.925.725.425.833.543.434.843.343.431.7
C24138.9124.2155.476.679.679.277.279.6145.1145.2143.3145.079.1143.6139.9144.7144.7139.2
C25129.2131.1139.173.373.273.974.873.3126.6127.0127.0126.774.1128.6129.0128.1128.1129.1
C26171.525.6195.468.523.667.669.325.5171.9172.8170.5172.967.6170.3170.4171.2171.2171.0
C2712.217.69.220.226.522.020.125.312.012.011.711.822.012.711.412.812.812.3
C2818.325.428.128.128.1--28.823.218.517.416.818.325.417.017.118.418.417.3
C2928.122.115.815.715.8--16.026.628.228.227.727.725.428.028.027.828.128.1
C3015.725.825.625.525.625.325.922.122.822.815.422.320.922.715.722.416.922.8
C1' OCOCH3 C31 C31 AcCH3 CH3COCH3COCH3CO
171.0 170.64 20.9 171.2 21.2 170.8170.5170.6
C2' 170.93 C32 C32 AcCH3 CH3COCH3COCH3CO
170.5 171.11 25.4 21.4 21.3 170.6171.021.03
C3' OCOCH3 AcCO CH3COCH3CO
21.3 20.83 170.7 21.421.3
C4' 20.99 AcCO CH3COCH3CO
20.9 21.29 171.0 21.321.4
NO.219b)220b)221b)222b)223b)224b)225b)226b)227b)228b)229b)230b)231b)232b)233b)234b)238b)239b)
C135.636.635.735.035.834.735.837.435.736.034.837.436.737.335.634.235.334.4
C227.334.827.827.934.527.534.134.034.334.527.634.027.434.634.223.934.327.2
C378.6216.878.978.5216.878.3216.6214.8216.5215.978.3215.277.5215.3218.179.9214.778.0
C438.547.538.738.847.038.646.746.946.846.838.646.940.543.946.737.547.238.5
C548.950.749.149.349.149.148.851.049.048.949.150.951.451.048.749.250.449.1
C622.823.723.026.827.826.527.633.827.729.126.633.733.333.927.626.637.126.6
C7121.6120.0120.367.066.566.966.2198.566.365.766.9198.7198.8199.566.266.1198.166.1
C8140.4142.8142.6157.2158.1156.8157.4149.7157.8159.8156.8149.8151.6149.7157.9157.4139.5155.9
C9146.2144.5146.0142.9141.4142.6141.1146.2141.3140.9142.7146.2146.0146.9141.1141.6162.7142.9
C1037.337.237.438.838.438.838.239.338.338.538.839.339.239.438.237.539.438.5
C11115.4117.2116.2198.2197.9197.8196.9194.1197.5198.0198.0194.1194.1199.4197.8199.523.8192.3
C1238.337.837.850.650.449.149.979.149.149.850.379.179.449.050.278.230.179.8
C1344.043.843.845.545.146.045.047.645.345.545.347.648.047.044.951.944.950.4
C1451.850.350.359.659.558.859.258.658.858.359.458.658.557.259.360.247.860.6
C1574.031.531.5218.1218.2217.7215.8205.8217.7215.5217.5205.9206.0207.3216.8217.128.5216.7
C1639.127.927.941.241.338.435.637.438.739.541.037.637.639.941.138.031.837.4
C1745.350.950.946.446.546.149.545.246.346.746.145.245.545.246.246.548.946.0
C1815.615.715.717.617.918.419.012.018.819.317.412.012.116.117.612.015.913.1
C1922.722.522.718.618.318.518.118.618.218.618.418.718.018.618.218.817.918.6
C2039.136.136.035.435.4143.985.933.0143.9145.835.133.133.035.435.231.735.931.8
C2112.518.418.418.318.2112.225.920.1112.3111.618.020.020.218.318.020.518.320.4
C2274.932.732.730.830.931.334.230.131.331.830.429.930.230.830.629.430.829.5
C2331.525.325.331.331.332.327.431.631.932.630.731.631.831.031.131.530.930.0
C24137.260.660.6173.8173.8177.3175173.6175.1173.2178.2178.7173.7173.8173.5177.8178.1178.2
C25129.960.760.7------------------------------
C26169.965.465.4------------------------------
C2712.314.214.2------------------------------
C2817.125.428.128.427.224.225.0--27.027.024.4--------27.925.328.0
C2927.922.115.815.620.928.126.9--20.820.928.1--------16.421.415.3
C3015.625.425.624.624.915.420.727.624.625.215.427.627.927.727.023.124.924.0
CH3CO Bu1'Bu1' C31 COOCH3 C31C31C31C31C31 COCH3
171.1 64.664.6 20.8 51.5 20.415.620.920.7161.0 170.5
CH3CO Bu2'Bu2' C32 C32C32C32C32 COCH3
20.87 30.930.9 20.4 20.821.420.324.6 20.7
NO.241b)242b)243b)244b)248b)249b)252b)253b)254b)255b)256b)261b)262a)263a)264a)266a)267b)268a)
C135.633.634.033.335.035.434.034.633.234.834.436.636.835.436.735.335.473.8
C234.327.433.827.427.934.533.633.827.327.627.434.835.028.327.928.927.739.8
C3216.977.6214.877.578.5215.9214.9215.177.478.278.1216.5215.372.070.779.378.875.5
C446.839.146.940.538.847.246.947.040.538.638.647.447.443.043.643.138.840.2
C548.850.851.051.449.349.650.950.951.449.149.150.750.942.544.550.250.249.1
C629.036.337.436.726.928.037.437.236.626.626.723.723.827.834.128.518.217.6
C768.8199.4198.5198.867.066.0198.4199.1198.066.066.1119.9121.666.7200.467.026.426.0
C8159.2151.6149.7151.6157.2158.6145.6146.2151.4156.5155.9142.6142.0158.8152.2158.0134.1134.1
C9140.3147.0146.2156.0142.9140.6149.6149.6145.4142.6142.9144.4145.3142.9147.4142.6134.4137.0
C1038.040.439.339.238.938.139.334.639.138.938.637.237.539.240.839.136.944.1
C11199.6199.9194.1194.1198.1199.9193.3198.0193.0197.0191.0117.0117.2198.3199.8198.420.925.1
C1251.849.679.179.450.678.578.648.878.950.279.137.838.751.149.951.130.732.0
C1346.644.347.648.045.551.947.944.348.245.449.843.744.545.644.545.644.444.3
C1453.957.058.658.559.660.558.957.158.959.361.050.252.659.257.659.049.850.4
C1572.6208.1205.8206.0218.1217.5203.8204.9203.9215.7214.527.973.6216.8208.0216.730.731.6
C1636.640.237.437.641.237.935.434.335.735.737.131.540.441.440.541.527.728.7
C1748.545.645.245.546.446.848.848.149.249.550.250.849.346.245.546.345.746.6
C1817.316.212.012.117.612.313.017.413.218.814.215.716.417.816.417.915.516.2
C1919.417.818.618.018.618.518.718.617.918.318.522.022.119.218.619.219.115.5
C2035.735.333.033.035.431.886.486.086.685.986.736.236.135.435.535.340.440.7
C2118.118.220.120.218.220.726.126.326.125.925.218.318.418.118.218.013.313.8
C2230.030.530.130.230.930.034.534.234.534.234.629.732.031.031.031.080.280.5
C2331.030.831.631.831.132.428.027.328.127.528.330.131.931.031.130.927.728.7
C24174.3178.0173.6173.7174.1173.9175.6175.8175.6175.9175.5178.2176.4174.0174.0174.1139.7140.5
C25--27.8----------------------66.665.1--128.1127.8
C26--15.5----------------------13.213.1--166.6166.2
C27--21.8----------------------24.821.6--17.118.7
C2827.4------28.426.527.627.627.928.128.125.425.6----23.727.928.2
C2920.7------15.621.420.420.315.515.415.422.422.3----64.215.415.4
C3019.4--27.627.924.623.521.121.321.624.724.525.317.9----24.924.324.9
CO- C31C31C1'C1'COCH3 COCH3 COCH3 CO-CO-CO-
OCH3 20.415.651.964.6170.1 170.1 170.3 OCH3OCH3OCH3
51.6 C32C32 C2'COCH3 COCH3 COCH3 51.451.451.4
20.821.4 30.921.0 21.0 21.2
NO.269b)270b)271b)272b)273b)274b)275b)276b)277a)278b)279b)280b)281b)282b)286287288b)289b)
C1143.7143.6144.2147.935.235.036.636.635.535.236.035.735.735.436.236.136.729.7
C2118.0118.1118.5116.734.328.334.834.829.334.333.627.735.427.533.733.634.922.8
C3167.1167.0166.8163.9213.277.0217.0217.078.1217.2216.278.0215.777.9216.5216.0216.977.5
C480.580.580.677.547.038.647.547.540.144.845.941.546.041.846.045.947.536.4
C549.049.049.292.649.849.650.850.850.549.440.839.340.739.439.440.750.747.7
C638.738.437.344.127.927.923.623.627.227.223.221.822.921.823.222.723.720.4
C727.627.227.226.865.866.6119.4119.471.770.160.558.759.159.062.962.6119.425.7
C8147.6147.0149.3149.5157.8156.8142.8142.7158.3158.366.071.462.162.964.357.6142.7137.6
C9130.5129.9131.8127.6140.9143.0144.4144.4140.7138.7163.4165.6167.6168.9164.8164.8144.3128.3
C10139.1139.3140.1132.937.839.237.237.139.337.540.237.940.838.040.340.737.239.4
C1126.926.867.728.0199.4200.5117.3117.2200.0199.7130.8128.7129.8128.5130.1129.7117.222.5
C1231.431.142.531.178.179.037.737.753.352.1201.2200.9199.8200.2202.8200.537.731.0
C1343.744.343.244.349.950.543.743.740.146.950.354.954.554.353.355.043.844.3
C1456.454.955.655.163.363.050.350.253.752.959.362.062.861.560.258.850.350.4
C1576.278.077.678.4215.5215.027.827.871.970.871.7209.6202.8203.176.6209.527.831.1
C1640.638.638.538.460.460.631.531.433.332.533.638.5125.2125.239.538.331.527.6
C1745.645.345.145.754.254.050.850.749.648.945.843.0181.6181.948.742.950.945.7
C1817.316.718.916.812.813.315.715.718.117.618.118.130.329.819.618.115.815.7
C19143.0142.8141.0139.418.319.222.022.020.719.621.618.324.925.921.321.622.1104.0
C2040.039.939.939.833.033.336.436.533.632.7157.3154.973.072.9158.6158.636.540.4
C2113.413.313.213.319.219.618.518.520.319.820.620.429.529.420.920.418.713.3
C2280.079.879.679.752.552.333.133.150.649.9126.0126.752.952.9126.3126.833.580.1
C2327.827.827.727.787.087.525.825.7209.3208.5198.8198.7206.2206.3199.2198.529.827.9
C24139.6139.4139.4139.340.640.478.876.847.846.947.647.747.847.847.647.677.2139.0
C25128.3128.4128.4128.434.334.873.673.536.334.834.834.934.533.133.734.973.9128.0
C26166.4166.3166.2166.2178.6179.066.568.7178.6176.4179.6179.7179.9179.9180.1180.269.6166.5
C2717.117.117.117.115.615.618.118.318.317.317.017.016.916.917.017.020.317.2
C2829.028.828.124.9----25.325.329.327.814.617.124.817.121.724.825.423.8
C2926.326.426.724.8----22.522.417.420.824.625.821.625.724.821.722.525.7
C3026.626.425.424.425.828.525.425.420.219.828.728.728.728.728.628.625.523.2
C1'C1'C1'C31C31C1'C1'C1'COCH3 C1'OCH3
170.4170.3170.121.316.0195.531.8102.752.1 195.355.2
C2'C2'C2'C32C32C2'C2'C2'C(CH3)2 C2'
21.421.421.325.224.6127.8140.624.1102.3 126.6
NO.290b)291b)292b)293a)294b)295b)296b)297e)298b)299a)300a)301a)302b)303b)304b)305b)306b)307b)
C127.5143.834.135.535.731.228.731.332.657.057.057.030.431.028.828.829.735.2
C227.1118.027.428.634.227.728.423.628.036.536.536.523.334.627.725.528.334.0
C3177.3167.076.577.6216.478.7179.078.378.9216.5216.5216.478.1216.6175.6174.5175.5214.9
C474.577.839.249.746.838.975.337.039.047.047.047.136.747.175.275.074.846.6
C555.148.950.349.748.950.247.946.050.155.455.455.545.339.747.948.047.849.3
C633.835.836.928.127.617.623.918.417.829.429.429.418.028.824.321.524.836.9
C727.127.1203.866.766.225.726.726.326.268.368.468.325.966.224.3117.926.0204.5
C8139.2146.0146.2158.7157.5137.1143.3134.4137.9136.4136.3136.3133.7132.9143.1134.1139.6150.9
C9121.7147.0155.9142.7141.2131.7126.1135.1130.4154.7154.7154.8134.776.3126.1141.1126.1153.2
C1091.5142.840.439.338.339.645.437.342.248.648.648.636.941.445.442.245.739.4
C1133.026.3198.5198.0196.823.020.821.222.083.583.683.520.826.222.6120.422.5200.9
C1230.731.179.350.950.131.031.030.831.037.437.437.430.834.231.239.431.249.6
C1344.544.354.145.845.144.444.345.044.445.645.645.744.345.251.443.744.148.2
C1450.554.950.659.059.350.251.549.950.462.362.462.449.5155.051.849.951.451.8
C1530.177.880.1215.0215.830.731.327.530.7215.0215.3214.827.077.530.531.530.872.9
C1627.138.5128.136.535.827.627.429.427.541.041.141.028.947.928.526.026.631.7
C1745.544.8157.749.749.045.845.947.747.146.846.946.647.049.746.947.547.839.2
C1815.516.726.018.618.115.615.916.416.617.717.717.716.317.215.716.015.816.6
C1941.5142.820.819.419.167.867.319.165.818.818.818.819.017.067.261.667.217.6
C2040.335.871.286.585.540.440.349.141.635.735.932.647.837.840.140.040.2124.4
C2113.312.832.825.826.013.313.4178.512.018.618.720.3175.213.312.912.613.3138.4
C2280.184.048.627.827.580.280.331.972.731.431.949.832.974.675.675.580.1107.7
C2327.963.6106.834.234.227.927.832.834.031.131.8208.9123.531.633.133.127.3153.6
C24139.7143.844.6176.7175.9139.6139.7156.0125.4174.1176.146.9132.3138.5141.0140.9142.934.3
C25128.0127.734.1----128.2128.234.3137.9----35.7155.4129.8128.2128.1128.038.5
C26166.5164.0178.7----166.6166.722.061.4----178.4106.7172.0172.4171.7166.3180.0
C2717.116.814.5----17.117.121.922.4----17.717.712.520.620.517.018.9
C2832.028.529.625.425.028.133.728.028.427.127.127.127.625.833.733.528.727.3
C2925.226.615.116.527.015.526.121.915.518.918.918.921.822.026.125.823.820.4
C3024.526.629.728.820.724.224.924.524.720.620.720.624.431.424.324.322.520.5
CO C1'C1'C1'C1'OCH3 C1' C1'C1'C1'
170.4 171.1170.7171.2170.551.4 94.5 170.6170.5170.4
NO.308a)309b)310a)311b)312a)315a)316b)NO.308a)309b)310a)311b)312a)315a)316b)
C132.731.838.036.637.135.532.4C1817.717.718.017.817.717.719.6
C230.830.429.629.930.128.832.2C1922.422.425.524.923.020.016.3
C3176.5173.9176.4174.7175.677.6214.1C2036.236.236.236.0139.940.1205.2
C4146.5146.487.386.1145.039.447.0C2118.518.518.118.119.017.531.2
C545.045.048.048.444.849.943.5C2231.927.731.931.3126.366.926.9
C635.535.432.132.527.029.036.7C2331.932.431.631.075.2--20.3
C767.967.872.973.161.369.5198.3C24176.5176.5176.4174.536.8--17.5
C8165.3165.7161.4161.266.5160.566.8C25--------34.3----
C9137.4137.1135.4135.1163.0141.968.1C26--------179.0----
C1041.341.241.641.143.839.137.4C27--------15.5----
C11200.4200.4199.8200.2130.0200.3200.6C28115.6115.771.371.3115.228.8--
C1252.152.050.950.8201.152.846.0C2923.423.225.025.323.016.7
C1347.341.245.345.259.147.745.5C3027.627.724.523.815.120.2
C1453.453.350.950.651.854.554.8 CH2O 3-OCH3OAc
C1532.431.930.129.371.872.6205.9 60.4 51.920.7
C1627.832.427.229.531.936.636.4 CH3CH2O 24-OCH3169.9
C1750.150.150.250.044.345.452.4 14.4 51.8
Notes: NO. 1 N-BU 2' 30.8, N-BU 3' 19.3, N-BU 4' 13.9; NO. 2 Bu 4' 13.9; NO. 3 Bu 4' 13.9; NO. 24 OCH2CH3 14.1; NO. 29 OCOCH3 20.9; NO. 41 15-COCH3 21.3; NO.65 15-OCOCH3 21.1; NO. 73 7-OCH3 55.6; NO. 74 7-OCH3 54.5; NO.77 AcCH3 21.4, AcCH3 21.0; NO. 78 3-OCOCH3 21.2, 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 79 22-OCOCH3 21.0; NO. 80 15-OCOCH3 21.1, 22-OCOCH3, 170.6, 22-OCOCH3 21.0; NO. 81 22-OCOCH3 21.1; NO. 82 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 83 AcCH3 21.1, AcCH3 21.3, AcCH3 21.3, CO 170.3, CO 170.3, CO 170.5; NO. 84 AcCH3 21.0, AcCH3 21.6, AcCH3 21.7, CO 170.6, CO 170.1, CO 170.2, OCH3 55.2; NO. 99 COOCH3 51.9; NO. 100 OCH3 51.9; NO. 101 OCH3 51.9, COCH3 20.9, COCH3 170.2; NO. 102 OCH3 51.8, COCH3 20.8, COCH3 170.1; NO. 103 OCH3 51.9; NO. 104 OCH3 51.9; NO. 105 OCH3 51.9; NO. 118 C3' 73.7, C4' 69.7, C5' 63.7, COCH3 170.9, COCH3 21.4; NO. 120 C2' 74.0, C3' 79.2, C4' 71.4, C5' 79.0, C6' 62.5; NO. 127 OCH3 52.0; NO. 138 COO-CH2CH3 60.9, COOCH2CH3 14.4, CO of AcO-C(3) 171.1, CH3 of AcO-C(3) 21.5; NO. 139 COOCH2CH3 60.8, COOCH2CH3 14.4; NO. 145 C24' 6.8; NO. 149 CH3CO 170.4; NO. 150 CH3CO 21.4, CH3CO 21.3; NO. 151 C23 31.8(24S), C24 75.6(24S), C25 149.8(24S), C26 111.5(24S), C27 18.1(24S); NO. 153 C24' 21.5; NO. 167 AcCO 170.8, AcCO 171.0.; NO. 172 AcCH3 21.2, AcCH3 21.4, AcCH3 21.5, CO 170.7, CO 170.9, CO 170.2; NO. 173 AcCH3 21.0, CO 170.6; NO. 174 AcCH3 21.0, AcCH3 21.3, CO 170.6, CO 170.6; NO. 176 AcCO 170.0, AcCH3 21.4, AcCH3 21.3, AcCH3 21.0; NO. 178 AcCH3 21.2, AcCH3 21.2; NO. 184 15-OCOCH3 21.4, 22-OCOCH3 170.6, 22-OCOCH3 21.0; NO. 185 AcCH3 21.5, CO 170.6, CO 171.2; NO. 186 AcCH3 21.7, CO 170.7, CO 170.9; NO. 193 C4' 20.9; NO. 222 Bu3' 19.3, Bu4' 13.9; NO. 223 Bu3' 19.3, Bu4' 13.9; NO. 226 COOCH3 20.8, OCH3 51.4, COCH3 170.0; NO. 230 COCH3 20.8, COCH3 170.1; NO. 231 OCH3 51.6, COCH3 20.9, COCH3 170.1; NO. 232 OCH3 51.7; NO. 233 C33 60.5, C34 14.2; NO. 243 OCH3 51.6, COCH3 20.8, COCH3 170.0; NO. 244 OCH3 51.6, COCH3 20.9, COCH3 170.1; NO. 249 C3' 19.3, C4' 13.9; NO. 275 C3' 145.2, C4' 34.5 C5' 25.6, C6' 122.1, C7' 136.9, C8' 39.0, C9' 25.6, C10' 125.5, C11' 134.5, C12' 38.7, C13' 13.8, C14' 16.2, C15', 169.0, C1'' 157.1, C2'' 112.7, C3'' 117.3, C4'' 148.2, C5'' 126.0, C6'' 119.8; NO. 276 C3' 133.3, C4' 35.9 C5' 28.5, C6' 124.6, C7' 136.7, C8' 38.9, C9' 27.3, C10' 126.8, C11' 135.8, C12' 69.0, C13' 13.7, C14' 16.2, C15' 172.3, C1'' 128.0, C2'' 149.3, C3'' 114.8, C4'' 151.2, C5'' 116.9, C6'' 117.8; NO. 277 C3' 27.0; NO. 278 CH3 26.4, CH3 23.5; NO. 288 C3' 146.3, C4' 34.6C5' 25.5, C6' 122.1, C7' 136.6, C8' 39.1, C9' 25.5, C10' 125.3, C11' 134.4, C12' 68.6, C13' 13.9, C14' 16.3, C15' 168.3, C1'' 157.0, C2'' 114.9, C3'' 117.2, C4'' 148.1, C5'' 126.1, C6'' 119.8; NO. 291 CH3 21.4; NO. 295 C2' 21.1; NO. 296 C2' 21.1; NO. 297 C2' 46.4, C3' 69.9 C4' 46.1, C5' 171. 9,3'-CH3 28.4, OCH3 51.2, C31 107.1; NO. 298 C2' 21.1; NO. 302 C2' 72.3, C3' 75.9, C4' 69.5, C5' 65.8, COCH3 170.9, COCH3 21.4, C241 25.7; NO. 303 22-OCOCH3 171.3, 22-OCOCH3, 21.2; NO. 304 C2' 20.7, C1'' 170.9, C2'' 21.1, OCH3 51.8; NO. 305 C2' 21.1, C1'' 170.8, C2'' 21.2, OCH3 51.8; NO. 306 C2' 20.7, OCH3 51.4. (a) Measured in C5D5N; (b) Measured in CDCl3; (c) Measured in CD3OD(50%) and CDCl3(50%); (d) Measured in DMSO-d6; (e) Measured in pyridine-d5; (f) Measured in CD3OD; (g) Measured in (CD3)2CO; (h) Measured in C6D6.

4. The Bioactivities of Ganoderma Triterpenes

4.1. Anti-Tumor Activity

Cancer has been acknowledged as a huge threat to human health and most governments are committed to diminish this threat. The urgent task of finding anti-tumor drugs with high efficiency and low toxicity have drawn countless researchers’ efforts directed to the discovery of lead compounds or bioactive ingredients from nature resources such as Ganoderma. The GTs were extensively evaluated for cytotoxic activities against a series of tumor cell lines. Compounds 45, 46, 164 and 204 showed cytotoxic effects against the tested tumor cell lines. Compound 46 exhibited the most potent cytotoxicity against LLC, T-47D, Sarcoma 180 and Meth-A tumor cells [25]. Compounds 62, 190 and 212 showed strong cytotoxic activities against human Hela cervical cancer cells [26]. According to Cheng’s report, the ganoderic alcohols showed stronger activities than ganoderic acids which implies that a hydroxy group substituted at 26 may be a very important structural feature for cytotoxic activity, however, the more hydroxyl groups there are, the lower the inhibitory activity will be [26]. Compounds 42 and 85 showed cytotoxicity against p388, Hela, BEL-7402, and SGC-7901 human cancer cell lines, with IC50 values in the 8–25 μM range [32]. Compounds 4752 were studied in vitro against Meth-A and LLC tumor cell lines [37]. Compound 187 displayed selective inhibitory activity against HL-60 cells, and compound 131 exhibited selective cytotoxic activity against MCF-7 cells. Compounds 7, 67 and 188 showed the ability to induce hPXR-mediated CYP3A4 expression [47]. Compounds 9, 23, 57 and 68 showed significant cytotoxic activity, with IC50 values of 18.7, 21.4, 16.2 and 20.1 μg/mL, respectively [48]. Compounds 77, 163, 170 and 173 were tested in vitro for their cytotoxic activities against 95D and Hela tumor cell lines with IC50 values ranging from 14.7 to 38.5 μM [49]. Compound 121 showed significant activity against T-24 cells, while compounds 119, 123, showed significant activity against T-24, HT-3, and CaSKi cells, respectively [60]. Compound 297 showed significant cytotoxic activity with an IC50 value of 2.5 μg/mL in the Hep-2 cell line [62]. Treatment of human hepatoma HuH-7 cells with compound 205 caused immediate inhibition of DNA synthesis as well as activation of ERK and JNK mitogen-activated protein kinases, and cell apoptosis. Molecular events of apoptosis including degradation of chromosomal DNA, decrease in the level of Bcl-xL, the disruption of mitochondrial membrane, cytosolic release of cytocherome c and activation of caspase-3 were elucidated. The ability of compound 205 to inhibit topoisomerases and to sensitize cancer cells towards apoptosis meets the criteria of a potential anticancer drug [88]. Compounds 30, 229 and 235 showed significant cytotoxic activities against Hep G2, Hep G2,2,15, and P-388 cell lines [91]. Compound 233 showed cytotoxicity against HL-60 and CA46 cancer cell lines [93]. Biological activity as an anti-tumor promoter was observed for compounds 279282 [101]. Compound 285 showed moderate cytotoxicity against liver cancer and lung cancer cell lines [27]. Compounds 140, 279, 281, 287, 292 and 312 inhibited the viability and growth of the HL-60 cell lines [103].

4.2. Anti-HIV and Anti-HIV-1 Protease Activity

It was reported that compounds 270, 272, 291 and 304306 were inhibitory against HIV-1 protease, with IC50 values for the most potent compounds ranging from 5 μg∙mL1 to 13 μg∙mL1 [102]. Moreover, compounds 190 and 210 were found to be active as anti-HIV-1 agents with an inhibitory concentration of 7.8 μg∙mL1 for both, and compounds 4, 11, 23, 28, 171 and 203 were moderately active inhibitors against HIV-1 protease with a 50% inhibitory concentration of 0.17–0.23 mM [18]. While compounds 5, 53, 201 and 204 showed significant anti-HIV-1 protease activity with IC50 values of 20–90 μM [38]. In addition, compounds 39, 224 and 255 inhibited human immunodeficiency virus-1 protease with IC50 values of 20–24 μM.

4.3. Neurotrophic Activity

A series of reports has shown that Ganoderma triterpenes exhibit neurotrophic activity. Bioassay results revealed that compounds 12 and 261 have nerve growth factor-like neuronal survival-promoting effects, whereas the two compounds mentioned above and compounds 10, 159 and 183 showed brain-derived neurotrophic factor-like neuronal survival-promoting activities [73]. Compounds 1 and 278, exhibiting specific anti-acetylc-holinesterase activity, are being examined as possible drug candidates for the treatment of Alzheimer’s and related neurodegenerative diseases. Compounds 62, 204, 210 and some other Ganoderma triterpenes exhibited moderate acetylcholinesterase-inhibitory activity, with IC50 values ranging from 9.40 to 31.03 μM. These results indicated that these lanostane triterpenes are preferential inhibitors of acetylcholinesterase and may be suitable as drug candidates [16].

4.4. Hepatoprotection

It is also reported that compound 11 showed significant hepatoprotective activity. However, increased doses of compound 11 (up to 10 times) did not further reduce GOT/GPT levels in the serum of the mice [107]. Compound 144 has an activity of lowering the levels GPT in mice with liver injury by CCl4 and GaNI and exhibits hepatoprotective effects [67].

4.5. Antiobesity Activity

In 2010, the inhibitory effect of triterpenes isolated from G. lucidum on adipocyte differentiation in 3T3-L1 cells was reported for the first time [17]. According to a report on the subsequent research, compound 249 reduced the triglyceride accumulation significantly by 72% at 80 μM and it effectively suppressed the glycerol-3-phosphate dehydrogenase activity in the cells. It suppressed the gene expressed of PPARγ, C/EBPα, and SREBP-1c in a dose-dependent manner during differentiation. These findings demonstrate that compound 249 contributes to the inhibitory effect on adipocyte differentiation in 3T3-L1 cells [96].

4.6. Hypoglycemic Activity

The inhibitory effect on aldose reductase was examined for compound 27 and its methyl ester. The results indicated that the IC50 of 27 is 22.8 μM, whereas that of its methyl ester is more than 200 μM, which suggested that a carboxyl group of side chain of compound 27 is essential for potent inhibitory activity because of much lower level of inhibitory activity of its methyl ester. However, the exact reason for the difference in inhibition between compound 27 and its methyl ester remains unclear [29]. Compound 169 was also found to have high α-glucosidase inhibition, with IC50 of 119.8 μM [108].

4.7. Other Bioactivities

Ganoderma has been investigated for other bioactivities. Compounds 45 and 58 were found to exhibit potent inhibitory activity against herpes simplex virus [42]. Compounds 13 and 15 were shown to inhibit histamine release from rat mast cells [21]. In the study on compounds 3 and 156, it was found they both exhibited inhibitory activities against the HMG-CoA reductase and acyl CoA acyltransferase [35]. Another study demonstrated that compounds 44 and 49 exhibited potent enhancement of ConA-induced mice splenocytes proliferation in vitro [36]. It was found that compounds 161, 189 and 316 possess the bioactivity to induce apoptosis in human promyelocytic leukemia HL-60 cells [75]. An investigation on the ability of some Ganoderma triterpenes to inhibit 5α-reductase in rat liver microsomes revealed that compounds 64, 161 and 206 showed the inhibitory activity. Further study suggested that a carboxyl group of the 17β-side chain of compound 206 was essential to elicit the inhibitory activity [89]. The in vitro tests showed that compounds 308 and 310 exhibited modest inhibitory activity against rabbit platelet aggregation induced by platelet activating factor (PAF), and compound 310 also displayed weak inhibition against platelet aggregation induced by adenosine diphosphate (ADP) [105]. The C-3 epimer of compound 172 also exhibited significant antimycobacterial activity against mycobacterium tuberculosis H37Ra [46].

5. Conclusions

Ganoderma triterpenes (GTs) are a class of compounds with various chemical structures and a diverse range of biological activities. Biomedical analysis has shown that triterpenes possess important pharmacological activities and are thought to be potential candidates for drug discovery, but their low abundance, complex procedures of extraction and purification, the difficult preparation of high purity triterpenoids from G .lucidum is currently limited at the laboratory scale. Thus, how to enhance the content of triterpenoids and improve the technology of the extraction and purification of triterpenoids from Ganoderma lucidum is a problem that needs to be solved. We can expect to enhance GT production through the regulation of GA biosynthesis, thus promoting the industrial development of G. lucidum and provide an important resource for the development and application of new antineoplastic, anti-HIV, and other drugs.
Based on the above analysis of structural complexity and functional group variety, it is especially important to prove the structure-function relationships to make up for the inadequacy of this aspect. Although extensive research has been done on this herb, there is still a lot of scope for further research, especially on the mechanisms of biological activity of GTs with emphasis on agents with anti-tumor, anti-HIV, neurotrophic properties. G. lucidum and G. sinense that are recorded in the pharmacopoeia of China in 2010 have been widely applied in China [8]. Their long-standing medicinal history indicates their irreplaceable functions. In further study, researchers may need to pay more attention to the two species, and focus on the active substances such as the triterpenes summarized above. To achieve better quality control, the studies on other species are also important, so that the differences between species can be illustrated clearly. Additionally, more important bioactive constituents should be integrated into the quality control system of Ganoderma. Further experiments including in vitro, in vivo and clinical studies should be encouraged to identify any potential side effects.

Acknowledgments

This work was supported by the National Science-technology Support Plan Project (NO. 2012BAI29B00).

Author Contributions

Qing Xia, Huazheng Zhang, Gaimei She, and Lanzhen Zhang have all been involved in drafting this review. Qing Xia and Huazheng Zhang contributed equally to this work. Xuefei Sun, Haijuan Zhao, Lingfang Wu and Xin Mao discussed the results and commented on the manuscript. Dan Zhu, Guanghui Yang, Yanyan Shao and Xiaoxue Zhang corrected the 13C-NMR data. All authors read and approved the final manuscript.

Conflicts of Interest

The authors declare that they have no competing interests.

References

  1. Xie, J.T.; Wang, C.Z.; Wicks, S.; Yin, J.J.; Kong, J.; Li, J.; Li, Y.C.; Yuan, C.S. Ganoderma lucidum extract inhibits proliferation of SW 480 human colorectal cancer cells. Exp. Oncol. 2006, 28, 25–29. [Google Scholar] [PubMed]
  2. Liu, G.Q.; Zhang, K.C. Mechanisms of the anticancer action of Ganoderma lucidum (Leyss. ex Fr.) Karst: A new understanding. J. Integr. Plant Biol. 2005, 47, 129–135. [Google Scholar] [CrossRef]
  3. Yuen, J.W.M.; Gohel, M.D.I. Anticancer effects of Ganoderma lucidum: A review of scientific evidence. Nutr. Cancer 2005, 53, 11–17. [Google Scholar] [CrossRef] [PubMed]
  4. Petrova, R.D.; Wasser, S.P.; Mahajna, J.A.; Denchev, C.M.; Nevo, E. Potential role of medicinal mushrooms in breast cancer treatment: Current knowledge and future perspectives. Int. J. Med. Mushrooms 2005, 7, 141–155. [Google Scholar] [CrossRef]
  5. Lin, Z.B.; Zhang, H.N. Antitumor and immunoregulatory activities of Ganoderma lucidum and its possible mechanisms. Acta Pharmacol. Sin. 2004, 25, 1387–1395. [Google Scholar] [PubMed]
  6. Gao, Y.H.; Zhou, S.F. Chemopreventive and tumoricidal properties of lingzhi mushroom Ganoderma lucidum (W.Curt.:Fr.) Lloyd (Aphyllophoromy cetideae). Part II. mechanism considerations (review). Int. J. Med. Mushrooms 2004, 6, 219–230. [Google Scholar] [CrossRef]
  7. Lee, S.Y.; Rhee, H.M. Cardiovascular effects of mycelium extract of Ganoderma lucidum: Inhibition of sympathetic outflow as a mechanism of its hypotensive action. Chem. Pharm. Bull. 1990, 38, 1359–1364. [Google Scholar] [CrossRef] [PubMed]
  8. National Pharmacopoeia Committee. Chinese Pharmacopoeia, 2010 ed.; Chemical Industry Press: Beijing, China, 2010; Part 1; pp. 174–175. [Google Scholar]
  9. Kubota, T.; Asaka, Y.; Miura, I.; Mori, H. Structure of Ganoderic acid A and B, two new lanostane type bitter triterpenes from Ganoderma lucidum (FR.) Karst. Helv. Chim. Acta 1982, 65, 611–619. [Google Scholar] [CrossRef]
  10. Luo, J.; Lin, Z.B. Advances of pharmacological effects of triterpenes from Ganoderma lucidum. Acta Pharmacol. Sin. 2002, 37, 574–578. [Google Scholar]
  11. Xie, J.T.; Wang, C.Z.; Wicks, S.; Yin, J.J.; Kong, J.; Li, J.; Li, Y.C.; Yuan, C.S. Anti-inflammatory and anti-tumor-promoting effects of triterpene acids and sterols from the fungus Ganoderma lucidum. Chem. Biodivers. 2007, 4, 224–231. [Google Scholar] [CrossRef] [PubMed]
  12. Boh, B.; Berovic, M.; Zhang, J.; Lin, Z.B. Ganoderma lucidum and its pharmaceutically active compounds. Biotechnol. Annu. Rev. 2007, 13, 265–301. [Google Scholar] [PubMed]
  13. Xu, Z.; Chen, X.; Zhong, Z.; Chen, L.; Wang, Y. Ganoderma lucidum polysaccharides: Immunomodulation and potential anti-tumor activities. Am. J. Chin. Med. 2011, 39, 15–27. [Google Scholar] [CrossRef] [PubMed]
  14. Liby, K.T.; Yore, M.M.; Sporn, M.B. Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer. Nat. Rev. Cancer 2007, 7, 357–369. [Google Scholar] [CrossRef]
  15. Hill, R.A.; Connolly, J.D. Triterpenoids. Nat. Prod. Rep. 2012, 29, 780–818. [Google Scholar]
  16. Lee, I.; Ahn, B.; Choi, J.; Hattori, M.; Min, B.; Bae, K. Selective cholinesterase inhibition by lanostane triterpenes from fruiting bodies of Ganoderma lucidum. Bioorg. Med. Chem. Lett. 2011, 21, 6603–6607. [Google Scholar] [CrossRef] [PubMed]
  17. Lee, I.; Seo, J.; Kim, J.; Kim, H.; Youn, U.; Lee, J.; Jung, H.; Na, M.; Hattori, M.; Min, B.; et al. Lanostane triterpenes from the fruiting bodies of Ganoderma lucidum and their inhibitory effects on adipocyte differentiation in 3T3-L1 cells. J. Nat. Prod. 2010, 73, 172–176. [Google Scholar] [CrossRef] [PubMed]
  18. El-Mekkawy, S.; Meselhy, M.R.; Nakamura, N.; Tezuka, Y.; Hattori, M.; Kakiuchi, N.; Shimotohno, K.; Kawahata, T.; Otake, T. Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum. Phytochemistry 1998, 49, 1651–1657. [Google Scholar] [CrossRef] [PubMed]
  19. Kikuchi, T.; Kanomi, S.; Murai, Y.; Kadota, S.; Tsubono, K.; Ogita, Z. Constituents of the fungus Ganoderma lucidum (FR.) Karst. III. Structure of Ganolucidic acids A and B, new lanostane-type triterpenoids. Chem. Pharm. Bull. 1986, 34, 4030–4036. [Google Scholar] [CrossRef]
  20. Kikuchi, T.; Matsuda, S.; Murai, Y.; Ogita, Z. Ganoderic acid G and I and Ganolucidic acid A and B, new triterpenoids from Ganoderma lucidum. Chem. Pharm. Bull. 1985, 33, 2628–2631. [Google Scholar] [CrossRef]
  21. Kohda, H.; Tokumoto, W.; Sakamoto, K.; Fujii, M.; Hirai, Y.; Yamasaki, K.; Komoda, Y.; Nakamura, H.; Ishihara, S. The biologically active constituents of Ganoderma lucidum (FR.) Karst. histamine release-inhibitory triterpenes. Chem. Pharm. Bull. 1985, 33, 1367–1374. [Google Scholar] [CrossRef] [PubMed]
  22. Kikuchi, T.; Matsuda, S.; Kadota, S.; Murai, Y.; Tsubono, K.; Ogita, Z. Constituents of the fungus Ganoderma lucidum (FR.) Karst. I. structure of Ganoderic acids of C2, E, I, and K, Lucidenic acid F and related compounds. Chem. Pharm. Bull. 1986, 34, 3695–3712. [Google Scholar] [CrossRef]
  23. Morigiwa, A.; Kitabatake, K.; Fujimoto, Y.; Ikekawa, N. Angiotensin converting enzyme-inhibitory triterpenes from Ganoderma lucidum. Chem. Pharm. Bull. 1986, 34, 3025–3028. [Google Scholar] [CrossRef] [PubMed]
  24. Luo, J.; Lin, Z.B. Srncture identification of triterpenes from fruiting bodies of Ganoderma lucidum by NMR spectra and X-ray diffraction analysis. Chin. Tradit. Herb. Drugs 2002, 33, 197–200. [Google Scholar]
  25. Gao, J.J.; Min, B.S.; Ahn, E.M.; Nakamura, N.; Lee, H.K.; Hattori, M. New triterpene aldehydes, lucialdehydes A-C, from Ganoderma lucidum and their cytotoxicity against murine and human tumor cells. Chem. Pharm. Bull. 2002, 50, 837–840. [Google Scholar] [CrossRef] [PubMed]
  26. Cheng, C.R.; Yue, Q.X.; Wu, Z.Y.; Song, X.Y.; Tao, S.J.; Wu, X.H.; Xu, P.P.; Liu, X.; Guan, S.H.; Guo, D.A. Cytotoxic triterpenoids from Ganoderma lucidum. Phytochemistry 2010, 71, 1579–1585. [Google Scholar] [PubMed]
  27. Kinge, T.R.; Mih, A.M. Secondary metabolites of oil palm isolates of Ganoderma zonatum Murill. from Cameroon and their cytotoxicity against five human tumour cell lines. Afr. J Biotechnol. 2011, 10, 8440–8447. [Google Scholar]
  28. Guan, S.H.; Yang, M.; Liu, X.; Xia, J.M.; Wang, X.M.; Jin, H.; Guo, D.A. Two new lanostanoid triterpenes from fruit body of Ganoderma lucidum—The major componet of Sunrecome. Nat. Prod. Commun. 2006, 1, 177–181. [Google Scholar]
  29. Fatmawati, S.; Shimizu, K.; Kondo, R. Ganoderic acid Df, a new triterpenoid with aldose reductase inhibirory activity from the fruiting body of Ganoderma lucidum. Fitoterapia 2010, 86, 1033–1036. [Google Scholar] [CrossRef]
  30. Kikuchi, T.; Kanomi, S.; Murai, Y.; Kadota, S.; Tsubono, K.; Ogita, Z.I. Constituents of the fungus Ganoderma lucidum (FR.) Karst. II.: Structure of Ganoderic acids F, G, and H, Lucidenic acids D2 and E2, and related compounds. Chem. Pharm. Bull. 1986, 34, 4018–4029. [Google Scholar] [CrossRef]
  31. Komoda, Y.; Nakamura, H.; Ishihara, S.; Uchida, M.; Kohda, H.; Yamasaki, K. Structure of new terpenoid constituents of Ganoderma lucidum (FR.) Karst (polyporaceae). Chem. Pharm. Bull. 1985, 33, 4829–4835. [Google Scholar] [CrossRef]
  32. Guan, S.H.; Xia, J.M.; Yang, M.; Wang, X.M.; Liu, X.; Guo, D.A. Cytotoxic lanostanoid triterpenes from Ganoderma lucidum. J. Asian Nat. Prod. Res. 2008, 10, 695–700. [Google Scholar] [CrossRef]
  33. Sato, N.; Zhang, Q.; Ma, C.M.; Hattori, M. Anti-human immunodeficiency virus-1 protease activity of new lanos-tane-type triterpenoids from Ganoderma sinense. Chem. Pharm. Bull. 2009, 57, 1076–1080. [Google Scholar] [CrossRef] [PubMed]
  34. Wang, F.; Liu, J.K. Highly oxygenated lanostane triterpenoids from the fungus Ganoderma applanatum. Chem. Pharm. Bull. 2008, 56, 1035–1037. [Google Scholar] [CrossRef] [PubMed]
  35. Li, C.J.; Li, Y.M.; Sun, H.H. New ganoderic acids, bioactive triterpenoid metabolites from the mushroom Ganoder-ma lucidum. Nat. Prod. Res. 2006, 20, 985–991. [Google Scholar] [CrossRef] [PubMed]
  36. Luo, J.; Zhao, Y.Y.; Lin, Z.B. A new lanostane-type triterpene from the fruiting bodies of Ganoderma lucidum. J. Asian Nat. Prod. Res. 2002, 4, 129–134. [Google Scholar] [CrossRef] [PubMed]
  37. Min, B.S.; Gao, J.J.; Nakamura, N.; Hattori, M. Triterpenes from the spores of Ganoderma lucidum and their cytotoxicity against Meth-A and LLC tumor cells. Chem. Pharm. Bull. 2000, 48, 1026–1033. [Google Scholar] [CrossRef] [PubMed]
  38. Min, B.S.; Nakamura, N.; Miyashiro, H.; Bae, KW.; Hattori, M. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease. Chem. Pharm. Bull. 1998, 46, 1607–1612. [Google Scholar] [CrossRef] [PubMed]
  39. Nishitoba, T.; Oda, K.; Sato, H.; Sakamura, S. Novel triterpeniods from the fungus Ganoderma lucidum. Agric. Biol. Chem. 1988, 52, 367–372. [Google Scholar] [CrossRef]
  40. Nishitoba, T.; Sato, H.; Oda, K.; Sakamura, S. Novel triterpeniods and a steroid from the fungus Ganoderma luci-dum. Agric. Biol. Chem. 1988, 52, 211–216. [Google Scholar] [CrossRef]
  41. Nishitoba, T.; Sato, H.; Shirasu, S.; Sakamura, S. Novel triterpeniods from the mycelial mat at the previous stage of fruiting of Ganoderma lucidum. Agric. Biol. Chem. 1987, 51, 619–622. [Google Scholar] [CrossRef]
  42. Niedermeyer, T.H.J.; Lindequist, U.; Renate, M.; Gordes, D.; Schmidt, E.; Thurow, K.; Lalk, M. Antiviral terpenoid constituents of Ganoderma pfeifferi. J. Nat. Prod. 2005, 68, 1728–1731. [Google Scholar] [CrossRef] [PubMed]
  43. Nishitoba, T.; Sato, H.; Sakamura, S. Novel mycelial components, Ganoderic acid Mg, Mh, Mi, Mj, and Mk, from the fungus Ganoderma lucidum. Agric. Biol. Chem. 1987, 51, 1149–1153. [Google Scholar] [CrossRef]
  44. González, A.G.; León, F.; Rivera, A.; Muñoz, C.M.; Bermejo, J. Lanostanoid triterpenes from Ganoderma lucidum. J. Nat. Prod. 1999, 62, 1770–1701. [Google Scholar]
  45. Cai, H.; Wang, F.S.; Yang, J.S.; Zhang, Y.M.; Hu, K.; Zhao, Y.J.; Bai, Y.; Zhang, Z.X. Studies on the triterpenoid constituents from the fruiting body Ganoderma lucidum (FR) Karst. Chin. J. Vet. Sci. 1997, 17, 511–513. [Google Scholar]
  46. Isaka, M.; Chinthanom, P.; Kongthong, S.; Srichomthong, K.; Choeklin, R. Lanostane triterpenes from cultures of the basidiomycete Ganoderma orbiforme BCC 22324. Phytochemistry 2013, 87, 133–139. [Google Scholar] [CrossRef] [PubMed]
  47. Liu, J.Q.; Wang, C.F.; Li, Y.; Luo, H.R.; Qiu, M.H. Isolation and bioactivity evaluation of terpenoids from the medicinal fungus Ganoderma sinense. Planta Med. 2012, 78, 368–376. [Google Scholar] [CrossRef] [PubMed]
  48. Ma, B.J.; Zhou, Y.; Ruan, Y.; Ma, J.C.; Ren, W.; Wen, C.N. Lanostane-type triterpenes from the sporoderm-broken spor-es of Ganoderma lucidum. J. Antibiot. 2012, 65, 165–167. [Google Scholar] [CrossRef] [PubMed]
  49. Li, Y.B.; Liu, R.M.; Zhong, J.J. A new ganoderic acid from Ganoderma lucidum mycelia and its stability. Fitoterapia 2013, 84, 115–122. [Google Scholar] [CrossRef] [PubMed]
  50. Hirotani, M.; Asaka, I.; Ino, C.; Furuya, T.; Shiro, M. Ganoderic acid derivatives and ergosta-4,7,22-triene-3,6-dione from Ganoderma lucidum. Phytochemistry 1987, 26, 2797–2803. [Google Scholar] [CrossRef]
  51. Shim, S.H.; Ryu, J.; Kim, J.S.; Kang, S.S.; Xu, Y.; Jung, S.H.; Lee, Y.S.; Lee, S.; Shin, K.H. New lanostane-type triterpenoids from Ganoderma applanatum. J. Nat. Prod. 2004, 67, 1110–1113. [Google Scholar] [CrossRef] [PubMed]
  52. Nishitoba, T.; Goto, S.; Sato, H.; Sakamura, S. Bitter triterpenoids from the fungus Ganoderma applanatum. Phytochemistry 1989, 28, 193–197. [Google Scholar] [CrossRef]
  53. Hao, R.X.; Zhang, J.S.; Tang, Q.J.; Hu, L.H.; Zheng, Z.P.; Pan, Y.J. Isolation, purification and identification of two new triterpenoid constituents from the fruiting bodies of Ganoderma lucidum. Mycosystema 2006, 25, 599–602. [Google Scholar]
  54. Kikuchi, T.; Matsuda, S.; Kadota, S.; Murai, Y.; Ogita, Z. Ganoderic acid D, E, F, and H and Lucidenic acid D, E, and F, new triterpenoids from Ganoderma lucidum. Chem. Pharm. Bull. 1985, 33, 2624–2627. [Google Scholar] [CrossRef]
  55. Hirotani, M.; Furuya, T. Ganoderic acid derivatives, highly oxygenated lanostane-type triterpenoids, from Ganoderma lucidum. Phytochemistry 1986, 25, 1189–1193. [Google Scholar] [CrossRef]
  56. Wang, C.F.; Liu, J.Q.; Yan, Y.X.; Chen, J.C.; Lu, Y.; Guo, Y.H.; Qiu, M.H. Three new triterpenoids containing four-membered ring from the fruiting body of Ganoderma sinense. Org. Lett. 2010, 12, 1656–1659. [Google Scholar] [CrossRef] [PubMed]
  57. Ma, J.Y.; Ye, Q.; Hua, Y.J.; Zhang, D.C.; Cooper, R.; Chang, M.N.; Chang, J.Y.; Sun, H.H. New lanostanoids from the mushroom Ganoderma lucidum. J. Nat. Prod. 2002, 65, 72–75. [Google Scholar] [CrossRef] [PubMed]
  58. Chen, M.; Zhang, M.; Sun, S.; Xia, B.; Zhang, H.Q. A new triterpene from the fruiting bodies of Ganoderma lucidum. Acta Pharm. Sin. 2009, 44, 768–770. [Google Scholar]
  59. Liu, C.; Chen, R.Y. A new triterpene from fungal fruiting bodies of Ganoderma sinense. Chin. Tradit. Herb. Drugs 2010, 41, 8–11. [Google Scholar]
  60. Su, H.J.; Fann, Y.F.; Chung, M.I.; Won, S.J.; Lin, C.N. New lanostanoids of Ganoderma tsugae. J. Nat. Prod. 2000, 63, 514–516. [Google Scholar] [CrossRef] [PubMed]
  61. Lin, C.N.; Fann, Y.F.; Chung, M.I. Steroids of formosan Ganoderma Tsugae. Phytochemistry 1997, 46, 1143–1146. [Google Scholar] [CrossRef]
  62. Niu, X.M.; Li, S.H.; Xiao, W.L.; Sun, H.D.; Che, C.T. Two new lanostanoids from Ganoderma resinaceum. J. Asian Nat. Prod. Res. 2007, 9, 659–664. [Google Scholar] [CrossRef] [PubMed]
  63. Guan, S.H.; Yang, M.; Wang, X.M.; Xia, J.M.; Zhang, Z.M.; Liu, X.; Guo, D.A. Structure elucidation and complete NMR spectral assignments of three new lanostanoid triterpenes with unprecedented Δ16,17 double bond from Ganoderma lucidum. Magn. Reson. Chem. 2007, 45, 789–791. [Google Scholar] [CrossRef] [PubMed]
  64. Nishitoba, T.; Sato, H.; Sakamura, S. Triterpenoids from the fungus Ganoderma lucidum. Phytochemistry 1987, 26, 1777–1784. [Google Scholar] [CrossRef]
  65. Li, Y.Y.; Mi, Z.Y.; Tang, Y.; Wang, G.; Li, D.S.; Tang, Y.J. Lanostanoids isolated from Ganoderma lucidum mycelium cultured by submerged fermentation. Helv. Chim. Acta 2009, 92, 1586–1593. [Google Scholar] [CrossRef]
  66. Chairul, S.M.; Hayashi, Y. Lanostanoid triterpenes from Ganoderma applanatum. Phytochemistry 1994, 35, 1305–1308. [Google Scholar] [CrossRef]
  67. Chen, R.Y.; Yu, D.Q. Studies on the triterpenoid constituents of the spores from Ganoderma lucidum karst. J. Chin. Pharm. Sci. 1993, 2, 91–96. [Google Scholar]
  68. Gan, K.H.; Kuo, S.H.; Lin, C.N. Steroidal constituents of Ganoderma applanatum and Ganderma neo-japonicum. J. Nat. Prod. 1998, 61, 1421–1422. [Google Scholar] [CrossRef] [PubMed]
  69. De Silva, E.D.; van der Sar, S.A.; Santha, R.L.; Wijesundera, R.L.; Cole, A.L.; Blunt, J.W.; Munro, M.H. Lanostane triterpenoids from the Sri Lankan Basidiomycete Ganoderma applanatum. J. Nat. Prod. 2006, 69, 1245–1248. [Google Scholar] [CrossRef] [PubMed]
  70. Qiao, Y.; Zhang, X.M.; Dong, X.C.; Qiu, M.H. A new 18(13→12β)-abeo-lanostadiene triterpenoid from Ganoderma fornicatum. Helv. Chim. Acta 2006, 89, 1038–1041. [Google Scholar] [CrossRef]
  71. Lin, L.J.; Shiao, M.S. Seven new triterpenes from Ganoderma lucidum. J. Nat. Prod. 1988, 51, 918–924. [Google Scholar] [CrossRef] [PubMed]
  72. Hirotani, M.; Ino, C.; Furuya, T. Comparative study on the strain-specific triterpenoid components of Ganoderma lucidum. Phytochemistry 1993, 33, 379–382. [Google Scholar] [CrossRef]
  73. Zhang, X.Q.; Ip, F.C.F.; Zhang, D.M.; Chen, L.X.; Zhang, W.; Li, Y.L.; Ip, N.Y.; Ye, W.C. Triterpenoids with neurotrophic activity from Ganoderma lucidum. Nat. Prod. Res. 2011, 25, 1607–1613. [Google Scholar] [CrossRef] [PubMed]
  74. Li, C.J.; Yin, J.H.; Guo, F.J.; Zhang, D.C.; Sun, H.H. Ganoderic acid Sz, a new lanostanoid from the mushroom Ganoderma lucidum. Nat. Prod. Res. 2005, 19, 461–465. [Google Scholar] [CrossRef] [PubMed]
  75. Gonzalez, A.G.; Leon, F.; Rivera, A.; Padron, J.I.; Ganzalez-Plata, J.; Zuluaga, J.C.; Quintana, J.; Estevez, F.; Bermejo, J. New lanostanoids from the Fungus Ganoderma concinna. J. Nat. Prod. 2002, 65, 417–421. [Google Scholar] [CrossRef] [PubMed]
  76. Arisawa, M.; Fujita, A.; Saga, M.; Fukumura, H.; Hayashi, T.; Shimizu, M.; Morita, N. Three new lanostanoids from Ganoderma lucidum. J. Nat. Prod. 1986, 49, 621–625. [Google Scholar] [CrossRef] [PubMed]
  77. Sato, H.; Nishitoba, T.; Shirasu, S.; Oda, K.; Sakamura, S. Ganoderiol A and B, new triteroenoids from the fungus Ganoderma lucidum (Reishi). Afr. Biol. Chem. 1986, 50, 2887–2890. [Google Scholar]
  78. Shiao, M.S.; Lin, L.J. Two new triterpenes of the fungus Ganoderma lucidum. J. Nat. Prod. 1987, 50, 886–890. [Google Scholar] [CrossRef]
  79. Keller, A.C.; Keller, J.; Maillard, M.P.; Hostettmann, K. A lanostane-type steroid from the fungus Ganoderma carnosum. Phytochemistry 1997, 46, 963–965. [Google Scholar] [CrossRef]
  80. Hirotani, M.; Ino, C.; Furuya, T.; Shiro, M. Ganoderic acids T, S and R, new triterpenoids from the cultured mycelia of Ganoderma lucidum. Chem. Pharm. Bull. 1986, 34, 2282–2285. [Google Scholar] [CrossRef]
  81. Shiao, M.S.; Lin, L.J.; Yeh, S.F. Triterpenes from Ganoderma lucidum. Phytochemistry 1988, 27, 2911–2914. [Google Scholar] [CrossRef]
  82. Lin, L.J.; Shiao, M.S.; Yea, S.F. Triterpenes from Ganoderma lucidum. Phytochemistry 1988, 27, 2269–2271. [Google Scholar] [CrossRef]
  83. Gerhäuser, C.; Zhang, W.D.; Ho-Chong-Line, N.; Fourasté, I. New lanostanoids from Ganoderma lucidum that induce NAD(P)H: Quinine oxidoreductase in cultured hepalclc 7 murine hepatoma cells. Planta Med. 2000, 66, 681–684. [Google Scholar] [CrossRef] [PubMed]
  84. Shiao, M.S.; Lin, L.J.; Yea, S.F. Triterpenes in Ganoderma lucidum. Phytochemistry 1988, 27, 873–875. [Google Scholar] [CrossRef]
  85. Yang, S.X.; Yu, Z.C.; Lu, Q.Q.; Shi, W.Q.; Laatsch, H.; Gao, J.M. Toxic lanostane triterpenes from the basidiomycete Ganoderma amboinense. Phytochem. Lett. 2012, 5, 576–580. [Google Scholar] [CrossRef]
  86. Qiao, Y.; Zhang, X.M.; Qiu, M.H. Two novel lanostane triterpenoids from Ganoderma Sinense. Molecules 2007, 12, 2038–2046. [Google Scholar] [CrossRef] [PubMed]
  87. Fujita, A.; Arisawa, M.; Saga, M.; Hayashi, T.; Fukumura, H.; Morita, N. Two new lanostanoids from Ganoderma lucidum. J. Nat. Prod. 1986, 49, 1122–1125. [Google Scholar] [CrossRef]
  88. Li, C.H.; Chen, P.Y.; Chang, U.M.; Kan, L.S.; Fang, W.H.; Tsai, K.S.; Lin, S.B. Ganoderic acid X, a lanostanoid triterpene, inhibits topoisomerases and induces apoptosis of cancer cells. Life Sci. 2005, 77, 252–265. [Google Scholar] [CrossRef] [PubMed]
  89. Liu, J.; Kurashiki, K.; Shimizu, K.; Kondo, R. Structure–activity relationship for inhibition of 5α-reductase by triterpenoids isolated from Ganoderma lucidum. Bioorg. Med. Chem. 2006, 14, 8654–8660. [Google Scholar] [CrossRef] [PubMed]
  90. Akihisa, T.; Tagata, M.; Ukiya, M.; Tokuda, H.; Suzuki, T.; Kimura, Y. Oxygenated lanostane-type triterpenoids from the fungus Ganoderma lucidum. J. Nat. Prod. 2005, 68, 559–563. [Google Scholar] [CrossRef] [PubMed]
  91. Wu, T.S.; Shi, L.S.; Kuo, S.C. Cytotoxicity of Ganoderma lucidum Triterpenes. J. Nat. Prod. 2001, 64, 1121–1122. [Google Scholar] [CrossRef] [PubMed]
  92. Weng, C.J.; Chau, C.F.; Chen, K.D.; Chen, D.H.; Yen, G.C. The anti-invasive effect of lucidenic acids isolated from a new Ganoderma lucidum strain. Mol. Nutr. Food Res. 2007, 51, 1472–1477. [Google Scholar] [CrossRef] [PubMed]
  93. Li, P.; Deng, Y.P.; Wei, X.X.; Xu, J.H. Triterpenoids from Ganoderma lucidum and their cytotoxic activities. Nat. Prod. Res. 2013, 27, 17–22. [Google Scholar] [CrossRef] [PubMed]
  94. Nishitoba, T.; Sato, H.; Kasai, T.; Kawagishi, H.; Sakamura, S. New bitter C27 and C30 terpenoids from the fungus Ganodema lucidum(Reishi). Agric. Biol. Chem. 1984, 48, 2905–2907. [Google Scholar] [CrossRef]
  95. Iwatsuki, K.; Akihisa, T.; Tokuda, H.; Ukiya, M.; Oshikubo, M.; Kimura, Y.; Asano, T.; Nomura, A.; Nishino, H. Lucidenic acids P and Q, methyl lucidenate P, and other triterpenoids from the fungus Ganoderma lucidum and their inhibitory effects on epstein-barr virus activation. J. Nat. Prod. 2003, 66, 1582–1585. [Google Scholar] [CrossRef] [PubMed]
  96. Lee, I.; Kim, H.; Youn, U.; Kim, J.; Min, B.; Jung, H.; Na, M.; Hattori, M.; Bae, K. Effect of lanostane triterpenes from the fruiting bodies of Ganoderma lucidum on adipocyte differentiation in 3T3-L1 cells. Planta Med. 2010, 76, 1558–1563. [Google Scholar] [CrossRef] [PubMed]
  97. El Dine, R.S.; el Halawany, A.M.; Nakamura, N.; Ma, C.M.; Hattori, M. New lanostane triterpene lactones from the vietnamese mushroom Ganoderma colossum (FR.) C. F. BAKER. Chem. Pharm. Bull. 2008, 56, 642–646. [Google Scholar] [CrossRef] [PubMed]
  98. Kleinwächter, P.; Anh, N.; Kiet, T.T.; Schlegel, B.; Dahse, H.M.; Härtl, A.; Gräfe, U. Colossolactones, new triterpenoid Metabolites from a Vietnamese mushroom Ganoderma colossum. J. Nat. Prod. 2001, 64, 236–239. [Google Scholar] [CrossRef] [PubMed]
  99. Chen, R.Y.; Yu, D.Q. Application of 2D NMR techniques in the structure determination of Ganosporelactone A and B. Acta Pharm. Sin. 1991, 26, 430–436. [Google Scholar]
  100. Sato, N.; Ma, C.M.; Komatsu, K.; Hattori, M. Triterpene-farnesyl hydroquinone conjugates from Ganoderma sinense. J. Nat. Prod. 2009, 72, 958–961. [Google Scholar] [CrossRef] [PubMed]
  101. Tokuyama, T.; Hayashi, Y.; Nishizawa, M.; Tokuda, H.; Chairul, S.M.; Hayashi, Y. Applanoxidic acids A, B, C, and D, biologically active tetracyclic triterpenes from Ganoderma applanatum. Phytochemistry 1991, 30, 4105–4109. [Google Scholar] [CrossRef]
  102. El Dine, R.S.; el Halawany, A.M.; Ma, C.M.; Hattori, M. Anti-HIV-1 protease activity of lanostane triterpenes from the vietnamese mushroom Ganoderma colossum. J. Nat. Prod. 2008, 71, 1022–1026. [Google Scholar] [CrossRef] [PubMed]
  103. Leon, F.; Valenica, M.; Rivera, A.; Nieto, I.; Quintana, J.; Estevez, F.; Bermejo, J. Novel cytostatic lanostanoid triterpenes from Ganoderma australe. Helv. Chim. Acta 2003, 86, 3088–3095. [Google Scholar] [CrossRef]
  104. Wang, F.S.; Cai, H.; Yang, J.S.; Zhang, Y.M.; Zhao, Y.J. Triterpenoids from the fruiting body of Ganoderma lucidum. J. Chin. Pharm. Sci. 1997, 6, 192–197. [Google Scholar]
  105. Niu, X.M.; Qiu, M.H.; Lu, Z.G.; Lu, Y.; Cao, P.; Zheng, Q. Two novel 3,4-seco-trinorlanostane triterpenoids isolated from Ganoderma fornicatum. Tetrahedron Lett. 2004, 45, 2989–2993. [Google Scholar] [CrossRef]
  106. Peng, X.R.; Liu, J.Q.; Xia, J.J.; Yang, Y.H.; Qiu, M.H. Two new triterpenoids from Ganoderma cochlear. Chin. Tradit. Herb. Drugs 2012, 43, 1045–1049. [Google Scholar]
  107. Su, C.H.; Lai, M.N.; Chan, M.H. Hepato-protective triterpenoids from Ganoderma tsugae Murrill. In Mushroom Biology and Mushroom Products; Chang, S., Buswell, J.A., Chiu, S., Eds.; The Chinese University Press: Hong Kong, China, 1993; pp. 275–283. [Google Scholar]
  108. Fatmawati, S.; Shimizu, K.; Kondo, R.; Ganoderol, B. A potent α-glucosidase inhibitor isolated from the fruiting body of Ganoderma lucidum. Phytomedicine 2011, 18, 1053–1055. [Google Scholar] [CrossRef] [PubMed]

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MDPI and ACS Style

Xia, Q.; Zhang, H.; Sun, X.; Zhao, H.; Wu, L.; Zhu, D.; Yang, G.; Shao, Y.; Zhang, X.; Mao, X.; et al. A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp. Molecules 2014, 19, 17478-17535. https://doi.org/10.3390/molecules191117478

AMA Style

Xia Q, Zhang H, Sun X, Zhao H, Wu L, Zhu D, Yang G, Shao Y, Zhang X, Mao X, et al. A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp. Molecules. 2014; 19(11):17478-17535. https://doi.org/10.3390/molecules191117478

Chicago/Turabian Style

Xia, Qing, Huazheng Zhang, Xuefei Sun, Haijuan Zhao, Lingfang Wu, Dan Zhu, Guanghui Yang, Yanyan Shao, Xiaoxue Zhang, Xin Mao, and et al. 2014. "A Comprehensive Review of the Structure Elucidation and Biological Activity of Triterpenoids from Ganoderma spp." Molecules 19, no. 11: 17478-17535. https://doi.org/10.3390/molecules191117478

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