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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
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