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.
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
1–
221 (
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,
1–
37 (
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,
11–
14,
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,
9–
17,
19–
23,
25,
27,
31,
34–
36 have hydroxy groups at C-7, and furthermore,
19,
20,
22 have α-configurations. What’s more, compounds
1,
4,
18,
24,
26,
28–
30,
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,
35–
37 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
5–
16,
21,
28–
30,
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
38–
70 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
71–
84 (
Figure 4) get an acetate substituent at C-22 and no substituent at C-11. Meanwhile, compounds
85–
98 (
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
99–
105 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
106–
110 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 (
112–
115), 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
117–
123,
124–
126,
127–
130,
131–
133,
134–
135,
136–
139,
140–
141,
142–
145 and
146–
147 possess extremely similar skeletons. Because of their distinctive skeletons,
148–
155 are listed independently. There are no double bonds between C-8 and C-9 in compounds
156–
221, 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
156–
196 (
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
197–
213 (
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
214–
219 (
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
222–
266 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
222–
260 (
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
263–
266 in
Figure 25 have hydroxy substituents at C-29. Compounds
267–
287 are divided into different groups on account of their characteristic skeletons. We list the structures of compounds
288–
307 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
313–
316 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
1–
37 in
Figure 2.
Table 1.
Ganoderma triterpenes 1–37 in Figure 2.
No. | Compound Name | Source | Ref. |
---|
1 | n-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] |
2 | Butyl ganoderate A | G. lucidum (fruit bodies) | [17] |
3 | Butyl ganoderate B | G. lucidum (fruit bodies) | [17] |
4 | Ganoderic acid α (12β-acetoxy-3β, 15β-dihydroxy-7,11,23-trioxo-5α-lanosta-8-en-26-oic acid) | G. lucidum (fruit bodies) | [18] |
5 | Ganolucidic acid A | G. lucidum (gill surface) | [19] |
6 | Methyl ganolucidate A (methyl 15α-hydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) | G. lucidum (gill surface) | [19,20] |
7 | Ganolucidic acid B | G. lucidum (gill surface) | [19] |
8 | Methyl ganolucidate B | G. lucidum (gill surface) | [19,20] |
9 | Ganoderic acid A (7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oic acid) | G. lucidum | [9,21] |
10 | Methyl ganoderate A (methyl 7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) | G. lucidum | [21] |
11 | Ganoderic acid B (3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oic acid) | G. lucidum | [21] |
12 | Methyl ganoderate B (methyl 3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate) | G. lucidum | [9,21] |
13 | Ganoderic acid C (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oic acid) | G. lucidum | [21] |
14 | Methyl ganoderate C | G. lucidum | [21] |
15 | Ganoderic acid D (7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oic acid) | G. lucidum | [21] |
16 | Methyl ganoderate D | G. lucidum | [21] |
17 | Methyl ganoderate C2 (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) | G. lucidum (gills) | [22] |
18 | Methyl ganoderate K | G. lucidum (gills) | [22,23] |
19 | Compound B8 | G. lucidum (gills) | [22] |
20 | Compound B9 | G. lucidum (gills) | [22] |
21 | 3β-Oxo-formyl-7β, 12β-dihydroxy-5α-lanost-11,15,23-trioxo-8-en(E)-26-oic acid | G. lucidum (fruit bodies) | [24] |
22 | Ganoderic acid B8 | G. lucidum (fruit bodies) | [25] |
23 | Ganoderic acid C1 | G. lucidum (fruit bodies) | [25] |
24 | 12β-Acetoxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acid ethyl ester | G. lucidum | [26] |
25 | 3β, 7β-Dihydroxy-12β-acetoxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid methyl ester | G. lucidum | [27] |
26 | 3β-Hydroxy-7,11,12,15,23-pentaoxolanost-8-en-26-oic acid | G. lucidum (fruit bodies) | [28] |
27 | Ganoderic acid Df (7β, 11β-dihydroxy-3,15,23-trioxo-5α-lanosta-8-en-26-oic acid) | G. lucidum | [29] |
28 | Ganoderic acid H | G. lucidum (gill surface) | [30] |
29 | Ganoderic acid F (12β-acetoxy-3,7,11,15-pentaoxo-5α-lanost-8-en-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
30 | Ganoderic acid E (3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
31 | Ganoderic acid K | G. lucidum (fruit bodies) | [32] |
32 | Ganoderic acid AM1 | G. lucidum (fruit bodies) | [32] |
33 | Ganoderic acid J | G. lucidum (fruit bodies) | [32] |
34 | Ganoderic acid C2 (3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanosta-8-en-26-oic acid) | G. lucidum (gills) | [22] |
35 | Ganoderic acid G (3β, 7β, 15β-trihydroxy-11,15,23-trioxo-5α-lanosta-8-en-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
36 | 7β, 12β-Dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8-en-26-oic acid | G. lucidum | [26] |
37 | 12β-Hydroxy-3,7,11,15,23-pentaoxo-5α-lanosta-8-en-26-oic acid | G. lucidum | [26] |
Table 2.
Ganoderma triterpenes (
38–
70) in
Figure 3.
Table 2.
Ganoderma triterpenes (38–70) in Figure 3.
No. | Compound Name | Source | Ref. |
---|
38 | Ganoderic acid GS-1 (7β-hydroxy-3,11,15-trioxolanosta-8,24(E)-dien-26-oic acid) | G. sinense (fruit bodies) | [33] |
39 | Ganoderic acid GS-2 (7β, 15α-dihydroxy-3,11-dioxolanosta-8,24(E)-dien-26-oic acid) | G. sinense (fruit bodies) | [33] |
40 | Ganoderic acid GS-3 (12β-acetoxy-3β, 7β-dihydroxy-11,15-dioxo-lanosta-8,24(E)-dien-26-oic acid) | G. sinense (fruit bodies) | [33] |
41 | Ganoderic acid AP2 (12β, 15α-diacetoxy-3β-hydroxy-11-oxolanost-8,24(E)-dien-26-oic acid) | G. applanatum (fruit bodies) | [34] |
42 | 23S-Hydroxy-3,7,11,15-tetraoxolanost-8,24E-diene-26-oic acid | G. lucidum (fruit bodies) | [32] |
43 | 7-Oxoganoderic acid Z (3β-hydroxy-7-oxo-5α-lanosta-8,24(E)-dien-26-oic acid) | G. lucidum (fruit bodies) | [35] |
44 | Ganoderic acid LM2 ((23S) 7β,-dihydroxy-3,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid) | G. lucidum (fruit bodies) | [36] |
45 | Lucialdehyde B ((24E)-3,7-dioxo-5α-lanosta-8,24-dien-26-al) | G. lucidum (fruit bodies) | [25] |
46 | Lucialdehyde C ((24E)-3β-hydroxy-7-oxo-5α-lanosta-8,24-dien-26-al) | G. lucidum (fruit bodies) | [25] |
47 | Ganoderic acid γ ((23S)-7β, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
48 | Ganoderic acid δ ((23S)-7α, 15α, 23-trihydroxy-3,11-dioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
49 | Ganoderic acid ε ((23S)-3β, 7β, 23-trihydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
50 | Ganoderic acid ζ ((23S)-3β, 23-dihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
51 | Ganoderic acid η ((23S)-3β, 7β, 12β, 23-tetrahydroxy-11,15-dioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
52 | Ganoderic acid θ ((23S)-3β, 12β, 23-trihydroxy-7,11,15-trioxolanosta-8,24(E)-diene-26-oic acid) | G. lucidum (spores) | [37] |
53 | Ganoderic acid β (3β, 7β-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid) | G. lucidum (spores) | [38] |
54 | Ganolucidic acid E (15α-hydroxy-3,11-dioxo-5α-lanosta-8,24E-dien-26-oic acid) | G. lucidum (fruit bodies) | [39] |
55 | Ganoderal B (7α-hydroxy-3-oxo-5α-lanosta-8,24E-dien-26-al) | G. lucidum | [40] |
56 | Ganoderic acid Ma (3α, 7α-diacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (fruit bodies) | [41] |
57 | Lucialdehyde D (3,7,11-trioxo-5α-lanosta-8,24-diene-26-al) | G. pfeifferi (fruit bodies) | [42] |
58 | Ganoderone A (5α-lanosta-8,24-diene-26-hydroxy-3,7-dione) | G. pfeifferi (fruit bodies) | [42] |
59 | ganoderic acid Mi (3α-acetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (mycelial mat) | [43] |
60 | 11α-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acid | G. lucidum | [26] |
61 | 11β-Hydroxy-3,7-dioxo-5α-lanosta-8,24(E)-dien-26-oic acid | G. lucidum | [26] |
62 | Lucidadiol (5α-lanosta-8,24-dien-3β, 26-dihydroxy-7-one) | G. lucidum | [44] |
63 | Lucidal (5α-lanosta-8,24E-dien-3β-hydroxy-7-on-26-al) | G. lucidum | [44] |
64 | Ganoderic acid DM (3,7-dioxo-8,24(E)-dien-lanosta-26-oic acid) | G. lucidum (cultured fruit bodies) | [45] |
65 | Ganoderic acid V | G. orbiforme | [46] |
66 | Ganolucidic acid γa (3β, 7β, 15α, 23-tetrahydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid) | G. sinense (fruit bodies) | [47] |
67 | Ganolucidate F (3β, 15α, 23-trihydroxy-11-oxo-5α-lanosta-8,24-dien-26-oic acid) | G. sinense (fruit bodies) | [47] |
68 | Lucialdehyde E (7β, 15α-dihydroxy-3,11-dioxo-5α-lanosta-8,24-dien-26-al) | G. lucidum (spores) | [48] |
69 | Ganolucidic acid D | G. lucidum (spores) | [37] |
70 | Ganoderic acid W | G. lucidum (fruit bodies) | [41] |
Figure 2.
Structures of compounds 1–37.
Figure 2.
Structures of compounds 1–37.
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 |
---|
1 | β-OH | =O | =O | β-O-Ac | =O | α-CH3 | COOBu |
2 | =O | β-OH | =O | H | α-OH | α-CH3 | COOBu |
3 | β-OH | β-OH | =O | H | =O | α-CH3 | COOBu |
4 | β-OH | =O | =O | β-O-Ac | α-OH | α-CH3 | COOH |
5 | =O | H | =O | H | α-OH | β-CH3 | COOH |
6 | =O | H | =O | H | α-OH | β-CH3 | COOCH3 |
7 | β-OH | H | =O | H | α-OH | β-CH3 | COOH |
8 | β-OH | H | =O | H | α-OH | β-CH3 | COOCH3 |
9 | =O | β-OH | =O | H | α-OH | β-CH3 | COOH |
10 | =O | β-OH | =O | H | α-OH | β-CH3 | COOCH3 |
11 | β-OH | β-OH | =O | H | =O | β-CH3 | COOH |
12 | β-OH | β-OH | =O | H | =O | β-CH3 | COOCH3 |
13 | β-OH | β-OH | =O | H | α-OH | β-CH3 | COOH |
14 | β-OH | β-OH | =O | H | α-OH | β-CH3 | COOCH3 |
15 | =O | β-OH | =O | H | =O | β-CH3 | COOH |
16 | =O | β-OH | =O | H | =O | β-CH3 | COOCH3 |
17 | β-OH | β-OH | =O | H | α-OH | α-CH3 | COOCH3 |
18 | β-OH | =O | =O | H | α-OH | α-CH3 | COOCH3 |
19 | =O | α-OH | =O | H | α-OH | α-CH3 | COOCH3 |
20 | β-OH | α-OH | =O | H | α-OH | α-CH3 | COOCH3 |
21 | O-CHO | β-OH | =O | β-OH | =O | β-CH3 | COOH |
22 | =O | α-OH | =O | H | α-OH | α-CH3 | COOH |
23 | =O | β-OH | =O | H | =O | α-CH3 | COOH |
24 | =O | =O | =O | β-O-COCH3 | =O | α-CH3 | COOEt |
25 | β-OH | β-OH | =O | β-O-COCH3 | =O | α-CH3 | COOCH3 |
26 | β-OH | =O | =O | =O | =O | α-CH3 | COOH |
27 | =O | β-OH | β-OH | H | =O | α-CH3 | COOH |
28 | β-OH | =O | =O | β-O-Ac | =O | β-CH3 | COOH |
29 | =O | =O | =O | β-O-Ac | =O | β-CH3 | COOH |
30 | =O | =O | =O | H | =O | β-CH3 | COOH |
31 | β-OH | β-OH | =O | β-O-Ac | =O | α-CH3 | COOH |
32 | β-OH | =O | =O | H | =O | α-CH3 | COOH |
33 | =O | =O | =O | H | α-OH | α-CH3 | COOH |
34 | β-OH | β-OH | =O | H | α-OH | α-CH3 | COOH |
35 | β-OH | β-OH | =O | β-OH | =O | β-CH3 | COOH |
36 | =O | β-OH | =O | β-OH | =O | α-CH3 | COOH |
37 | =O | =O | =O | β-OH | =O | α-CH3 | COOH |
Figure 3.
Structures of compounds 38–70.
Figure 3.
Structures of compounds 38–70.
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
---|
38 | =O | β-OH | =O | H | =O | α-CH3 | H | COOH |
39 | =O | β-OH | =O | H | α-OH | α-CH3 | H | COOH |
40 | β-OH | β-OH | =O | β-O-Ac | =O | α-CH3 | H | COOH |
41 | β-OH | H | =O | β-O-Ac | α-O-Ac | α-CH3 | H | COOH |
42 | =O | =O | =O | H | =O | α-CH3 | β-OH | COOH |
43 | β-OH | =O | H | H | H | β-CH3 | H | COOH |
44 | =O | OH | =O | H | =O | α-CH3 | OH | COOH |
45 | =O | =O | H | H | H | α-CH3 | H | CHO |
46 | β-OH | =O | H | H | H | α-CH3 | H | CHO |
47 | =O | β-OH | =O | H | α-OH | α-CH3 | β-OH | COOH |
48 | =O | α-OH | =O | H | α-OH | α-CH3 | β-OH | COOH |
49 | β-OH | β-OH | =O | H | =O | α-CH3 | β-OH | COOH |
50 | β-OH | =O | =O | H | =O | α-CH3 | β-OH | COOH |
51 | β-OH | β-OH | =O | β-OH | =O | α-CH3 | β-OH | COOH |
52 | β-OH | =O | =O | β-OH | =O | α-CH3 | β-OH | COOH |
53 | β-OH | β-OH | =O | H | =O | α-CH3 | H | COOH |
54 | =O | H | =O | H | α-OH | β-CH3 | H | COOH |
55 | =O | α-OH | H | H | H | β-CH3 | H | CHO |
56 | α-O-Ac | α-O-Ac | H | H | α-OH | β-CH3 | H | COOH |
57 | =O | =O | =O | H | H | α-CH3 | H | CHO |
58 | =O | =O | H | H | H | α-CH3 | H | CH2OH |
59 | α-O-Ac | α-O-CH3 | H | H | α-OH | β-CH3 | H | COOH |
60 | =O | =O | α-OH | H | H | α-CH3 | H | COOH |
61 | =O | =O | β-OH | H | H | α-CH3 | H | COOH |
62 | β-OH | =O | H | H | H | α-CH3 | H | CH2OH |
63 | β-OH | =O | H | H | H | α-CH3 | H | CHO |
64 | =O | =O | H | H | H | α-CH3 | H | COOH |
65 | =O | α-OH | H | H | α-O-Ac | α-CH3 | H | COOH |
66 | β-OH | β-OH | =O | H | α-OH | α-CH3 | β-OH | COOH |
67 | β-OH | H | =O | H | α-OH | α-CH3 | β-OH | COOH |
68 | =O | β-OH | =O | H | α-OH | α-CH3 | H | CHO |
69 | =O | H | =O | H | α-OH | α-CH3 | β-OH | COOH |
70 | α-O-Ac | α-OH | H | H | α-O-Ac | β-CH3 | H | COOH |
Table 3.
Ganoderma triterpenes 71–98 in Figure 4 and Figure 5.
No. | Compound Name | Source | Ref. |
---|
71 | Ganoderic acid Mb (3α, 15α, 22-triacetoxy-7α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (fruit bodies) | [41] |
72 | Ganoderic acid Mc (3α, 7α, 22-triacetoxy-15α-hydroxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (fruit bodies) | [41] |
73 | Ganoderic acid Md (3α, 22-diacetoxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (fruit bodies) | [41] |
74 | Ganoderic acid Mg (3α, 22-diacetoxy-15α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (mycelial mat) | [43] |
75 | Ganoderic acid Mh (3α, 22-diacetoxy-7α, 15α-dihydroxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (mycelial mat) | [43] |
76 | Ganoderic acid Mj (22-acetoxy-3α-hydroxy-7α-methoxy-5α-lanost-8,24E-dien-26-oic acid) | G. lucidum (mycelial mat) | [43] |
77 | 3α, 22β-Diacetoxy-7α-hydroxyl-5α-lanost-8,24E-dien-26-oic acid | G. lucidum (mycelial mat) | [49] |
78 | Ganorbiformin B | G. orbiforme | [46] |
79 | Ganorbiformin C | G. orbiforme | [46] |
80 | Ganorbiformin D | G. orbiforme | [46] |
81 | Ganorbiformin E | G. orbiforme | [46] |
82 | Ganorbiformin F | G. orbiforme | [46] |
83 | Ganoderic acid O ((22S, 24E)-3α, l5α, 22-triacetoxy-7α-hydroxy-5α-lanosta-7,24-dien-26-oic acid) | G. lucidum (cultured mycelium) | [50] |
84 | 7-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] |
85 | 12β-Acetoxy-3β-hydroxy-7,11,15,23-tetraoxo-lanost-8,20E-diene-26-oic acid | G. lucidum (fruit bodies) | [32] |
86 | 23-Dihydroganoderenic acid D (7β, 23ξ-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic acid) | G. applanatum (fruit bodies) | [51] |
87 | Methyl ganoderenate D (7β-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic acid methyl ester) | G. applanatum (fruit bodies) | [51] |
88 | Ganoderenic acid A ((20E)-7β, 15α-dihydroxy-3,11,23-trioxo-5α-lanost-8,20-dien-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
89 | Ganoderenic acid B ((20E)-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanost-8,20-dien-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
90 | Ganoderenic acid C ((20E)-3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8,20-dien-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
91 | Ganoderenic acid D ((20E)-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8,20-dien-26-oic acid) | G. lucidum (dried fruit bodies) | [31] |
92 | 12β-Acetoxy-7β-hydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20-dien-26-oic acid | G. lucidum | [26] |
93 | Ganoderenic acid F (3,7,11,15,23-pentaoxo-5α-lanosta-8,20E-dien-26-oic acid) | G. applanatum (fruit bodies) | [52] |
94 | Ganoderenic acid G (15α-hydroxy-3,7,11,23-tetraoxo-5α-lanosta-8,20E-dien-26-oic acid) | G. applanatum (fruit bodies) | [52] |
95 | Methy ganoderenate H (methyl 3β-hydroxy-7,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate) | G. applanatum (fruit bodies) | [52] |
96 | Methyl ganoderenate I (3β, 15α-dihydroxy-7,11,23-trioxo-5α-lanosta-8,20E-dien-26-oate) | G. applanatum (fruit bodies) | [52] |
97 | Ganoderenic acid H | G. lucidum (fruit bodies) | [32] |
98 | 12β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxo-5α-lanosta-8,20-dien-26-oic acid | G. lucidum | [26] |
Figure 4.
Structures of compounds 71–84.
Figure 4.
Structures of compounds 71–84.
Cpd | R1 | R2 | R3 | R4 | R5 |
---|
71 | α-O-Ac | α-OH | α-O-Ac | β-CH3 | ξ-O-Ac |
72 | α-O-Ac | α-O-Ac | α-OH | β-CH3 | ξ-O-Ac |
73 | α-O-Ac | α-O-CH3 | H | β-CH3 | ξ-O-Ac |
74 | α-O-Ac | α-O-CH3 | α-OH | β-CH3 | ξ-O-Ac |
75 | α-O-Ac | α-OH | α-OH | β-CH3 | ξ-O-Ac |
76 | α-OH | α-O-CH3 | H | β-CH3 | ξ-O-Ac |
77 | α-O-Ac | α-OH | H | α-CH3 | β-O-Ac |
78 | β-O-Ac | =O | H | α-CH3 | β-O-Ac |
79 | β-OH | =O | H | α-CH3 | β-O-Ac |
80 | =O | α-OH | α-O-Ac | α-CH3 | β-O-Ac |
81 | =O | α-OH | H | α-CH3 | β-O-Ac |
82 | =O | α-O-CH3 | H | α-CH3 | β-O-Ac |
83 | α-O-Ac | α-OH | α-O-Ac | α-CH3 | β-O-Ac |
84 | α-O-Ac | α-O-CH3 | α-O-Ac | α-CH3 | β-O-Ac |
Figure 5.
Structures of compounds 85–98.
Figure 5.
Structures of compounds 85–98.
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 |
---|
85 | β-OH | =O | β-O-Ac | =O | β-CH3 | =O | COOH |
86 | =O | β-OH | H | =O | β-CH3 | ξ-OH | ξ-COOH |
87 | =O | β-OH | H | =O | β-CH3 | =O | ξ-COOCH3 |
88 | =O | β-OH | H | α-OH | β-CH3 | =O | COOH |
89 | β-OH | β-OH | H | =O | β-CH3 | =O | COOH |
90 | β-OH | β-OH | H | α-OH | β-CH3 | =O | COOH |
91 | =O | β-OH | H | =O | β-CH3 | =O | COOH |
92 | =O | β-OH | β-O-Ac | =O | β-CH3 | =O | COOH |
93 | =O | =O | H | =O | β-CH3 | =O | COOH |
94 | =O | =O | H | α-OH | β-CH3 | =O | COOH |
95 | β-OH | =O | H | =O | β-CH3 | =O | COCH3 |
96 | β-OH | =O | H | α-OH | β-CH3 | =O | COCH3 |
97 | β-OH | =O | H | =O | β-CH3 | =O | COOH |
98 | β-OH | β-OH | β-O-Ac | =O | α-CH3 | =O | COOH |
Table 4.
Ganoderma triterpenes 99–123 in Figure 6, Figure 7, Figure 8 and Figure 9.
No. | Compound Name | Source | Ref. |
---|
99 | Methyl ganoderate D (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) | G. lucidum (fruit bodies) | [53,54] |
100 | Methyl ganoderate E (methyl 3β, 7β, 15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) | G. lucidum (gills) | [54,55] |
101 | Methyl ganoderate F (methyl 12β-acetoxy-3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oate) | G. lucidum (gills) | [56] |
102 | Methyl ganoderate H (methyl 3β-hydroxy-12β-acetoxy-7,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) | G. lucidum (gills) | [30,56] |
103 | Methyl ganoderate G (methyl 3β, 7β, 12β-trihydroxy-11,15,23-trioxo-5α-lanost-8-en-26-oate) | G. lucidum | [20] |
104 | Compound C5 | G. lucidum (gill surface) | [30] |
105 | Compound C6 | G. lucidum (gill surface) | [30] |
106 | Ganoderic acid AP3 (15α, 20ξ-dihydroxy-3,7,11,23-tetraoxolanost-8-en-26-oic acid) | G. applanatum (fruit bodies) | [34] |
107 | 23-Dihydroganoderic acid I (3β, 7β, 20,23ξ-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic acid) | G. applanatum (fruit bodies) | [51] |
108 | 23-Dihydroganoderic acid N (7β, 20,23ξ-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid) | G. applanatum (fruit bodies) | [51] |
109 | 20-Hydroxylganoderic acid G | G. lucidum (fruit bodies) | [57] |
110 | Ganoderic acid I | G. lucidum (gills) | [22] |
111 | Lucidumol A ((24S)-24,25-dihydroxylanost-8-ene-3,7-dione) | G. lucidum (spores) | [38] |
112 | Ganoderiol C (7α-ethoxy-24,25,26-trihydroxy-5α-lanost-8-en-3-one) | G. lucidum (fruit bodies) | [39] |
113 | Ganoderiol D (24,25,26-trihydroxy-5α-lanost-8-en-3,7-dione) | G. lucidum (fruit bodies) | [39] |
114 | Ganoderiol G (24,25,26-trihydroxy-7α-methoxy-5α-lanost-8-en-3-one) | G. lucidum (fruit bodies) | [39] |
115 | Ganoderiol H (3β, 24,25,26-tetrahydroxy-5α-lanost-8-en-7-one) | G. lucidum (fruit bodies) | [39] |
116 | Ganoderitriol M ((24S)-lanosta-7-oxo-8-en-3β, 24,25-triol) | G. lucidum (fruit bodies) | [58] |
117 | Sinensoic acid (3,26-dihydroxy-5-lanosta-8,24E-dien-21-oic acid) | G. sinense (fruit bodies) | [59] |
118 | Tsugarioside B (3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-d-xyloside) | G. tsugae (fruit bodies) | [60] |
119 | Tsugaric acid A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid) | G. tsugae | [61] |
120 | Ganosinoside A (3-oxo-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside) | G. sinense (fruit bodies) | [47] |
121 | Tsugarioside A (3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid ester β-d-glucoside) | G. tsugae (fruit bodies) | [60] |
122 | 3-Oxo-5α-lanosta-8,24-dien-21-oic acid | G. resinaceum (fruit bodies) | [62] |
123 | 3β-Hydroxy-5α-lanosta-8,24-dien-21-oic acid | G. tsugae (fruit bodies) | [60] |
Figure 6.
Structures of compounds 99–105.
Figure 6.
Structures of compounds 99–105.
Cpd | R1 | R2 | R3 | R4 |
---|
99 | β-OH | β-OH | H | α-OH |
100 | =O | =O | H | =O |
101 | =O | =O | β-O-Ac | =O |
102 | β-OH | =O | β-O-Ac | =O |
103 | β-OH | β-OH | β-OH | =O |
104 | =O | β-OH | OH | =O |
105 | β-OH | =O | OH | =O |
Figure 7.
Structures of compounds 106‒110
Figure 7.
Structures of compounds 106‒110
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
---|
106 | =O | =O | H | α-OH | β-CH3 | ξ-OH | =O | COOH |
107 | β-OH | β-OH | H | =O | α-CH3 | β-OH | ξ-OH | ξ-COOH |
108 | =O | β-OH | H | =O | α-CH3 | β-OH | ξ-OH | ξ-COOH |
109 | β-OH | β-OH | β-OH | =O | β-CH3 | β-OH | =O | COOH |
110 | β-OH | β-OH | =O | =O | α-CH3 | ξ-OH | =O | COOH |
Figure 8.
Structures of compounds 111‒116
Figure 8.
Structures of compounds 111‒116
Cpd | R1 | R2 | R3 | R4 | R5 |
---|
111 | =O | =O | α-CH3 | α-OH | CH3 |
112 | =O | α-O-Et | β-CH3 | ξ-OH | CH2OH |
113 | =O | =O | β-CH3 | ξ-OH | CH2OH |
114 | =O | α-O-CH3 | β-CH3 | ξ-OH | CH2OH |
115 | β-OH | =O | β-CH3 | ξ-OH | CH2OH |
116 | β-OH | =O | α-CH3 | α-OH | CH3 |
Figure 9.
Structures of compounds 117‒123.
Figure 9.
Structures of compounds 117‒123.
Cpd | R1 | R2 | R3 |
---|
117 | β-OH | α-COOH | CH2OH |
118 | α-O-Ac | CH2O-β-D-xylosyl | CH3 |
119 | α-O-COCH3 | α-COOH | CH3 |
120 | =O | α-COO-β-D-glucopyranosyl | CH3 |
121 | α-O-Ac | α-COOH | CH3 |
122 | =O | α-COOH | CH3 |
123 | β-OH | α-COOH | CH3 |
Table 5.
Ganoderma triterpenes 124–147 in Figure 10, Figure 11, Figure 12, Figure 13, Figure 14, Figure 15, Figure 16 and Figure 17 and Ganoderma triterpenes 148–155 in Figure 18.
No. | Compound Name | Source | Ref. |
---|
124 | 3β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid | G. lucidum (fruit bodies) | [63] |
125 | 3β, 7β-Dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid methyl ester | G. lucidum (fruit bodies) | [63] |
126 | 12β-Acetoxy-3β, 7β-dihydroxy-11,15,23-trioxolanost-8,16-dien-26-oic acid | G. lucidum (fruit bodies) | [63] |
127 | Methyl ganoderate I | G. lucidum | [20,22] |
128 | Methyl ganoderate AP (methyl 12β, l5α, 20-trihydroxy-3,7,11,23- tetraoxo-5α-lanost-8-en-26-oate) | G. applanatum (fruit bodies) | [52] |
129 | Methyl ganoderate N (Methyl 7β, 20-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) | G. lucidum (fruit bodies) | [64] |
130 | Methyl ganoderate M (methyl 7β, 12α-dihydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oate) | G. lucidum (fruit bodies) | [64] |
131 | Ganoderiol E (3β, 26,27-trihydroxy-5α-lanosta-8,24-dien-7-one) | G. lucidum (fruit bodies) | [39] |
132 | Ganoderiol I (15α, 26,27-trihydroxy-5α-lanosta-8,24-dien-3-one) | G. lucidum (fruit bodies) | [39] |
133 | Ganoderiol J (26,27-dihydroxy-5α-lanosta-8,24-dien-3,7-dione) | G. sinense (fruit bodies) | [47] |
134 | Epoxyganoderiol A (24S, 25S-epoxy-7α, 26-dihydroxy-5α-lanost-8-en-3-one) | G. lucidum | [40] |
135 | Ganoderone C (5α-lanosta-8-ene-24,25-epoxy-26-hydroxy-3,7-dione) | G. pfeifferi (fruit bodies) | [42] |
136 | 3-O-Acetylganoderic acid B (3β-acetoxy-7β-hydroxy-11,15,23-trioxolanost-8-en-26-oic acid) | G. lucidum (mycelia) | [65] |
137 | 3-O-Acetylganoderic acid K (3β-acetyloxy-15α-hydroxy-7,11,23-trioxolanost-8-en-26-oic acid) | G. lucidum (mycelia) | [65] |
138 | Ethyl 3-O-acetylganoderate B | G. lucidum (mycelia) | [65] |
139 | Ethyl ganoderate J | G. lucidum (mycelia) | [65] |
140 | Applanoxidic acid G (15β, 20-dihydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid) | G. applanatum | [66] |
141 | Applanoxidic acid H (3β, 12α, 20-trihydroxy-7α, 8α-epoxydioxo-5α-lanosta-9(11),16-dien-26-oic acid) | G. applanatum | [66] |
142 | 8β, 9α-Dihydroganoderic acid J | G. lucidum (fruit bodies) | [57] |
143 | Methyl 8β, 9α-dihydroganoderate J | G. lucidum (fruit bodies) | [57] |
144 | Ganosporeric acid A (3,7,11,12,15,23-hexaoxo-5α-lanosta-8-en-26-oic acid) | G. lucidum (spores) | [67] |
145 | 24ξ-Methyl-5α-lanosta-25-one | G. applanatum (fruit bodies) | [68] |
146 | 3α-Carboxyacetoxy-24-methylene-23-oxolanost-8-en-26-oic acid | G. applanatum (fruit bodies) | [69] |
147 | 3α-Carboxyacetoxy-24-methyl-23-oxolanost-8-en-26-oic acid | G. applanatum (fruit bodies) | [69] |
148 | Fornicatin C ((3β)-3-hydroxy-18(13→12β)-abeo-lanosta-13(17),24-dien-18-oic acid) | G. fornicatum (fruit bodies) | [70] |
149 | 3-Epipachymic acid (3α-acetoxy-16α-hydroxy-24-methylene-5α-lanost-8-en-21-oic acid) | G. resinaceum (fruit bodies) | [62] |
150 | 3β, 15α-Diacetoxylanosta-8,24-dien-26-oic acid | G. lucidum (mycelia) | [71] |
151 | Tsugaric acid C ((24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid) | G. tsugae (fruit bodies) | [60] |
152 | Ganoderic acid V1 ((24E)-3β, 20ξ-dihydroxy-7,11,15-trioxo-5α-lanosta-8,24-dien-26-oic acid) | G. lucidum | [72] |
153 | Tsugaric acid B (3α-acetoxy-16α-hydroxy-24ξ-methyl-5α-lanosta-8,25-dien-21-oic acid) | G. tsugae | [61] |
154 | Methyl ganoderenate E (7β, 12β-dihydroxy-3,11,15,23-tetraoxo-5α-lanosta-8,20E-dien-26-oate) | G. lucidum (fruit bodies) | [64] |
155 | 8β, 9α-Dihydroganoderic acid C | G. lucidum (mycelia) | [65] |
Figure 10.
Structures of compounds 124–126.
Figure 10.
Structures of compounds 124–126.
Cpd | R1 | R2 |
---|
124 | H | COOH |
125 | H | COOCH3 |
126 | β-O-Ac | COOH |
Figure 11.
Structures of compounds 127–130.
Figure 11.
Structures of compounds 127–130.
Cpd | R1 | R2 | R3 | R4 |
---|
127 | β-OH | β-OH | H | =O |
128 | =O | =O | β-OH | α-OH |
129 | =O | β-OH | H | =O |
130 | =O | β-OH | α-OH | =O |
Figure 12.
Structures of compounds 131‒133.
Figure 12.
Structures of compounds 131‒133.
Cpd | R1 | R2 | R3 | R4 |
---|
131 | β-OH | =O | H | β-CH3 |
132 | =O | β-CH3 | α-OH | β-CH3 |
133 | =O | =O | H | α-CH3 |
Figure 13.
Structures of compounds 134 and 135.
Figure 13.
Structures of compounds 134 and 135.
Cpd | R1 | R2 |
---|
134 | α-OH | β-CH3 |
135 | =O | α-CH3 |
Figure 14.
Structures of compounds 136‒139.
Figure 14.
Structures of compounds 136‒139.
Cpd | R1 | R2 | R3 | R4 |
---|
136 | β-O-Ac | β-OH | =O | COOH |
137 | β-O-Ac | =O | α-OH | COOH |
138 | β-O-Ac | β-OH | =O | COOEt |
139 | =O | =O | α-OH | COOEt |
Figure 15.
Structures of compounds 140‒141.
Figure 15.
Structures of compounds 140‒141.
Cpd | R1 | R2 | R3 |
---|
140 | =O | =O | β-OH |
141 | β-OH | α-OH | =O |
Figure 16.
Structures of compounds 142‒145.
Figure 16.
Structures of compounds 142‒145.
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 |
---|
142 | =O | =O | =O | H | α-OH | β-CH3 | =O | H | COOH |
143 | =O | =O | =O | H | α-OH | β-CH3 | =O | H | COOCH3 |
144 | =O | =O | =O | =O | =O | β-CH3 | =O | H | COOH |
145 | H | H | H | H | H | α-CH3 | H | ξ-CH3 | =O |
Figure 17.
Structures of compounds 146‒147.
Figure 17.
Structures of compounds 146‒147.
Figure 18.
Structures of compounds 148‒155.
Figure 18.
Structures of compounds 148‒155.
![Molecules 19 17478 g018]()
Table 6.
Ganoderma triterpenes 156–196 in Figure 19.
No. | Compound Name | Source | Ref. |
---|
156 | 15-Hydroxy-ganoderic acid S (15α-hydroxy-3-oxo-5α-lanosta-7,9(11),24(E)-trien-26-oic acid) | G. lucidum (fruit bodies) | [35] |
157 | 3α, 16α-Dihydroxylanosta-7,9(11),24-trien-21-oic acid | G. applanatum (fruit bodies) | [69] |
158 | 3α, 16α, 26-Trihydroxylanosta-7,9(11),24-trien-21-oic acid | G. applanatum (fruit bodies) | [69] |
159 | Ganoderic acid S1 | G. lucidum (fruit bodies) | [73] |
160 | Ganoderic acid SZ (3-oxo-lanosta-7,9(11),24(Z)-trien-26-oic acid) | G. lucidum (fruit bodies) | [74] |
161 | 5α-Lanosta-7,9(11),24-triene-15α-26-dihydroxy-3-one | G. concinna | [75] |
162 | Ganoderic acid Me (3α, 15α-diacetoxy-5α-lanost-7,9(11),24E-trien-26-oic acid) | G. lucidum (cultured mycelial mat) | [41] |
163 | Ganoderic acid Mf (3α-acetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid) | G. lucidum (cultured mycelial mat) | [41] |
164 | Ganodermenonol (26-hydroxy-5α-lanosta-7,9(11),24-trien-3-one) | G. lucidum (dried fruit bodies) | [76] |
165 | Ganodermadiol (5α-lanosta-7,9(11),24-triene-3β, 26-diol) | G. lucidum (dried fruit bodies) | [76] |
166 | Ganodermatriol (5α-lanosta-7,9(11),24-triene-3β, 26,27-triol) | G. lucidum (fruit bodies) | [77] |
167 | Ganodermic acid S (lanosta-7,9(11),24-trien-3β, 15α-diacetoxy-26-oic acid) | G. lucidum | [78] |
168 | Carnosodione (26,27-dihydroxylanosta-7,9(11),24-trien-3,16-dione) | G. carnosum (fruit bodies) | [79] |
169 | Canoderol B ((24E)-5α-lanosta-7,9(11),24-trien-3,26-diol) | G. lucidum | [23] |
170 | Ganoderic acid Mk (3α, 22-diacetoxy-15α-hydroxy-5α-lanost-7,9(11),24E-trien-26-oic acid) | G. lucidum (mycelia mat) | [43] |
171 | Ganoderiol B (15α, 26,27-trihydroxy-5α-lanosta-7,9(11),24-trien-3-one) | G. lucidum (fruit bodies) | [77] |
172 | Ganoderic acid T ((22S, 24E)-3α, 15α, 22-triacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid) | G. lucidum (cultured mycelia) | [80] |
173 | Ganoderic acid S ((22S, 24E)-22-acetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (cultured mycelia) | [23,80] |
174 | Ganoderic acid R ((22S, 24E)-3α, 22-diacetoxy-5α-lanosta-7,9,(11),24-trien-26-oic acid) | G. lucidum (cultured mycelia) | [80] |
175 | Ganorbiformin G | G. orbiforme | [46] |
176 | Lanosta-7,9(11),24-trien-3β, 15α, 22β-triacetoxy-26-oic acid | G. lucidum | [81] |
177 | Lanosta-7,9(11),24-trien-15α-acetoxy-3α-hydroxy-23-oxo-26-oic acid | G. lucidum | [81] |
178 | Lanosta-7,9(11),24-trien-3α, l5α-diacetoxy-23-oxo-26-oic acid | G. lucidum | [81] |
179 | Lanosta-7,9(11),24-trien-3α, 15α-hydroxy-23-oxo-26-oic acid | G. lucidum | [81] |
180 | Lanosta-7,9(11),24-trien-3α-acetoxy-15α, 22β-dihydroxy-26-oic acid | G. lucidum | [81] |
181 | Ganodermic acid T-N (3β-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (mycelia) | [82] |
182 | Ganodermic acid T-O (3β-acetoxy-15α-hydroxy-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (mycelia) | [82] |
183 | Ganodermic acid T-Q (3β-oxo-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (mycelia) | [82] |
184 | Compound 10 | G. orbiforme | [46] |
185 | Ganoderic acid P ((22S, 24E)-15α, 22-diacetoxy-3α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (cultured mycelium) | [50] |
186 | Ganoderic acid Q ((22S, 24E)-3α, 22-diacetoxy-15α-hydroxy-5α-lanosta-7,9(11),24-trien-26-oic acid) | G. lucidum (cultured mycelium) | [50] |
187 | Ganoderic acid Jc (15α, 23-dihydroxy-3-oxo-5α-lanosta-7,9(11),24-trien-26-oic acid) | G. sinense (fruit bodies) | [47] |
188 | Ganodermatetraol (3β, 15α, 26,27-tetrahydroxy-5α-lanosta-7,9(11),24-triene) | G. sinense (fruit bodies) | [47] |
189 | 5α-Lanosta-7,9(11),24-triene-3β-hydroxy-26-al | G. concinna | [75] |
190 | Ganoderiol F (26,27-dihydroxy-5α-lanosta-7,9(11),24-trien-3-one) | G. lucidum (fruit bodies) | [39] |
191 | 26,27-Dihydroxy-5α-lanosta-7,9(11),24-triene-3,22-dione | G. lucidum (basidiocarp) | [83] |
192 | 26-Hydroxy-5α-lanosta-7,9(11),24-triene-3,22-dione | G. lucidum (basidiocarp) | [83] |
193 | Ganodermic acid P1 (lanosta-7,9(11),24-trien-3α, 22β-diacetoxy-15α-hydroxy-26-oic acid) | G. lucidum (mycelia) | [84] |
194 | Ganodermic acid P2 (lanosta-7,9(11),24-trien-15α, 22β-diacetoxy-3β-hydroxy-26-oic acid) | G. lucidum (mycelia) | [84] |
195 | Lanosta-7,9(11),24-trien-3β, 15α, 22-triacetoxy-26-oic acid | G. amboinense (fruit bodies) | [85] |
196 | 16α-Hydroxy-3-oxolanosta-7,9(11),24-trien-21-oic acid | G. applanatum (fruit bodies) | [69] |
Table 7.
Ganoderma triterpenes (
197–
213) in
Figure 20.
Table 7.
Ganoderma triterpenes (197–213) in Figure 20.
No. | Compound Name | Source | Ref. |
---|
197 | Lucialdehyde A ((24E)-3β-hydroxy-5α-lanosta-7,9(11),24-trien-26-al) | G. lucidum (fruit bodies) | [25] |
198 | Ganoderiol a triacetate (3β, 24,26-triacetoxy-5α-lanosta-7, 9(11)-dien-25-ol) | G. sinense (fruit bodies) | [86] |
199 | Ganoderal A | G. lucidum | [23] |
200 | Ganoderol A | G. lucidum | [23] |
201 | Lucidumol B ((24S)-lanosta-7,9(11)-diene-3β, 24,25-triol) | G. lucidum (spores) | [38] |
202 | Ganodermanontiol (24,25,26-trihydroxy-5α-lanosta-7,9(11)-dien-3-one) | G. lucidum (spores) | [67] |
203 | Ganoderiol A (5α-lanosta-7,9(11)-dien-3β, 24,25,26-tetraol) | G. lucidum (fruit bodies) | [77] |
204 | Ganodermanondiol | G. lucidum (fruit bodies) | [87] |
205 | Ganoderic acid X (3α-hydroxy-15α-acetoxy-lanosta-7,9(11),24-trien-26-oic acid) | G. amboinense | [88] |
206 | Ganoderic acid TR | G. lucidum | [89] |
207 | Ganodermic acid Ja (lanosta-7,9(11),24-trien-3α, 15α-dihydroxy-26-oic acid) | G. lucidum (mycelia) | [84] |
208 | Ganodermic acid Jb (lanosta-7,9(11),24-trien-3β, 15α-dihydroxy-26-oic acid) | G. lucidum (mycelia) | [84] |
209 | Ganodermic acid R (lanosta-7,9(11),24-trien-3α, 15α-diacetoxy-26-oic acid) | G. lucidum | [78] |
211 | 15α-Hydroxy-3-oxo-5α-lanosta-7,9,24(E)-triene-26-oic acid | G. lucidum | [26] |
212 | 15α, 26-Dihydroxy-5α-lanosta-7,9,24(E)-trien-3-one | G. lucidum | [26] |
213 | 3β-Hydroxy-5α-lanosta-7,9,24(E)-trien-26-oic acid | G. lucidum | [26] |
Figure 19.
Structures of compounds 156–196.
Figure 19.
Structures of compounds 156–196.
![Molecules 19 17478 g019]()
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | |
---|
156 | =O | α-OH | H | β-CH3 | H | H | COOH | CH3 | |
157 | α-OH | H | α-OH | α-COOH | H | H | CH3 | CH3 | |
158 | α-OH | H | α-OH | α-COOH | H | H | CH2OH | CH3 | |
159 | =O | H | H | α-CH3 | H | H | COOH | CH3 | |
160 | =O | H | H | β-CH3 | H | H | COOH | CH3 | |
161 | =O | α-OH | H | α-CH3 | H | H | CH2OH | CH3 | |
162 | α-O-Ac | α-O-Ac | H | β-CH3 | ξ-H2 | H | COOH | CH3 | |
163 | β-O-Ac | α-OH | H | β-CH3 | ξ-H2 | H | COOH | CH3 | |
164 | =O | H | H | α-CH3 | H | H | CH2OH | CH3 | |
165 | β-OH | H | H | α-CH3 | H | H | CH2OH | CH3 |
166 | β-OH | H | H | α-CH3 | H | H | CH2OH | CH2OH |
167 | β-O-Ac | α-O-Ac | H | β-CH3 | H | H | COOH | CH3 |
168 | =O | H | O | β-CH3 | H | H | CH2OH | CH2OH |
169 | β-OH | H | H | β-CH3 | H | H | CH2OH | CH3 |
170 | α-O-Ac | α-OH | H | β-CH3 | ξ-O-Ac | H | COOH | CH3 |
171 | =O | α-OH | H | α-CH3 | H | H | CH2OH | CH2OH |
172 | α-O-Ac | α-O-Ac | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
173 | α-OH | H | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
174 | α-O-Ac | H | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
175 | =O | H | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
176 | β-O-Ac | α-O-Ac | H | β-CH3 | β-O-Ac | H | COOH | CH3 |
177 | α-OH | α-O-Ac | H | β-CH3 | H | =O | COOH | CH3 |
178 | α-O-Ac | α-O-Ac | H | β-CH3 | H | =O | COOH | CH3 |
179 | α-O-Ac | α-OH | H | β-CH3 | H | =O | COOH | CH3 |
180 | α-O-Ac | α-OH | H | β-CH3 | H | H | COOH | CH3 |
181 | β-OH | α-O-Ac | H | β-CH3 | H | H | COOH | CH3 |
182 | β-O-Ac | α-OH | H | β-CH3 | H | H | COOH | CH3 |
183 | =O | α-O-Ac | H | β-CH3 | H | H | COOH | CH3 |
184 | =O | α-O-Ac | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
185 | α-OH | α-O-Ac | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
186 | α-O-Ac | α-OH | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
187 | =O | α-OH | H | α-CH3 | H | OH | COOH | CH3 |
188 | β-OH | α-OH | H | α-CH3 | H | H | CH2OH | CH2OH |
189 | β-OH | H | H | α-CH3 | H | H | CHO | CH3 |
190 | =O | H | H | β-CH3 | H | H | CH2OH | CH2OH |
191 | =O | H | H | α-CH3 | =O | H | CH2OH | CH2OH |
192 | =O | H | H | α-CH3 | =O | H | CH2OH | CH3 |
193 | α-O-Ac | α-OH | H | β-CH3 | O-Ac | H | COOH | CH3 |
194 | β-OH | α-O-Ac | H | β-CH3 | O-Ac | H | COOH | CH3 |
195 | β-O-Ac | α-O-Ac | H | α-CH3 | β-O-Ac | H | COOH | CH3 |
196 | =O | H | α-OH | α-COOH | H | H | CH3 | CH3 |
Figure 20.
Structures of compounds 197–213.
Figure 20.
Structures of compounds 197–213.
Cpd | R1 | R2 | R3 | R4 | R5 | R6 |
---|
197 | β-OH | H | α-CH3 | △24,25 | △24,25 | CHO |
198 | β-O-Ac | H | α-CH3 | OAc | OH | CH2-O-Ac |
199 | =O | H | β-CH3 | △24,25 | △24,25 | CHO |
200 | =O | H | β-CH3 | △24,25 | △24,25 | CH2OH |
201 | β-OH | H | α-CH3 | α-OH | OH | CH3 |
202 | =O | H | β-CH3 | α-OH | H | CH2OH |
203 | β-OH | H | α-CH3 | OH | OH | CH2OH |
204 | =O | H | α-CH3 | OH | OH | CH3 |
205 | β-OH | α-O-Ac | β-CH3 | H | H | COOH |
206 | =O | α-OH | α-CH3 | △24,25 | △24,25 | COOH |
207 | α-OH | α-OH | β-CH3 | △24,25 | △24,25 | COOH |
208 | β-OH | α-OH | β-CH3 | △24,25 | △24,25 | COOH |
209 | α-O-Ac | α-O-Ac | β-CH3 | △24,25 | △24,25 | COOH |
210 | =O | H | α-CH3 | OH | OH | CH2OH |
211 | =O | α-OH | α-CH3 | △24,25 | △24,25 | COOH |
212 | =O | α-OH | α-CH3 | △24,25 | △24,25 | CH2OH |
213 | β-OH | H | α-CH3 | △24,25 | △24,25 | COOH |
Table 8.
Ganoderma triterpenes (214–221) in Figure 21 and Figure 22.
No. | Compound Name | Source | Ref. |
---|
214 | 3α, 15α, 22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
215 | 3β, 15α, 22β-Trihydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
216 | 3α, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
217 | 3β, 15α-Diacetoxy-22α-hydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
218 | 22β-Acetoxy-3α, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
219 | 22β-Acetoxy-3β, 15α-dihydroxylanosta-7,9(11),24-trien-26-oic acid | G. lucidum (mycelia) | [71] |
220 | Epoxyganoderiol B (24S, 25S-epoxy-26-hydroxy-5α-lanosta-7,9(11)-diene-3-one) | G. lucidum | [40] |
221 | Epoxyganoderiol C (24S, 25S-epoxy-5α-lanosta-7,9(11)-diene-3β, 26-diol) | G. lucidum | [40] |
Figure 21.
Structures of compounds 214–219.
Figure 21.
Structures of compounds 214–219.
Cpd | R1 | R2 | R3 |
---|
214 | α-OH | α-OH | α-OH |
215 | β-OH | α-OH | β-OH |
216 | α-O-Ac | α-O-Ac | α-OH |
217 | β-O-Ac | α-O-Ac | α-OH |
218 | α-OH | α-OH | β-O-Ac |
219 | β-OH | α-OH | β-O-Ac |
Figure 22.
Structure of compounds 220–221.
Figure 22.
Structure of compounds 220–221.
Table 9.
Ganoderma triterpenes (
222–
260) in
Figure 23.
Table 9.
Ganoderma triterpenes (222–260) in Figure 23.
No. | Compound Name | Source | Ref. |
---|
222 | Butyl lucidenate N | G. lucidum (fruit bodies) | [17] |
223 | Butyl lucidenate A | G. lucidum (fruit bodies) | [17] |
224 | 20(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] |
225 | 20-Hydroxylucidenic acid A (7β, 20ξ-dihydroxy-3,11,15-trioxo-25,26,27-trinorlanost-8-en-24-oic acid) | G. sinense (fruit bodies) | [33] |
226 | Methyl lucidenate D (methyl 12β-acetoxy-3,7,11,15-tetraoxo-5α-lanost-8-en-24-oate) | G. lucidum (fruit bodies) | [53,54] |
227 | 20(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] |
228 | Methyl 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] |
229 | Lucidenic 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] |
230 | Lucidenic 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] |
231 | Methyl lucidenate E | G. lucidum (gills) | [54] |
232 | Methyl lucidenate F | G. lucidum (gills) | [23,54] |
233 | Ethyl lucidenates A (ethyl 7β-hydroxy-4,4,14α-trimethyl-3,11,15-trioxo-5α-chol-8-en-24-oate) | G. lucidum (fruit bodies) | [93] |
234 | 3β-Oxo-formyl-7β, 12β-dihydroxy-4,4,14α-trimethyl-5α-chol-11,15-dioxo-8-en(E)-24-oic acid | G. lucidum | [24] |
235 | Lucidenic 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] |
236 | Lucidenic 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] |
237 | Lucidenic 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] |
238 | 4,4,14α-Trimethyl-3,7-dioxo-5α-chol-8-en-24-oic acid | G. lucidum | [26] |
239 | Lucidenic 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] |
240 | Methyl lucidenate P | G. lucidum (fruit bodies) | [95] |
241 | Methyl lucidenate Q (methyl-7β, 15α-dihydroxy-25,26,27-trinor-3,11-dioxolanost-8-en-24-oate) | G. lucidum (fruit bodies) | [95] |
242 | 3β-Hydroxy-4,4,14-trimethyl-7,11,15-trioxochol-8-en-24-oic acid | G. lucidum (fruit bodies) | [28] |
243 | Methyl lucidenate D2 | G. lucidum (gill surface) | [30] |
244 | Methyl lucidenate E2 | G. lucidum (gill surface) | [30] |
248 | Methyl lucidenate N (methyl 3β, 7β-dihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oate) | G. lucidum (fruit bodies) | [96] |
249 | t-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] |
250 | Methyl lucidenate A | G. lucidum (fruit bodies) | [93] |
251 | Lucidenic acid D2 | G. lucidum (fruit bodies) | [95] |
252 | 20-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] |
253 | 20-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] |
254 | 20-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] |
255 | 20-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] |
256 | 20-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] |
257 | Lucidenic acid F | G. lucidum (gills) | [22] |
258 | Methyl lucidenate C | G. lucidum | [26] |
259 | Lucidenic acid E2 | G. lucidum (fruit bodies) | [95] |
260 | Lucideric acid A | G. lucidum | [26] |
Figure 23.
Structures of compounds 222–260.
Figure 23.
Structures of compounds 222–260.
![Molecules 19 17478 g023]()
Cpd | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
---|
222 | β-OH | β-OH | =O | H | =O | α-CH3 | H | COOBu |
223 | =O | β-OH | =O | H | =O | α-CH3 | H | COOBu |
224 | β-OH | β-OH | =O | H | =O | CH2 | △20,21 | COOH |
225 | =O | β-OH | =O | H | =O | β-CH3 | ξ-OH | COOH |
226 | =O | =O | =O | β-O-Ac | =O | β-CH3 | H | COOCH3 |
227 | =O | β-OH | =O | H | =O | CH2 | △20,21 | COOH |
228 | =O | β-OH | =O | H | =O | CH2 | △20,21 | COOCH3 |
229 | β-OH | β-OH | =O | H | =O | α-CH3 | H | COOH |
230 | =O | =O | =O | β-O-Ac | =O | β-CH3 | H | COOH |
231 | β-OH | =O | =O | β-O-Ac | =O | β-CH3 | H | COOCH3 |
232 | =O | =O | =O | H | =O | β-CH3 | H | COOCH3 |
233 | =O | OH | =O | H | =O | α-CH3 | H | COOEt |
234 | β-O-CHO | β-OH | =O | OH | =O | β-CH3 | H | COOH |
235 | =O | β-OH | =O | H | =O | β-CH3 | H | COOH |
236 | =O | β-OH | =O | β-OH | =O | β-CH3 | H | COOH |
237 | β-OH | β-OH | =O | β-OH | =O | β-CH3 | H | COOH |
238 | =O | =O | H | H | H | α-CH3 | H | COOH |
239 | β-OH | β-OH | =O | β-O-Ac | =O | α-CH3 | H | COOH |
240 | β-OH | β-OH | =O | β-O-Ac | =O | α-CH3 | H | COOCH3 |
241 | =O | β-OH | =O | H | α-OH | α-CH3 | H | COOCH3 |
242 | β-OH | =O | =O | H | =O | α-CH3 | H | COOH |
243 | =O | =O | =O | O-Ac | =O | β-CH3 | H | COOCH3 |
244 | β-OH | =O | =O | O-Ac | =O | β-CH3 | H | COOCH3 |
245 | =O | =O | =O | α-OH | =O | β-CH3 | H | COOCH3 |
246 | β-OH | =O | =O | β-OH | =O | β-CH3 | H | COOCH3 |
247 | β-OH | α-OH | =O | H | α-OH | β-CH3 | H | COOCH3 |
248 | β-OH | β-OH | =O | H | =O | α-CH3 | H | COOCH3 |
249 | =O | β-OH | =O | β-OH | =O | α-CH3 | H | COOBu |
250 | =O | β-OH | =O | H | =O | α-CH3 | H | COOCH3 |
251 | =O | =O | =O | β-O-Ac | =O | α-CH3 | H | COOH |
252 | =O | =O | =O | β-O-Ac | =O | β-CH3 | ξ-OH | COOH |
253 | =O | =O | =O | H | =O | β-CH3 | ξ-OH | COOH |
254 | β-OH | =O | =O | β-O-Ac | =O | β-CH3 | ξ-OH | COOH |
255 | β-OH | β-OH | =O | H | =O | β-CH3 | ξ-OH | COOH |
256 | β-OH | β-OH | =O | β-O-Ac | =O | β-CH3 | ξ-OH | COOH |
257 | =O | =O | =O | H | =O | α-CH3 | H | COOH |
258 | β-OH | β-OH | =O | H | =O | α-CH3 | H | COOCH3 |
259 | β-OH | =O | =O | β-O-Ac | =O | α-CH3 | H | COOH |
260 | =O | β-OH | =O | H | =O | α-CH3 | H | COOH |
Table 10.
Ganoderma triterpenes 261–280 in Figure 24, Figure 25, Figure 26, Figure 27, Figure 28, Figure 29, Figure 30 and Figure 31.
No. | Compound Name | Source | Ref. |
---|
261 | 4,4,14α-Trimethyl-5α-chol-7,9(11)-dien-3-oxo-24-oic acid | G. lucidum (dried fruit bodies) | [73] |
262 | Ganoderic acid Jd (15α-hydroxy-3-oxo-5α-lano-sta-7,9(11)-dien-24-oic acid) | G. sinense (fruit bodies) | [47] |
263 | Methyl 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] |
264 | Methyl lucidenate I (3β-hydroxy-4α-hydroxymethyl-4β, 14α-dimethyl-7,11,15-trioxo-5α-chol-8-en-24-oate) | G. lucidum (fruit bodies) | [64] |
265 | Methyl 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] |
266 | Methyl lucidenate Ha | G. sinense (fruit bodies) | [47] |
267 | Colossolactone I ((22S)-3-β-hydroxylanosta-8,24-dien-26,22-olide) | G. colossum | [97] |
268 | Colossolactone II ((22S)-1,3-β-dihydroxylanosta-8,24-dien-26,22-olide) | G. colossum | [97] |
269 | Colossolactone D | G. colossum (fruit bodies) | [98] |
270 | Colossolactone E | G. colossum (fruit bodies) | [98] |
271 | Colossolactone F | G. colossum (fruit bodies) | [98] |
272 | Colossolactone G | G. colossum (fruit bodies) | [98] |
273 | Ganosporelactone A | G. lucidum (spores) | [99] |
274 | Ganosporelactone B | G. lucidum (spores) | [99] |
275 | Ganosinensin 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] |
276 | Ganosinensin 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] |
277 | Ganodermacetal (methyl 7β, 15α-isopropylide-nedioxy-3β-hydroxy-11,23-dioxo-5α-lanost-8-en-26-oate) | G. amboinense (fruit bodies) | [85] |
278 | Methyl ganoderate A acetonide (methyl 7β, 15α-isopropylidenedioxy-3,11,23-trioxo-5α-lanost-8-en-26-oate) | G. lucidum (fruit bodies) | [16] |
279 | Applanoxidic acid A (15α-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid) | G. applanatum | [101] |
280 | Applanoxidic 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 261–262.
Figure 24.
Structures of compounds 261–262.
Figure 25.
Structures of compounds 263–266.
Figure 25.
Structures of compounds 263–266.
Cpd | R1 | R2 | R3 |
---|
263 | β-OH | H | β-CH3 |
264 | =O | H | β-CH3 |
265 | =O | β-OH | β-CH3 |
266 | β-OH | H | α-CH3 |
Figure 26.
Structures of compounds 267–268.
Figure 26.
Structures of compounds 267–268.
Figure 27.
Structures of compounds 269–272.
Figure 27.
Structures of compounds 269–272.
Cpd | R1 | R2 | R3 |
---|
269 | α-H | β-H | β-OH |
270 | α-H | β-H | β-O-Ac |
271 | α-H | β-OH | β-O-Ac |
272 | ξ-OH | H | β-O-COCH3 |
Figure 28.
Structures of compounds 273–274.
Figure 28.
Structures of compounds 273–274.
Figure 29.
Structures of compounds 275–276.
Figure 29.
Structures of compounds 275–276.
Figure 30.
Structures of compounds 277–278.
Figure 30.
Structures of compounds 277–278.
Cpd | R1 | R2 |
---|
277 | β-OH | COOH |
278 | =O | COOCH3 |
Figure 31.
Structures of compounds 279–280.
Figure 31.
Structures of compounds 279–280.
Cpd | R1 | R2 |
---|
279 | =O | α-OH |
280 | β-OH | =O |
Table 11.
Ganoderma triterpenes
281–
287,
288–
307,
308–
311,
312,
313–
315,
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 281–287, 288–307, 308–311, 312, 313–315, 316 in Figure 32, Figure 33, Figure 34, Figure 35, Figure 36, Figure 37, Figure 38, Figure 39 and Figure 40.
No. | Compound Name | Source | Ref. |
---|
281 | Applanoxidic acid C (20-hydroxy-7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),16-dien-26-oic acid) | G. applanatum | [101] |
282 | Applanoxidic acid D (3β, 20-dihydroxy-7α, 8α-epoxy-12,15,23-trioxo-5α-lanosta-9(11),16-dien-26-oic acid) | G. applanatum | [101] |
283 | Lanosta-7,9(11),24-trien-3-one15,26-dihydroxy | G. zonatum Murill. | [27] |
284 | Lanosta-7,9(11),24-trien-26-oic,3-hydroxy | G. zonatum Murill. | [27] |
285 | Ganoderic acid Y ((24E)-3-ol-5α-lanosta-7,9(11),24-trien-26-oic acid) | G. zonatum Murill. | [27] |
286 | Applanoxidic acid E (15β-hydroxy-7α, 8α-epoxy-3,12,23-trioxo-5α-lanosta-9(11),20E-dien-26-oic acid) | G. applanatum | [66] |
287 | Applanoxidic acid F (7α, 8α-epoxy-3,12,15,23-tetraoxo-5α-lanosta-9(11),20E-dien-26-oic acid) | G. applanatum | [66] |
288 | Ganosinensin 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] |
289 | Colossolactone III ((22S)-3β, 19-epoxy-lanosta-8,24-dien-26,22-olide) | G. colossum | [97] |
290 | Colossolactone IV ((22S)-A,B-dihomo-19-nor-4-oxalanosta-8,24-dien-26,22-olide) | G. colossum | [97] |
291 | Colossolactone 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] |
292 | Austrolactone ((23S, 25S)-12α, 23-epoxy-3β, 15β, 20α-trihydroxy-7,11-dioxo-5α-lanosta-8,16-dien-23,26-olide) | G. australe | [103] |
293 | Ganolactone B (3β, 7β-dihydroxy-11,15-dioxolanosta-8-en-24→20 lactone) | G. sinense (fruit bodies) | [86] |
294 | Ganolactone (7β-hydroxy-3,11,15-trioxo-lanosta-8-en-24→20s lactone) | G. lucidum (fruit bodies) | [104] |
295 | Colossolactone B | G. colossum (fruit bodies) | [98] |
296 | Colossolactone C | G. colossum (fruit bodies) | [98] |
297 | 3α-(3-Hydroxy-5-methoxy-3-methyl-1,5-dioxopentyloxy)-24-methylene-5α-lanost-8-en-21-oic acid | G. resinaceum (fruit bodies) | [62] |
298 | Colossolactone A | G. colossum (fruit bodies) | [98] |
299 | Methyl ganosinensate A | G. sinense (fruit bodies) | [56] |
300 | Ganosinensic acid A | G. sinense (fruit bodies) | [56] |
301 | Ganosinensic acid B | G. sinense (fruit bodies) | [56] |
302 | Tsugarioside C (3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside) | G. tsugae (fruit bodies) | [60] |
303 | Ganorbiformin A | G. colossum (fruit bodies) | [46] |
304 | Colossolactone 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] |
305 | Colossolactone 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] |
306 | Colossolactone VII ((22S)-3,4-seco-19-acetoxy-4-hydroxylanosta-8,24-dien-26,22-olide 3-methyl ester) | G. colossum (fruit bodies) | [102] |
307 | Furanoganoderic 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] |
308 | Fornicatin 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] |
309 | Fornicatin 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] |
310 | Fornicatin 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] |
311 | Fornicatin H (4, 7β-epoxy-28-hydroxy-11-oxo-3,4-seco-25,26,27-trinorlansta-8-en-3,24-diester) | G. cochlear (sporophore) | [106] |
312 | Australic 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] |
313 | Lucidone A | G. tsugae | [107] |
314 | Lucidenol | G. tsugae | [107] |
315 | Ganosineniol A | G. sinense (fruit bodies) | [47] |
316 | 8α, 9α-Epoxy-4,4,14α-trimethyl-3,7,11,15,20-pentaoxo-5α-pregnane | G. concinna | [75] |
Figure 32.
Structures of compounds 281–282.
Figure 32.
Structures of compounds 281–282.
Figure 33.
Structures of compounds 283–285.
Figure 33.
Structures of compounds 283–285.
Cpd | R | R2 |
---|
283 | α-OH | COOH |
284 | =O | CH2OH |
285 | β-OH | COOH |
Figure 34.
Structures of compounds 286–287.
Figure 34.
Structures of compounds 286–287.
Figure 35.
Structures of compounds 288–307.
Figure 35.
Structures of compounds 288–307.
Figure 36.
Structures of compounds 308–309.
Figure 36.
Structures of compounds 308–309.
Figure 37.
Structure of compounds 310–311.
Figure 37.
Structure of compounds 310–311.
Cpd | R1 | R2 |
---|
310 | COOH | COOH |
311 | COOCH3 | COOCH3 |
Figure 38.
Structure of compound 312.
Figure 38.
Structure of compound 312.
Figure 39.
Structures of compounds 313–315.
Figure 39.
Structures of compounds 313–315.
Cpd | R1 | R2 |
---|
313 | =O | =O |
314 | =O | OH |
315 | α-OH | CH2OH |
Figure 40.
Structure of compound 316.
Figure 40.
Structure of compound 316.