CC BY
0Molecules 2007, 12, 2038-2046
molecules
ISSN 1420-3049
© 2007 by MDPI www.mdpi.org/molecules
Full Paper
Two Novel Lanostane Triterpenoids from Ganoderma Sinense
Ying Qiao, Xian-min Zhang and Ming-hua Qiu *
State Key Laboratory Phytochemistry and Plant Resource in West China, Kunming Institute of Botany, The Chinese Academy of Sciences, Kunming 650204, P.R. China; E-mails: qiaoying@gmail.com; wjj-94@163.com
* Author to whom correspondence should be addressed; E-mail: mhchiu@mail.kib.ac.cn; Tel: (+86)871-5223327; Fax: (+86)871-5223255
Received: 17 May 2007; in revised form: 20 August 2007 / Accepted: 20 August 2007 /Published: 23 August 2007
Abstract: Two novel lanostane-type triterpenes, Ganolactone B and Ganoderiol A triacetate, were isolated from the fruiting bodies of G. sinense, together with six known compounds. The structures of the two new triterpenes were determined as 3^,7^-dihydroxy-11,15-dioxo-lanosta-8-en-24^20 lactone (1) and 3^,24,26-triacetoxy-5a-lanosta-7,9(11)-dien-25-ol (2), respectively, by chemical and spectroscopic means.
Keywords: Ganolactone B, Ganoderiol A triacetate, Ganoderma Sinenes.
Introduction
The fruiting body of the fungus Ganoderma lucidum Karst.(Polyporaceae) has attracted much attention as a well-known traditional Chinese medicine that has been used clinically in China, Japan, and Korea for a long time. Over the past recent two decades, more than 130 highly oxygenated lanostane-type triterpenoids have been isolated from the fruiting bodies, spores and culture mycelia of Ganoderma spp., including common fungal steroids derived from ergosterol. Some of them are known to possess varied bioactive properties. Other Ganoderma spp. have also been used in traditional Chinese, Japanese and Korean medicines, and their pharmacological activities as antitumor [1,2] and antihypertensive agents [3], their use in the treatment of chronic bronchitis and diabetes or their liver
protective [4], antioxidant [5] and anti-HIV activity [6] were studied. In this paper, we wish to report the structural elucidation by extensive spectroscopic analyses of two new components isolated together with known six compounds (Figure 1) from the fruiting bodies of G. sinense.
Ri OAc
CH2R4 R3
R2 R3 R4
OAc OH OAc
OH OH OH
A24(25) oh oh
OH OH OH
Figure 1. Cont.
Dried chipped fruiting bodies of G. sinense were soaked overnight in acetone at room temperature to give an extract which was suspended in water and successively partitioned with petroleum ether, CHCl3, EtOAc and n-BuOH, respectively. The CHCl3 layer was chromatographed on silica gel to separate it into six fractions. Some of these were subjected to silica gel column chromatography to give two new triterpene compounds, which we have named Ganolactone B (3^,7^-dihydroxy-11,15-dioxo-lanosta-8-en-24^-20 lactone, 1), Ganoderiol A triacetate (3^,24,26-triacetoxy-5a-lanosta-7,9(11)-dien-25-ol, 2), together with six known compounds: Ganoderiol A (3)[7], Ganodermatriol (4), Ganodermanontriol (5), 20(21)-dehydrolucidenic acid (6) [8], Ganoderic acid D (7) [9] and Ganoderic acid A (8) [10].
Ganolactone B (1): colorless needles, m.p. > 300°C, [a]D 183°(c=0.3, MeOH). Compound 1 gave a quasi-molecular ion peak at m/z 459 [M+H]+ in its positive FABMS spectrum, and was assigned a molecular formula of C27H38O6, which was confirmed by HRESIMS (C27H3sO6Na, 481.2579; calcd. for C27H38O6Na, 481.2566) and NMR spectral data (Table 1). The IR spectrum [3433 (br, OH), 1769, 1719, 1655 (C=O), 1207, 1143 and 1065 (C-O and COOC)] indicated the presence of hydroxyl and
carbonyl groups. The UV data [(MeOH) Xmax(logs) nm: 255 (0.17)] indicated the presence of an a,P-unsaturated carbonyl group. The 1H-NMR spectrum of 1 (Table 1), analyzed together with the compound's HMQC spectrum, exhibited singlet signals (3H each) of six methyl groups at Sr 107, 1.24, 1.36, 1.39, 1.40, 1.44 and two oxygenated methine protons at Sr 3.46 (1H, dd, J=5.5, 11.0Hz, 3a-H) and 5.19 (1H, t, 8.4Hz, 7a-H). The 13C-NMR spectrum displayed signals characteristic of six methyl groups, an oxygen-bearing quaternary carbon at Sc 86.49 (s), two hydroxyl-bearing methine carbons at Sc 77.59 (d) and 66.70 (d), an «^-unsaturated C=O at Sc 197.98 (s), 158.71 (s), 142.65 (s), a ketone carbon at Sc 214.96 (s), and a carboxyl group at Sc 176.69 (s). These data suggested a polyoxygenated lanostane-type triterpene with a structure very similar to Ganolactone A, including its chemical configuration at C-20 [11]. Ganolactone B (1) had a signal at Sc 86.49 (s). This indicated that linking group was at C-20. The connectivities of 1 were established by interpretation of the HMBC spectrum (Figure 2). In the HMBC experiment, Sc 86.49 (s, C-20) showed correlation with two secondary methyl group signals Sr 2.81, 2.66 (each 1H, H-16), Sr 2.68, 2.49 (each 1H, H-22) and one methyl signal Sr 1.39 (3H, H-21). From the above observation and on the basis of all the above results the structure of Ganolactone B was established as 3p,7P-dihydroxy-11,15-dioxo-lanosta-8-en-24^-20 lactone.
Figure 2. key HMBC(^*) correlations of Ganolactone B (1).
Compound 2 gave colorless needles, mp 232~233°C, [a]D 80°(c=0.1, C5D5N) and a quasi-molecular ion peak at m/z 601 [M+H]+ in its positive FABMS spectrum, and was thus assigned a molecular formula of C36H56O7, which was confirmed by HRESIMS (C36H56O7Na, 623.3923; calcd. for C36H56O7Na, 623.3920) and NMR spectral data (Table 1). Its UV spectrum was similar to that of Ganoderiol A [7], indicating the presence a heteroannular diene system in this molecule. The IR spectrum [3492 (br, OH), 1735, 1719 (C=O), 1233, 1152 and 1031 (C-O and COOC)] indicated the presence of hydroxyl and carbonyl groups. The 1H-NMR spectrum of 2 showed singlets for three acetyl methyl group at Sr 2.05, 2.07 and 2.10 (3H each). The 13C-NMR spectrum of 2 verified the presence of three carbons attached to oxygen at Sc 68.45 (t), 76.64 (d) and 80.83 (d), three carbonyl carbons for acetyl moieties at Sc 170.64 (s), 170.93 (s), and 171.11 (s), and three acetyl methyl carbons at Sc 20.83 (q), 20.98 (q), and 21.29 (q). From these spectral data, the structure of this compound was
established as 3^,24,26-triacetoxy-5a-lanosta-7, 9(11)-dien-25-ol, for which we propose the name Ganoderiol A triacetate.
Table 1. 1H-NMR and 13C-NMR data of compounds 1 and 2.
No. 1 2
8c 8h (J = Hz) 8c 8h (J = Hz)
C5D5N CDCl3
1 35.47 t 3.22 m (a) 35.41 t -
1.20 m (P) -
2 28.59 t 1.89 m (a) 22.77 t -
1.89 m (в) -
3 77.59 d 3.46 dd(10.96, 5.43) (a) 80.83 d 4.51 dd (12.68, 3.56) (a)
4 49.68 s - 37.62 s -
5 49.65 d 1.10 t(16.97, 12.99) (a) 49.26 d -
6 28.14 t 2.37 m (a) 24.26 t -
1.90 m (в) -
7 66.70 d 5.19 t(16.97, 12.99) (a) 119.97 d 5.45 m (a)
8 158.71 s - 142.70 s -
9 142.65 s - 146.65 s -
10 39.29 s - 37.80 s -
11 197.98 s - 116.50 d 5.30 d (4.64)
12 50.94 t 3.09 d(16.88) (a) 37.24 t -
2.95 d(16.78) (в) -
13 45.78 s - 43.74 s -
14 59.03 s - 50.32 s -
15 214.96 s - 25.99 t -
16 36.53 t 2.81 dd(18.30, 10.17) (a) 31.45 t -
2.66 dd(18.30, 10.32) (fi) -
17 49.65 d 2.65 dd(11.98, 7.26) (a) 50.77 d -
18 18.64 q 1.40 s 16.92 q 0.54 s
19 19.40 q 1.36 s 22.82 q 0.99 s
20 86.49 s - 36.45 d -
21 25.79 q 1.39 s 18.56 q 0.94 d(5.28)
22 27.84 t 2.28 m (a) 32.62 t -
2.49 m (в) -
23 34.20 t 2.08 m (a) 27.78 t -
1.85 m (в) -
24 176.69 s - 76.64 d 4.89 dd(9.80, 1.96)
25 - - 73.27 s -
26 - - 68.45 t -
27 - - 20.19 q 1.19 s
28 25.39 q 1.44 s 28.08 q 0.86 s
29 16.47 q 1.24 s 15.66 q 0.86 s
30 28.75 q 1.07 s 25.53 q 0.94 s
OCOMe - - 170.64 s -
- - 170.93 s -
- - 171.11 s -
OCOMe - - 20.83 q 2.05(3H, s)
- - 20.99 q 2.07(3H, s)
- - 21.29 q 2.10(3H, s)
Experimental
General
Melting points were measured on a XRB-1 micro hot-stage melting point apparatus and are uncorrected. Optical rotations were measured with a DIP-370 automatic polarimeter. UV spectra were measured with a Shimadzu double-beam instrument. IR spectra were obtained on a Bio-Rad FTS-135 infrared spectrophotometer. 1H-, 13C-NMR and 2D-NMR spectra were recorded on a Bruker AM-400 MHz or a DRX-500 spectrometer with TMS as internal standard.
Plant Material
The fruiting bodies of G. sinenes were purchased from the Kunming natural medicine market, Yunnan Province, P. R. China in July 2005. The botanical identification was made by Prof. Yang Zhuliang (Kunming Institute of Botany, The Chinese Academy of Sciences).
Extraction and Isolation
Dried chipped fruiting bodies of G. sinense (8 kg) were soaked overnight in acetone at room temperature to afford an extract which was suspended in water and successively partitioned with petroleum ether (PE), CHCl3, EtOAc, and n-BuOH, respectively. The CHCl3 extracts were concentrated in vacuo to afford a residue (115 g), which was subjected to silica gel column chromatography, using a CHCl3-Me2CO gradient (from 100% CHCl3 to CHCl3-Me2CO 1:1) as eluent to separate it into six fractions (Fr. A - F). Fr. D (19.5 g) was subjected repeatedly to silica gel chromatography and eluted stepwise with PE-Me2CO (from 100% PE to PE-Me2CO 1:1) to afford compounds 2 (17 mg), 3 (29 mg), 4 (22 mg) and 5 (13 mg), respectively. Fr. E (8.3 g) was rechromatographed on a silica gel column chromatography by elution with PE-Me2CO (5:1 v/v, 3:1, 1:1) to yield 1 (36 mg). Fr. F (4.7g) was rechromatographed on a silica gel column chromatography by elution with PE- Me2CO (2:1 v/v, 1:2). Further purification of Fr. F-4 (1.7 g) was achieved by a reversed phase C-18 (from MeOH- H2O 40% to 65%) to give compounds 6 (12 mg), 7 (11 mg) and 8 (9 mg), respectively.
Ganolactone B (1): colorless needles, m.p. > 300°C, [a]D9183°(c=0.3, MeOH); positive FABMS m/z 459[M+H]+, HRESIMS (calcd. for C27H38O6: 458.2579); IR(KBr)cm-1: 3433 (br, OH), 1769, 1719, 1655 (C=O), 1207, 1143 and 1065 (C-O and COOC); UV (MeOH) Xmx (logs) nm:255(0.17); 1H- and 13C-NMR spectral data, see Table 1.
3p,24,26-Triacetoxy-5a-lanosta-7,9(11)-dien-25-ol (Ganoderiol A triacetate) (2): Colorless needles, mp 232~233°C, [a]l9D 80°(c=0.1, C5D5N); positive FABMS m/z 601 [M+H]+; HRESIMS (calcd. for C36H56O7: 600.3920); IR (KBr) cm-1: 3492 (br, OH), 1735, 1719 (C=O), 1233, 1152 and 1031 (C-O and COOC); UV (MeOH) ^ (logs) nm: 243 (0.30); 1H- and 13C-NMR spectral data, see Table 1.
Ganoderiol A (3): colorless needles, mp 232~234°C, [a]D +20°(c=0.10, EtOH); HREIMS m/z 474.3740 (calcd for C30H50O4: 474.3709); UV (EtOH) Vax (logs) nm: 253 (8058), 244 (962), 253 (6518); IR (KBr) cm-1: 3350, 2950, 2900, 2850, 1430, 1360, 1060; 1H-NMR (C5D5N) ¿h: 5.55 (1H, m, H-7), 5.40 (1H, m, H-12), 3.83, 3.47 (1H each, d, J=10.6Hz, 26-H), 3.46 (1H, t, J=12.1Hz, C-24), 3.24 (1H, dd, J=10.5 and 5.0 Hz, H-3), 1.11 (3H, s, H-27), 1.01 (3H, s, H-19), 0.98 (3H, s, H-28), 0.92 (3H, d, J=6.2Hz H-21), 0.88 (3H, s, H-29), 0.88 (3H, s, H-30), 0.67 (3H, s, H-18); 13C-NMR (C5D5N) ¿c: 36.40 (t, C-1), 28.86 (t, C-2), 78.12 (d, C-3), 39.37 (s, C-4), 49.83 (d, C-5), 23.56 (t, C-6), 120.99 (d, C-7), 143.03 (s, C-8), 146.61 (s, C-9), 37.85 (s, C-10), 116.58 (s, C-11), 38.14 (t, C-12), 44.13 (s,C-13), 50.68 (s, C-14), 28.17 (t, C-15), 31.91 (t, C-16), 51.50 (d, C-17), 16.64 (q, C-18), 23.11 (q, C-19), 37.15 (d, C-20), 19.06 (q, C-21), 34.40 (t, C-22), 28.94 (t, C-23), 77.23 (d, C-24), 74.79 (s, C-25), 69.28 (t, C-26), 20.15 (q,C-27), 28.94 (q, C-28), 16.07 (q, C-29), 25.89 (q, C- 30).
Ganodermatriol (4): white powder, mp 180~190°C; [a]D2+9°(c=0.04, EtOH); HREIMS m/z 456.3612 (calcd for C30H48O3: 456.3605); UV (EtOH) W (logs) nm: 237 (4740), 245 (5400), 253 (3650); 1H-NMR (C5D5N) ¿h: 5.56 (1H, J=7.5 , H-24), 5.48 (1H, m, H-7), 5.32 (1H brd, J=6.2Hz, H-11), 4.33 (2H, s, H-27), 4.21 (2H, s, H-26), 3.24 (3H, dd, J=10.6 and 4.8 Hz H-3), 1.01 (3H, s, H-19), 0.98 (3H, s, H-28), 0.91 (3H, d , J=6.2Hz, H-21), 0.88 (3H, s, H-29), 0.88 (3H, s, H-30), 0.67 (3H, s, H-18); 13C-NMR (C5D5N) ¿c: 36.42 (t, C-1), 28.74 (t, C-2), 78.12 (d, C-3), 39.37 (s, C-4), 49.84 (d, C-5), 23.57 (t, C-6), 121.06 (d,C-7), 142.98 (s, C-8), 146.64 (s, C-9), 37.86 (s, C-10), 116.54 (s, C-11), 38.11 (t, C-12), 44.13 (s,C-13), 50.69 (s, C-14), 28.16 (t, C-15), 31.90 (t,C-16), 51.24 (d, C-17), 16.65 (q, C-18), 23.10 (q, C-19), 36.42 (d, C-20), 18.62 (q, C-21), 36.91 (t, C-22), 24.66 (t, C-23), 127.74 (d, C-24), 140.75 (s, C-25), 65.51 (t, C-26), 58.59 (q,C-27), 28.86 (q, C-28), 16.02 (q, C-29), 25.87 (q, C- 30).
Ganodermanontriol (5): colorless prisms, mp 168~170°C; [a]D4+41°(c=0.20, MeOH); HREIMS m/z 472.3540 (calcd. for C30H48O4: 472.3550); 1H-NMR (C5D5N) ¿h: 5.51 (1H, d, J=6.2Hz, H-7), 5.39 (1H, d, J= 5.9Hz, H-11), 3.83, 3.48 (1H each, d, J=11.3Hz, 26-H), 3.46 (1H, t, J=11.0Hz, C-24), 1.20 (3H, s, H-19), 1.13 (3H, s, H-28), 1.11 (3H, s, H-27), 1.09 (3H, s, H-29), 0.92 (3H, d, J=6.2Hz, H-21), 0.88 (3H, s, H-30), 0.60 (3H, s, H-18); 13C-NMR (C5D5N) ¿c: 36.86 (t, C-1), 34.39 (t, C-2), 215.18 (s, C-3), 47.52 (s, C-4), 51.11 (d, C-5), 23.92 (t, C-6), 120.43 (d,C-7), 143.14 (s, C-8), 146.97 (s, C-9),
37.13 (s, C-10), 117.69 (s, C-11), 37.50 (t, C-12), 44.08 (s,C-13), 50.60 (s, C-14), 31.39 (t, C-15),
28.14 (t, C-16), 51.11 (d, C-17), 16.06 (q, C-18), 22.11 (q, C-19), 36.55 (d, C-20), 19.06 (q, C-21), 34.39 (t, C-22), 28.94 (t, C-23), 77.24 (d, C-24), 74.79 (s, C-25), 69.28 (t, C-26), 20.14 (q,C-27), 25.66 (q, C-28), 22.39 (q, C-29), 25.66 (q, C- 30).
20(21)-Dehydrolucidenic acid A (6): colorless needles, mp 135-137°C; [a]D5+69.9°(c 0.20, CHO3); HREIMS m/z456.2512 (calcd. for C27H36O6 [M], 456.2511); UV (MeOH) ^ (logs) nm: 253 (3.78); IR (KBr) cm-1: 3445, 1735, 1702, 1659, 897; 1H-NMR (CHO3) ¿h 5.06 (1H, s, H-21), 4.91 (1H, s, H-21), 1.39 (3H, s, H-30), 1.25 (3H, s, H-19), 1.13 (3H, s, H-28), 1.10 (3H, s, H-29), 0.89 (3H, s, H-19); 13C-NMR (CHO3) ¿c: 35.64 (t, C-1), 34.27 (t, C-2), 216.57 (s, C-3), 46.78 (s, C-4),49.07 (d, C-5), 27.66 (t, C-6), 66.34 (d,C-7), 157.75 (s, C-8), 141.15 (s, C-9), 38.31 (s, C-10), 197.49 (s, C-11), 49.07 (t, C-12), 45.26 (s,C-13), 58.82 (s, C-14), 217.67 (s, C-15), 38.64 (t,C-16), 46.24 (d, C-17), 18.82 (q, C-18), 18.14 (q, C-19), 143.91 (s, C-20), 112.35 (t, C-21), 31.28 (t, C-22), 32.26 (t, C-23), 176.88 (s, C-24), 27.03(q, C-28), 20.78(q, C-29), 24.55(q, 30).
Ganoderic acid D (7): colorless needles, mp 201~203°C: [a]D2+185°(c=0.10, EtOH); HREIMS m/z 530.2875 (calcd. for C30H42O8: 530.2881); UV (EtOH) ^ (logs) nm: 253 (8800); IR (KBr) cm-1: 3410, 3400~2500 (br), 1730, 1720, 1660; 1H-NMR (C5D5N) ¿h 5.16 (1H, dd, J=8.4 and 8.4Hz, H-7), 4.69 (1H, s, H-12), 1.47 (3H, s, H-28), 1.43 (3H, s, H-19), 1.41 (3H, d, J=6.7Hz, C-21), 1.36 (3H, d, J=7.3Hz, C-27), 1.22 (3H, s, H-18), 1.15 (3H, s, H-30), 1.07 (3H, s, H-29); 13C-NMR (C5D5N) ¿c: 35.47 (t, C-1), 34.59 (t, C-2), 216.64 (s, C-3), 46.93 (s, C-4), 49.34 (d, C-5), 28.94 (t, C-6), 65.72 (d, C-7), 159.83 (s, C-8), 140.90 (s, C-9), 38.23 (s, C-10), 201.07 (s, C-11), 79.26 (d, C-12), 51.78 (s, C-13), 59.91 (s, C-14), 215.26 (s, C-15), 39.24 (t,C-16), 46.93 (d, C-17), 13.03 (q, C-18), 18.37 (q, C-19), 29.09 (d, C-20), 21.89 (q, C-21), 49.02 (t, C-22), 209.04 (s, C-23), 46.93 (t, C-24), 46.93 (d, C-25), 178.26 (s, C-26), 17.66 (q,C-27), 24.01 (q, C-28), 21.14 (q, C-29), 26.60 (q, C- 30).
Ganoderic acid A (8): colorless needles, mp 233~236°C; [a]D2+150°(c=0.13, CHCl3); HREIMS m/z 516.3070 (calcd. for C30H42O8: 516.3087); UV (EtOH) ^ (logs) nm: 254 (3.70); IR (KBr) cm-1: 3400, 2700~2300 (br), 1700, 1655, 1270, 1000; 1H-NMR (C5D5N) ¿h 5.23 (1H, dd, J=9.2 and 7.8Hz, H-15), 4.94 (1H, dd, J=9.7 and 7.6Hz, H-7), 1.51 (3H, s, H-28), 1.41 (3H, s, H-19), 1.33 (3H, d, J=7.3Hz, C-27), 1.15 (3H, s, H-30), 1.11 (3H, s, H-29), 1.07 (3H, s, H-18), 0.95 (3H, d, J=6.2Hz, C-21); 13C-NMR (C5D5N) ¿c: 36.07 (t, C-1), 34.63 (t, C-2), 216.11 (s, C-3), 47.10 (s, C-4), 49.04 (d, C-5), 29.69 (t, C-6), 68.76 (d,C-7), 161.51 (s, C-8), 139.98 (s, C-9), 38.35 (s, C-10), 199.70 (s, C-11), 52.44 (t, C-12), 46.78 (s, C-13), 54.76 (s, C-14), 72.22 (d, C-15), 36.96 (t, C-16), 48.68 (d, C-17), 17.54 (q, C-18), 19.58 (q, C-19), 33.10 (d, C-20), 19.77 (q, C-21), 49.97 (t, C-22), 208.95 (s, C-23), 47.15 (t, C-24), 35.60 (d, C-25), 176.23 (s, C-26), 17.65 (q,C-27), 20.29 (q, C-28), 20.87 (q, C-29), 27.26 (q, C- 30).
Acknowledgements
This project was supported by the XiBuZhiGuang Program from CAS and Natural Science Foundation of Yunnan (2005C0010Z), and the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institue of Botany, Chinese Academy of Sciences.
Reference
1. Cao, Q. Z.; Lin, Z. B. Antitumor and anti-angiogenic activity of Ganoderma lucidum polysaccharides peptide. Acta. Pharm. Sin. 2004, 25, 833-838.
2. Morigiwa, A.; Kitabatake, K.; Fujjimoto, Y. Angitensin convetting enzymeinbibitory triterpenes from Ganoderma lucidum. Chem. Pharm. Bull. 1986, 34, 3025-3018.
3. Zhang, W. M.; Sun, X. M.; Wu, S. L. Studies on the regulation of the blood fat function of Ganoderma lucidum spores powder. Chin. Wild Plant Resour. 2001, 20, 14-16.
4. Zeng, X. L.; Bao, H.Y. Advances of Researches on triterpene constituents and pharmacology of Ganoderma lucidum. J. Fung. Res. 2004, 2, 68-77.
5. Li, P. Z.; Zhang, K. C. Studies on pH controlled fermentation of bioactive exopolysaccharides by Ganoderma lucidum. Microbiology 2000, 27, 5-8.
6. Min, B. S.; Nakamura, N.; Miyashio, H. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease. Chem. Pharm. Bull. 1998, 46, 1607-1612.
7. Sato, H.; Nishitoba, T.; Shirasu, S. Ganoderiol A and Ganoderiol B, new triterpenoids from the fungus Ganoserma Lucidum(Reishi). Agric. Biol. Chem. 1986, 50, 2887-2890.
8. Akihisa, T.; Tagata, M.; Ukiya, M.; Tokuda, H.; Suzuki, T.; Kimura, Y. Oxygenated lanostane-type triterpenoids from the fungus Ganoserma Lucidum. J. Nat. Prod. 2005, 68, 559-563.
9. Nishitoba, T.; Sato, H.; Sakamura, S. New terpenoids from Ganoserma Lucidum and their bitterness. Agric. Boil.Chem. 1985, 49, 1547-1549.
10. Kohda, H.; Tokumoto, W.; Sakamoto, K.; Fujii, M.; Hirai, Y.; Yamasaki, K.; Komoda, Y.; Nakamura, H.; Ishihara S. The biologically active constituents of Ganoserma Lucidum(FR.)Karst. Histamine release-inhibitory triterpenes. Chem. Pharm. Bull. 1985, 33, 1367-1374.
11. Wang, F. S.; Cai, H.; Yang, J. S. Triterpenoids from the fruiting body of Ganoderma lucidum. Acta. Pharm. Sin. 1997, 32, 447-450.
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