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DOI: 10.1055/s-0031-1280441
© Georg Thieme Verlag KG Stuttgart · New York
Isolation and Bioactivity Evaluation of Terpenoids from the Medicinal Fungus Ganoderma sinense
Publikationsverlauf
received August 13, 2011
revised Nov. 8, 2011
accepted Nov. 22, 2011
Publikationsdatum:
12. Dezember 2011 (online)

Abstract
A new pentanorlanostane, ganosineniol A (1), eight new lanostane triterpenoids, ganosinoside A (2), ganoderic acid Jc (3), ganoderic acid Jd (4), ganodermatetraol (5), ganolucidic acid γa (6), ganolucidate F (7), ganoderiol J (8), and methyl lucidenate Ha (9), and a new sesquiterpenoid, ganosinensine (10), together with eleven known triterpenoids (11–21), were isolated from the fruiting bodies of the fungus Ganoderma sinense. Chemical structures were determined based on spectroscopic evidence, including 1D, 2D NMR, and mass spectral data. Furthermore, all isolates were tested for cytotoxic activity and induction ability of hPXR-mediated CYP3A4 expression. Among them, ganoderic acid Jc (3) displayed selective inhibitory activity against HL-60 cells (IC50 = 8.30 µM), and ganoderiol E (11) exhibited selective cytotoxic activity against MCF-7 cells (IC50 = 6.35 µM). Meanwhile, compounds 5, 7, and ganolucidic acids B and C (19, 20) showed induction ability of hPXR-mediated CYP3A4 expression.
Key words
Ganoderma sinense - Ganodermataceae - triterpenoids - sesquiterpene - cytotoxicity - CYP3A4 induction
References
- 1 Lu W L, Lin Z P, Lin Z B. Lucid ganoderma
. Chapter 5. Beijing: Science Press; 1985: 108-122
Reference Ris Wihthout Link
- 2
Chen R Y, Yu D Q.
Progress of studies on the chemical constituents of Ganoderma triterpene.
Acta Pharm Sin.
1990;
25
940-953
Reference Ris Wihthout Link
- 3
Lee I S, Kim H J, Youn U J, Kim J P, Min B S, Jung H J, Na M K, Hattori M, Bae K H.
Effect of lanostane triterpenes from the fruiting bodies of Ganoderma lucidum on adipocyte differentiation in 3T3-L1 cells.
Planta Med.
2010;
76
1558-1563
Reference Ris Wihthout Link
- 4
Dine R S E, Halawany A M E, Ma C M.
Anti-HIV-1 protease activity of lanostane triterpens from the Vietnamese mushroom
Ganoderma colossum.
J Nat Prod.
2008;
71
1022-1026
Reference Ris Wihthout Link
- 5
Niedermeyer T H J, Lindequist U, Mentel R, Gördes D, Schmidt E, Thurow K, Lalk M.
Antiviral terpenoid constituents of Ganoderma pfeifferi.
J Nat Prod.
2005;
68
1728-1731
Reference Ris Wihthout Link
- 6
Gao J J, Min B S, Ahn E M, Nakamura N, Lee H K, Hattori M.
New triterpene aldehides luciadehides A–C from ganoderma and their cytotoxicity against murine and human tumor cells.
Chem Pharm Bull.
2002;
50
837-840
Reference Ris Wihthout Link
- 7
Fatmawati S, Shimizu K, Kondo R.
Inhibition of aldose reductase in vitro by constituents of Ganoderma lucidum.
Planta Med.
2010;
76
1691-1693
Reference Ris Wihthout Link
- 8
Ko H H, Hung D F, Wang J P, Lin C N.
Antiinflammatory triterpenoids and steroids from Ganoderma lucidum and G. tsugae.
Phytochemistry.
2008;
69
234-239
Reference Ris Wihthout Link
- 9
Qiao Y, Zhang X M, Qiu M H.
Two novel lanostane triterpenoids from Ganoderma sinense.
Molecules.
2007;
12
2038-2046
Reference Ris Wihthout Link
- 10
Sato N, Ma C M, Komatsu K, Hattori M.
Triterpene-farnesyl hydroquinone conjugates from Ganoderma sinense.
J Nat Prod.
2009;
72
958-961
Reference Ris Wihthout Link
- 11
Liu C, Chen R Y.
A new triterpene from fungal fruiting bodies of Ganoderma sinense.
Zhongcaoyao.
2010;
41
8-11
Reference Ris Wihthout Link
- 12
Liu C, Zhao F, Chen R Y.
A novel alkaloid from the fruiting bodies of Ganoderma sinense.
Chin Chem Lett.
2010;
21
197-199
Reference Ris Wihthout Link
- 13
Wang C F, Liu J Q, Yan Y X, Chen J C, Lu Y, Guo Y H, Qiu M H.
Three new triterpenoids containing four-membered ring from the fruiting body of Ganoderma sinense.
Org Lett.
2010;
12
1656-1659
Reference Ris Wihthout Link
- 14
Mu Y, Zhang J N, Zhang S M, Zhou H H, Toma D, Ren S R, Huang L, Yaramus M, Raum A, Venkataramanan R, Xie W.
Traditional Chinese medicines Wu Wei Zi (Schisandra chinensis Baill) and Gan Cao (Glycyrrhiza uralensis Fisch) activate pregnane X receptor and increase warfarin clearance in rats.
J Pharmacol Exp Ther.
2006;
316
1369-1377
Reference Ris Wihthout Link
- 15
Hu D L, Wang G, Li Z, Fan L, Tan Z R, Wang D, Zhou H H.
Establishment of in vitro screening system for CYP3A4 and CYP2B6 inducers.
China Med Eng.
2007;
15
646-649
Reference Ris Wihthout Link
- 16
Mosmann T.
Growth and survival: application to proliferation and cytotoxicity assays.
J Immunol Methods.
1983;
65
55-63
Reference Ris Wihthout Link
- 17
Reed L J, Muench H.
A simple method of estimating fifty percent endpoints.
Am J Hyg.
1938;
27
493-497
Reference Ris Wihthout Link
- 18
Kohda H, Tokumoto W, Sakamoto K, Fujii M, Hirai Y, Yamasaki K, Komoda Y, Nakamura H, Ishihara S, Uchida M.
The biologically active constituents of Ganoderma lucidum (Fr.) Karst. histamine release-inhibitory triterpenes.
Chem Pharm Bull.
1985;
33
1367-1374
Reference Ris Wihthout Link
- 19
Lin L J, Shiao M S, Yeh S F.
Seven new triterpenes from Ganoderma lucidum.
J Nat Prod.
1988;
51
918-924
Reference Ris Wihthout Link
- 20
Gan K H, Fann Y F, Hsu S H, Kuo K W, Lin C N.
Mediation of the cytotoxicity of lanostanoids and steroids of Ganoderma tsugae through apoptosis and cell cycle.
J Nat Prod.
1998;
61
485-487
Reference Ris Wihthout Link
- 21
Arisawa M, Fujita A, Saga M, Jukumura H, Hayashi T, Shimizu M, Morita N.
Three new lanostanoids from Ganoderma lucidum.
J Nat Prod.
1986;
49
621-625
Reference Ris Wihthout Link
- 22
Min B S, Gao J J, Nakamura N, Hattori M.
Triterpenes from the spores of Ganoderma lucidum and their cytotoxicity against Meth-A and LLC tumor cells.
Chem Pharm Bull.
2000;
48
1026-1033
Reference Ris Wihthout Link
- 23
Nishitoba T, Oda K, Sato H, Sakamura S.
Novel triterpenoids from the fungus Ganoderma lucidum.
Agric Biol Chem.
1988;
52
367-372
Reference Ris Wihthout Link
- 24
Nishitoba T, Sato H, Sakamura S.
Triterpenoids from the fungus Ganoderma lucidum.
Phytochemistry.
1987;
26
1777-1784
Reference Ris Wihthout Link
- 25
Rosslein L, Tamm C, Zürcher W.
Sambucinic acid, a new metabolite of Fusarium sambucinum.
Helv Chim Acta.
1988;
71
588-595
Reference Ris Wihthout Link
- 26
Fujita A, Arisawa M, Saga M, Hayashi T, Morita N.
Two new lanostanoids from Ganoderma lucidum.
J Nat Prod.
1986;
49
1122-1125
Reference Ris Wihthout Link
- 27
Sato H, Nishitoba T, Shirasu S, Oda K, Sakamura S.
Ganoderiol A and B, new triterpenoids from the fungus Ganoderma lucidum (Reishi).
Agric Biol Chem.
1986;
50
2887-2890
Reference Ris Wihthout Link
- 28
Kikuchi T, Matsuda S, Kadota S, Murai Y, Ogita Z.
Ganoderic acid-D, acid-E, acid-F and acid-H and lucidenic acid-D, acid-E, acid-F,
new triterpenoids from Ganoderma lucidum.
Chem Pharm Bull.
1985;
33
2624-2627
Reference Ris Wihthout Link
- 29
Kikuchi T, Kanomi S, Murai Y, Kadota S, Tsubono K, Ogita Z.
Constituents of the fungus Ganoderma lucidum (Fr.) Karst. III. Structure of ganolucidic acids A and B, new lanostane-type triterpenoids.
Chem Pharm Bull.
1986;
34
4030-4036
Reference Ris Wihthout Link
- 30
Nishitoba T, Sato H, Sakamura S.
New terpenoids, ganoderic acid J and ganolucidic acid C, from the fungus Ganoderma lucidum.
Agric Biol Chem.
1985;
49
3637-3638
Reference Ris Wihthout Link
- 31
Gonzalez A G, Leon F, Rivera A, Munoz C M, Bermejo J.
Lanostanoid triterpenes from Ganoderma lucidum.
J Nat Prod.
1999;
62
1700-1701
Reference Ris Wihthout Link
- 32
Frederick G J.
23,24,25,26,27-Pentanorlanost-8-en-3β,22-diol from Verticillium lecanii.
Phytochemistry.
1984;
23
1721-1723
Reference Ris Wihthout Link
- 33
Lin J H, Lu A Y.
Inhibition and induction of cytochrome P450 and the clinical implications.
Clin Pharmacokinet.
1998;
35
361-390
Reference Ris Wihthout Link
Prof. Dr. Ming-Hua Qiu
State Key Laboratory of Photochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences
Lanhei Road, 132
Kunming 650204
Yunnan
P. R. China
Telefon: +86 87 15 22 32 57
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eMail: mhchiu@mail.kib.ac.cn