Download PDF
Planta Med 2012; 78(4): 368-376
DOI: 10.1055/s-0031-1280441
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Isolation and Bioactivity Evaluation of Terpenoids from the Medicinal Fungus Ganoderma sinense

Jie-Qing Liu1 , Cui-Fang Wang1 , Yan Li 1 , Huai-Rong Luo1 , Ming-Hua Qiu1
  • 1State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, P. R. China
Further Information

Publication History

received August 13, 2011 revised Nov. 8, 2011

accepted Nov. 22, 2011

Publication Date:
12 December 2011 (online)

    Permissions and Reprints

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

Supporting Information

References

  • 1 Lu W L, Lin Z P, Lin Z B. Lucid ganoderma . Chapter 5. Beijing: Science Press; 1985: 108-122
    Google Scholar
  • 2 Chen R Y, Yu D Q. Progress of studies on the chemical constituents of Ganoderma triterpene.  Acta Pharm Sin. 1990;  25 940-953
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 7 Fatmawati S, Shimizu K, Kondo R. Inhibition of aldose reductase in vitro by constituents of Ganoderma lucidum.  Planta Med. 2010;  76 1691-1693
    Google Scholar
  • 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
    Google Scholar
  • 9 Qiao Y, Zhang X M, Qiu M H. Two novel lanostane triterpenoids from Ganoderma sinense.  Molecules. 2007;  12 2038-2046
    Google Scholar
  • 10 Sato N, Ma C M, Komatsu K, Hattori M. Triterpene-farnesyl hydroquinone conjugates from Ganoderma sinense.  J Nat Prod. 2009;  72 958-961
    Google Scholar
  • 11 Liu C, Chen R Y. A new triterpene from fungal fruiting bodies of Ganoderma sinense.  Zhongcaoyao. 2010;  41 8-11
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 16 Mosmann T. Growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
    Google Scholar
  • 17 Reed L J, Muench H. A simple method of estimating fifty percent endpoints.  Am J Hyg. 1938;  27 493-497
    Google Scholar
  • 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
    Google Scholar
  • 19 Lin L J, Shiao M S, Yeh S F. Seven new triterpenes from Ganoderma lucidum.  J Nat Prod. 1988;  51 918-924
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 23 Nishitoba T, Oda K, Sato H, Sakamura S. Novel triterpenoids from the fungus Ganoderma lucidum.  Agric Biol Chem. 1988;  52 367-372
    Google Scholar
  • 24 Nishitoba T, Sato H, Sakamura S. Triterpenoids from the fungus Ganoderma lucidum.  Phytochemistry. 1987;  26 1777-1784
    Google Scholar
  • 25 Rosslein L, Tamm C, Zürcher W. Sambucinic acid, a new metabolite of Fusarium sambucinum.  Helv Chim Acta. 1988;  71 588-595
    Google Scholar
  • 26 Fujita A, Arisawa M, Saga M, Hayashi T, Morita N. Two new lanostanoids from Ganoderma lucidum.  J Nat Prod. 1986;  49 1122-1125
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 32 Frederick G J. 23,24,25,26,27-Pentanorlanost-8-en-3β,22-diol from Verticillium lecanii.  Phytochemistry. 1984;  23 1721-1723
    Google Scholar
  • 33 Lin J H, Lu A Y. Inhibition and induction of cytochrome P450 and the clinical implications.  Clin Pharmacokinet. 1998;  35 361-390
    Google Scholar

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

Phone: +86 87 15 22 32 57

Fax: +86 87 15 22 32 55

Email: mhchiu@mail.kib.ac.cn

>