Planta Med 2001; 67(9): 811-814
DOI: 10.1055/s-2001-18854
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

Anticomplement Activity of Terpenoids from the Spores of Ganoderma lucidum

Byung Sun Min1 , Jiang Jing Gao1 , Masao Hattori1 , Hyeong Kyu Lee2 , Young Ho Kim3
  • 1 Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
  • 2 Natural Product Biosynthesis Research Unit, Korea Research Institute of Bioscience and Biotechnology, Teajon, Korea
  • 3 College of Pharmacy, Chungnam National University, Taejon, Korea
Further Information

Publication History

November 10, 2000

March 31, 2001

Publication Date:
06 December 2001 (online)

Abstract

A new lanostane-type terpenoid, lucidenic acid SP1 (1), was isolated from a CHCl3-soluble fraction of Ganoderma lucidum spores together with four other known compounds (2 - 5). The structure of lucidenic acid SP1 was determined to be 3β,7β-dihydroxy-4,4,14α-trimethyl-11,15-dioxo-5α-chol-8-en-24-oic acid by spectroscopic means including 2D-NMR. Twelve triterpenes (1 - 12) isolated from G. lucidum spores were investigated in vitro for their anticomplementary activity. Compounds 1 - 5 were inactive, whereas ganoderiol F (8), ganodermanondiol (9) and ganodermanontriol (10) showed a strong anticomplement activity against the classical pathway (CP) of the complement system with IC50 values of 4.8, 41.7, and 17.2 μM, respectively. The potency of these triterpene alcohols (8 - 10) in inhibiting CP activity was improved when the number of hydroxymethyl groups on the side chain moiety is increased. On the other hand, the ganoderic acids 1 - 7, which contain a carboxyl group in the side chain, and lucidumols A and B (11, 12) had little activity on this system.

References

  • 1 Kim H W, Shim M J, Kim B K. Medicinal Components and Their Structures of Ganoderma lucidum . Seoul National University Seoul; 1998: 1-3
  • 2 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.  Chemical & Pharmaceutical Bulletin. 1985;  33 1367-74
  • 3 Sonoda Y, Sekigawa Y, Sato Y. In vitro effects of oxygenated lanosterol derivatives on cholesterol biosynthesis from 24,25-dihydrolanosterol.  Chemical & Pharmaceutical Bulletin. 1988;  36 966-73
  • 4 Komoda Y, Shimizu M, Sonoda Y, Sato Y. Ganoderic acid and its derivatives as cholesterol synthesis inhibitors.  Chemical & Pharmaceutical Bulletin. 1989;  37 531-3
  • 5 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.  Chemical & Pharmaceutical Bulletin. 2000;  48 1026-33
  • 6 Kino K, Yamashita A, Yamaoka K, Watanabe J, Tanaka S, Ko K, Shimizu K, Tsuno H. Isolation and characterization of a new immunomodulatory protein, Lingzhi-8 (LZ-8), from Ganoderma lucidum .  The Journal of Biological Chemistry. 1989;  264 472-8
  • 7 Miyazaki T, Nishijima M. Studies on fungal polysaccharides. XXVII. Structural examination of a water-soluble, antitumor polysaccharide of Ganoderma lucidum .  Chemical & Pharmaceutical Bulletin. 1981;  29 3611-6
  • 8 El-Mekkawy S, Meselhy M R, Nakamura N, Tezuka Y, Hattori M, Kaiuchi N, Shimotohno K, Kawahata T, Otake T. Anti-HIV-1 and anti-HIV-1 protease substances from Ganoderma lucidum .  Phytochemistry. 1998;  49 1651-7
  • 9 Min B S, Nakamura N, Miyashiro H, Bae K H, Hattori M. Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease.  Chemical & Pharmaceutical Bulletin. 1998;  46 1607-12
  • 10 Lichman A K, Pober J S. Cellular and Molecular Immunology. W. B. Saunders Company Philadelphia; 1997: 315-38
  • 11 Yamada H, Ohtani K, Kiyohara H, Cyong J C, Otsuka Y, Ueno Y, Omura S. Purification and chemical properties of anti-complementary polysaccharide from the leaves of Artemisia princeps .  Planta Medica. 1985;  51 121-5
  • 12 Peake P W, Pussell B A, Martyn P, Timmermans V, Charlesworth J A. The inhibitory effect of rosmarinic acid on complement involves the C5 convertase.  International Journal of Immunopharmacology. 1991;  13 853-7
  • 13 Kim D S, Oh S R, Lee I S, Jung K Y, Park J D, Kim S I, Lee H K. Anticomplementary activity of ginseng saponins and their degradation products.  Phytochemistry. 1998;  47 397-9
  • 14 Jung K Y, Oh S R, Park S H, Lee I S, Ahn K S, Lee J J, Lee H K. Anti-complementary activity of tiliroside from the flower buds of Magnolia fargesii .  Biological & Pharmaceutical Bulletin. 1998;  21 1077-8
  • 15 Kubota T, Asaka Y, Miura H. Structures of ganoderic acid A and B, two new lanostane type bitter triterpenes from Ganoderma lucidum (Fr.) Karst.  Helvetica Chimica Acta. 1982;  65 611-9
  • 16 Kikuchi T, Kanomi S, Murai Y, Katoda S, Tsubono K, Ogita Z. Constituents of the fungus Ganoderma lucidum (Fr.) Karst. II. Structures of ganoderic aicds F, G, and H, Lucidenic acids D2 and E2, and related compounds.  Chemical & Pharmaceutical Bulletin. 1986;  34 4018-29
  • 17 Nishitoba T, Sato H, Kasai T, Kawagishi H, Sakamura S. New bitter C27 and C30 terpenoids from the fungus Ganoderma lucidum .  Agricultural Chemistry and Biotechnology. 1984;  48 2905-7
  • 18 Matsuda H, Tomohiro N, Yoshikawa M, Kubo M, Studies on Alismatis R hizoma. II. Anti-complementary activities of methanol extract and terpene components from Alismatis Rhizoma (dried rhizome of Alisma orientale).  Biological & Pharmaceutical Bulletin. 1998;  21 1317-21

Dr. Young Ho Kim

College of Pharmacy

Chungnam National University

Taejon 305-764

Korea

Email: yhk@cnu.ac.kr

Fax: +82-42-823-6566

Phone: Tel.: +82-42-821-5933

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