Download PDF
Planta Med 2003; 69(6): 568-571
DOI: 10.1055/s-2003-40639
Letter
© Georg Thieme Verlag Stuttgart · New York

A Bioactive Triterpenoid and Vulpinic Acid Derivatives from the Mushroom Scleroderma citrinum

Somdej Kanokmedhakul1 , Kwanjai Kanokmedhakul1 , Thirada Prajuabsuk1 , Kasem Soytong2 , Palangpon Kongsaeree3 , Apichart Suksamrarn4
  • 1Department of Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
  • 2Department of Plant Pest Management, Faculty of Agricultural Technology, King Mongkut’s Institute of Technology Ladkrabang, Bangkok, Thailand
  • 3Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand
  • 4Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand
Further Information

Publication History

Received: October 4, 2002

Accepted: February 15, 2003

Publication Date:
16 July 2003 (online)

Also available at
    Permissions and Reprints

Abstract

A new lanostane-type triterpenoid, (20S,22S,23E)-22-O-acetyl-25-hydroxylanosta-8,23(E)-dien-3-one (1), isolated as a new natural product for the first time, methyl 4,4′-dimethoxyvulpinate (2), together with the known compound 4,4′-dimethoxyvulpinic acid (3) were isolated from the mushroom Scleroderma citrinum. Their structures were determined using spectroscopic and chemical methods, and an X-ray analysis was performed to confirm structure of 1. Compound 1 exhibited significant antiviral activity against Herpes simplex type 1. Compound 3 and two of its derivatives, the dibromo derivative 5 and acetate derivative 6, exhibited activity towards Mycobacterium tuberculosis. In addition, 5 and 6 also showed cytotoxicity against the NCI-H187 cell line.

References

  • 1 Bresinsky A, Besl H, Bisset N G. A colour atlas of poisonous fungi. London; Wolf Publishing 1990: pp. 174-5
    Search in Google Scholar
  • 2 Singh P, Anchel M. Atromentic acid from Clitocybe illudens .  Phytochemistry. 1971;  10 3259-62
    CrossrefPubMedSearch in Google Scholar
  • 3 Steffan B, Steglich W. Pigments from the cap cuticle of the bay boletus (Xerocomus badius).  Angew Chem Int Ed Engl. 1984;  23 445-7
    PubMedSearch in Google Scholar
  • 4 Foden F R, McCormick J, O’Mant D M. Vulpinic acids as potential anti-inflammatory agents. 1. Vulpinic acids with substituents in the aromatic rings.  J Med Chem. 1975;  18 199-203
    CrossrefPubMedSearch in Google Scholar
  • 5 Marumoto R, Pilzlaboratorium R, Hyogo A, Kilpert C, Steglich W. Neue Pulvinsäurederivate aus Pulveroboletus arten (Boletales).  Z Naturforsch. 1986;  41c 363-5
    PubMedSearch in Google Scholar
  • 6 Cantrell C L, Lu T, Fronczek F R, Fischer N H. Antimycobacterial cycloartanes from Borrichia frutescens .  J Nat Prod. 1996;  59 1131-6
    CrossrefPubMedSearch in Google Scholar
  • 7 Lobo A M, Macedo D AP, Prabhakar S, Godinho L S, Jones R, Rzepa H S, Williams D J. Triterpenoids of the fungus Pisolithus tinctorius .  Phytochemistry. 1988;  27 3569-74
    CrossrefPubMedSearch in Google Scholar
  • 8 Tanaka R, Kasubuchi K, Kita S, Matsunaga S. Obtusifoliol and related steroids from the whole herb of Euphorbia chamaesyce .  Phytochemistry. 1999;  51 457-63
    CrossrefPubMedSearch in Google Scholar
  • 9 Cantrell C L, Franzblau S G, Fischer N H. Antimycobacterial plant terpenoids.  Planta Med. 2001;  67 685-94
    Thieme ConnectPubMedSearch in Google Scholar
  • 10 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren J T, Bokesch H, Kenney S, Boyd M R. New colorimetric cytotoxicity assay for anticancer-drug screening.  J Natl Cancer Inst. 1990;  82 1107-12
    CrossrefPubMedSearch in Google Scholar
  • 11 Collins L, Franzblau S G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium .  Antimicrob Agents Ch. 1997;  41 1004-9
    PubMedSearch in Google Scholar

Asst. Prof. Dr. Somdej Kanokmedhakul

Department of Chemistry

Faculty of Science

Khon Kaen University

Khon Kaen 40002

Thailand

Email: somdej@kku.ac.th

Fax: +66-043-243338