Download PDF
Planta Med 2001; 67(3): 279-281
DOI: 10.1055/s-2001-11997
Letter

© Georg Thieme Verlag Stuttgart · New York

A New Antimycobacterial, 3β-Acetoxy-15α,22-dihydroxyhopane, from the Insect Pathogenic Fungus Aschersonia tubulata

Surat Boonphong1 , Prasat Kittakoop2,*, Masahiko Isaka2 , Prasit Palittapongarnpim2 , Amonlaya Jaturapat2 , Kannawat Danwisetkanjana2 , Morakot Tanticharoen2 , Yodhathai Thebtaranonth2, 3
  • 1 Department of Chemistry, Faculty of Science, Naresuan University, Phitsanulok, Thailand
  • 2 National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Bangkok, Thailand
  • 3 Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand
Further Information

Publication History

April 7, 2000

July 16, 2000

Publication Date:
31 December 2001 (online)

Also available at
    Permissions and Reprints

Abstract

Bioassay-guided fractionation of the cell extract of the insect pathogenic fungus Aschersonia tubulata BCC 1785 led to the isolation of dustanin (1), 3β,15α,22-trihydroxyhopane (3), 5α,8α-epidioxy-24(R)-methylcholesta-6,22-diene-3β-ol (6), together with the new 3β-acetoxy-15α,22-dihydroxyhopane (4). Chemical structures of these compounds were elucidated by spectral analyses as well as chemical transformation. Compounds 1 and 4 exhibited antimycobacterial activity with the minimum inhibitory concentration (MIC) of 12.5 μg/ml.

References

  • 1 Tsuda Y, Isobe K. A new pentacyclic triterpenoid as a fungal metabolite.  Tetrahedron Letters. 1965;  3337-43
    CrossrefPubMedSearch in Google Scholar
  • 2 Corbett R E, Young H. Lichens and fungi. Part III. Structural elucidation of 15α,22-dihydroxyhopane from Sticta billardierii Del.  J. Chem. Soc. (C). 1966;  1564-7
    PubMedSearch in Google Scholar
  • 3 Van Eijk G W, Roeijmans H J, Seykens D. Hopanoids from the entomogenous fungus Aschersonia aleyrodis .  Tetrahedron Letters. 1986;  27 2533-4
    CrossrefPubMedSearch in Google Scholar
  • 4 Takahashi R, Tanaka O, Shibata S. Occurrence of 15α-acetoxy-22-hydroxyhopane and phlebic acid A in the lichen, Peltigera aphthosa .  Phytochemistry. 1969;  8 2345-9
    CrossrefPubMedSearch in Google Scholar
  • 5 Sheffer M, Fried A, Gottlieb H E, Tietz A, Avron M. Lipid composition of the plasma membrane of the halotolerant alga, Dunaliella salina .  Biochim. Biophys. Acta. 1986;  857 165-72
    PubMedSearch in Google Scholar
  • 6 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 .  Antimicrobial Agents and Chemotherapy. 1997;  4 1004-9
    PubMedSearch in Google Scholar
  • 7 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.  Journal of National Cancer Institute. 1990;  82 1107-12
    CrossrefPubMedSearch in Google Scholar
  • 8 Cantrell C L, Rajab M S, Franzblau S G, Fronczek F R, Fischer N H. Antimycobacterial ergosterol-5,8-endoperoxide from Ajuga remota .  Planta Medica. 1999;  65 732-4
    Thieme ConnectPubMedSearch in Google Scholar
  • 9 Cantrell C L, Lu T, Fronczek F R, Fischer N H, Adams L B, Franzblau S G. Antimycobacterial cycloartanes from Borrichia frutescens .  J. Nat. Prod.. 1996;  59 (12) 1131-6
    CrossrefPubMedSearch in Google Scholar
  • 10 Cantrell C L, Rajab M S, Franzblau S G, Fischer N H. Antimycobacterial triterpenes from Melia volkensii .  J. Nat. Prod.. 1999;  62 (4) 546-8
    CrossrefPubMedSearch in Google Scholar
  • 11 Fischer N H, Lu T, Cantrell C L, Castañeda-Acosta J, Quijano L, Franzblau S G. Antimycobacterial evaluation of germacranolides.  Phytochemistry. 1998;  49 (2) 559-64
    CrossrefPubMedSearch in Google Scholar
  • 12 Cantrell C L, Abate L, Fronczek F R, Franzblau S G, Quijano L, Fischer N H. Antimycobacterial Eudesmanolides from Inula helenium and Rudbeckia subtomentosa .  Planta Medica. 1999;  65 (4) 351-5
    Thieme ConnectPubMedSearch in Google Scholar
  • 13 Rajab M S, Cantrell C L, Franzblau S G, Fischer N H. Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.  Planta Medica. 1998;  64 (1) 2-4
    Thieme ConnectPubMedSearch in Google Scholar
  • 14 Lu T, Cantrell C L, Robbs S L, Franzblau S G, Fischer N H. Antimycobacterial matricaria esters and lactones from Astereae species.  Planta Medica. 1998;  64 (7) 665-7
    Thieme ConnectPubMedSearch in Google Scholar

Dr. Prasat Kittakoop

National Center for Genetic Engineering and Biotechnology


National Science and Technology Development Agency

73/1, Rama VI Road

Bangkok 10400

Thailand

Email: prasat@biotec.or.th

Fax: +66-2-6448107