RSS-Feed abonnieren
PDF herunterladen
DOI: 10.1055/s-2004-818951
Anti-HIV-1 Cycloartanes from Leaves and Twigs of Gardenia thailandica
We are grateful to the Higher Education Development Project: Postgraduate Education and Research Program in Chemistry (PERCH), the National Research Council of Thailand (NRCT) and the Thailand Research Fund (TRF) through a Senior Scholar Award to VR for the financial support. We also thank the Development and Promotion of Science and Technology Talent Project (DPST) for providing a scholarship to ASPublikationsverlauf
Received: August 25, 2003
Accepted: January 10, 2004
Publikationsdatum:
19. April 2004 (online)
Abstract
Thailandiol (1), gardenolic acid A (2), quadrangularic acid E (3) and 3β-hydroxy-5α-cycloart-24(31)-en-28-oic acid (4) have been isolated from the leaves and twigs of Gardenia thailandica Tirveng (order: Rubiales; family: Rubiaceae). In addition, 5-hydroxy-7,2′,3′,4′,5′,6′-hexamethoxyflavone (5), 5,7-dihydroxy-2′,3′, 4′,5′,6′-pentamethoxyflavone (6), 5-hydroxy-7,2′,3′,4′,5′-pentamethoxyflavone (7) and 5,7-dihydroxy-2′,3′,4′,5′-tetramethoxyflavone (8) were also isolated from the same source. The structures were elucidated by spectroscopic methods. Crude extracts and compounds 1 - 4 displayed anti-HIV-1 activities as determined by using the Δ Tat/RevMC99 virus and 1A2 cell line system. The EC50 values determined by the syncytium assay ranged from < 7.8 to 110 μg/mL. They also exhibited moderate to high activities in reverse transcriptase (RT) assay; the IC50 values of compounds 1 - 4, ranged from < 22.5 to 156.8 μg/mL.
References
- 1 Richman D D, Grimes J M, Lagaleos S W. Effect of stage of disease and drug dose on zidovudine susceptibilities of human immunodeficiency virus. J AIDS. 1990; 3 743-6
- 2 Wainberg M A, Friesland G. Public health implications of antiretroviral therapy and HIV drug resistance. JAMA. 1998; 279 1977-83
- 3 Silva G L, Gil R R, Cui B, Chai H, Santisuk T, Srisook E, Reutrakul V, Tuchinda P, Sophasan S, Sujarit S, Upathum S, Lynn S M, Farthing J E, Yang S -L, Lewis J A, O′Neill M J, Farnsworth N R, Cordell G A, Pezzuto J M, Kinghorn A D. Novel cytotoxic ring-A seco-cycloartane triterpenes from Gardenia coronaria and G. sootepensis . Tetrahedron. 1997; 53 529-38
- 4 Tuchinda P, Pompimon W, Reutrakul V, Pohmakotr M, Yoosook C, Kongyai N, Sophasan S, Sujarit K, Upathum S, Santisuk T. Cytotoxic and anti-HIV-1 constituents of Gardenia obtusifolia and their modified compounds. Tetrahedron. 2002; 58 8073-86
- 5 Cabrera G M, Gallo M, Seldes A M. Cycloartane derivatives from Tillandsia usneoides . J Nat Prod. 1996; 59 343-7
- 6 Gutierrez-Lugo M -T, Singh M P, Maiese W M, Timmermann B N. New antimicrobial cycloartane triterpenes from Acalypha communis . J Nat Prod. 2002; 65 872-5
- 7 Qin G -W, Fan Z -Y, Xu R -S. Studies on the chemical constituents of antifertility plant Gardenia jasminoides Ellis II. The structure of gardenolic acid A. Youji Huaxue. 1989; 9 263-5
- 8 Banskota A H, Tezuka Y, Phung L K, Tran K Q, Saiki I, Miwa Y, Taga T, Kadota S. Cytotoxic cycloartane-type triterpenes from Combretum quadrangulare . Bioorg Med Chem Lett. 1998; 8 3519-24
- 9 Banskota A H, Tezuka Y, Tran K Q, Tanaka K, Saiki I, Kadota S. Methyl quadrangularates A - D and related triterpenes from Combretum quadrangulare . Chem Pharm Bull. 2000; 48 496-504
- 10 Juma B F, Yenesew A, Midiwo J O, Waterman P G. Flavones and phenylpropenoids in the surface exudate of Psiadia punctulata . Phytochemistry. 2001; 57 571-4
- 11 El-Feraly F S, Mossa J S, Al-Yahya M A, Hifnawy M S, Hafez M M, Hufford C D. Two flavones from Psiadia arabica . Phytochemistry. 1990; 29 3372-3
- 12 Zhang H -J, Tan G T, Hoang V D, Hung N V, Cuong N M, Soejarto D D, Pezzuto J M, Fong H HS. Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea . J Nat Prod. 2003; 66 263-8
- 13 Tan G T, Pezzuto J M, Kinghorn A D, Hughes S H. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. J Nat Prod. 1991; 54 143-54
- 14 Kiser R, Makovsky S, Terpening S J, Liang N, Clayton D J. Assessment of a cytoprotection assay for the discovery and evaluation of anti-human immunodeficiency virus compounds utilizing a genetically-impaired virus. J Virol Meth. 1996; 58 99-109
- 15 Nara P L, Hatch W C, Dunlop N M, Robey W G, Arthur L O, Gonda M A, Fischinger P J. Simple, rapid, quantitative, syncytium forming microassay for the detection of human immunodeficiency virus neutralizing antibody. AIDS Res Hum Retrovir. 1987; 3 283-302
- 16 Weislow O S, Kiser R, Fine D L, Bader J, Shoemarker R H, Boyd M R. New soluble-formazan assay for HIV-1 cytopathic effects: Application to high flux screening of synthetic and natural products for AIDS-antiviral activity. J Natl Cancer Inst. 1989; 81 577-86
Dr. Patoomratana Tuchinda
Department of Chemistry
Faculty of Science
Mahidol University
Rama 6 Road
Bangkok 10400
Thailand
Telefon: +66-2-201-5159
Fax: +66-2-247-7050
eMail: scptc@mahidol.ac.th