Planta Med 2010; 76(4): 368-371
DOI: 10.1055/s-0029-1186193
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Anti-HIV‐1 and Anti-Inflammatory Lupanes from the Leaves, Twigs, and Resin of Garcinia hanburyi

Vichai Reutrakul1 , Natthinee Anantachoke1 , 2 , Manat Pohmakotr1 , Thaworn Jaipetch1 , 3 , Chalobon Yoosook4 , Jittra Kasisit4 , Chanita Napaswa4 , Ampai Panthong5 , Thawatchai Santisuk6 , Samran Prabpai1 , Palangpon Kongsaeree1 , Patoomratana Tuchinda1
  • 1Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand
  • 2Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok, Thailand
  • 3Department of Basic Science, Mahidol University Kanchanaburi Campus, Kanchanaburi, Thailand
  • 4Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, Thailand
  • 5Department of Pharmacology, Faculty of Medicine, Chiang Mai University, Chiang Mai, Thailand
  • 6The Forest Herbarium, Royal Forest Department, Bangkok, Thailand
Further Information

Publication History

received July 10, 2009 revised September 10, 2009

accepted September 14, 2009

Publication Date:
14 October 2009 (online)

Abstract

Two new lupanes, 2α-acetoxy-3β-hydroxy-19β-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) (1) and 2α-hydroxy-3β-acetoxy-19β-hydrogen-lup-20(29)-en-28-oic acid (3-acetoxyalphitolic acid) (2), together with the known betulinic acid (3), betulin (4), and stimasterol-3-O-β-D-glucopyranoside (5), were isolated from the leaves and twigs of Garcinia hanburyi. Compounds 13 were also isolated from the resin of this plant. The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. All of the lupanes (14) displayed anti-HIV‐1 activities in the anti-HIV‐1 reverse transcriptase (IC50 values 16.3–116.9 µg/mL) and syncytium assays (EC50 5.6–73.6 µg/mL, SI 1.7–3.3). Moreover compounds 14 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.

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Prof. Vichai Reutrakul

Department of Chemistry and Center for Innovation in Chemistry
Faculty of Science
Mahidol University

Rama 6 Road

Bangkok 10400

Thailand

Phone: + 66 22 01 51 52

Fax: + 66 26 44 51 26

Email: scvrt@mahidol.ac.th