Anti-HIV-1 and anti-inflammatory lupanes from the leaves, twigs, and resin of Garcinia hanburyi

Vichai Reutrakul; Natthinee Anantachoke; Manat Pohmakotr; Thaworn Jaipetch; Chalobon Yoosook; Jittra Kasisit; Chanita Napaswa; Ampai Panthong; Thawatchai Santisuk; Samran Prabpai; Palangpon Kongsaeree; Patoomratana Tuchinda

doi:10.1055/s-0029-1186193

Anti-HIV-1 and anti-inflammatory lupanes from the leaves, twigs, and resin of Garcinia hanburyi

Planta Med. 2010 Mar;76(4):368-71. doi: 10.1055/s-0029-1186193. Epub 2009 Oct 14.

Authors

Vichai Reutrakul, Natthinee Anantachoke, Manat Pohmakotr, Thaworn Jaipetch, Chalobon Yoosook, Jittra Kasisit, Chanita Napaswa, Ampai Panthong, Thawatchai Santisuk, Samran Prabpai, Palangpon Kongsaeree, Patoomratana Tuchinda

PMID: 19830655
DOI: 10.1055/s-0029-1186193

Abstract

Two new lupanes, 2 alpha-acetoxy-3 beta-hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) ( 1) and 2 alpha-hydroxy-3 beta-acetoxy-19 beta-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- beta- D-glucopyranoside ( 5), were isolated from the leaves and twigs of GARCINIA HANBURYI. Compounds 1- 3 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 ( 1- 4) displayed anti-HIV-1 activities in the anti-HIV-1 reverse transcriptase (IC (50) values 16.3-116.9 microg/mL) and syncytium assays (EC (50) 5.6-73.6 microg/mL, SI 1.7-3.3). Moreover compounds 1- 4 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.

Copyright Georg Thieme Verlag KG Stuttgart New York.

Publication types

Letter
Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Anti-Inflammatory Agents / therapeutic use
Antiviral Agents / isolation & purification
Antiviral Agents / pharmacology*
Antiviral Agents / therapeutic use
Disease Models, Animal
Edema / drug therapy*
Garcinia / chemistry*
Giant Cells / drug effects
Glucosides / isolation & purification
HIV-1 / drug effects*
Inflammation / drug therapy
Inhibitory Concentration 50
Molecular Structure
Phytotherapy
Plant Extracts / chemistry
Plant Extracts / pharmacology*
Plant Extracts / therapeutic use
Plant Leaves
Plant Stems
RNA-Directed DNA Polymerase / metabolism
Resins, Plant
Stigmasterol / analogs & derivatives
Stigmasterol / isolation & purification
Triterpenes / isolation & purification
Triterpenes / pharmacology*
Triterpenes / therapeutic use
X-Ray Diffraction

Substances

Anti-Inflammatory Agents
Antiviral Agents
Glucosides
Plant Extracts
Resins, Plant
Triterpenes
stigmasterol 3-O-beta-D-glucopyranoside
Stigmasterol
RNA-Directed DNA Polymerase