A new diarylheptanoid from the rhizomes of Zingiber mekongense.
A new diarylheptanoid, (3S,5S)-3,5-diacetoxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane (1), together with the known docosyl trans-ferulate (2), (1S,2S,4S)-p-menthan-1,2,4-triol (3), 5αH-eudesmane-4α,11-diol (4), 5αH-eudesmane-4β,11-diol (5), 4α,10β-dihydroxy-1βH,5αH-guaia-6-ene (guaianediol) (6), (+)-galanolactone (7), (E)-labda-8(17),12(13)-dien-15,16-olide (8), labda-8(17),13(14)-dien-15,16-olide (9), 3,5-dihydroxy-7,4'-dimethoxyflavone (10) and 3,5,3'-trihydroxy-7,4'-dimethoxyflavone (11) were isolated from the rhizomes of Zingiber mekongense. Their structures were determined by spectroscopic methods. The stereochemistry of 1 was proved through chemical conversion. Compounds 1, 4-7 and 9-11 exhibited anti-HIV-1 activities in the anti-syncytium assay using (∆Tat/rev)MC99 virus and 1A2 cell line system, while only compounds 7 and 11 were found active in the HIV-1 reverse transcriptase assay.
Department of Chemistry and Center for Innovation in Chemistry, PERCH, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand.
Arthittaya
A
Chareonkla
Manat
M
Pohmakotr
Vichai
V
Reutrakul
Chalobon
C
Yoosook
Jitra
J
Kasisit
Chanita
C
Napaswad
Patoomratana
P
Tuchinda
D019380:Anti-HIV Agents / Q000302:isolation & purification*; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification*; D004353:Drug Evaluation, Preclinical; D006536:Heptanes / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D027343:Rhizome / Q000737:chemistry; D030521:Zingiberaceae / Q000737:chemistry*
C560385:(3S,5S)-3,5-diacetoxy-1,7-bis(3,4,5-trimethoxyphenyl)heptane; D019380:Anti-HIV Agents; D036381:Diarylheptanoids; D006536:Heptanes