Absolute stereochemistry and anti-HIV activity of minquartynoic acid, a polyacetylene from Ochanostachys amentacea.
Anti-HIV bioassay-guided fractionation of an organic extract of Ochanostachys amentacea provided an HIV-inhibitory polyacetylenic acid. The identity of this compound was established as (-)-17-hydroxy-9,11,13,15-octadecatetraynoic acid (1), also known as minquartynoic acid, by comparison of its physical and spectral data with previously reported values. Analysis of Mosher's ester derivatives of the methyl ester of 1 allowed assignment of S absolute stereochemistry to the lone chiral center. In an in vitro XTT-based anti-HIV assay, 2-5 micrograms/mL of minquartynoic acid (1) effectively inhibited human lymphoblastoid cell killing by HIV-1.
Rashid
M A
MA
Laboratory of Drug Discovery Research and Development, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, NCI-FCRDC, Building 1052, Room 121, Frederick, MD 21702-1201, USA.
Gustafson
K R
KR
Cardellina
J H
JH
Boyd
M R
MR
D000480:Alkynes; D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D019684:Magnoliopsida / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D053279:Polyynes; D013237:Stereoisomerism
D000480:Alkynes; D019380:Anti-HIV Agents; D005231:Fatty Acids, Unsaturated; C417933:minquartynoic acid; D053279:Polyynes