Absolute stereochemistry and anti-HIV activity of miquartynoic acid, a polyacetylene from Ochanostachys amentacea

Mohammad A. Rashid, Kirk R. Gustafson, John H. Cardellina II and Michael R. Boyd, Nat.Prod.Lett. 15: 21-26, 2001.

Abstract:

Anti-HIV bioassay-guided fractionation of an organic extract of Ochanostachys amentacea provided an HIV-inhiitory 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 XTT-based anti-HIV assay, 2-5 µg/mL of minquartynoic acid (1) effecitively inhibited lymphoblastoid cell killing by HIV-1.

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