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HIV-inhibitory natural products part 61 - Absolute stereochemistry and anti-HIV activity of minquartynoic acid, a polyacetylene from Ochanostachys amentacea

  1. Author:
    Rashid, M. A.
    Gustafson, K. R.
    Cardellina, J. H.
    Boyd, M. R.
  2. Author Address

    NCI, Lab Drug Discovery Res & Dev, Dev Therapeut Program, Div Canc Treatment & Diag, FCRDC, Frederick, MD 21702 USA.
    1. Year: 2001
  1. Journal: Natural Product Letters
    1. 15
    2. 1
    3. Pages: 21-26
  2. Type of Article: Article
  1. Abstract:

    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 mug/mL of minquartynoic acid (1) effectively inhibited human lymphoblastoid cell killing by HIV-1.

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