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Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly

  1. Author:
    Marquez, B. L.
    Watts, K. S.
    Yokochi, A.
    Roberts, M. A.
    Verdier-Pinard, P.
    Jimenez, J. I.
    Hamel, E.
    Scheuer, P. J.
    Gerwick, W. H.

  2. Author Address

    Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA Oregon State Univ, Dept Biochem & Biophys, Corvallis, OR 97331 USA Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA Gerwick WH Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA
    1. Year: 2002
  2. Journal: Journal of Natural Products
    1. 65
    2. 6
    3. Pages: 866-871
  4. Type of Article: Article
  1. Abstract:

    Hectochlorin (1) was isolated from marine isolates of Lyngbya majuscula collected from Hector Bay, Jamaica, and Boca del Drago Beach, Bocas del Toro, Panama. The planar structure was deduced by one-and two-dimensional NMR spectroscopy. X-ray crystallography was used to determine the absolute stereochemistry of hectochlorin as 2S,3S, 14S,22S. Hectochlorin is equipotent to jasplakinolide (5) in its ability to promote actin polymerization, but unlike jasplakinolide, is unable to displace a fluorescent phalloidin analogue from polymerized actin. In addition, hectochlorin shows both a unique profile of cytotoxicity by the COMPARE algorithm and potent inhibitory activity toward the fungus Candida albicans. Structurally, hectochlorin resembles dolabellin and the recently reported lyngbyabellin class of compounds.

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