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Pyranocoumarins From Tropical Species of the Genus Calophyllum - a Chemotaxonomic Study of Extracts in the National Cancer Institute Collection

  1. Author:
    McKee, T. C.
    Covington, C. D.
    Fuller, R. W.
    Bokesch, H. R.
    Young, S.
    Cardellina, J. H.
    Kadushin, M. R.
    Soejarto, D. D.
    Stevens, P. F.
    Cragg, G. M.
    Boyd, M. R.

  2. Author Address

    Boyd MR NCI LAB DRUG DISCOVERY RES & DEV DEV THERAPEUT PROGRAM DIV CANC TREATMENT DIAGNOSIS BLDG 1052 FREDERICK, MD 21702 USA NCI LAB DRUG DISCOVERY RES & DEV DEV THERAPEUT PROGRAM DIV CANC TREATMENT DIAGNOSIS FREDERICK, MD 21702 USA
    1. Year: 1998
  2. Journal: Journal of Natural Products
    1. 61
    2. 10
    3. Pages: 1252-1256
  4. Type of Article: Article
  1. Abstract:

    (+)-Calanolide A, a novel dipyranocoumarin from the Malesian tree Calophyllum lanigerum var. austrocoriaceum, and a closely related compound, (-)-calanolide B, isolated from Calophyllum teysmannii var. inophylloide, are representatives of a distinct class of nonnucleoside HIV-1 specific reverse-transcriptase inhibitor under development as an AIDS chemotherapeutic. NCI repository specimens totalling 315 organic extracts from 31 taxa of Calophyllum were analyzed for related pyranocoumarins using a simple TLC system. A total of 127 extracts was initially classified as ''positive''; eight out of the 31 taxa examined, representing perhaps 28 species already described (1/7-1/8 of all the species in this genus), contained prenylated coumarins, suggesting that these compounds, while sometimes abundantly present, are not widespread in the genus. Representative members of the TLC-positive extracts were partitioned between CH2Cl2 and 25% aqueous MeOH; the CH2Cl2-soluble materials were then analyzed by TLC and H-1 NMR to confirm the presence of pyranocoumarins. The anti-HIV activity of the partitioned extracts are also presented. This study suggested that there are several distinctive coumarin chemotaxonomic markers distinguishing species of this genus. [References: 32]

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