Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia

Jian Qiao Gu, Tyler N. Graf, Dongho Lee, Hee Byung Chai, Qiuwen Mi, Leonardus B S Kardono, Fransisca M. Setyowati, Rachman Ismail, Soedarsono Riswan, Norman R. Farnsworth, Geoffrey A. Cordell, John M. Pezzuto, Steven M. Swanson, David J. Kroll, Joseph O. Falkinham, Monroe E. Wall, Mansukh C. Wani, A. Douglas Kinghorn, Nicholas H. Oberlies

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80 Citations (Scopus)

Abstract

Bioactivity-directed fractionation of extracts of two Diospyros maritima bark samples from Indonesia, one collected at sea level in a beach forest in Java and the other collected at a slight elevation away from the sea shore on the island of Lombok, yielded a diverse set of secondary metabolites. The naphthoquinone plumbagin (1), although found in extracts of both specimens, constituted a much larger percentage of the former sample, which also yielded a series of plumbagin dimers, maritinone (2), chitranone (3), and zeylanone (4). The latter sample yielded a new naphthoquinone derivative, (4S)-shinanolone (5), and a new natural product coumarin, 7,8-dimethoxy-6-hydroxycoumarin (6), along with three other analogues of plumbagin, 2-methoxy-7-methyljuglone (7), 3-methoxy-7-methyljuglone (8), and 7-methyljuglone (9). The structures of compounds 5 and 6 were elaborated by physical, spectral, and chemical methods. All of the isolates were evaluated in both cytotoxicity and antimicrobial assays, and structure-activity relationships of these naphthoquinones are proposed. Plumbagin (1) and maritinone (2) were evaluated also for in vivo antitumor activity in the hollow fiber assay, but both were found to be inactive.

Original languageEnglish
Pages (from-to)1156-1161
Number of pages6
JournalJournal of Natural Products
Volume67
Issue number7
DOIs
Publication statusPublished - 2004 Jul 1
Externally publishedYes

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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    Gu, J. Q., Graf, T. N., Lee, D., Chai, H. B., Mi, Q., Kardono, L. B. S., Setyowati, F. M., Ismail, R., Riswan, S., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Swanson, S. M., Kroll, D. J., Falkinham, J. O., Wall, M. E., Wani, M. C., Kinghorn, A. D., & Oberlies, N. H. (2004). Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia. Journal of Natural Products, 67(7), 1156-1161. https://doi.org/10.1021/np040027m