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Author Notes:

o whom correspondence should be addressed. Tel: (662) 915-5730. Fax: (662) 915-6975. Email: mthamann@olemiss.edu

We are indebted to Subagus Wahyuono and Achmad Mursyidi from Gadjah Mada University, Indonesia, for assistance with sample collection, John Trott and Sharon Sanders for in vitro malaria assays, and Phillip E. Fanwick, Department of Chemistry, Purdue University, for the X-ray diffraction data.

We gratefully acknowledge Sharon C. Sanders and Belynda G. Smiley, the National Center for Natural Products Research, for bioassays.

Subjects:

Research Funding:

This work was supported by NIH (RO1AI36596, KO2AI01502), UNDP/World Bank/WHO special program for Research and Training in Tropical Diseases (TDR# 990119).

R.F.S. is supported by the Emory University Center for AIDS Research and Department of Veterans Affairs.

Keywords:

  • Science & Technology
  • Life Sciences & Biomedicine
  • Plant Sciences
  • Chemistry, Medicinal
  • Pharmacology & Pharmacy
  • CHEMISTRY, MEDICINAL
  • PHARMACOLOGY & PHARMACY
  • PLANT SCIENCES
  • MARINE NATURAL-PRODUCTS
  • MAGNETIC-RESONANCE
  • XESTOSPONGIA
  • 8-HYDROXYMANZAMINE-A
  • AGENTS
  • ACIDS

New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an indonesian sponge

Tools:

Journal Title:

Journal of Natural Products

Volume:

Volume 66, Number 6

Publisher:

, Pages 823-828

Type of Work:

Article | Post-print: After Peer Review

Abstract:

Eleven manzamine type alkaloids, two β-carbolines, and five nucleosides have been isolated from an Indonesian sponge. Among these are the previously characterized 12,34-oxamanzamine A, 12,34-oxamanzamine E, manzamine A (1), 8-hydroxymanzamine A, 6-deoxymanzamine X, manzamine E (2), manzamine X, manzamine F (4), norharman, thymine, 2′,3′-didehydro-2′,3′-dideoxyuridine, uracil, thymidine, and 2′-deoxyuridine. The structures for the five new compounds have been assigned as 32,33-dihydro-31-hydroxymanzamine A (3), 32,33-dihydro-6-hydroxymanzamine A-35-one (5), des-N-methylxestomanzamine A (6), 32,33-dihydro-6,31-dihydroxymanzamine A (7), and 1,2,3,4-tetrahydronorharman-1-one (8), on the basis of NMR and X-ray data. The bioactivity and SAR of the manzamines against malaria, TB, and leishmania are also presented. The structural revision of two previously reported pyrazoles as uracil and thymine is also discussed.

Copyright information:

© 2003 American Chemical Society and American Society of Pharmacognosy

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