Three New Manzamine Alkaloids from a Common Indonesian Sponge and Their Activity against Infectious and Tropical Parasitic Diseases

Three new manzamine-type alkaloids, 12,34-oxamanzamine E (3), 8-hydroxymanzamine J (4), and 6-hydroxymanzamine E (8), as well as 12 previously characterized manzamine alkaloids have been isolated from a common Indonesian sponge of the genus Acanthostrongylophora. The structures of the new compounds...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-08, Vol.67 (8), p.1314-1318
Main Authors: Rao, Karumanchi V, Kasanah, Noer, Wahyuono, Subagus, Tekwani, Babu L, Schinazi, Raymond F, Hamann, Mark T
Format: Article
Language:English
Subjects:
Acanthostrongylophora
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Animals
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
Anti-Infective Agents - chemistry
Anti-Infective Agents - isolation & purification
Anti-Infective Agents - pharmacology
Antimalarials - chemistry
Antimalarials - isolation & purification
Antimalarials - pharmacology
Antiprotozoal Agents - chemistry
Antiprotozoal Agents - isolation & purification
Antiprotozoal Agents - pharmacology
Biological and medical sciences
Carbolines - chemistry
Carbolines - isolation & purification
Carbolines - pharmacology
General pharmacology
Human immunodeficiency virus 1
Indonesia
Leishmania
Marine
Medical sciences
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium tuberculosis
Mycobacterium tuberculosis - drug effects
Nuclear Magnetic Resonance, Biomolecular
Petrosiidae
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera
Porifera - chemistry
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Summary:Three new manzamine-type alkaloids, 12,34-oxamanzamine E (3), 8-hydroxymanzamine J (4), and 6-hydroxymanzamine E (8), as well as 12 previously characterized manzamine alkaloids have been isolated from a common Indonesian sponge of the genus Acanthostrongylophora. The structures of the new compounds have been established on the basis of 1D and 2D NMR spectroscopic analysis and comparison of the data to literature values of related compounds. The biological activities and structure−activity relationship of the manzamines against malaria, Mycobacterium tuberculosis, Leishmania, HIV-1, and AIDS opportunistic infections are discussed. A plausible pathway for the formation of the 12,34-oxaether bridge in compound 3 is also provided.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0400095