Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / chemistry
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Alkaloids / isolation & purification*
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Alkaloids / pharmacology
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Animals
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / isolation & purification*
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Anti-HIV Agents / pharmacology
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Anti-Infective Agents / chemistry
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Anti-Infective Agents / isolation & purification*
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Anti-Infective Agents / pharmacology
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Antimalarials / chemistry
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Antimalarials / isolation & purification*
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Antimalarials / pharmacology
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Antiprotozoal Agents / chemistry
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Antiprotozoal Agents / isolation & purification*
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Antiprotozoal Agents / pharmacology
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Carbolines / chemistry
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Carbolines / isolation & purification*
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Carbolines / pharmacology
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Indonesia
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Microbial Sensitivity Tests
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Molecular Structure
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Mycobacterium tuberculosis / drug effects
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Nuclear Magnetic Resonance, Biomolecular
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Porifera / chemistry*
Substances
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12,34-oxamanzamine E
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6-hydroxymanzamine E
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8-hydroxymanzamine J
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Alkaloids
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Anti-HIV Agents
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Anti-Infective Agents
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Antimalarials
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Antiprotozoal Agents
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Carbolines