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 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.
Rao
Karumanchi V
KV
The Department of Pharmacognosy and National Center for the Development of Natural Products, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
Kasanah
Noer
N
Wahyuono
Subagus
S
Tekwani
Babu L
BL
Schinazi
Raymond F
RF
Hamann
Mark T
MT
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002243:Carbolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007214:Indonesia; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
C492402:12,34-oxamanzamine E; C492404:6-hydroxymanzamine E; C492403:8-hydroxymanzamine J; D000470:Alkaloids; D019380:Anti-HIV Agents; D000890:Anti-Infective Agents; D000962:Antimalarials; D000981:Antiprotozoal Agents; D002243:Carbolines