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

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 8; pp. 1314 - 1318
• Main Authors: Rao, Karumanchi V, Kasanah, Noer, Wahyuono, Subagus, Tekwani, Babu L, Schinazi, Raymond F, Hamann, Mark T
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-08-2004; Glendale, AZ American Society of Pharmacognosy
• 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; Asia; Indonesia; ISEW, Indonesia; Antimalarial; HIV-1 virus; Angular nitrogen heterocycle; Marine environment; Alkaloid; Bacteria; Antiviral; Antiinfectious; Antituberculous agent; Kinetoplastida; Protozoa; Opportunistic infection; Pharmacognosy; Retroviridae; Animal origin; Polycyclic compound; Lentivirus; In vitro; Biological activity; Virus; Mycobacterium tuberculosis; Mycobacteriales; Porifera; Leishmania; Mycobacteriaceae; Parasiticide; Isolation; Actinomycetes; Sponge; Human immunodeficiency virus; Invertebrata; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0400095

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.