1. Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera.
- Author
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Fan G, Li Z, Shen S, Zeng Y, Yang Y, Xu M, Bruhn T, Bruhn H, Morschhäuser J, Bringmann G, and Lin W
- Subjects
- Alkaloids isolation & purification, Alkaloids pharmacology, Animals, Anti-HIV Agents isolation & purification, Anti-HIV Agents pharmacology, Cell Line, China, HIV Envelope Protein gp41 antagonists & inhibitors, HIV Envelope Protein gp41 metabolism, HIV-1 drug effects, Humans, Structure-Activity Relationship, Sulfates chemistry, Viral Proteins antagonists & inhibitors, Viral Proteins metabolism, vif Gene Products, Human Immunodeficiency Virus antagonists & inhibitors, vif Gene Products, Human Immunodeficiency Virus metabolism, Alkaloids chemistry, Anti-HIV Agents chemistry, Porifera chemistry, Pyrroles chemistry
- Abstract
Fifteen new DOPA-derived pyrrole alkaloids, named baculiferins A-O (2-16), were isolated from the Chinese marine sponge Iotrochota baculifera, together with the known alkaloids purpurone (1) and ningalin A (17). Most of the new compounds contain one to three O-sulfate units. Their structures were determined by extensive spectroscopic analysis including (1)H and (13)C NMR (COSY, HMQC, HMBC) and ESIMS data. A possible pathway for the biosynthetic origin of the isolated alkaloids is proposed, in which DOPA is assumed to be a joint biogenetic precursor. Baculiferins C, E-H, and K-N (4, 6-9, 12-15) were found to be potent inhibitors against the HIV-1 IIIB virus in both, MT4 and MAGI cells. Additional bioassay revealed that baculiferins could dramatically bind to the HIV-1 target proteins Vif, APOBEC3G, and gp41, for which structure-activity relationships are discussed., (Copyright (c) 2010 Elsevier Ltd. All rights reserved.) more...
- Published
- 2010
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