Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera

Bioorganic & Medicinal Chemistry
Guotao FanWenhan Lin

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.

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Citations

Apr 7, 2012·Chemical Reviews·Arndt W SchmidtHans-Joachim Knölker
Feb 23, 2011·Marine Drugs·Manickam Sugumaran, William E Robinson
Feb 24, 2015·Marine Drugs·Christian Bailly
Jul 30, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Insaf FilaliHichem Ben Jannet
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Oct 4, 2017·Mini Reviews in Medicinal Chemistry·Tingting LiJianrong Li
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Jul 11, 2020·Biomolecules·Gennaro RiccioChiara Lauritano
May 1, 2021·Marine Drugs·Disha VarijakzhanChou-Min Chong
Aug 3, 2021·ACS Chemical Biology·Jianrong LiuWenhan Lin

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