title: Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera.
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.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, People's Republic of China.
authors.forename: Guotao
authors.initials: G
authors.lastname: Fan
authors.forename: Zelin
authors.initials: Z
authors.lastname: Li
authors.forename: Shi
authors.initials: S
authors.lastname: Shen
authors.forename: Yi
authors.initials: Y
authors.lastname: Zeng
authors.forename: Yishu
authors.initials: Y
authors.lastname: Yang
authors.forename: Minjuang
authors.initials: M
authors.lastname: Xu
authors.forename: Torsten
authors.initials: T
authors.lastname: Bruhn
authors.forename: Heike
authors.initials: H
authors.lastname: Bruhn
authors.forename: Joachim
authors.initials: J
authors.lastname: Morschhäuser
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
authors.forename: Wenhan
authors.initials: W
authors.lastname: Lin
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D002460:Cell Line; D002681:China; D015700:HIV Envelope Protein gp41 / Q000037:antagonists & inhibitors / Q000378:metabolism; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D011161:Porifera / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000737:chemistry; D014764:Viral Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D054320:vif Gene Products, Human Immunodeficiency Virus / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D000470:Alkaloids; D019380:Anti-HIV Agents; D015700:HIV Envelope Protein gp41; D011758:Pyrroles; D013431:Sulfates; D014764:Viral Proteins; C514787:gp41 protein, Human immunodeficiency virus 1; D054320:vif Gene Products, Human Immunodeficiency Virus; C514847:vif protein, Human immunodeficiency virus 1