title: Urupocidin A: a new, inducing iNOS expression bicyclic guanidine alkaloid from the marine sponge Monanchora pulchra.
abstract: Urupocidins A and B (1 and 2), bisguanidine alkaloids with an unprecedented skeleton system, derived from polyketide precursors and containing an unusual N-alkyl-N-hydroxyguanidine moiety, have been isolated from the sponge Monanhora pulchra. The structures of 1 and 2, including absolute configuration, were established using the detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound 1 increases nitric oxide production in murine macrophages via inducing iNOS expression.
authors.affiliation: G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences , Vladivostok-22, Prospect 100-let, Vladivostok 159, Russia.
authors.forename: Tatyana N
authors.initials: TN
authors.lastname: Makarieva
authors.forename: Ekaterina K
authors.initials: EK
authors.lastname: Ogurtsova
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Denisenko
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Ksenya M
authors.initials: KM
authors.lastname: Tabakmakher
authors.forename: Alla G
authors.initials: AG
authors.lastname: Guzii
authors.forename: Evgeny A
authors.initials: EA
authors.lastname: Pislyagin
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Es'kov
authors.forename: Valery B
authors.initials: VB
authors.lastname: Kozhemyako
authors.forename: Dmitry L
authors.initials: DL
authors.lastname: Aminin
authors.forename: Yun-Ming
authors.initials: YM
authors.lastname: Wang
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D006146:Guanidines / Q000737:chemistry* / Q000494:pharmacology*; D006898:Hydroxylamines; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D006146:Guanidines; D006898:Hydroxylamines; C000597826:urupocidin A; C000597827:urupocidin B; D009569:Nitric Oxide; C029604:hydroxyguanidine; C496319:NOS2 protein, human; D052247:Nitric Oxide Synthase Type II