title: Neopetrocyclamines A and B, polycyclic diamine alkaloids from the sponge Neopetrosia cf exigua.
abstract: Two new polycyclic alkaloids, neopetrocyclamines A and B (1 and 2), along with the known metabolites papuamine (3) and haliclonadiamine (4), were isolated from the Indonesian sponge Neopetrosia cf exigua. Neopetrocyclamine A contains a formamidinium moiety, a rare functional group. While these compounds share the same basic biosynthetic building blocks, the size of the ring system differs in 1 and 2 because of the formamidinium moiety. Biological evaluations of 1-4 revealed that papuamine is cytotoxic against glioblastoma SF-295 cells (GI50 = 0.8 μM).
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, United States.
authors.forename: Zhibin
authors.initials: Z
authors.lastname: Liang
authors.affiliation: ‡University of Hawaii Cancer Center, 701 Ilalo Street, Honolulu, Hawaii 96813, United States.
authors.forename: Florian J
authors.initials: FJ
authors.lastname: Sulzmaier
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, United States.
authors.forename: Wesley Y
authors.initials: WY
authors.lastname: Yoshida
authors.affiliation: §National Centre Coasts and Oceans, National Institute of Water and Atmospheric Research, 41 Market Place, Auckland Central 1010, New Zealand.
authors.forename: Michelle
authors.initials: M
authors.lastname: Kelly
authors.affiliation: ‡University of Hawaii Cancer Center, 701 Ilalo Street, Honolulu, Hawaii 96813, United States.
authors.forename: Joe W
authors.initials: JW
authors.lastname: Ramos
authors.affiliation: †Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, United States.|‡University of Hawaii Cancer Center, 701 Ilalo Street, Honolulu, Hawaii 96813, United States.
authors.forename: Philip G
authors.initials: PG
authors.lastname: Williams
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003959:Diamines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007214:Indonesia; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011083:Polycyclic Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D003959:Diamines; D011083:Polycyclic Compounds; C585612:haliclonadiamine; C000598717:neopetrocyclamine A; C000598718:neopetrocyclamine B; C585611:papuamine