title: Nuttingins A-F and malonganenones D-H, tetraprenylated alkaloids from the Tanzanian gorgonian Euplexaura nuttingi.
abstract: Six new tetraprenylated purine alkaloids, designated nuttingins A-F (1-6), were isolated together with three known malonganenones, A-C (12-14), and five new closely related malonganenones, D-H (7-11), from the gorgonian Euplexaura nuttingi collected in Pemba Island, Tanzania. The structures of the compounds were elucidated by interpretation of 1D and 2D NMR data including 15N chemical shifts obtained from 1H-15N HMBC spectra. Nuttingins A-E (1-5) and malonganenones D-G (7-10) displayed inhibitory activity against both K562 and UT7 tumor cell lines, compounds 3-5 being the most active ones, approximately 3-fold more potent than the others. Compounds 1-5 and 7-11 also induce apoptosis in transformed mammalian cells at a concentration of 1.25 microg/mL.
authors.affiliation: School of Chemistry, Department of Zoology, and Department of Cell and Developmental Biology, Tel-Aviv University, Ramat Aviv 69978, Israel.
authors.forename: Hagit
authors.initials: H
authors.lastname: Sorek
authors.forename: Amira
authors.initials: A
authors.lastname: Rudi
authors.forename: Yehuda
authors.initials: Y
authors.lastname: Benayahu
authors.forename: Nathalie
authors.initials: N
authors.lastname: Ben-Califa
authors.forename: Drorit
authors.initials: D
authors.lastname: Neumann
authors.forename: Yoel
authors.initials: Y
authors.lastname: Kashman
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D003063:Cnidaria / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020014:K562 Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013636:Tanzania
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents