title: Two new tryptamine derivatives, leptoclinidamide and (-)-leptoclinidamine B, from an Indonesian ascidian Leptoclinides dubius.
abstract: Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C²-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and its N-acetyl derivative (4). Compound 1 was an amide of tryptamine with two β-alanine units. Although the planar structure of 2 is identical to that of the known compound (+)-leptoclinidamine B (5), compound 2 was determined to be the enantiomer of 5 based on amino acid analysis using HPLC methods. Compounds 1 to 4 were evaluated for cytotoxicity against two human cancer cell lines, HCT-15 (colon) and Jurkat (T-cell lymphoma) cells, but none of the compounds showed activity.
authors.affiliation: Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamazaki
authors.affiliation: Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan.|Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
authors.forename: Defny S
authors.initials: DS
authors.lastname: Wewengkang
authors.affiliation: Laboratory of Taxonomy, Department of Biology, Faculty of Science, Toho University, Miyama, Funabashi 274-8510, Japan.
authors.forename: Teruaki
authors.initials: T
authors.lastname: Nishikawa
authors.affiliation: Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Henki
authors.initials: H
authors.lastname: Rotinsulu
authors.affiliation: Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
authors.forename: Remy E P
authors.initials: REP
authors.lastname: Mangindaan
authors.affiliation: Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan.
authors.forename: Michio
authors.initials: M
authors.lastname: Namikoshi
mesh_terms: D000107:Acetylation; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D059001:Aquatic Organisms / Q000378:metabolism*; D045744:Cell Line, Tumor; D003110:Colonic Neoplasms / Q000188:drug therapy; D055808:Drug Discovery; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D019156:Indian Ocean; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology*; D007214:Indonesia; D019169:Jurkat Cells; D007661:Ketoses / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D015458:Leukemia, T-Cell / Q000188:drug therapy; D015394:Molecular Structure; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology*; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D014561:Urochordata / Q000378:metabolism*
chemical_list: C421662:2-(mannopyranosyl)-tryptophan; D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D026121:Indole Alkaloids; D007661:Ketoses; D014363:Tryptamines; C573582:leptoclinidamide; C540544:leptoclinidamine B; D014364:Tryptophan