1. Two new tryptamine derivatives, leptoclinidamide and (-)-leptoclinidamine B, from an Indonesian ascidian Leptoclinides dubius.
- Author
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Yamazaki H, Wewengkang DS, Nishikawa T, Rotinsulu H, Mangindaan REP, and Namikoshi M
- Subjects
- Acetylation, Alkaloids chemistry, Alkaloids isolation & purification, Alkaloids metabolism, Alkaloids pharmacology, Animals, Anti-Bacterial Agents chemistry, Anti-Bacterial Agents isolation & purification, Anti-Bacterial Agents metabolism, Antineoplastic Agents chemistry, Antineoplastic Agents isolation & purification, Antineoplastic Agents metabolism, Cell Line, Tumor, Colonic Neoplasms drug therapy, Drug Discovery, Escherichia coli drug effects, Humans, Indian Ocean, Indole Alkaloids chemistry, Indole Alkaloids metabolism, Indonesia, Jurkat Cells, Ketoses chemistry, Ketoses isolation & purification, Ketoses metabolism, Ketoses pharmacology, Leukemia, T-Cell drug therapy, Molecular Structure, Stereoisomerism, Tryptamines chemistry, Tryptamines metabolism, Tryptophan analogs & derivatives, Tryptophan chemistry, Tryptophan isolation & purification, Tryptophan metabolism, Tryptophan pharmacology, Anti-Bacterial Agents pharmacology, Antineoplastic Agents pharmacology, Aquatic Organisms metabolism, Indole Alkaloids isolation & purification, Indole Alkaloids pharmacology, Tryptamines isolation & purification, Tryptamines pharmacology, Urochordata metabolism
- 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.
- Published
- 2012
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