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.
Keywords:
Indonesian ascidian; Leptoclinides dubius; alkaloid; leptoclinidamide; leptoclinidamine; tryptamine.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetylation
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Alkaloids / chemistry
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Alkaloids / isolation & purification
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Alkaloids / metabolism
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Alkaloids / pharmacology
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Animals
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / metabolism
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Anti-Bacterial Agents / pharmacology*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / isolation & purification
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology*
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Aquatic Organisms / metabolism*
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Cell Line, Tumor
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Colonic Neoplasms / drug therapy
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Drug Discovery
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Escherichia coli / drug effects
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Humans
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Indian Ocean
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Indole Alkaloids / chemistry
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Indole Alkaloids / isolation & purification*
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Indole Alkaloids / metabolism
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Indole Alkaloids / pharmacology*
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Indonesia
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Jurkat Cells
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Ketoses / chemistry
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Ketoses / isolation & purification
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Ketoses / metabolism
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Ketoses / pharmacology
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Leukemia, T-Cell / drug therapy
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Molecular Structure
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Stereoisomerism
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Tryptamines / chemistry
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Tryptamines / isolation & purification*
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Tryptamines / metabolism
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Tryptamines / pharmacology*
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Tryptophan / analogs & derivatives
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Tryptophan / chemistry
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Tryptophan / isolation & purification
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Tryptophan / metabolism
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Tryptophan / pharmacology
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Urochordata / metabolism*
Substances
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2-(mannopyranosyl)-tryptophan
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Alkaloids
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Anti-Bacterial Agents
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Antineoplastic Agents
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Indole Alkaloids
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Ketoses
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Tryptamines
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leptoclinidamide
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leptoclinidamine B
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Tryptophan