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Mar. Drugs 2012, 10(2), 349-357; doi:10.3390/md10020349
Article

Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius

1
,
1,2
,
3
,
1
,
2
 and
1,*
1 Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Komatsushima, Aoba-ku, Sendai 981-8558, Japan 2 Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia 3 Laboratory of Taxonomy, Department of Biology, Faculty of Science, Toho University, Miyama, Funabashi 274-8510, Japan
* Author to whom correspondence should be addressed.
Received: 27 December 2011 / Revised: 23 January 2012 / Accepted: 7 February 2012 / Published: 10 February 2012
(This article belongs to the Special Issue Alkaloid Analogs)
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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: leptoclinidamide; leptoclinidamine; tryptamine; alkaloid; Indonesian ascidian; Leptoclinides dubius leptoclinidamide; leptoclinidamine; tryptamine; alkaloid; Indonesian ascidian; Leptoclinides dubius
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Yamazaki, H.; Wewengkang, D.S.; Nishikawa, T.; Rotinsulu, H.; Mangindaan, R.E.P.; Namikoshi, M. Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius. Mar. Drugs 2012, 10, 349-357.

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