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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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