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

Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C(2)-α-D-mannosylpyranosyl-L-tryptophan (3). The structure of 1 was assigned on the basis of spectroscopic data for 1 and i...

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Autores principales: Yamazaki, Hiroyuki, Wewengkang, Defny S., Nishikawa, Teruaki, Rotinsulu, Henki, Mangindaan, Remy E. P., Namikoshi, Michio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297002/
https://www.ncbi.nlm.nih.gov/pubmed/22412806
http://dx.doi.org/10.3390/md10020349
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author Yamazaki, Hiroyuki
Wewengkang, Defny S.
Nishikawa, Teruaki
Rotinsulu, Henki
Mangindaan, Remy E. P.
Namikoshi, Michio
author_facet Yamazaki, Hiroyuki
Wewengkang, Defny S.
Nishikawa, Teruaki
Rotinsulu, Henki
Mangindaan, Remy E. P.
Namikoshi, Michio
author_sort Yamazaki, Hiroyuki
collection PubMed
description Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C(2)-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.
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spelling pubmed-32970022012-03-12 Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius Yamazaki, Hiroyuki Wewengkang, Defny S. Nishikawa, Teruaki Rotinsulu, Henki Mangindaan, Remy E. P. Namikoshi, Michio Mar Drugs Article Two new tryptamine-derived alkaloids, named as leptoclinidamide (1) and (-)-leptoclinidamine B (2), were isolated from an Indonesian ascidian Leptoclinides dubius together with C(2)-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. MDPI 2012-02-10 /pmc/articles/PMC3297002/ /pubmed/22412806 http://dx.doi.org/10.3390/md10020349 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Yamazaki, Hiroyuki
Wewengkang, Defny S.
Nishikawa, Teruaki
Rotinsulu, Henki
Mangindaan, Remy E. P.
Namikoshi, Michio
Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title_full Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title_fullStr Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title_full_unstemmed Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title_short Two New Tryptamine Derivatives, Leptoclinidamide and (-)-Leptoclinidamine B, from an Indonesian Ascidian Leptoclinides dubius
title_sort two new tryptamine derivatives, leptoclinidamide and (-)-leptoclinidamine b, from an indonesian ascidian leptoclinides dubius
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297002/
https://www.ncbi.nlm.nih.gov/pubmed/22412806
http://dx.doi.org/10.3390/md10020349
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