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Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata

Two new nitrogen-containing verticillene diterpenoids, cespilamides A and B (1 and 2), three new nitrogen-containing sesquiterpenoids, cespilamides C–E (3–5), and five new norverticillene and verticillene diterpenoids, cespitaenins A–E (6–10), were isolated from the Taiwanese soft coral Cespitularia...

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Autores principales: Wang, Shih-Sheng, Cheng, Yuan-Bin, Lin, Yu-Chi, Liaw, Chia-Ching, Chang, Jiun-Yang, Kuo, Yao-Haur, Shen, Ya-Ching
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4584355/
https://www.ncbi.nlm.nih.gov/pubmed/26389921
http://dx.doi.org/10.3390/md13095796
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author Wang, Shih-Sheng
Cheng, Yuan-Bin
Lin, Yu-Chi
Liaw, Chia-Ching
Chang, Jiun-Yang
Kuo, Yao-Haur
Shen, Ya-Ching
author_facet Wang, Shih-Sheng
Cheng, Yuan-Bin
Lin, Yu-Chi
Liaw, Chia-Ching
Chang, Jiun-Yang
Kuo, Yao-Haur
Shen, Ya-Ching
author_sort Wang, Shih-Sheng
collection PubMed
description Two new nitrogen-containing verticillene diterpenoids, cespilamides A and B (1 and 2), three new nitrogen-containing sesquiterpenoids, cespilamides C–E (3–5), and five new norverticillene and verticillene diterpenoids, cespitaenins A–E (6–10), were isolated from the Taiwanese soft coral Cespitularia taeniata. Compound 1 possesses an unusual oxazo ring system at C-10 while compound 2 displays an unprecedented C–C bond cleavage between C-10 and C-11 with an N-ethylphenyl group at C-10. Biogenetic pathways of 1 and 2 are proposed. The absolute configuration of 1 was confirmed by Mosher’s method and molecular mechanics calculations (MM2). The cytotoxicities of compounds 1–10 were evaluated against a small panel of human cancer cell lines.
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spelling pubmed-45843552015-10-05 Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata Wang, Shih-Sheng Cheng, Yuan-Bin Lin, Yu-Chi Liaw, Chia-Ching Chang, Jiun-Yang Kuo, Yao-Haur Shen, Ya-Ching Mar Drugs Article Two new nitrogen-containing verticillene diterpenoids, cespilamides A and B (1 and 2), three new nitrogen-containing sesquiterpenoids, cespilamides C–E (3–5), and five new norverticillene and verticillene diterpenoids, cespitaenins A–E (6–10), were isolated from the Taiwanese soft coral Cespitularia taeniata. Compound 1 possesses an unusual oxazo ring system at C-10 while compound 2 displays an unprecedented C–C bond cleavage between C-10 and C-11 with an N-ethylphenyl group at C-10. Biogenetic pathways of 1 and 2 are proposed. The absolute configuration of 1 was confirmed by Mosher’s method and molecular mechanics calculations (MM2). The cytotoxicities of compounds 1–10 were evaluated against a small panel of human cancer cell lines. MDPI 2015-09-15 /pmc/articles/PMC4584355/ /pubmed/26389921 http://dx.doi.org/10.3390/md13095796 Text en © 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Shih-Sheng
Cheng, Yuan-Bin
Lin, Yu-Chi
Liaw, Chia-Ching
Chang, Jiun-Yang
Kuo, Yao-Haur
Shen, Ya-Ching
Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title_full Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title_fullStr Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title_full_unstemmed Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title_short Nitrogen-Containing Diterpenoids, Sesquiterpenoids, and Nor-Diterpenoids from Cespitularia taeniata
title_sort nitrogen-containing diterpenoids, sesquiterpenoids, and nor-diterpenoids from cespitularia taeniata
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4584355/
https://www.ncbi.nlm.nih.gov/pubmed/26389921
http://dx.doi.org/10.3390/md13095796
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