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Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030
1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C(5)-curcumin. Intrigued by the potent antitumor activity of C(5)-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, t...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332050/ https://www.ncbi.nlm.nih.gov/pubmed/26305242 http://dx.doi.org/10.3390/molecules200815374 |
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author | Kohyama, Aki Yamakoshi, Hiroyuki Hongo, Shoko Kanoh, Naoki Shibata, Hiroyuki Iwabuchi, Yoshiharu |
author_facet | Kohyama, Aki Yamakoshi, Hiroyuki Hongo, Shoko Kanoh, Naoki Shibata, Hiroyuki Iwabuchi, Yoshiharu |
author_sort | Kohyama, Aki |
collection | PubMed |
description | 1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C(5)-curcumin. Intrigued by the potent antitumor activity of C(5)-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C(5)-curcuminoids], we previously conducted a structure–activity relationship study of C(5)-curcuminoids and showed that highly active GO-Y030 [1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one (4)] is the most promising antitumor compound. In this study, a panel of C(5)-curcuminoids based on GO-Y030, consisting of 30 new and 10 known compounds, was synthesized to elucidate in detail which moiety of GO-Y030 is significant for antitumor activity. The results confirmed that both the cross-conjugated dienone moiety and the 3,5-bis(methoxymethoxy) substituent are important for the antitumor activity. |
format | Online Article Text |
id | pubmed-6332050 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-63320502019-01-24 Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 Kohyama, Aki Yamakoshi, Hiroyuki Hongo, Shoko Kanoh, Naoki Shibata, Hiroyuki Iwabuchi, Yoshiharu Molecules Article 1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C(5)-curcumin. Intrigued by the potent antitumor activity of C(5)-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C(5)-curcuminoids], we previously conducted a structure–activity relationship study of C(5)-curcuminoids and showed that highly active GO-Y030 [1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one (4)] is the most promising antitumor compound. In this study, a panel of C(5)-curcuminoids based on GO-Y030, consisting of 30 new and 10 known compounds, was synthesized to elucidate in detail which moiety of GO-Y030 is significant for antitumor activity. The results confirmed that both the cross-conjugated dienone moiety and the 3,5-bis(methoxymethoxy) substituent are important for the antitumor activity. MDPI 2015-08-24 /pmc/articles/PMC6332050/ /pubmed/26305242 http://dx.doi.org/10.3390/molecules200815374 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 Kohyama, Aki Yamakoshi, Hiroyuki Hongo, Shoko Kanoh, Naoki Shibata, Hiroyuki Iwabuchi, Yoshiharu Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title | Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title_full | Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title_fullStr | Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title_full_unstemmed | Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title_short | Structure-Activity Relationships of the Antitumor C(5)-Curcuminoid GO-Y030 |
title_sort | structure-activity relationships of the antitumor c(5)-curcuminoid go-y030 |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332050/ https://www.ncbi.nlm.nih.gov/pubmed/26305242 http://dx.doi.org/10.3390/molecules200815374 |
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