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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...

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Detalles Bibliográficos
Autores principales: Kohyama, Aki, Yamakoshi, Hiroyuki, Hongo, Shoko, Kanoh, Naoki, Shibata, Hiroyuki, Iwabuchi, Yoshiharu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
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.
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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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