Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation
Three new diarylheptanoids, a 1:2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene (9) and 1-(4-hydroxyphenyl)...
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th-mahidol.188922018-07-12T09:50:35Z Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation Apichart Suksamrarn Mathurose Ponglikitmongkol Kanjana Wongkrajang Anon Chindaduang Suthadta Kittidanairak Aroon Jankam Boon ek Yingyongnarongkul Narin Kittipanumat Ratchanaporn Chokchaisiri Pichit Khetkam Pawinee Piyachaturawat Ramkhamhaeng University Mahidol University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics Three new diarylheptanoids, a 1:2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene (9) and 1-(4-hydroxyphenyl)-7-phenyl-(4E,6E)-4,6-heptadien-3-one (16), and nine known diarylheptanoids, 2, 8, 10-12, 14, a 3:1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ERβ gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an olefinic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1-position of the heptyl chain. © 2008 Elsevier Ltd. All rights reserved. 2018-07-12T02:17:58Z 2018-07-12T02:17:58Z 2008-07-15 Article Bioorganic and Medicinal Chemistry. Vol.16, No.14 (2008), 6891-6902 10.1016/j.bmc.2008.05.051 09680896 2-s2.0-47349084839 https://repository.li.mahidol.ac.th/handle/123456789/18892 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=47349084839&origin=inward |
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Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics Apichart Suksamrarn Mathurose Ponglikitmongkol Kanjana Wongkrajang Anon Chindaduang Suthadta Kittidanairak Aroon Jankam Boon ek Yingyongnarongkul Narin Kittipanumat Ratchanaporn Chokchaisiri Pichit Khetkam Pawinee Piyachaturawat Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
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Three new diarylheptanoids, a 1:2 mixture of (3S)- and (3R)-1-(4-methoxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol (13a and 13b) and 1-(4-hydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-one (15), together with two synthetically known diarylheptanoids 1,7-diphenyl-(1E,3E,5E)-1,3,5-triene (9) and 1-(4-hydroxyphenyl)-7-phenyl-(4E,6E)-4,6-heptadien-3-one (16), and nine known diarylheptanoids, 2, 8, 10-12, 14, a 3:1 mixture of 17a and 17b, and 18, were isolated from the rhizomes of Curcuma comosa Roxb. The absolute stereochemistry of the isolated compounds has also been determined using the modified Mosher's method. The isolated compounds and the chemically modified analogues were evaluated for their estrogenic-like transcriptional activity using RT-PCR in HeLa cell line. Some of the isolated diarylheptanoids and their modified analogues exhibited estrogenic activity comparable to or higher than that of the phytoestrogen genistein. Based on the transcriptional activation of both estrogenic targets, Bcl-xL and ERβ gene expression, the structural features for a diarylheptanoid to exhibit high estrogenic activity are the presence of an olefinic function conjugated with the aromatic ring at the 7-position, a keto group at the 3-position, and a phenolic hydroxyl group at the p-position of the aromatic ring attached to the 1-position of the heptyl chain. © 2008 Elsevier Ltd. All rights reserved. |
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Ramkhamhaeng University |
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Ramkhamhaeng University Apichart Suksamrarn Mathurose Ponglikitmongkol Kanjana Wongkrajang Anon Chindaduang Suthadta Kittidanairak Aroon Jankam Boon ek Yingyongnarongkul Narin Kittipanumat Ratchanaporn Chokchaisiri Pichit Khetkam Pawinee Piyachaturawat |
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Apichart Suksamrarn Mathurose Ponglikitmongkol Kanjana Wongkrajang Anon Chindaduang Suthadta Kittidanairak Aroon Jankam Boon ek Yingyongnarongkul Narin Kittipanumat Ratchanaporn Chokchaisiri Pichit Khetkam Pawinee Piyachaturawat |
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Apichart Suksamrarn |
title |
Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
title_short |
Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
title_full |
Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
title_fullStr |
Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
title_full_unstemmed |
Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation |
title_sort |
diarylheptanoids, new phytoestrogens from the rhizomes of curcuma comosa: isolation, chemical modification and estrogenic activity evaluation |
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2018 |
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https://repository.li.mahidol.ac.th/handle/123456789/18892 |
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1763491548143550464 |