Estrogenic Activity of Chemical Constituents from Tephrosia candida.

MEF Hegazy; El-Hamd H. Mohamed Abou; Ali M. El-Halawany; Pierre C. Djemgou; Abdelaaty A. Shahat; Paul Pare

doi:10.1021/np100378d

Estrogenic Activity of Chemical Constituents from Tephrosia candida.

MEF Hegazy, El-Hamd H. Mohamed Abou, Ali M. El-Halawany, Pierre C. Djemgou, Abdelaaty A. Shahat, Paul Pare

Research output: Contribution to journal › Article

Abstract

In a continued investigation of medicinal plants from the genus Tephrosia, phytochemical analysis of a methylene chloridemethanol (1:1) extract of the air-dried aerial parts of Tephrosia candida afforded two new 8-prenylated flavonoids, namely, tephrocandidins A (1) and B (2), a new prenylated chalcone, candidachalcone (3), a new sesquiterpene (4), and a previously reported pea flavonoid phytoalexin, pisatin (5). The structures of 14 were established by spectroscopic methods, including HREIMS, and 1H, 13C, DEPT, HMQC, and HMBC NMR experiments. The most potent estrogenic activity of these isolated natural products in an estrogen receptor (ERR) competitive-binding assay was for 3, which exhibited an IC50 value of 80 μM, compared with 18 nM for the natural steroid 17β-estradiol. Results were interpreted via virtual docking of isolated compounds to an ERR crystal structure.

Original language	English
Pages (from-to)	937-942
Journal	Journal Natural Products
DOIs	https://doi.org/10.1021/np100378d
State	Published - Apr 21 2011

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Hegazy, MEF., Abou, E-H. H. M., El-Halawany, A. M., Pierre C. Djemgou, Shahat, A. A., & Pare, P. (2011). Estrogenic Activity of Chemical Constituents from Tephrosia candida. Journal Natural Products, 937-942. https://doi.org/10.1021/np100378d

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title = "Estrogenic Activity of Chemical Constituents from Tephrosia candida.",

abstract = "In a continued investigation of medicinal plants from the genus Tephrosia, phytochemical analysis of a methylene chloridemethanol (1:1) extract of the air-dried aerial parts of Tephrosia candida afforded two new 8-prenylated flavonoids, namely, tephrocandidins A (1) and B (2), a new prenylated chalcone, candidachalcone (3), a new sesquiterpene (4), and a previously reported pea flavonoid phytoalexin, pisatin (5). The structures of 14 were established by spectroscopic methods, including HREIMS, and 1H, 13C, DEPT, HMQC, and HMBC NMR experiments. The most potent estrogenic activity of these isolated natural products in an estrogen receptor (ERR) competitive-binding assay was for 3, which exhibited an IC50 value of 80 μM, compared with 18 nM for the natural steroid 17β-estradiol. Results were interpreted via virtual docking of isolated compounds to an ERR crystal structure.",

author = "MEF Hegazy and Abou, {El-Hamd H. Mohamed} and El-Halawany, {Ali M.} and {Pierre C. Djemgou} and Shahat, {Abdelaaty A.} and Paul Pare",

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doi = "10.1021/np100378d",

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AU - Hegazy, MEF

AU - Abou, El-Hamd H. Mohamed

AU - El-Halawany, Ali M.

AU - Pierre C. Djemgou,

AU - Shahat, Abdelaaty A.

AU - Pare, Paul

PY - 2011/4/21

Y1 - 2011/4/21

N2 - In a continued investigation of medicinal plants from the genus Tephrosia, phytochemical analysis of a methylene chloridemethanol (1:1) extract of the air-dried aerial parts of Tephrosia candida afforded two new 8-prenylated flavonoids, namely, tephrocandidins A (1) and B (2), a new prenylated chalcone, candidachalcone (3), a new sesquiterpene (4), and a previously reported pea flavonoid phytoalexin, pisatin (5). The structures of 14 were established by spectroscopic methods, including HREIMS, and 1H, 13C, DEPT, HMQC, and HMBC NMR experiments. The most potent estrogenic activity of these isolated natural products in an estrogen receptor (ERR) competitive-binding assay was for 3, which exhibited an IC50 value of 80 μM, compared with 18 nM for the natural steroid 17β-estradiol. Results were interpreted via virtual docking of isolated compounds to an ERR crystal structure.

AB - In a continued investigation of medicinal plants from the genus Tephrosia, phytochemical analysis of a methylene chloridemethanol (1:1) extract of the air-dried aerial parts of Tephrosia candida afforded two new 8-prenylated flavonoids, namely, tephrocandidins A (1) and B (2), a new prenylated chalcone, candidachalcone (3), a new sesquiterpene (4), and a previously reported pea flavonoid phytoalexin, pisatin (5). The structures of 14 were established by spectroscopic methods, including HREIMS, and 1H, 13C, DEPT, HMQC, and HMBC NMR experiments. The most potent estrogenic activity of these isolated natural products in an estrogen receptor (ERR) competitive-binding assay was for 3, which exhibited an IC50 value of 80 μM, compared with 18 nM for the natural steroid 17β-estradiol. Results were interpreted via virtual docking of isolated compounds to an ERR crystal structure.

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