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 chloride-methanol (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 1-4 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 (ERα) 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 ERα crystal structure.
authors.affiliation: Chemistry of Medicinal Plants Department, and Center of Excellence for Advanced Sciences, National Research Centre, El-Tahrir Street, Dokki, Giza, 12622, Egypt.
authors.forename: Mohamed-Elamir F
authors.initials: ME
authors.lastname: Hegazy
authors.forename: Abou
authors.initials: A
authors.lastname: El-Hamd H Mohamed
authors.forename: Ali M
authors.initials: AM
authors.lastname: El-Halawany
authors.forename: Pierre C
authors.initials: PC
authors.lastname: Djemgou
authors.forename: Abdelaaty A
authors.initials: AA
authors.lastname: Shahat
authors.forename: Paul W
authors.initials: PW
authors.lastname: Paré
mesh_terms: D002163:Cameroon; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D047628:Estrogen Receptor alpha / Q000187:drug effects; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D048789:Phytoestrogens / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D036343:Pterocarpans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D031304:Tephrosia / Q000737:chemistry*; D000094162:Phytoalexins
chemical_list: D047188:Chalcones; D047628:Estrogen Receptor alpha; D005419:Flavonoids; D048789:Phytoestrogens; D036343:Pterocarpans; D012717:Sesquiterpenes; C560114:1beta-hydroxy-6,7alpha-dihydroxyeudesm-4(15)-ene; C506487:ESR1 protein, human; C560113:candidachalcone; C560111:tephrocandidin A; C560112:tephrocandidin B; C003161:pisatin; D000094162:Phytoalexins