InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+ |
PACBGANPVNHGNP-RUDMXATFSA-N |
COc1cc(O)ccc1C(=O)\C=C\c1ccc(O)cc1 |
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Caesalpinia sappan
(NCBI:txid483143)
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Found in
heartwood
(PO:0004512).
Methanolic extract of dried heart wood of C.sappan(Caesalpinia001)
See:
PubMed
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metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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View more via ChEBI Ontology
(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
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2'-O-methylisoliquiritigenin
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UniProt
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4,4'-dihydroxy-2'-methoxychalcone
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ChEMBL
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3060129
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Reaxys Registry Number
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Reaxys
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Lai WC, Wang HC, Chen GY, Yang JC, Korinek M, Hsieh CJ, Nozaki H, Hayashi K, Wu CC, Wu YC, Chang FR (2011) Using the pER8:GUS reporter system to screen for phytoestrogens from Caesalpinia sappan. Journal of natural products 74, 1698-1706 [PubMed:21800859] [show Abstract] Arabidopsis thaliana pER8:GUS, a low-cost, highly efficient, and convenient transgenic plant system, was used to assay the estrogen-like activity of 30 traditional Chinese medicines. The MeOH extract of Caesalpinia sappan exhibited significant bioactivity in this assay, and subsequent bioactivity-guided fractionation of the extract led to the isolation of one new compound, (S)-3,7-dihydroxychroman-4-one (1), and 10 known compounds. Both the plant pER8:GUS and in vitro estrogen response element reporter assays were used to evaluate the estrogenic activity of the isolated compounds, and these two systems produced comparable results. Compounds 6, 8, and 11 showed significant estrogenic activity comparable to genistein. These active compounds were determined to be nontoxic new sources of phytoestrogens. In addition, compounds 2 and 3 inhibited ERE transcription induced by 17β-estradiol. A docking model revealed that compounds 6, 8, and 11 showed high affinity to the estrogen receptor. The pER8:GUS reporter system was demonstrated to be a useful and effective technique in phytoestrogen discovery. |
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