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Longeracemosones A–F, Aromatase Inhibitors from Dunbaria longeracemosa
Author(s) -
Prachyawarakorn Vilailak,
Mahidol Chulabhorn,
Ruchirawat Somsak
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100410
Subject(s) - chemistry , aromatase , stereochemistry , antioxidant , chemical transformation , organic chemistry , medicine , cancer , breast cancer
Six dihydroflavonols, longeracemosones A–F ( 1 – 6 ), together with two known flavonoids, mundulinol ( 7 ) and sericetin ( 8 ), have been isolated from Dunbaria longeracemosa . The structures of the isolated compounds were elucidated by spectroscopic analysis and the absolute configurations were determined by analysis of the CD spectra and by the modified Mosher's method. A novel conversion of the linear chromene in 1 to the angular chromene in 2 was observed and the mechanism of this unique transformation is proposed. The isolated compounds were evaluated for their cytotoxic and antioxidant activity and compounds 3 , 4 , and 7 exhibited potent aromatase inhibitory activity with IC 50 values of 0.3, 0.4, and 1.2 μ M , respectively.