Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity
Kanda Panthong, Sakchai Hongthong, Chutima Kuhakarn, Pawinee Piyachaturawat, Kanoknetr Suksen, Ampai Panthong, Natthakarn Chiranthanut, Palangpon Kongsaeree, Samran Prabpai, Narong Nuntasaen, Vichai Reutrakul
The chemical study on the heartwoods extract of Ventilago harmandiana (Rhamnaceae) resulted in the isolation of ten previously undescribed pyranonaphthoquinones (ventilanones A−J), an undescribed anthraquinone (ventilanone K), together with eight known anthraquinone derivatives. Their structures were elucidated by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone A was established from single crystal X-ray crystallographic analysis of its p-bromobenzenesulfonate ester derivative using Cu Kα radiation. The absolute configurations of the other related compounds were identified by comparison of their ECD data with those of ventilanone A and related known compounds. Cytotoxic and anti-inflammatory activities of some of the isolated compounds were evaluated. Ventilanone A and ventilanone C exhibited moderate cytotoxicity against P-388 cell line. Ventilanone D exhibited significant anti-inflammatory activity while ventilanone A and ventilanone C showed moderate activity.
Absorption, Quantitation, Agriculture and environmental, Medicinal