Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity

• Main Authors: Kanda Panthong, Sakchai Hongthong, Chutima Kuhakarn, Pawinee Piyachaturawat, Kanoknetr Suksen, Ampai Panthong, Natthakarn Chiranthanut, Palangpon Kongsaeree, Samran Prabpai, Narong Nuntasaen, Vichai Reutrakul
• Format: Journal
• Published: 2020
• Subjects: Agricultural and Biological Sciences; Biochemistry, Genetics and Molecular Biology
• Online Access: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85073677804&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/68209
• Institution: Chiang Mai University

© 2019 Elsevier Ltd 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.