Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity. (January 2020)

• Record Type: Journal Article
• Authors: Panthong, Kanda; Hongthong, Sakchai; Kuhakarn, Chutima; Piyachaturawat, Pawinee; Suksen, Kanoknetr; Panthong, Ampai; Chiranthanut, Natthakarn; Kongsaeree, Palangpon; Prabpai, Samran; Nuntasaen, Narong; Reutrakul, Vichai
• Is Part Of: Phytochemistry. Volume 169(2020)
• Publication Date: 2020-01
• Subjects: Ventilago harmandiana -- Rhamnaceae -- Pyranonaphthoquinone -- Anthraquinone -- Anti-inflammatory; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.112182
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: 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. Graphical abstract: Ten undescribed pyranonaphthoquinones and an undescribed anthraquinone were isolated from the heartwood of Ventilago harmandiana (Rhamnaceae). The structure of compound 1 was elucidated by single crystal X-ray crystallographic analysis of its p -bromobenzenesulfonate ester derivative 1a . Image 1 Highlights: Investigation of Ventilago harmandiana plant was reported for the first time. Ten undescribed pyranonaphthoquinones and an undescribed anthraquinone were discovered. Structures were elucidated using NMR, X-ray and ECD. Ventilanones A and C displayed moderate cytotoxic activity. Ventilanones A and D exhibited promising anti-inflammatory activity.