Polyoxygenated Cyclohexenes and Their Chlorinated Derivatives from the Leaves of Uvaria cherrevensis

Abstract

The chemical study of leaf extracts from Uvaria cherrevensis resulted in the identification of 11 new polyoxygenated cyclohexenes, cherrevenols A–K (1–11), and a new seco-cyclohexene derivative, cherrevenol L (12). Nine known compounds (13–21) were also isolated. Three of the isolated compounds are chlorinated polyoxygenated cyclohexenes. The structures of these compounds were determined using spectroscopic methods and, in some cases (compounds 2, 6, 8, and 10), single-crystal X-ray crystallographic structural analysis or chemical correlation (compounds 6 and 7). Compounds 6 and 7 were both isolated as scalemic mixtures (ee 23–24%).

α-Glucosidase inhibitory activity of compounds isolated from the twig and leaf extracts of Desmos dumosus

“…The isolation and elucidation of EtOAc extracts of twigs and leaves from D. dumosus was purified by repeated chromatographic techniques to obtain fourteen flavonoids, a chalcone, two benzyl benzoates, two coumarins, eight aristolactam alkaloids, a seco-cyclohexenes, and a cyclohexenes compounds (Figure 4 [36], flexuvarin B (27) [37], cherrevenol A (28) [38], and benzoic acid (29) [39]. These structures were confirmed by comparisons of their spectroscopic and chemical properties with previously reported data.…”

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

“…Two new compounds 1 and 2 were obtained from the leaf extract, while three new compounds 3-5 were obtained from the flower extract. The known compounds were characterized by the comparison of their physical properties and spectroscopic data with the previous reports and identified as flexuvarin B (6) (Hsu et al, 2016), flexuvarin C (7) (Hsu et al, 2016), flexuvarin D (8) (Hsu et al, 2016), chrysin (9) (Meesakul et al, 2017), 5-hydroxy-7-methoxyflavone (tectochrysin) (10) (Righi et al, 2010), pinocembrin (11) (Meesakul et al, 2017), pinocembrin 7-O-benzoate (12) (Hoeneisen et al, 1993), 2 0 -hydroxy-4 0 ,6 0 -dibenzyloxychalcone (13) (Drewes and van Vuuren, 2008), zeylenone (14) (Suthiphasilp et al, 2019), 1R,6S-cherrevenol A (15) (Auranwiwat et al, 2019), and (À)-(5R)-desmoscochinoxepinone B (16) (Meesakul et al, 2019) (Figure 2).…”

(R)-3-(8'-Hydroxyfarnesyl)-indole and other chemical constituents from the flowers of Anomianthus dulcis and their antimalarial and cytotoxic activities

“…The crude extract and some secondary metabolites from this plant showed antibacterial (Ubonopas et al 2014;Kadchumsang et al 2015), anticancer, anti-Herpes Simplex Virus I (Ubonopas et al 2014), antispasmodic, (Wiya et al 2018) and antioxidant activities (Kadchumsang et al 2015). Furthermore, previous investigations of plants from the Uvaria genus have found several types of secondary metabolites such as polyoxygenated cyclohexenes (Ho et al 2015;Okpekon et al 2015;Hsu et al 2016;Auranwiwat et al 2017;Awale et al 2017;Auranwiwat et al 2019a;Auranwiwat et al 2019b), flavonoids (Salae et al 2017;Auranwiwat et al 2018), alkaloids (Auranwiwat et al 2018), naphthalenes (Auranwiwat et al 2017;Salae et al 2017), xanthenes (Macabeo et al 2014) and lignan glycosides (Nguyen et al 2015). Some of these chemical constituents have shown significant bioactivities, including anticancer (Macabeo et al 2014;Ho et al 2015;Awale et al 2017), anti-inflammatory (Hsu et al 2016), antimalarial (Auranwiwat et al 2017;Salae et al 2017), antimicrobial (Okpekon et al 2015), antiglycation and antioxidant activities (Thomas and Essien 2018).…”