Four new C-benzyl flavonoids from the fruit of Uvaria cherrevensis

Abstract

The phytochemical investigation of the fruit extracts of Uvaria cherrevensis led to the isolation and characterization of four new C-benzyl flavonoids; cherrevenones A-D (1-4) together with 11 known compounds. The isolated compounds were characterized using spectroscopic techniques. Compounds 1, 3, 5 and 11 showed moderate inhibitory activities against the P. falciparum strains TM4/8.2 and K1CB1 with IC values ranging from 21.0 ± 3.10 - 33.7 ± 7.69 and 21.0 ± 5.44 - 43.5 ± 11.9 μM, respectively. Compounds 1, 2, 5, 10 and 11 exhibited strong cytotoxic activities against KB cells with IC values ranging from 0.60 ± 0.17 - 4.91 ± 2.69 μM which were similar to their cytotoxic activities found against Vero cells, except for compound 5, which was non-toxic to Vero cells.

Structure elucidation of cyclohexene (9Z)-octadec-9-enyl ethers isolated from the leaves of Uvaria cherrevensis (Annonaceae)

“…2 Previous studies on U. cherrevensis, Annonaceae family, found various types of secondary metabolites, including alkaloids, cyclohexenes, flavonoids, naphthalene derivatives, and terpenoids. [3][4][5][6][7][8] We report here the first isolation of cyclohexene (9Z)-octadec-9-enyl ethers, cherrevenols M-O (1)(2)(3), from the leaf extracts of U. cherrevensis. The application of 13 C NMR and Ozone Induced Dissociation (OzID) mass spectrometry were used to determine the (Z) configuration and C-9 position of the olefinic moiety of the C-18 ether side chains, respectively.…”

“…Antimalarial activity against Plasmodium falciparum TM4/8.2 (a wild type sensitive strain) and K1CB1 (multidrug resistant strain) was carried out as described in a previous report. 6 The cytotoxicity against normal Vero cells (kidney epithelial cells of African green monkey, Cercopithecus aethiops) and KB cells (human mouth epidermal carcinoma cells) were also carried out as previously described. 6…”

“…6 The cytotoxicity against normal Vero cells (kidney epithelial cells of African green monkey, Cercopithecus aethiops) and KB cells (human mouth epidermal carcinoma cells) were also carried out as previously described. 6…”

(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).…”

Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones

“…Enamino ketones 2a-2o are colorless crystalline solids that are stable on storage. They can be used as building blocks for the synthesis of various trifluoromethyl-substituted carbo-and heterocycles containing a (2-hydroxynaphthalen-1-yl)methyl or 2-hydroxybenzyl group, the latter being a structural fragment of many natural compounds [34][35][36].…”