Anthelmintic flavonoids and other compounds from Combretum glutinosum Perr. ex DC (Combretaceae) leaves

Abstract

A chemical study of the hydro-ethanol extract of the leaves of Combretum glutinosum resulted in the isolation of nine compounds, including 5-demethylsinensetin (1), umuhengerin (2), (20S,24R)-ocotillone (3), lupeol (4), β-sitosterol (5), oleanolic acid (6), betulinic acid (7), corymbosin (8) and β-sitosterol glucoside (9). Four compounds have been isolated for the first time from the genus Combretum [viz. (1), (2), (3) and (8)]. The crystal structures of flavonoid (2), C20H20O8, Z′ = 2, and triterpene (3), C30H50O3, Z′ = 1, have been determined for the first time; the latter confirmed the absolute configuration of native (20S,24R)-ocotillone previously derived from the crystal structures of related derivatives. The molecules of (3) are linked into supramolecular chains by intermolecular O—H...O hydrogen bonds. The crude extracts obtained by aqueous decoction and hydro-ethanolic maceration, as well as the nine isolated compounds, were tested for their anthelmintic activity on the larvae and adult worms of Haemonchus contortus, a hematophage that causes parasitic disorders in small ruminants. The evaluated anthelmintic activity showed that the extracts at different doses, as well as all the compounds tested at 150 µg ml−1, inhibited the migration of the larvae and the motility of the adult worms of the parasite compared with the phosphate buffer solution negative reference control. The best activity was obtained with flavonoids (1), (2) and (8) on both stages of the parasite. The flavones that showed good activity can be used for the further development of other derivatives, which could increase the anthelmintic efficacy.

Computational evaluation of potential ACE1 inhibitors from selected antihypertensive plants

“…The bioactive compounds used in this study were retrieved from literature where the medicinal plants of interest had been characterized (Akoh et al 2021;Edewor and Olajire 2011;Fadeyi et al 2015;Toklo et al 2021). The PubChem compound database was used to retrieve the chemical composition of the bioactive compounds (Balogun et al 2021).…”

Natural products as anthelmintics: safeguarding animal health

“…45 Flavones from the West African medicinal plant Combretum glutinosum (Combretaceae) capable of inhibiting the motility of adult H. contortus include 5-desmethylsinensetin (3.45) (EC 75 150 mg mL −1 ), umuhengerin (3.46) (EC 53 150 mg mL −1 ) and corymbosin (3.47) (EC 48 150 mg mL −1 ). 77 An H. contortus egg hatch inhibition bioassay guided fractionation of the Mexican medicinal plant Bacharis conferta (Asteraceae)traditionally used as fodder for farm animalsled to the isolation of isokaempferide 3.48 (LC 50 80 mg mL −1 at 48 h). 78 A similar fractionation of leaves from the Mexican smooth mesquite tree Prosopis laevigata (Fabaceae) yielded the H. contortus egg hatching inhibitor isorhamnetin (3.49) (EC 100 70 mg mL −1 at 48 h), although 3.49 proved inactive when tested against H. contortus L3 larvae (LC 50 > 1000 mg mL −1 ).…”

“…Flavones from the West African medicinal plant Combretum glutinosum (Combretaceae) capable of inhibiting the motility of adult H. contortus include 5-desmethylsinensetin ( 3.45 ) (EC 75 150 μg mL −1 ), umuhengerin ( 3.46 ) (EC 53 150 μg mL −1 ) and corymbosin ( 3.47 ) (EC 48 150 μg mL −1 ). 77…”

Ethnomedicinal Information on Plants Used for the Treatment of Bone Fractures, Wounds, and Sprains in the Northern Region of the Republic of Benin

“…Te seed oil is used as fuel and lubricant [26,27] Ceibapentains A and B, linarin, 3,4-dihydroxybenzoic acid, cinchonains ia and ib, N-trans-cafeoyl-DOPA-methyl ester, monoterpene, and sesquiterpene hydrocarbons [28,29] Chasmanthera dependens Hochst Treatment of venereal diseases, fractures, sprains, muscular pains (leaves) and is used as uterine stimulant [30] Berberine [30], tertiary nonphenolic alkaloids (tetrahydropalmatine, liriodenine, lysicamine, oxoglaucine, glaucine, anonaine, nornuciferine, norglaucine, O,O-dimethylcorytuberine, and anomaine), govanine (� (−) -tetrahydropseudocolumbamine), coreximine, bisnorargemonine, pallidine, and quaternary alkaloids (jatrorrhizine, columbamine, pseudocolumbamine, magnoforine, and palmatine) [31,32] Combretum collinum Fresen Treatment of wounds, ulcers, rheumatism, microbial infections, gastrointestinal problems, cough, and bronchitis with the leaves [33] Myricetin-3-O-rhamnoside, myricetin-3-O-glucoside stilbenoids (combretastatins), phenanthrenes, and mollic acid [33] Combretum glutinosum Perr. Ex DC Treatment of scrotal elephantiasis, dysentery, typhoid fever, eye sore and earache, fever, stomachache malaria, diarrhoea, ring worms, bronchitis, hypertension, and syphilis [34,35] 2,3-(5′)-Hexahydroxydiphenoyl-D-glucose, punicalin, punicalagin, umuhengerin and combreglutinin, betulinic acid, β-sitosterol glucoside, 5-demethylsinensetin, (20S,24R)-ocotillone, lupeol, β-sitosterol, oleanolic acid, and corymbosin [35] Combretum sericeum G.Don Treatment of diarrhoea, gastrointestinal disorders, conjunctivitis, fever, pneumonia, malaria, and use as repellent [36,37] -Crossopteryx febrifuga (Afzel. ex G.Don) Bents Treatment of dysentery, diarrhoea and fever [38], pain, malaria, septic wounds, and respiratory infections [39] Epimeric mixtures of 3β-urs-12,20(30)-diene-27,28-dioic acid and 18epi-3β-urs-12,20(30)-diene-27,28-dioic acid, 3β-D-glucopyranosylurs-12,20(30)-diene-27,28-dioic acid and 18-epi-3β-D-glucopyranosylurs-12,20(30)-diene-27,28-dioic acid, triterpenoid (β-chinovin), vitexin and isovitexin xylosides, quercetin-3-rutinoside, and alkaloids (crossopterine) [40] Eleusine indica (L.) Gaertn Use as diuretic, anthelmintic, febrifuge, diaphoretic, and treatment of cough [41] Flavonoids schaftoside, vitexin, isovitexin, and 6′-O-palmitoyl derivatives, β-sitosterol, β-sitosterol glucoside, and stigmasterol [42] Evidence-Based Complementary and Alternative Medicine Flueggea virosa, (Roxb.…”