Farnesyl glycosides and one new triterpenoid saponin from the roots of Lecaniodiscus cupanioides Planch. ex Benth

Chemical investigation of the methanol extract of the roots of Lecaniodiscus cupanioides led to the isolation and characterisation of three new sesquiterpene glycosides, named cupanioidesosides A (1), B (2) and C (3), together with one new triterpenoid saponin named lecanioside A (4), Their structures were established by extensive analysis of spectroscopic methods including 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and HRESIMS. The four new compounds were evaluated for their antiproliferative activity against the Caco-2 cell line (human epithelial cell line). None of the isolated compounds showed positive activity in our assay. Our findings represent a valuable contribution to the chemotaxonomy Lecaniodiscus genus of the subfamily of Sapindoideae of Sapindaceae family, known to be a rich source of farnesol glycosides

Phenolic compounds from the roots of Ochna schweinfurthiana and their antioxidant and antiplasmodial activities

peer reviewedAn investigation of compounds extracted from Ochna schweinfurthiana roots with ethyl acetate led to the isolation of three new compounds 4‴-methoxylophirone A (1), 4,4′,4‴–trimethoxylophirone A (2) and (4E;7Z)-3,8-dicarboxy-1-(O-β-D-glucopyranosyl-(1 → 6)-O-β-D-glucopyranosyl-2,9-dihydroxyhexeicosa-4,7-diene (3). Six known compounds were also identified, including Calodenone (4), Calodenine B (5), Lophirone A (6), Gerontoisoflavone A(7), 16α,17-dihydroxy-ent-kauran-19-oic acid (8) and 3β-O-D-glucopyranosyl-β-sitosterol (9). This report describes the first time that compounds 4-8 have been isolated from this plant, while 8 has never been identified in the genus Ochna. Some of the isolated compounds were evaluated for their antiplasmodial activity against the chloroquine-sensitive Plasmodium falciparum strain 3D7 and antioxidant activity using DPPH radical scavenging and Ferric reducing-antioxidant power (FRAP) assays. Compound 5 exhibited prominent radical scavenging and FRAP activities, while 7 had weak activity. Compound 1 showed good in vitro anti-plasmodial activity. The structures of the isolated compounds were elucidated by spectroscopic methods and comparisons with prior data in the literature. © 2016 Phytochemical Society of Europ

Nitrile glucosides and serotobenine from Campylospermum glaucum and Ouratea turnarea

peer reviewedTwo nitrile glucosides (1S,3S,4S,5R)-4-benzoyloxy-2-cyanomethylene-3,5-dihydroxycyclohexyl-1-O-be ta-glucopyranoside (campyloside A) and (1S,3S,4S,5R)-5-benzoyloxy-2-cyanomethylene-3-hydroxy-4-(2-pyrrolcarboxylo xy)cyclohexyl-1-O-beta-glucopyranoside (campyloside B) were isolated from the stem roots of Campylospermum glaucum, whereas serotobenine was isolated from Ouratea turnarea. The structure elucidations were based on spectroscopic evidence. The biological assays of compounds and crude extract of plant species showed good antimicrobial activity of crude extracts against Gram-positive cocci

Triterpenoid saponins from Calliandra calothyrsus Meisn. and their antiproliferative activity against two digestive carcinoma human cell lines

The chemical investigation of the flowers and twigs of Calliandra calothyrsus (Fabaceae) led to the isolation of three new oleanane-type triterpenoid saponins, named calothyrsusosides A-C (1-3). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR and 2D NMR (H-1, H-1 NMR DOSY, C-13 NMR, COSY, HSQC, HMBC, HSQC-TOCSY and NOESY) and by comparison with literature data. Compounds 1 and 2 were tested for their antiproliferative activity against two digestive carcinoma human cell lines: Hep3B (hepatocellular carcinoma) and Caco-2 (epithelial colorectal adenocarcinoma). Both compounds exhibited an antiproliferative activity against the Hep3B cell line, with IC50 values of 6.0 and 6.5 mu M, respectively, while no effect was detected against the epithelial colorectal adenocarcinoma Caco-2 (CC50 > 25 mu M)

New triterpenoid saponin from the stems of Albizia adianthifolia (Schumach.) W.Wight

As part of our continuing study of apoptosis-inducing saponins from CameroonianAlbiziagenus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated fromAlbizia adianthifoliastems. The structure of the new saponin (1), was established on the basis of extensive analysis of 1 D and 2 D NMR (H-1-,C-13-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[beta-D-xylopyranosyl-(1 -> 2)-beta-D-fucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)octa-2,7-dienoyl]-(beta-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-beta-D-glucopyranosyl-(1 -> 3)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1 -> 4)]-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranosyl ester (1).The pro-apoptotic activity of the new isolated saponin1was evaluated, using Annexin V-FITC binding assay, on the A431 human epidermoid cancer cell. The result showed that adianthifolioside J (1) displayed weak pro-apoptotic activity

Triterpenoid saponins from the stem barks of Chytranthus klaineanus Radlk. ex Engl

In our continuing studies on saponins from Cameroonian medicinal plants, phytochemical investigation of Chytranthus klaineanus stem barks led to the isolation of three new oleanane-type saponins, named Klaineanosides A-C(1-3). Their structures were established by extensive analysis of their spectral data, mainly 1D(H-1, C-13 NMR, and DEPT) and 2D (COSY, HSQC, NOESY, HSQC-TOCSY, and HMBC) NMR experiments, and mass spectrometry as 3-O-beta-D-glucopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[-beta-D-xylopyranosyl(1 -> 3)-beta-D-xylopyranosyl(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)]-alpha-L-arabinopyranosylhederagenin(1), 3-O-beta-D-glucopyr-anosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)[ beta-D-xylopyranosyl(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)]-alpha-L-arabinopyr-anosylhederagenin(2), and 3-O-beta-D-xylopyranosyl(1 -> 4)-beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosylhederagenin(3). These triterpene saponins 1-3 have hederagenin as aglycone with a-(3)Rha-(2)Ara-(3)hederagenin oligosaccharidic sequence usually found in Sapindaceae family