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Beaudelaire Kemvoufo Ponou Rémy Bertrand Teponno Massimo Ricciutelli Télesphore Bénoit Nguelefack Luana Quassinti Massimo Bramucci Giulio Lupidi Luciano Barboni Léon Azefack Tapondjou 《化学与生物多样性》2011,8(7):1301-1309
Two new oleanane‐type triterpenes named ivorengenin A (=3‐oxo‐2α,19α,24‐trihydroxyolean‐12‐en‐28‐oic acid; 1 ) and ivorengenin B (=4‐oxo‐19α‐hydroxy‐3,24‐dinor‐2,4‐secoolean‐12‐ene‐2,28‐dioic acid; 2 ), together with five known compounds, arjungenin, arjunic acid, betulinic acid, sericic acid, and oleanolic acid, were isolated from the barks of Terminalia ivorensis A. Chev . (Combretaceae). Their structures were established on the basis of 1D‐ and 2D‐NMR data, and mass spectrometry. A biogenetic pathway to the formation of these compounds from sericic acid, isolated as the major compound from this plant, was proposed. The antioxidant activities of different compounds were investigated by means of the 2,2‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) and 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) assays, and IC50 values were calculated and compared with Trolox activity. Antiproliferative activities of the isolated compounds were also evaluated against MDA‐MB‐231, PC3, HCT116, and T98G human cancer cell lines, against which the compounds showed significant cytotoxic activities. 相似文献
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Beaudelaire Kemvoufo Ponou Rémy Bertrand Teponno Massimo Ricciutelli Luana Quassinti Massimo Bramucci Giulio Lupidi Luciano Barboni Léon Azefack Tapondjou 《Phytochemistry》2010,71(17-18):2108-2115
Three saponins, including two dimeric triterpenoid glucosides possessing an unusual skeleton, ivorenosides A and B, and a monomeric triterpenoid saponin (ivorenoside C), together with the known sericoside, were isolated from the bark of Terminalia ivorensis. Their structures were established on the basis of 1D and 2D NMR data, chemical methods and tandem MS–MS spectrometry as a dimer of β-d-glucopyranosyl-18,19-seco-2α,3β,19,19,24-pentahydroxyolean-12-en-28-oate and β-d-glucopyranosyl-2α,3β,19α,24-tetrahydroxyolean-12-en-28-oate (ivorenoside A, 1), a dimer of β-d-glucopyranosyl-18,19-seco-24-carboxyl-2α,3β,19,19-tetrahydroxyolean-12-en-28-oate and β-d-glucopyranosyl-2α,3β,19α,24-tetrahydroxyolean-12-en-28-oate (ivorenoside B, 2) and β-d-glucopyranosyl-2α,3β,19β,24-tetrahydroxyolean-11-oxo-olean-12-en-28-oate (ivorenoside C, 3). Ivorenosides A and B are the first examples in nature of dimeric triterpenoid saponins with a 18,19-seco E ring of one of the two units. These isolated compounds were evaluated for their antioxidant properties and further for their cytotoxic activity against four human cancer cell lines. Ivorenoside B and C exhibited scavenging activity against DPPH and ABTS+ radicals with IC50 values comparable with that of the standard drug Trolox and ivorenoside A showed antiproliferative activity against MDA-MB-231 and HCT116 human cancer cell lines with IC50 values of 3.96 and 3.43 μM, respectively. 相似文献
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Tapondjou LA Nyaa LB Tane P Ricciutelli M Quassinti L Bramucci M Lupidi G Ponou BK Barboni L 《Carbohydrate research》2011,346(17):2699-2704
Three new triterpenoid saponins, elucidated as 3-O-β-d-glucopyranosyloleanolic acid 28-O-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranoside (parkioside A, 1), 3-O-[β-d-apifuranosyl-(1→3)-β-d-glucopyranosyl]oleanolic acid 28-O-[β-d-apifuranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)β-d-xylopyranoside (parkioside B, 2) and 3-O-β-d-glucuronopyranosyl-16α-hydroxyprotobassic acid 28-O-α-l-rhamnopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranoside (parkioside C, 3), were isolated from the n-BuOH extract of the root bark of Butyrospermum parkii, along with the known 3-O-β-d-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities. Compound 2 showed cytotoxic activity against A375 and T98G cell lines, with IC50 values of 2.74 and 2.93 μM, respectively. Furthermore, it showed an antioxidant activity comparable to that of Trolox or butylated hydroxytoluene (BHT), used as controls, against 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), oxygen and nitric oxide radicals. 相似文献
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Rémy B. Teponno Beaudelaire K. Ponou Léon A. Tapondjou Luciano Barboni 《Phytochemistry letters》2013,6(2):310-314
A new clerodane diterpenoid, bafoudiosbulbin H (1), was isolated from the flowers of Dioscorea bulbifera L. var sativa. Its acetylation using acetic anhydride-pyridine and catalytic amount of 4-DMAP at 60 °C yielded bafoudiosbulbin H acetate (2) together with a clerodane with an unprecedented acylation pattern (bafoudiosbulbin H1, 3). The reaction of the known bafoudiosbulbin G (4) in the same conditions yielded demethylbafoudiosbulbin G (5). Structural elucidation of 5 led to the revision of the stereochemistry previously assigned to 4. Structures were elucidated using spectroscopic techniques, including 1D and 2D NMR (1H, 13C, HSQC, COSY, HMBC, ROESY, NOESY) and mass spectrometry (HRESIMS). 相似文献
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