Article Dans Une Revue Carbohydrate Research Année : 2021

Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn

Résumé

In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 3)-β-d-fucopyranosyl} polygalacic acid 28-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl ester (1), 3-O-{α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 3)-[α-l-arabinofuranosyl-(1 → 4)]-α-l-rhamnopyranosyl-(1 → 3)-β-d-fucopyranosyl} polygalacic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl ester (2), and 3-O-{α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 3)-β-d-fucopyranosyl} polygalacic acid 28-O-[α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
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hal-03542561 , version 1 (02-08-2023)

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Eutrophe Le Doux Kamto, Olivier Placide Noté, Mc Jesus Kinyok, Anke Wilhelm, Joséphine Ngo Mbing, et al.. Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn. Carbohydrate Research, 2021, 507, pp.108374. ⟨10.1016/j.carres.2021.108374⟩. ⟨hal-03542561⟩
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