Triterpene saponins from Billia rosea

Five previously undescribed triterpene saponins, billiosides A-E, and a known analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. Ulloa & P. Jørg. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, TOCSY, NOESY,...

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Bibliographic Details
Published in:	Phytochemistry (Oxford) Vol. 141; pp. 105 - 113
Main Authors:	De Freitas, Luis, Jimenez, Doris, Pimentel, Sherley, Mitaine-Offer, Anne-Claire, Pouységu, Laurent, Quideau, Stéphane, Paululat, Thomas, Gonzalez-Mujica, Freddy, Rojas, Luis B., Rodríguez, María, Lacaille-Dubois, Marie-Aleth
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 01-09-2017
Subjects:	Animals Billia rosea Glucose - metabolism Glucose-6-phosphatase Hippocastanaceae - chemistry Hypoglycemic Agents - isolation & purification Hypoglycemic Agents - pharmacology Intestinal Absorption - drug effects Intestinal glucose absorption Intestines - drug effects Microsomes, Liver - drug effects Molecular Structure Rats Sapindaceae Saponins - isolation & purification Saponins - pharmacology Seeds - chemistry Triterpene saponins Triterpenes - isolation & purification Triterpenes - pharmacology Billia rosea Triterpene saponins Glucose-6-phosphatase Sapindaceae Intestinal glucose absorption
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Summary:	Five previously undescribed triterpene saponins, billiosides A-E, and a known analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. Ulloa & P. Jørg. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments (1H, 13C, DEPT, COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC) and mass spectrometry as (3β,21β,22α)-3-[(2-O-β-D-glucopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21-[((2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl)oxy]-22-(acetyloxy)-24-hydroxyolean-12-en-28-oic acid, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranoside, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-xylopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-β-D-glucopyranoside, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-β-D-glucopyranoside, (3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, and dipteroside A. Billiosides B and C exhibited moderate effects when tested as hepatic glucose-6-phosphatase inhibitors and as glucose intestinal absorption inhibitors, using in situ rat intestinal segments. Chemical investigation of the seeds of Billia rosea led to the isolation of five previously undescribed triterpene saponins, billiosides A-E along with a known analogue. Billiosides B, and C exhibited moderate antihyperglycemic activity. [Display omitted] •Five previously undescribed triterpene saponins were isolated from Billia rosea.•Their structures were elucidated by combined NMR and MS analyses.•Billiosides B and C displayed moderate antihyperglycemic activity.
ISSN:	0031-9422 1873-3700
DOI:	10.1016/j.phytochem.2017.04.023