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Phytochemistry. 2017 Sep;141:105-113. doi: 10.1016/j.phytochem.2017.04.023. Epub 2017 Jun 7.

Triterpene saponins from Billia rosea.

Author information

1
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 Dijon Cedex, France; Laboratorio de Productos Naturales, Escuela de Química, Facultad de Ciencias, Universidad Central de Venezuela, Caracas 47102, Venezuela.
2
Laboratorio de Productos Naturales, Escuela de Química, Facultad de Ciencias, Universidad Central de Venezuela, Caracas 47102, Venezuela.
3
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 Dijon Cedex, France.
4
Institut des Sciences Moléculaires, CNRS-UMR 5255 et Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 Rue Robert Escarpit, 33607 Pessac Cedex, France.
5
Universität Siegen, OC-II, Naturwissenschaftlich-Technische Fakultät, Adolf-Reichwein-Str. 2, D-57076 Siegen, Germany.
6
Sección de Bioquímica Médica, Instituto de Medicina Experimental, Facultad de Medicina, Universidad Central de Venezuela, Caracas 50587, Venezuela.
7
Laboratorio de Productos Naturales, Departamento de Quimica, Facultad de Ciencias, Universidad de los Andes, Mérida 5101, Venezuela.
8
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 Dijon Cedex, France. Electronic address: m-a.lacaille-dubois@u-bourgogne.fr.

Abstract

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.

KEYWORDS:

Billia rosea; Glucose-6-phosphatase; Intestinal glucose absorption; Sapindaceae; Triterpene saponins

PMID:
28599241
DOI:
10.1016/j.phytochem.2017.04.023
[Indexed for MEDLINE]

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