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
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.
Laboratorio de Productos Naturales, Escuela de Química, Facultad de Ciencias, Universidad Central de Venezuela, Caracas 47102, Venezuela.
Phytochemistry. 2017 Sep;141:105-113. doi: 10.1016/j.phytochem.2017.04.023. Epub 2017 Jun 7.
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 (H, C, 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.
从玫瑰比利亚（Planch. & Linden）C. Ulloa & P. Jørg.的种子中分离出了5种此前未描述的三萜皂苷，即比利亚皂苷A - E，以及一种已知类似物。通过广泛的一维和二维核磁共振实验（氢谱、碳谱、DEPT、COSY、TOCSY、NOESY、ROESY、HSQC和HMBC）和质谱分析，确定了它们的结构分别为(3β,21β,22α)-3-[(2 - O - β - D - 吡喃葡萄糖基 - O - [α - L - 阿拉伯吡喃糖基-(1→4)]-β - D - 吡喃葡萄糖基)氧基]-21-[((2E,6S)-2,6 - 二甲基 - 6 - 羟基辛 - 2,7 - 二烯酰)氧基]-22-(乙酰氧基)-24 - 羟基齐墩果-12 - 烯-28 - 酸、(3β,21β,22α)-3-[(2 - O - β - D - 吡喃半乳糖基 - β - D - 吡喃葡萄糖基)氧基]-21,22 - 二羟基齐墩果-12 - 烯-28 - 基O - α - L - 阿拉伯吡喃糖基-(1→4)-β - D - 吡喃葡萄糖苷、(3β,
