Laboratoire d'Innovation Thérapeutique, UMR 7200, Faculté de Pharmacie, CNRS-Université de Strasbourg, 74 route du Rhin, F-67401 Illkirch, Cedex, France; Laboratoire de Pharmacochimie des Substances Naturelles, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé I, BP 812, Yaoundé, Cameroon.
Laboratoire de Pharmacochimie des Substances Naturelles, Département de Chimie Organique, Faculté de Sciences, Université de Yaoundé I, BP 812, Yaoundé, Cameroon.
Fitoterapia. 2018 Sep;129:34-41. doi: 10.1016/j.fitote.2018.06.008. Epub 2018 Jun 12.
As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides GI (13). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (H-, C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-β-d-xylopyranosyl-(1 → 3)-[5-O-acetyl-α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (1), 3-O-[β-d-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-β-d-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (2), and 3-O-[β-d-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-d-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl ester (3). The apoptotic effect of saponins 1-3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1-3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
作为我们对喀麦隆 Albizia 属皂苷促凋亡功能研究的一部分，对 Albizia adianthifolia 的根进行了植物化学研究，分离得到三种新的三萜皂苷，命名为 adianthifoliosides GI（13）。根据 1D 和 2D NMR（H-、C NMR、DEPT、COSY、TOCSY、NOESY、HSQC、HSQC-TOCSY 和 HMBC）和 HRESIMS 实验的广泛分析以及化学证据，确定了它们的结构，并通过化学证据确定为 3-O-[β-d-吡喃葡萄糖基-(1 → 2)-β-D-岩藻吡喃糖基-(1 → 6)-β-d-吡喃葡萄糖基]-21-O-{(2E,6S)-2-(羟甲基)-6-甲基-6-O-{4-O-[(2E,6S)-2,6-二甲基-6-O-(β-D-奎尼烯酰基)辛二烯酰基]-(β-D-奎尼烯酰基)辛二烯酰基}赤藓酸-28-O-β-d-吡喃木糖基-(1 → 3)-[5-O-乙酰基-α-L-阿拉伯呋喃糖基-(1 → 4)]-α-L-鼠李吡喃糖基-(1 → 2)-β-d-吡喃葡萄糖基酯（1）、3-O-[β-d-吡喃葡萄糖基-(1 → 2)-β-D-岩藻吡喃糖基-(1 → 6)-β-d-吡喃葡萄糖基]-21-O-{(2E,6S)-2-(羟甲基)-6-甲基-6-O-{4-O-[(2E,6S)-2,6-二甲基-6-O-(β-D-奎尼烯酰基)辛二烯酰基]-(β-D-奎尼烯酰基)辛二烯酰基}赤藓酸 28-O-β-d-吡喃木糖基-(1 → 3)-[α-L-阿拉伯呋喃糖基-1 → 4)]-α-L-鼠李吡喃糖基-(1 → 2)-β-d-吡喃葡萄糖基酯（2）和 3-O-[β-d-吡喃葡萄糖基-(1 → 2)-β-D-岩藻吡喃糖基-(1 → 6)-β-d-吡喃葡萄糖基]-21-O-{(2E,6S)-2-(羟甲基)-6-甲基-6-O-{4-O-[(2E,6S)-2,6-二甲基-6-O-(β-D-奎尼烯酰基)辛二烯酰基]-(β-D-奎尼烯酰基)辛二烯酰基}-4-O-[(2E,6S)-2,6-二甲基-6-O-(β-D-奎尼烯酰基)辛二烯酰基]-β-D-奎尼烯酰基}赤藓酸 28-O-β-d-吡喃木糖基-(1 → 3)-[α-L-阿拉伯呋喃糖基-1 → 4)]-α-L-鼠李吡喃糖基-(1 → 2)-β-d-吡喃葡萄糖基酯（3）。对化合物 1-3 的凋亡作用进行了评估，结果表明化合物 1-3 以剂量依赖性方式诱导人表皮癌细胞（A431）凋亡。
