PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, BP 87900, CEDEX, 21079 Dijon, France.
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
Molecules. 2021 Nov 11;26(22):6805. doi: 10.3390/molecules26226805.
Four oleanane-type glycosides were isolated from a horticultural cultivar "Green Elf" of the endemic (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3--β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C, 3--β-d-galactopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C, and the known 3--β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C (Eryngioside L). From the roots, the known 3--β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3--β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C, and Eryngioside L were evaluated.
从新西兰特有植物(藤黄科)园艺品种“Green Elf”的叶子中分离得到四种齐墩果烷型糖苷:三种酰化巴卡亭 III 糖苷,其中两种为新结构,分别为 3--β-d-吡喃葡萄糖基-(1→2)-[α-l-阿拉伯吡喃糖基-(1→3)]-β-d-吡喃葡萄糖醛酸基-21--当归酰基-28--乙酰基巴卡亭 III、3--β-d-半乳糖吡喃基-(1→2)-[α-l-阿拉伯吡喃糖基-(1→3)]-β-d-吡喃葡萄糖醛酸基-21--当归酰基-28--乙酰基巴卡亭 III 和已知的 3--β-d-吡喃葡萄糖基-(1→2)-[α-l-阿拉伯吡喃糖基-(1→3)]-β-d-吡喃葡萄糖醛酸基-21--当归酰基-28--乙酰基巴卡亭 III(Eryngioside L)。从根部分离得到已知的 3--β-d-吡喃葡萄糖基-(1→2)-β-d-吡喃半乳糖基-(1→2)-β-d-吡喃葡萄糖醛酸齐墩果酸(Sandrosaponin X)。通过光谱方法(包括 1D 和 2D-NMR 实验和质谱(ESI-MS))阐明了它们的结构。根据它们与 Gymnemic 酸的结构相似性,评估了叶和根的水醇提取物、粗皂苷混合物、3--β-d-吡喃葡萄糖基-(1→2)-[α-l-阿拉伯吡喃糖基-(1→3)]-β-d-吡喃葡萄糖醛酸基-21--当归酰基-28--乙酰基巴卡亭 III 和 Eryngioside L 对甜味 TAS1R2/TAS1R3 受体的抑制活性。