State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China.
Carbohydr Res. 2012 Nov 1;361:19-26. doi: 10.1016/j.carres.2012.07.027. Epub 2012 Aug 8.
Phytochemical investigation of the bulbs of Lilium brownii var. viridulum led to the isolation of seven new steroidal saponins (1-7), along with eight known analogues (8-15). The new steroidal saponins were identified as 27-O-[(3S)-3-O-β-D-glucopyranosyl 3-methylglutaroyl]isonarthogenin 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1), (24S,25S)-3β,17α,24-trihydroxy-5α-spirostan-6-one 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (2), tenuifoliol 3-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (3), 26-O-β-D-glucopyranosylnuatigenin (4), 26-O-β-D-glucopyranosylnuatigenin 3-O-β-D-glucopyranoside (5), 26-O-β-D-glucopyranosylnuatigenin 3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]}-β-D-glucopyranoside (6), 26-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosylnuatigenin 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (7), using a combination of spectroscopic evidence and chemical methods. The carbohydrate chain of a sugar linked to C-3 of the HMG group (3-hydroxy-3-methylglutarate) in compound 1 is rarely found in nature. Compound 2 possesses a new (24S,25S)-3β,17α,24-trihydroxy-5α-spirostan-6-one aglycon moiety. The disaccharide chain linked to C-26 hydroxy group of the furospirostanol in compound 7 has not been observed from natural sources.
从百合属植物黄花百合的鳞茎中分离得到了七种新甾体皂苷（1-7）和八种已知类似物（8-15）。通过波谱数据和化学方法鉴定了这七种新甾体皂苷的结构，分别为 27-O-[(3S)-3-O-β-D-吡喃葡萄糖基 3-甲基戊二酰基]异次黄烷苷元 3-O-[α-L-鼠李吡喃糖基-(1→2)]-β-D-吡喃葡萄糖苷（1）、(24S,25S)-3β,17α,24-三羟基-5α-螺甾烷-6-酮 3-O-[α-L-鼠李吡喃糖基-(1→2)]-β-D-吡喃葡萄糖苷（2）、纤细薯蓣皂苷元 3-O-[β-D-吡喃葡萄糖基-(1→4)]-β-D-吡喃葡萄糖苷（3）、26-O-β-D-吡喃葡萄糖基诺皂角苷元（4）、26-O-β-D-吡喃葡萄糖基诺皂角苷元 3-O-β-D-吡喃葡萄糖苷（5）、26-O-β-D-吡喃葡萄糖基诺皂角苷元 3-O-{α-L-鼠李吡喃糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→6)]}-β-D-吡喃葡萄糖苷（6）、26-O-[β-D-吡喃葡萄糖基-(1→2)]-β-D-吡喃葡萄糖基诺皂角苷元 3-O-[α-L-鼠李吡喃糖基-(1→2)]-β-D-吡喃葡萄糖苷（7）。化合物 1 中 HMG 基团（3-羟基-3-甲基戊二酸）连接的糖的糖链在自然界中很少见。化合物 2 具有一个新的（24S,25S）-3β,17α,24-三羟基-5α-螺甾烷-6-酮苷元部分。化合物 7 中呋甾烷醇 26-羟基连接的二糖链在天然产物中尚未观察到。
