麦冬皂苷D | 65604-80-0

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 麦冬皂苷D
• 中文别名: 麦冬皂苷D'；麦冬皂苷 D'
• 英文名称: ophiopogonin D'
• 英文别名: diosgenyl α-L-rhamnopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranoside；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS: 65604-80-0
• 化学式: C₄₄H₇₀O₁₆
• 分子量: 855.03
• InChiKey: DQYACEDUQHWXQZ-QOYNBSPSSA-N

物化性质

• 密度：
  1.40
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  60
• 可旋转键数：
  7
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  236
• 氢给体数：
  8
• 氢受体数：
  16

制备方法与用途

生物活性

Ophiopogonin D' 是从麦冬 (Ophiopogon japonicus) 的块茎中分离出的一种罕见天然存在的 C29 甾体糖苷。研究表明，它对两种人肿瘤细胞系 MG-63 和 SNU387 具有细胞毒活性，IC50 值分别为 3.09 μM 和 3.63 μM，并且以剂量依赖方式激活了 SIRT1。

靶点

SIRT1

化学性质

Ophiopogonin D' 是一种白色结晶粉末，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于麦冬 (Ophiopogon japonicus)。

用途

用于含量测定、鉴定以及药理实验等。

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 麦冬皂苷D
  参考文献：
  名称：

  Chemical Synthesis of Several 2'-O-, 3'-O-Glycosylated Diosgenyl β-D-Glucopyranosides

  摘要：

  Six 2'-O-, 3'-O-glycosylated diosgenyl beta-D-glucopyranosides (4-9), which have a typical structural pattern of diosgenyl saponins, were synthesized; their synthetic routes are discussed.

  DOI：

  10.1080/07328309908544058

文献信息

• Steroidal saponins from the bulbs of Lilium longiflorum and their antitumour-promoter activity
  作者：Yoshihiro Mimaki、Osamu Nakamura、Yutaka Sashida、Yoshiko Satomi、Atsuko Nishino、Hoyoku Nishino

  DOI：10.1016/0031-9422(94)85030-5

  日期：1994.1

  3-O-(O-alpha-L-rhamnopyranosyl-(1 --> 2)- O-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside). The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

  从长花百合的新鲜鳞茎中分离出两种新的螺甾醇皂苷和两种新的呋甾醇皂苷以及几种已知的皂苷。新化合物的结构被确定为 (25S)-spirost-5-ene-3 beta, 27-diol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O- [alpha -L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)，(25R)-27-O-[(S)-3-羟基-3-甲基戊二酰基]-spirost-5-ene-3 β,27二醇3-O-(O-α-L-吡喃鼠李糖基-(1-->2)-O-[α-L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)， 22-O-甲基-26-O-β-D-吡喃葡萄糖基-(25R)-furost-5-ene-3 beta,22 xi, 26-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1 -->2)-O-[α-L
• Steroidal glycosides, indiosides A-E, from Solanum indicum
  作者：Shoji Yahara、Takanori Nakamura、Yukimi Someya、Tomoko Matsumoto、Tomoyuki Yamashita、Toshihiro Nohara

  DOI：10.1016/s0031-9422(96)00395-0

  日期：1996.12

  Together with isoanguivine, protodioscin, solasonine and solamargine, five new steroidal glycosides, named indiosides A-E were obtained from Solanum indicum (indiosides A and B from the fruits, indiosides C-E from the roots). Their structures were characterized as: (23S, 25R, 26R)-spirost-5-en-3 beta, 23, 26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside} (indioside A); (25R)-26-O-beta-D-glucopyranosyl-22 alpha-methoxyfurost-5-en-3 beta, 26-diol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside} (indioside B); (25R)-26-O-beta-D-glucopyranosyl-furost-5-en-3 beta, 22 zeta, 26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-galactopyranoside} (indioside C); (25R)-26-O-(beta-D-glucopyranosyl)-furost-5-en-3 beta, 22 xi, 26-triol 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)- [beta-D-glucopyranosyl-(1 --> 3)]-beta-D-galactopyranoside} (beta-solatrioside) (indioside D); diosgenin 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-galactopyranoside} (indioside E). Copyright (C) 1996 Elsevier Science Ltd
• Chemical Synthesis of Several 2'-<i>O</i>-, 3'-<i>O</i>-Glycosylated Diosgenyl β-D-Glucopyranosides
  作者：Chuan Li、Biao Yu、Yongzheng Hui

  DOI：10.1080/07328309908544058

  日期：1999.1

  Six 2'-O-, 3'-O-glycosylated diosgenyl beta-D-glucopyranosides (4-9), which have a typical structural pattern of diosgenyl saponins, were synthesized; their synthetic routes are discussed.