白头翁甙 C | 57539-70-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 白头翁甙 C
• 中文别名: 白头翁甙C
• 英文名称: 3β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester
• 英文别名: hederagenin 28-O-4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside>；kalopanax saponin G；kalopanaxsaponin g；kizuta saponin K3；pulsatiloside C；cussonoside A；[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 57539-70-5
• 化学式: C₄₈H₇₈O₁₈
• 分子量: 943.137
• InChiKey: YGSBJLPWANWGED-HYXYOFMCSA-N

物化性质

• 沸点：
  1001.7±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  66
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  295
• 氢给体数：
  11
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 白头翁甙 C 在 吡啶 作用下， 生成 [(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-acetyloxy-9-(acetyloxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
  参考文献：
  名称：

  13C NMR spectra of acetylated hederagenin glycosides

  摘要：

  DOI：

  10.1007/bf00567289
• 作为产物：
  描述：

  nipponoside A 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以30 mg的产率得到白头翁甙 C
  参考文献：
  名称：

  Triterpenoid Saponins of Acanthopanax nipponicus Leaves

  摘要：

  Five new triterpenoid saponins, nipponosides A-E (1, 3-6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A-E were characterized as the 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-beta-D-glucopyranoside, gypsogenin 3-O-beta-D-glucopyranoside, 3 beta,23,29-trihydroxyolean-12-en-28-oic acid, and 3 beta,20 alpha,2 3-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.

  DOI：

  10.1021/np9804334

文献信息

• Studies on the constituents of Hedera rhombea Bean. IV. On the hederagenin glycosides. (2)
  作者：HARUHISA KIZU、SATOSHI HIRABAYASHI、MIZUMI SUZUKI、TSUYOSHI TOMIMORI

  DOI：10.1248/cpb.33.3473

  日期：——

  On the basis of chemical and physicochemical evidence, the structures of two new hederagenin bisdesmosides, named Kizuta saponins K8 (X) and K11 (I), which were isolated from the stem and bark of Hedera rhombea BEAN (Araliaceae), were established to be as follows : X, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester ; I, 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl (1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. A glucoside mixture (XIII) was considered to be a mixture of the β-D-glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol based on chemical and physicochemical evidence.

  基于化学和物理化学证据，确定了从常春藤（Hedera rhombea BEAN，五加科）的茎和树皮中分离出的两种新的常春素双甙的结构，分别命名为Kizuta皂苷K8（X）和K11（I），其结构如下：X为3-O-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基-(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯；I为3-O-α-L-鼠李呋喃糖基-(1→2)-α-L-阿拉伯呋喃糖基-常春素28-O-α-L-鼠李呋喃糖基(1→4)-6-O-乙酰基-β-D-葡萄吡喃糖基-(1→6)-β-D-葡萄吡喃糖基酯。基于化学和物理化学证据，认为葡萄糖苷混合物（XIII）是油菜甾醇（微量）、豆甾醇和β-谷甾醇的β-D-葡萄吡喃糖苷混合物。
• 13C NMR spectra of acetylated hederagenin glycosides
  作者：A. I. Kalinovskii、N. I. Chetyrina

  DOI：10.1007/bf00567289

  日期：——
• Triterpenoid Saponins of <i>Acanthopanax nipponicus</i> Leaves
  作者：Masazumi Miyakoshi、Katsuya Shirasuna、Yasuaki Hirai、Kazushi Shingu、Susumu Isoda、Junzo Shoji、Yoshiteru Ida、Torao Shimizu

  DOI：10.1021/np9804334

  日期：1999.3.1

  Five new triterpenoid saponins, nipponosides A-E (1, 3-6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A-E were characterized as the 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-beta-D-glucopyranoside, gypsogenin 3-O-beta-D-glucopyranoside, 3 beta,23,29-trihydroxyolean-12-en-28-oic acid, and 3 beta,20 alpha,2 3-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.