sapindoside C | 904684-90-8

• 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
• 英文名称: sapindoside C
• 英文别名: hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-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-carboxylic acid
• CAS: 904684-90-8
• 化学式: C₅₂H₈₄O₂₁
• 分子量: 1045.23
• InChiKey: BECKQSNYULYJHB-LQKGKWEGSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  334
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  sapindoside C 在 Helix pomatia enzyme 作用下， 以 水 为溶剂， 生成 sapindoside B
  参考文献：
  名称：

  Triterpene Glycosides from Kalopanax septemlobum. II. Glycosides E, K, and L from Leaves of Kalopanax septemlobum var. maximowiczii Introduced to Crimea

  摘要：

  已知的hederagenin 3-O-β-D-吡喃葡萄糖基-(1→4)-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖苷（sapindoside C）及其28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯和28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯，为新三萜糖苷，从引种至克里米亚的刺楸（Kalopanax septemlobum var. maximowiczii）叶中分离得到。这些化合物的结构通过化学方法和二维核磁共振波谱技术确定。

  DOI：

  10.1007/s10600-005-0140-9
• 作为产物：
  描述：

  hederagenin 3-(O-β-D-glucopyranosyl-1-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl)-28-O-(α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 生成 sapindoside C
  参考文献：
  名称：

  Triterpene Glycosides from Kalopanax septemlobum. II. Glycosides E, K, and L from Leaves of Kalopanax septemlobum var. maximowiczii Introduced to Crimea

  摘要：

  已知的hederagenin 3-O-β-D-吡喃葡萄糖基-(1→4)-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖苷（sapindoside C）及其28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯和28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯，为新三萜糖苷，从引种至克里米亚的刺楸（Kalopanax septemlobum var. maximowiczii）叶中分离得到。这些化合物的结构通过化学方法和二维核磁共振波谱技术确定。

  DOI：

  10.1007/s10600-005-0140-9

文献信息

• Antifungal Activity of Modified Hederagenin Glycosides from the Leaves of Kalopanax pictum var. chinense.
  作者：Min-Won LEE、Sung Uk KIM、Dug-Ryoung HAHN

  DOI：10.1248/bpb.24.718

  日期：——

  Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albicans at the minimal inhibitory concentrations of 6.25—25 μm/ml. The hederagenin glycosides were isolated from the leaves of Kalopanax pictum var. chinense.

  从常春藤甙元的双甙部分降解物中得到的单甙对犬小孢子菌、粗球孢子菌、须毛癖菌、新型隐球菌和白色念珠菌表现出显著的抗真菌效应，其最低抑制浓度为6.25—25μm/ml。这些常春藤甙是从刺揪中国变种的叶中分离得到的。
• Metabolism of Kalopanaxsaponin K by Human Intestinal Bacteria and Antirheumatoid Arthritis Activity of Their Metabolites.
  作者：Dong-Hyun Kim、Eun-Ah Bae、Myung Joo Han、Hee-Juhn Park、Jong-Won Choi

  DOI：10.1248/bpb.25.68

  日期：——

  When kalopanaxsaponin K (KPK) from Kalopanax pictus was incubated for 24 h at 37 °C with human intestinal microflora, KPK was mainly metabolized to kalopanaxsaponin I (KPI) via kalopanaxsaponin H (KPH) rather than via kalopanaxsaponin J (KPJ), and then transformed to kalopanaxsaponin A (KPA) and hederagenin. Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. transformed KPK to KPI and KPA and hederagenin via KPH or KPJ. However, Lactobacillus sp. and Streptococcus sp. transformed KPK to KPI, KPA, and hederagenin only via KPJ. The metabolite KPA of KPK showed potent antirheumatoid arthritis activity.

  当来自毛蕊花的甘露皂苷K（KPK）在37°C下与人类肠道微生物菌群孵育24小时后，KPK主要通过甘露皂苷H（KPH）代谢为甘露皂苷I（KPI），而不是通过甘露皂苷J（KPJ），然后转化为甘露皂苷A（KPA）和赫达根醇（hederagenin）。拟杆菌属（Bacteroides sp.）、双歧杆菌属（Bifidobacterium sp.）和梭菌属（Fusobacterium sp.）通过KPH或KPJ将KPK转化为KPI、KPA和赫达根醇。然而，乳酸菌属（Lactobacillus sp.）和链球菌属（Streptococcus sp.）仅通过KPJ将KPK转化为KPI、KPA和赫达根醇。KPK的代谢物KPA显示出强大的抗类风湿关节炎活性。
• Triterpene Glycosides from Kalopanax septemlobum. III. Glycosides D2, I1, and K1 from Leaves of Kalopanax septemlobum var. maximowiczii Introduced in Crimea
  作者：V. I. Grishkovets、D. A. Panov、E. A. Palii、V. V. Kachala、A. S. Shashkov

  DOI：10.1007/s10600-005-0141-8

  日期：2005.5

  The new caffeylated triterpene glycosides hederagenin 3-O-(6-O-caffeyl-β-D-glucopyranosyl)-(1→4)-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-β-L-arabinopyranoside and its 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl and 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters were isolated from leaves of Kalopanax septemlobum var. maximowiczii introduced in Crimea. The structures of these compounds were established using chemical methods and NMR spectroscopy.

  从克里米亚引进的七叶树变种maximowiczii的叶中分离出新的咖啡酰基三萜糖苷hederagenin 3-O-(6-O-caffeyl-β-D-glucopyranosyl)-(1→4)-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-O-β-L-arabinopyranoside及其28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl和28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl酯。这些化合物的结构通过化学方法和核磁共振光谱确定。
• Triterpene Glycosides from Kalopanax septemlobum. II. Glycosides E, K, and L from Leaves of Kalopanax septemlobum var. maximowiczii Introduced to Crimea
  作者：D. A. Panov、V. I. Grishkovets、V. V. Kachala、A. S. Shashkov

  DOI：10.1007/s10600-005-0140-9

  日期：2005.5

  The known hederagenin 3-O-β-D-glucopyranosyl-(1→4)-O-β-D-xylopyranosyl-(1→ 3)-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranoside (sapindoside C) and its 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl and 28-O-α-L-rhamnopyranosyl-(1→4)-O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl esters, new triterpene glycosides, were isolated from leaves of Kalopanax septemlobum var. maximowiczii introduced to Crimea. The structures of these compounds were established using chemical methods and two-dimensional NMR spectroscopy.

  已知的hederagenin 3-O-β-D-吡喃葡萄糖基-(1→4)-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖苷（sapindoside C）及其28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯和28-O-α-L-吡喃鼠李糖基-(1→4)-O-6-O-乙酰基-β-D-吡喃葡萄糖基-(1→6)-O-β-D-吡喃葡萄糖基酯，为新三萜糖苷，从引种至克里米亚的刺楸（Kalopanax septemlobum var. maximowiczii）叶中分离得到。这些化合物的结构通过化学方法和二维核磁共振波谱技术确定。