sapindoside B | 3582-25-0

• 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 B
• 英文别名: hederagenin 3-O-β-D-xylopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside；hederagenin 3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside；3-O-β-[D-xylopyranosyl-(1→ 3)-α-L-rhamnopyranosyl-(1→ 2)-α-L-arabinpyranosyl]-hederagenin；(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-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: 3582-25-0；30994-75-3
• 化学式: C₄₆H₇₄O₁₆
• 分子量: 883.084
• InChiKey: IAGSHEHQJJTLLR-FNINEVAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  255
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  sapindoside B 以 甲醇 、 溶剂黄146 为溶剂， 反应 15.0h， 以84%的产率得到
  参考文献：
  名称：

  Yoshikawa, Masayuki; Wang, Hui Kang; Tosirisuk, Veeraphan, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 8, p. 3057 - 3060

  摘要：

  DOI：
• 作为产物：
  描述：

  hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 在 氢氧化钾 、 氨 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 sapindoside B
  参考文献：
  名称：

  Triterpene Glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from Leaves of Kalopanax septemlobum var. Maximowichii Introduced to Crimea

  摘要：

  从引入克里米亚的刺楸变种Kalopanax septemlobum var. maximowichii叶中，通过色谱方法分离出了已知的8种常春藤苷元和新的三萜皂苷3-O-β-D-吡喃木糖基-(1→3)-O-α-L-吡喃鼠李糖基-(1→2)-O-α-L-吡喃阿拉伯糖基-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-吡喃葡萄糖基酯常春藤苷元。在鵺中首次观察到已知的3-O-α-L-吡喃阿拉伯糖基-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-吡喃葡萄糖基酯常春藤苷元。

  DOI：

  10.1007/s10600-005-0110-2

文献信息

• Acetylated Triterpene Saponins from the Thai Medicinal Plant, Sapindus emarginatus.
  作者：Tripetch KANCHANAPOOM、Ryoji KASAI、Kazuo YAMASAKI

  DOI：10.1248/cpb.49.1195

  日期：——

  From the pericarps of Sapindus emarginatus (Sapindaceae), three new acetylated triterpene saponins were isolated together with hederagenin and five known triterpene saponins, as well as one known sweet acyclic sesquiterpene glycoside, mukurozioside IIb. The structures of new compounds were elucidated as hederagenin 3-O-(2-O-acetyl-beta-D-xylopyranosyl)-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha

  从无患子无患子（Sapindaceae）的果皮中，分离出三种新的乙酰化的三萜皂苷与二十碳皂苷元和五种已知的三萜皂苷，以及一种已知的甜美的无环倍半萜烯糖苷mukurozioside IIb。阐明了新化合物的结构，如二十三碳精3-O-（2-O-乙酰基-β-D-吡喃吡喃糖基）-（1-> 3）-α-L-鼠李糖基-（1-> 2）-α -L-阿拉伯吡喃果糖苷，23-O-乙酰基-角域生成素3-O-（4-O-乙酰基-β-D-吡喃木糖基）-（1-> 3）-α-L-鼠李糖基-（1-> 2 ）-α-L-阿拉伯吡喃糖苷和齐墩果酸3-O-（4-O-乙酰基-β-D-吡喃吡喃糖基）-（1-> 3）-α-L-鼠李糖基吡喃糖基-（1-> 2）- α-L-阿拉伯吡喃糖苷的化学和光谱数据。
• 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。
• 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。
• Met abolism of Kalopanaxsaponin B and H by Human Intestinal Bacteria and A ntidiabetic Activity of Their Metabolites.
  作者：Dong-Hyun KIM、Ki-Woong YU、Eun-Ah BAE、Hee-Juhn PARK、Jong-Won CHOI

  DOI：10.1248/bpb.21.360

  日期：——

  To investigate the relationship between the intestinal bacterial metabolism of kalopanaxsaponin B and H from Kalopanix pictus (Araliaceae), and their antidiabetic effect, kalopanaxsaponin B and H were metabolized by human interstinal microfiora and the antidiabetic activity of their metabolites was measured. Human intestinal microflora metabolized kalopanaxsaponin B to kalopanaxaponin A, hederagenin 3-O-α-L-arabinopyranoside and hedaragenin. The main metabolites of kalopanaxsaponin B were kalopanaxsaponin A and hederagenin. Kalopanaxsaponin H was metabolized to kalopanaxsaponin A and I, hederagenin 3-O-α-L-arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin H were kalopanaxsaponin I and hederagenin. Among kalopanaxsaponin B, H and their metabolites, kalopanaxsaponin A showed the most potent antidiabetic activity, followed by hederagenin. However, the main components, kalopanaxsaponin B and H, in K. pictus were inactive.

  为了研究从光叶肾蕨（Araliaceae）提取得到的卡罗潘沙苷B和H的肠道细菌代谢与其抗糖尿病效果之间的关系，研究人员对人类肠道微生物群进行了卡罗潘沙苷B和H的代谢，测量了其代谢产物的抗糖尿病活性。人类肠道微生物群将卡罗潘沙苷B代谢为卡罗潘沙苷A、hederagenin 3-O-α-L-arabinopyranoside和hederagenin。卡罗潘沙苷B的主要代谢产物是卡罗潘沙苷A和hederagenin。卡罗潘沙苷H则被代谢为卡罗潘沙苷A和I、hederagenin 3-O-α-L-arabinopyranoside和hederagenin。卡罗潘沙苷H的主要代谢产物是卡罗潘沙苷I和hederagenin。在卡罗潘沙苷B、H及其代谢产物中，卡罗潘沙苷A表现出最强的抗糖尿病活性，其次是hederagenin。然而，卡罗潘沙苷B和H这两个主要成分在K. pictus中是无活性的。
• 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。