3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-7(8),25(26)-dien-16-one | 1220913-36-9

• 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: 3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-7(8),25(26)-dien-16-one
• 英文别名: holotoxin E；(2S,5S,6S,9S,12R,13R,16S,18R)-16-[(2S,3R,4S,5R)-3-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-2-yl]oxy-2,6,13,17,17-pentamethyl-6-(4-methylpent-4-enyl)-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-1(20)-ene-4,8-dione
• CAS: 1220913-36-9
• 化学式: C₆₅H₁₀₂O₃₁
• 分子量: 1379.51
• InChiKey: HJSPQVGDFJDQOW-DBYZLMMVSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  96
• 可旋转键数：
  20
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  467
• 氢给体数：
  15
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  3β-O-{2-O-[3-O-methyl-β-D-glucopyranosyl-(1->3)-β-D-xylopyranosyl-(1->4)-β-D-quinovopyranosyl]-4-O-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl]-β-D-xylopranosyl}holosta-7(8),25(26)-dien-16-one 在 三氟乙酸 、 吡啶 、 盐酸羟胺 、 乙酸酐 作用下， 以 水 为溶剂， 反应 4.0h， 生成 D-木糖 、 6-脱氧-D-葡萄糖 、 葡萄糖 、 3-O-甲基-D-葡萄糖 、 3β-hydroxyholosta-9(11),25(26)-dien-16-one
  参考文献：
  名称：

  Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka

  摘要：

  A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A(1) (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A(1) and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Delta(25) terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Delta(9(11)) to Delta(7) in the aglycone moiety contributes little to the bioactivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2011.10.080

文献信息

• Antifungal nortriterpene and triterpene glycosides from the sea cucumber Apostichopus japonicus Selenka
  作者：Zenglei Wang、Hongwei Zhang、Weihua Yuan、Wei Gong、Hua Tang、Baoshu Liu、Karsten Krohn、Ling Li、Yanghua Yi、Wen Zhang

  DOI：10.1016/j.foodchem.2011.10.080

  日期：2012.5

  A nortriterpene glycoside, 26-nor-25-oxo-holotoxin A(1) (1), four triterpene glycosides, including both holostane and non-holostane types analogues, holotoxins D-G (2-5), together with three known triterpene glycosides, holotoxins A(1) and B (6, 7), and cladoloside B (8), were isolated from the warty sea cucumber Apostichopus japonicus Selenka, a traditional tonic with high economic value in China. The structures of the new compounds were elucidated by a combination of detailed spectroscopic analysis and chemical methods. This is the first report of a nortriterpene glycoside isolated from sea cucumbers. These compounds showed potent antifungal activities in the in vitro biotest. A preliminary structure-activity analysis suggests that the 18(20) lactone group and the Delta(25) terminal double bond may increase the activity. The component of the carbohydrate chain seems play an important role whereas the double bond transformation from Delta(9(11)) to Delta(7) in the aglycone moiety contributes little to the bioactivity. (C) 2011 Elsevier Ltd. All rights reserved.