eryloside P

• 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: eryloside P
• 英文别名: 3β-O-{[β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl-(1->3)-α-L-arabinopyranosyl-(1->3)]-[β-D-galactopyranosyl-(1->2)-α-L-arabinopyranosyl}-14-carboxy-24-methylenelanost-8(9)-en-3β-ol；(3S,5R,10S,13R,14S,17R)-3-[(2S,3R,4S,5S)-4-[(2S,3R,4R,5S)-5-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-5-hydroxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-14-carboxylic acid
• 化学式: C₆₄H₁₀₄O₃₀
• 分子量: 1353.51
• InChiKey: TWNNTRBCJKBPIJ-AMZGHUIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  94
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  472
• 氢给体数：
  17
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  eryloside P 在 盐酸 作用下， 反应 2.0h， 生成 D-吡喃木糖 、 D-葡萄糖 、 D-吡喃葡萄糖 、 L-(+)-arabinose
  参考文献：
  名称：

  Isolation and Structures of Erylosides from the Carribean Sponge Erylus formosus

  摘要：

  Nine new triterpene glycosides, erylosides F-1-F-4 (1-4), M (5), N (6), O (7), P (8), and Q (9), along with previously known erylosides F (10) and H (11) were isolated from the sponge Erylus formosus collected from the Mexican Gulf (Puerto Morelos, Mexico). Structures of 1-4 were determined as the corresponding biosides having aglycons related to penasterol with additional oxidation patterns in their side chains. Erylosides 5-9 contain new variants of carbohydrate chains with three (5, 6), four (7), and six (8, 9) sugar units, respectively. Erylosides 5, 7, 8, and 6, 9 contain 14-carboxy-24-methylenelanost-8(9)-en-3 beta-ol and penasterol as aglycons, respectively. In contrast with its epimer 2, the compound 3 induced the early apoptosis of Ehrlich carcinoma cells at a concentration of 100 mu g/mL, while 1 and 10 activated the Ca2+ influx into mouse spleenocytes (130% of the control) at the same doses.

  DOI：

  10.1021/np060364q

文献信息

• Isolation and Structures of Erylosides from the Carribean Sponge <i>Erylus formosus</i>
  作者：Alexandr S. Antonov、Anatoly I. Kalinovsky、Valentin A. Stonik、Shamil S. Afiyatullov、Dmitry L. Aminin、Pavel S. Dmitrenok、Ernesto Mollo、Guido Cimino

  DOI：10.1021/np060364q

  日期：2007.2.1

  Nine new triterpene glycosides, erylosides F-1-F-4 (1-4), M (5), N (6), O (7), P (8), and Q (9), along with previously known erylosides F (10) and H (11) were isolated from the sponge Erylus formosus collected from the Mexican Gulf (Puerto Morelos, Mexico). Structures of 1-4 were determined as the corresponding biosides having aglycons related to penasterol with additional oxidation patterns in their side chains. Erylosides 5-9 contain new variants of carbohydrate chains with three (5, 6), four (7), and six (8, 9) sugar units, respectively. Erylosides 5, 7, 8, and 6, 9 contain 14-carboxy-24-methylenelanost-8(9)-en-3 beta-ol and penasterol as aglycons, respectively. In contrast with its epimer 2, the compound 3 induced the early apoptosis of Ehrlich carcinoma cells at a concentration of 100 mu g/mL, while 1 and 10 activated the Ca2+ influx into mouse spleenocytes (130% of the control) at the same doses.