cyclopassifloside II | 292167-39-6

• 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: cyclopassifloside II
• 英文别名: I(2)-D-Glucopyranosyl (1I+/-,3I(2),4I+/-,24S)-1,3,24-trihydroxy-24-(hydroxymethyl)-9,19-cyclolanostan-28-oate；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-dihydroxy-15-[(2R,5S)-5-hydroxy-5-(hydroxymethyl)-6-methylheptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylate
• CAS: 292167-39-6
• 化学式: C₃₇H₆₂O₁₁
• 分子量: 682.893
• InChiKey: ZNQCKSPNGMMRRF-GOUYUMKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 cyclopassifloside II 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Four Cycloartane Triterpenoids and Six Related Saponins from Passiflora edulis

  摘要：

  Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7), IV (8), V (9), and VI (10), were isolated from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A-D were assigned as 22(R),24(S)-1 alpha,3 beta,22,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; 24(5)-1 alpha,3 beta,24,31-tetrahydroxy-24-methycycloartan-28-oic acid; 20(S),24(S)-1 alpha,3 beta,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1 alpha,3 beta,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were established as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Finally, cyclopassiflosides III and V were demonstrated as the 28,31-bis-O-beta-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).

  DOI：

  10.1021/np000126+

文献信息

• Four Cycloartane Triterpenoids and Six Related Saponins from <i>Passiflora edulis</i>
  作者：Kazuko Yoshikawa、Susumu Katsuta、Junko Mizumori、Shigenobu Arihara

  DOI：10.1021/np000126+

  日期：2000.9.1

  Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7), IV (8), V (9), and VI (10), were isolated from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A-D were assigned as 22(R),24(S)-1 alpha,3 beta,22,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; 24(5)-1 alpha,3 beta,24,31-tetrahydroxy-24-methycycloartan-28-oic acid; 20(S),24(S)-1 alpha,3 beta,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1 alpha,3 beta,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were established as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Finally, cyclopassiflosides III and V were demonstrated as the 28,31-bis-O-beta-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).