sarasinoside A₁ | 114099-54-6

• 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: sarasinoside A₁
• 英文别名: Sarasinoside A1；N-[(2S,3R,4R,5R,6R)-2-[(3R,4S,5R,6S)-5-[(2S,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-[[(3S,5R,10S,13R,14R,17R)-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-4-oxohept-5-en-2-yl]-1,2,3,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 114099-54-6
• 化学式: C₆₂H₁₀₀N₂O₂₆
• 分子量: 1289.47
• InChiKey: YMIDOMYJFRKBJR-ONJRYDCZSA-N

物化性质

• 熔点：
  209-212 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  90
• 可旋转键数：
  20
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  431
• 氢给体数：
  15
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  sarasinoside A₁ 在 β-glucosidase 作用下， 生成 sarasinoside A₁-pro-3
  参考文献：
  名称：

  Structures of sarasinosides a1, b1, and c1; New norlanostane-triterpenoid oligoglycosides from the palauan marine sponge Asteropus sarasinosum.

  摘要：

  从帕劳海生海绵 Asteropus sarasinosum 中分离出 9 种新的正羊毛甾烷三萜寡糖苷（sarasinoside），并根据化学性质确定了三种主要寡糖苷的结构，即 sarasinoside A1 (7)、B1 (8) 和 C1 (4)。物理化学证据，包括皂醇的 X 射线分析。

  DOI：

  10.1248/cpb.35.5036

文献信息

• Structures of sarasinosides a1, b1, and c1; New norlanostane-triterpenoid oligoglycosides from the palauan marine sponge Asteropus sarasinosum.
  作者：Isao Kitagawa、Motomasa Kobayashi、Yoshihiro Okamoto、Masayuki Yoshikawa、Yoshihiro Hamamoto

  DOI：10.1248/cpb.35.5036

  日期：——

  Nine new norlanostane-triterpenoid oligoglycosides (sarasinoside) were isolated from the Palauan marine sponge Asteropus sarasinosum and the structures of three major oligoglycosides named sarasinosides A1 (7), B1 (8), and C1 (4) have been determined on the basis of chemical and physicochemical evidence including the x-ray analysis of the sapogenol.

  从帕劳海生海绵 Asteropus sarasinosum 中分离出 9 种新的正羊毛甾烷三萜寡糖苷（sarasinoside），并根据化学性质确定了三种主要寡糖苷的结构，即 sarasinoside A1 (7)、B1 (8) 和 C1 (4)。物理化学证据，包括皂醇的 X 射线分析。
• SCHMITZ, FRANCIS J.;KSEBATI, MOHAMAD B.;GUNASEKERA, SARATH P.;AGARWAL, SA+, J. ORG. CHEM., 53,(1988) N 25, C. 5941-5947
  作者：SCHMITZ, FRANCIS J.、KSEBATI, MOHAMAD B.、GUNASEKERA, SARATH P.、AGARWAL, SA+

  DOI：——

  日期：——
• Marine Natural Products. XXVIII. The Structures of Sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, Nine New Norlanostane-Triterpenoidal Oligoglycosides from the Palauan Marine Sponge Asteropus sarasinosum.
  作者：Motomasa KOBAYASHI、Yoshihiro OKAMOTO、Isao KITAGAWA

  DOI：10.1248/cpb.39.2867

  日期：——

  The chemical structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine 30-norlanostane-triterpenoidal oligoglycosides isolated from the Palauan marine sponge Asteropus sarasinosum have been elucidated on the basis of chemical and physicochemical evidence. Sarasinosides A2 (2) and A3 (3) were shown to be the 7, 9(11)-diene and 8, 14-diene analogs of sarasinoside A1 (1), whereas sarasinosides B2 (7) and B3 (9) were the 7, 9(11)-diene and 8, 14-diene analogs of sarasinoside B1 (5), respectively. Similar structural correlations of sarasinosides C2 (6) and C3 (8) with sarasinoside C1 (4) were demonstrated. These sarasinosides characteristically contain one mole each of N-acetyl-glucosamine and N-acetylgalactosamine in their oligosaccharide moieties.

  根据化学和物理化学证据，阐明了从帕劳海洋海绵 Asteropus sarasinosum 分离出的九种 30-去甲龙脑三萜类低聚糖苷的化学结构。研究表明，沙拉苷 A2 (2) 和 A3 (3) 分别是沙拉苷 A1 (1) 的 7、9(11)-二烯和 8、14-二烯类似物，而沙拉苷 B2 (7) 和 B3 (9) 分别是沙拉苷 B1 (5) 的 7、9(11)-二烯和 8、14-二烯类似物。沙拉糖苷 C2 (6) 和 C3 (8) 与沙拉糖苷 C1 (4) 也有类似的结构关联。这些沙星苷的特点是在其寡糖分子中分别含有一摩尔的 N-乙酰氨基葡萄糖和 N-乙酰半乳糖胺。