soyasaponin I methyl ester | 86764-13-8

• 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: soyasaponin I methyl ester
• 英文别名: 22β,24-dihydroxyolean-12-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranosiduronic acid methyl ester；methyl (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylate
• CAS: 86764-13-8
• 化学式: C₄₉H₈₀O₁₈
• 分子量: 957.163
• InChiKey: ZEIAROWTCSYWFT-QVOSIWNASA-N

物化性质

• 沸点：
  991.6±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  67
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  284
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  soyasaponin I methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2S,3R,4R,5R,6S)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,4S,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
  参考文献：
  名称：

  满天金（Desmodium styracifolium）成分的研究。

  摘要：

  从Desmodii Herba [满地香（Desmodium styracifolium（Osbeck）Merr）干燥的整株植物中分离出了两个三萜皂苷（1和2）。（豆科）]及其化学结构被表征为大豆皂苷I和新的皂苷3-O- [α-L-鼠李糖基-（1 ---- 2）-β-D-吡喃半乳糖基-（1 ---- 2）通过化学和光谱方法分别测定β-D-D-葡萄糖醛酸吡喃糖基]大豆皂酚E。

  DOI：

  10.1248/cpb.37.2229
• 作为产物：
  描述：

  重氮甲烷 、 大豆皂苷 Bb 以 乙醚 为溶剂， 生成 soyasaponin I methyl ester
  参考文献：
  名称：

  Oleanene glycosides from seeds of Trifolium alexandrinum

  摘要：

  From the seeds of Trifolium alexandrinum, two new oleanene-type triterpene glycosides were isolated as their methyl esters, together with five known saponins. The structures of the isolated compounds were determined by NMR and mass spectral analyses.

  DOI：

  10.1016/0031-9422(95)00430-f

文献信息

• Study on the constituents of Desmodium styracifolium.
  作者：Tomoko KUBO、Syuichi HAMADA、Toshihiro NOHARA、Zhi-rou WANG、Hideo HIRAYAMA、Keiichi IKEGAMI、Ken YASUKAWA、Michio TAKIDO

  DOI：10.1248/cpb.37.2229

  日期：——

  Two triterpenoid saponins (1 and 2) were isolated from Desmodii Herba [the dried whole plants of Desmodium styracifolium (Osbeck) Merr. (Leguminosae)] and their chemical structures were characterized as soyasaponin I and a new saponin, 3-O-[alpha-L-rhamnopyranosyl-(1----2)-beta-D-galactopyranosyl- (1----2)-beta-D-glucuronopyranosyl]soyasapogenol E, respectively, by chemical and spectroscopic means

  从Desmodii Herba [满地香（Desmodium styracifolium（Osbeck）Merr）干燥的整株植物中分离出了两个三萜皂苷（1和2）。（豆科）]及其化学结构被表征为大豆皂苷I和新的皂苷3-O- [α-L-鼠李糖基-（1 ---- 2）-β-D-吡喃半乳糖基-（1 ---- 2）通过化学和光谱方法分别测定β-D-D-葡萄糖醛酸吡喃糖基]大豆皂酚E。
• Oleanene glycosides from seeds of Trifolium alexandrinum
  作者：Khaled M. Mohamed、Kazuhiro Ohtani、Ryoji Kasai、Kazuo Yamasaki

  DOI：10.1016/0031-9422(95)00430-f

  日期：1995.11

  From the seeds of Trifolium alexandrinum, two new oleanene-type triterpene glycosides were isolated as their methyl esters, together with five known saponins. The structures of the isolated compounds were determined by NMR and mass spectral analyses.
• Effects of Triterpenoids from Pueraria lobata on Immunohemolysis: β-D-Glucuronic Acid Plays an Active Role in Anticomplementary Activity in Vitro
  作者：Sei-Ryang Oh、Junei Kinjo、Yuichi Shii、Tuyoshi Ikeda、Toshihiro Nohara、Kyung Seop Ahn、Jung Hee Kim、Hyeong-Kyu Lee

  DOI：10.1055/s-2000-8614

  日期：2000.8

  The anticomplementary properties of kaikasaponin III (4) and soyasaponin I (8) from Pueraria lobata and their hydrolytic analogs were investigated in vitro. Diglycosidic saponins [kaikasaponin I (3), soyasaponin III (7)] showed most potent anticomplementary activities, followed by monoglycosidic saponins [soyasapogenol B monoglucuronide (6), sophoradiol monoglucuronide (2)] and triglycosidic saponins [soyasaponin I (8), kaikasaponin III (4)], whereas sophoradiol (1) and soyasapogenol B (5) showed enhancement of hemolysis under the presence of serum on the classical pathway of complement system. But all of them showed very weak or no anticomplementary activities on the alternative pathway of complement system. The anticomplementary activity of the saponins was influenced by the nature of glucuronic acid, where the free acid forms (-COOH) showed much more potent activity than the sodium salt forms (-COO - Na+) or methyl ester forms (-COOCH3), and the reduced forms (-CH2OH) decreased the activity significantly.

  在体外研究了来自葛根的凯卡皂苷 III (4) 和大豆皂苷 I (8) 及其水解类似物的抗补体特性。二糖苷皂苷 [kaikasaponin I (3)、大豆皂苷 III (7)] 显示出最有效的抗补体活性，其次是单糖苷皂苷 [soyasapogenol B monoglucuronide (6)、sophoradiol monoglucuronide (2)] 和三糖苷皂苷 [soyasaponin I (8)、kaikasaponin] III (4)]，而槐二醇 (1) 和大豆皂醇 B (5) 在补体系统经典途径中在血清存在下显示出溶血增强。但它们对补体系统旁路途径的抗补体活性均非常弱或无抗补体活性。皂苷的抗补体活性受到葡萄糖醛酸性质的影响，其中游离酸形式（-COOH）比钠盐形式（-COO - Na+）或甲酯形式（-COOCH3）表现出更强的活性，并且还原形式（-CH2OH）显着降低活性。