23-O-β-D-glucopyranosyl-3β,20S,23S,30-tetrahydroxydammar-24-en-16-on-3-yl O-α-L-fucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranoside

• 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: 23-O-β-D-glucopyranosyl-3β,20S,23S,30-tetrahydroxydammar-24-en-16-on-3-yl O-α-L-fucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranoside
• 英文别名: protojujuboside B₁；(3S,5R,8R,9R,10R,13R,14S,17S)-3-[(2S,3R,4S,5S)-4-[(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-5-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-14-(hydroxymethyl)-17-[(2S,4R)-2-hydroxy-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-4,4,8,10-tetramethyl-1,2,3,5,6,7,9,11,12,13,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
• 化学式: C₅₈H₉₆O₂₇
• 分子量: 1225.38
• InChiKey: JWDBYPGADNNYPU-JZQJKUAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  85
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  433
• 氢给体数：
  16
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  23-O-β-D-glucopyranosyl-3β,20S,23S,30-tetrahydroxydammar-24-en-16-on-3-yl O-α-L-fucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->2)-β-D-glucopyranosyl-(1->3)]-α-L-arabinopyranoside 在 盐酸 、 甲醇 作用下， 反应 1.0h， 以0.9 mg的产率得到香果灵内酯
  参考文献：
  名称：

  Bioactive Saponins and Glycosides. XIV. Structure Elucidation and Immunological Adjuvant Activity of Novel Protojujubogenin Type Triterpene Bisdesmosides, Protojujubosides A, B, and B1, from the Seeds of Zizyphus jujuba var. spinosa (Zizyphi Spinosi Semen).

  摘要：

  继阐明了大枣苷 A1 和 C 以及乙酰大枣苷 B 之后，又从大枣种子 Zizyphus jujuba MILL. var. spinosa HU 的种子 Zizyphi Spinosi Semen 中分离出了新型原大枣苷类三萜双二苷，即原大枣苷 A、B 和 B1。原大枣苷 A、B 和 B1 的结构是根据化学和物理化学证据确定的，其中包括利用酶水解将原大枣苷转化为已知的大枣苷。研究发现，原大枣苷 A 和大枣苷 A、B 和 C 具有很强的免疫佐剂活性。

  DOI：

  10.1248/cpb.47.1744

文献信息

• Bioactive Saponins and Glycosides. XIV. Structure Elucidation and Immunological Adjuvant Activity of Novel Protojujubogenin Type Triterpene Bisdesmosides, Protojujubosides A, B, and B1, from the Seeds of Zizyphus jujuba var. spinosa (Zizyphi Spinosi Semen).
  作者：Hisashi MATSUDA、Toshiyuki MURAKAMI、Akira IKEBATA、Johji YAMAHARA、Masayuki YOSHIKAWA

  DOI：10.1248/cpb.47.1744

  日期：——

  Following the elucidation of jujubosides A1 and C and acetyljujuboside B, novel protojujubogenin type triterpene bisdesmosides, protojujubosides A, B, and B1, were isolated from Zizyphi Spinosi Semen, the seeds of Zizyphus jujuba MILL. var. spinosa HU. The structures of protojujubosides A, B, and B1 were determined on the basis of chemical and physicochemical evidence, which included the conversion of protojujubosides to known jujubosides using enzymatic hydrolysis. Protojujubosides A and jujubosides A, B, and C were found to show potent immunological adjuvant activity.

  继阐明了大枣苷 A1 和 C 以及乙酰大枣苷 B 之后，又从大枣种子 Zizyphus jujuba MILL. var. spinosa HU 的种子 Zizyphi Spinosi Semen 中分离出了新型原大枣苷类三萜双二苷，即原大枣苷 A、B 和 B1。原大枣苷 A、B 和 B1 的结构是根据化学和物理化学证据确定的，其中包括利用酶水解将原大枣苷转化为已知的大枣苷。研究发现，原大枣苷 A 和大枣苷 A、B 和 C 具有很强的免疫佐剂活性。