蜡果杨梅酸 B | 55497-79-5

• 物质功能分类: 天然产物 - 萜类
• 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
• 中文名称: 蜡果杨梅酸 B
• 中文别名: 蜡果杨梅酸B
• 英文名称: Myriceric acid B
• 英文别名: (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 55497-79-5
• 化学式: C₃₉H₅₄O₇
• 分子量: 634.854
• InChiKey: IZCSLJUDQLFLNO-YYGQYJBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

忍冬酸B是一种有效的HIV-1进入抑制剂，能够靶向gp41。此外，它还具有抗肿瘤作用。

反应信息

• 作为反应物：
  描述：

  蜡果杨梅酸 B 在 三氯化铁 作用下， 以 丙酮 为溶剂， 生成 rhoipteleic acid B 、 rhoipteleic acid A
  参考文献：
  名称：

  Two diastereomeric triterpene-lignan esters having dimeric structure and their biosynthetically related triterpene caffeate from Rhoiptelea chiliantha

  摘要：

  27-Caffeoyloxy-3-beta-hydroxyolean-12-en-28-oic acid (1) and rhoipteleic acids A (2) and B (3), diastereomeric esters composed of two triterpene units and enantiomeric lignan carboxylic acids, were isolated from the bark of Rhoiptelea chiliantha. The structures have been determined on the basis of spectroscopic and chemical evidence including biomimetic synthesis of 2 and 3 from 1.

  DOI：

  10.1016/s0040-4039(00)73041-3
• 作为产物：
  描述：

  在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以2.3%的产率得到蜡果杨梅酸 B
  参考文献：
  名称：

  Endothelin Receptor Antagonist Triterpenoid, Myriceric Acid A, Isolated from Myrica cerifera, and Structure Activity Relationships of Its Derivatives.

  摘要：

  作为第一种非肽类内皮素受体拮抗剂，新的三萜类化合物——美洲杜鹃酸A（myiceric acid A，50-235）（1）是从海梅果（Myrica cerifera）中分离得到的。美洲杜鹃酸A（1）不仅抑制了内皮素-1诱导的细胞质游离Ca<2+>浓度的增加（IC50 = 11±2 nM），还抑制了[<125&I]内皮素-1在大鼠主动脉平滑肌细胞中的结合（Ki = 66±15 nM）。此外，还分离出了两种新的相关三萜类化合物，美洲杜鹃酸C（6）和美洲杜鹃酸D（8）。进一步地，对这些天然产物的化学修饰导致合成了硫酸酯衍生物（13、14、15），其对内皮素受体的亲和力提高了1.5到20倍。讨论了美洲杜鹃酸及其衍生物的结构活性关系。

  DOI：

  10.1248/cpb.44.343

文献信息

• Chilianthins A-F, Six Triterpene Esters Having Dimeric Structures from Rhoiptelea chiliantha DIELS et HAND.-MAZZ.
  作者：Zhi-Hong JIANG、Takashi TANAKA、Isao KOUNO

  DOI：10.1248/cpb.44.1669

  日期：——

  Five triterpene-lignan esters, chilianthins A-E (2-6) and a triterpene-naphthalene carboxylic acid ester, chilianthin F (7), were isolated from the bark of Rhoiptelea chiliantha DIELS et HAND.-MAZZ. (Rhoipteleaceae), together with a known triterpene caffeate, 27-caffeoyloxy-3β-hydroxyolean-12-en-28-oic acid (myriceric acid B, 1). Their structures were elucidated on the basis of spectroscopic and chemical evidence. Chilianthins A (2), B (3), C (4) and E (6) were biomimetically synthesized from 1 by oxidative coupling.

  从 Rhoiptelea chiliantha DIELS et HAND.-MAZZ 的树皮中分离出五种三萜-木脂素酯，chilianthins A-E (2-6) 和三萜-萘羧酸酯，chilianthin F (7)。 （Rhoipteleaceae），以及已知的三萜咖啡酸酯，27-咖啡酰氧基-3β-羟基齐墩果酸-12-en-28-oic酸（杨梅酸B，1）。它们的结构是根据光谱和化学证据阐明的。 Chilianthins A (2)、B (3)、C (4) 和 E (6) 是通过氧化偶联从 1 仿生合成的。
• Endothelin Receptor Antagonist Triterpenoid, Myriceric Acid A, Isolated from Myrica cerifera, and Structure Activity Relationships of Its Derivatives.
  作者：Kensuke SAKURAWI、Fumio YASUDA、Takehiko TOZYO、Miharu NAKAMURA、Tomohiro SATO、Junko KIKUCHI、Yoshihiro TERUI、Yuji IKENISHI、Tsuyoshi IWATA、Kazuhiro TAKAHASHI、Toshiro KONOIKE、Shin-ichi MIHARA、Masafumi FUJIMOTO

  DOI：10.1248/cpb.44.343

  日期：——

  As the first non-peptide endothelin receptor antagonist form a higher plant, a new triter penoid, myiceric acid A (50-235) (1) was isolated from the bayberry, Myrica cerifera. myriceric acid A (1) inhibited not only an endothelin-1-induced increase in cytosolic free Ca&glt;2+> concentration (IC50=11±2nM) but [<125&t;I]endothelin-1 binding in rat aortic smooth muscle cells (Ki=66±15nM). Two new related triterpenoids, myriceric acid C (6), and myriceric acid D (8), were also isolated. Furthermore, the chemical modification of these natural products led to the synthesis of sulfated derivative (13, 14, 15) which showed 1.5 to 20 times higher affinity for endothelin receptors. The structure activity relationships of myriceric acids and their derivatives are discussed.

  作为第一种非肽类内皮素受体拮抗剂，新的三萜类化合物——美洲杜鹃酸A（myiceric acid A，50-235）（1）是从海梅果（Myrica cerifera）中分离得到的。美洲杜鹃酸A（1）不仅抑制了内皮素-1诱导的细胞质游离Ca<2+>浓度的增加（IC50 = 11±2 nM），还抑制了[<125&I]内皮素-1在大鼠主动脉平滑肌细胞中的结合（Ki = 66±15 nM）。此外，还分离出了两种新的相关三萜类化合物，美洲杜鹃酸C（6）和美洲杜鹃酸D（8）。进一步地，对这些天然产物的化学修饰导致合成了硫酸酯衍生物（13、14、15），其对内皮素受体的亲和力提高了1.5到20倍。讨论了美洲杜鹃酸及其衍生物的结构活性关系。
• Two diastereomeric triterpene-lignan esters having dimeric structure and their biosynthetically related triterpene caffeate from Rhoiptelea chiliantha
  作者：Zhi-Hong Jiang、Takashi Tanaka、Isao Kouno

  DOI：10.1016/s0040-4039(00)73041-3

  日期：1994.3

  27-Caffeoyloxy-3-beta-hydroxyolean-12-en-28-oic acid (1) and rhoipteleic acids A (2) and B (3), diastereomeric esters composed of two triterpene units and enantiomeric lignan carboxylic acids, were isolated from the bark of Rhoiptelea chiliantha. The structures have been determined on the basis of spectroscopic and chemical evidence including biomimetic synthesis of 2 and 3 from 1.