A₁-barrigenol | 15448-03-0

• 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: A₁-barrigenol
• 英文别名: A1-Barrigenol；(3S,4aR,6aR,6bS,7R,8S,8aS,9S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,7,8,9-tetrol
• CAS: 15448-03-0
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: MBKUYULYIBPFSF-OJSXYETASA-N

物化性质

• 熔点：
  293-295 °C
• 沸点：
  599.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  A₁-barrigenol 、 苯甲酰氯 在 吡啶 作用下， 生成 3β.15α.22α.28-tetrabenzoyloxy-oleanen-(12)-ol-(16α)
  参考文献：
  名称：

  Nozoe; Kinugasa, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1935, vol. 56, p. 704,708

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 、 potassium dihydrogenphosphate 、 hesperidinase 、 silver carbonate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 A₁-barrigenol
  参考文献：
  名称：

  Triterpenoid saponins from leaves of Pittosporum undulatum

  摘要：

  DOI：

  10.1016/0031-9422(83)80166-6

文献信息

• Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (<i>Camellia sinensis</i>)
  作者：Hisashi Matsuda、Makoto Hamao、Seikou Nakamura、Haruka Kon’i、Megumi Murata、Masayuki Yoshikawa

  DOI：10.1248/cpb.60.674

  日期：——

  Effects of principal saponins, chakasaponins I-III, from the flower buds of Camellia sinensis cultivated in Fujian province, China on plasma triglyceride (TG) and glucose levels in olive oil or sucrose-loaded mice were examined. Chakasaponins I-III at 50 and 100 mg/kg significantly inhibited increases in plasma TG and glucose levels. Furthermore, they prevented gastric emptying, suggesting that the

  研究了来自中国福建省茶树的花蕾中的主要皂苷，chakasaponins I-III对载有橄榄油或蔗糖的小鼠血浆甘油三酸酯（TG）和葡萄糖水平的影响。Chakasaponins I-III的浓度为50和100 mg / kg，可显着抑制血浆TG和葡萄糖水平的升高。此外，它们阻止了胃排空，表明前者的抑制作用部分取决于对胃排空的抑制。此外，基于化学和物理化学证据，阐明了一种新的酰化的齐墩果烷型三萜寡糖甙，chakasaponin IV的化学结构。
• Cytotoxic Oxygenated Triterpenoid Saponins from <i>Symplocos chinensis</i>
  作者：Guangmiao Fu、Yue Liu、Shishan Yu、Xiangzhong Huang、Youcai Hu、Xiaoguang Chen、Furong Zhang

  DOI：10.1021/np060160+

  日期：2006.12.1

  A n-butanol-soluble fraction of an ethanolic extract from the roots of Symplocos chinensis showed cytotoxic activity against several cancer cell lines. Bioassay-guided purification led to the isolation and characterization of eight new triterpenoid saponins, symplocososides L-S (1-8). The structures of 1-8 were elucidated as glycosides based on oxygenated aglycons by spectroscopic and chemical methods

  来自中华plo的根的乙醇提取物的正丁醇可溶级分显示出对几种癌细胞系的细胞毒活性。生物测定指导的纯化导致了八种新的三萜皂苷，symplocososides LS（1-8）的分离和表征。通过光谱和化学方法，基于氧化的糖苷配基阐明1-8的结构为糖苷。这些化合物及其水解产物，以及早先从中华葡萄球菌根获得的一些其他类似物，在一个小型癌细胞组中进行了细胞毒性评估。
• Ternstroenols A – E: Undescribed pentacyclic triterpenoids from the Australian rainforest plant Ternstroemia cherryi
  作者：Ahilya Singh、Jason K. Cullen、Zara C. Bruce、Paul Reddell、Gerald Münch、Ritesh Raju

  DOI：10.1016/j.phytochem.2020.112426

  日期：2020.8

  Chromatographic separation of the extracts of the Australian rainforest plant Ternstroemia cherryi led to the isolation of five undescribed barrigenol-like triterpenoids, ternstroenols A - E, from the fruits and three known ones from the leaves. Ternstroenols A - E represent a new form of structural diversity, being the first in its kind to incorporate a trans- 2, 4, 6- decatrienoyl moiety at C-22. The structures of the ternstroenols were assigned by detailed spectroscopic analysis, degradation and chemical derivatization. All compounds exhibited potent antiinflammatory activity in LPS and IFN-gamma activated RAW 264.7 macrophages, with IC50, values as low as 0.7 mu M. Despite the remarkable potency, high levels of unwanted cell growth inhibition was also observed, which prompted their cytotoxic evaluation in U87/U251 human glioblastoma cell lines.
• Nozoe; Kinugasa, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1935, vol. 56, p. 864,868
  作者：Nozoe、Kinugasa

  DOI：——

  日期：——
• Ito et al., Tetrahedron Letters, 1967, p. 2289
  作者：Ito et al.

  DOI：——

  日期：——