R1-barrigenol | 15399-43-6

• 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: R1-barrigenol
• 英文别名: R₁-barrigenol；(4aS)-3c,4t,5t,6t,10c-Pentahydroxy-2,2,6at,6bc,9,9,12ac-heptamethyl-4ar-hydroxymethyl-(8atH,12btH,14bcH)-Δ¹⁴-eicosahydro-picen；Oleanen-(12)-hexol-(3β,15α,16α,21β,22α,28)；R₁-Barrigenol；R1-Barrigenol (3β,15α,16α,21β,22α,28-Hexahydroxy-oleanen-(12))；Desacylsaniculagenin-A；(3R,4R,4aS,5S,6R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,6,10-pentol
• CAS: 15399-43-6
• 化学式: C₃₀H₅₀O₆
• 分子量: 506.723
• InChiKey: DZVVEETZRZUXLI-RVWOYFKVSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  615.9±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 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：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  R1-barrigenol 、 乙酸酐 在 吡啶 作用下， 生成 R1-barrigenol pentaacetate
  参考文献：
  名称：

  Ito et al., Tetrahedron Letters, 1967, p. 2289

  摘要：

  DOI：
• 作为产物：
  描述：

  ranuncoside I 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以6 mg的产率得到R1-barrigenol
  参考文献：
  名称：

  Oleanane glycosides from Hydrocotyle ranunculoides

  摘要：

  Six new oleanane glycosides, ranuncosides I-VI, have been isolated from Hydrocotyle ranunculoides. Their structures have been determined on the basis of chemical and spectroscopic studies.

  DOI：

  10.1016/s0031-9422(00)89746-0

文献信息

• Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of <i>Camellia oleifera</i>—Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects—
  作者：Sachiko Sugimoto、Guihua Chi、Yasuyo Kato、Seikou Nakamura、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.57.269

  日期：——

  The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera ABEL were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-soluble fractions also showed inhibitory effects on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl radical and superoxide. From the 1-butanol-soluble fraction, four new acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, were isolated and their structures were elucidated on the basis of chemical and physicochemical evidence. On the other hand, quercetin 3-O-α-L-rhamnopyranoside and kaempferol 3-O-α-L-rhamnopyranoside were isolated from the ethyl acetate- and 1-butanol-soluble fractions as the principal constituents, and their gastroprotective effects were examined.

  山茶花（Camellia oleifera ABEL）花蕾的甲醇提取物及其丁醇可溶部分对大鼠乙醇和吲哚美辛诱导的胃黏膜损伤显示出抑制作用。乙酸乙酯和丁醇可溶部分还表现出对大鼠晶状体醛糖还原酶的抑制作用以及对1,1-二苯基-2-苦基肼自由基和超氧自由基的清除效果。从丁醇可溶部分中分离出四种新的酰化齐墩果烷型三萜寡糖苷，命名为玉茶皂苷A、B、C和D，其结构根据化学和物理化学证据得以阐明。另一方面，从乙酸乙酯和丁醇可溶部分中分离出槲皮素3-O-α-L-鼠李糖苷和山柰酚3-O-α-L-鼠李糖苷作为主要成分，并对其胃保护作用进行了研究。
• Medicinal Flowers. XXXVI.<sup>1</sup><sup>)</sup> Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese <i>Camellia japonica</i>
  作者：Seikou Nakamura、Katsuyoshi Fujimoto、Souichi Nakashima、Takahiro Matsumoto、Tomoko Miura、Kaoru Uno、Hisashi Matsuda、Masayuki Yoshikawa

  DOI：10.1248/cpb.60.752

  日期：——

  Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E–H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.

  从中国云南省栽培的茶花花蕾中分离得到4个酰化的齐墩果烷型三萜低聚糖苷——山茶皂苷E~H，以及4个已知的三萜低聚糖苷。通过化学和物理化学证据阐明了新三萜低聚糖苷的化学结构。研究了这些三萜低聚糖苷组分对茶碱刺激的B16黑色素瘤4A5细胞黑素生成的抑制作用。
• 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。
• Isolation and structure elucidation of four new triterpenoid estersaponins from fruits of Pittosporum tobira ait.
  作者：Ilaria D'Acquarica、Maria Cristina Di Giovanni、Francesco Gasparrini、Domenico Misiti、Claudio D'Arrigo、Nicolina Fagnano、Decimo Guarnieri、Giovanni Iacono、Giuseppe Bifulco、Raffaele Riccio

  DOI：10.1016/s0040-4020(02)01364-9

  日期：2002.12

  Four new triterpenoid estersaponins, tentatively designated as IIIA2 (1), IIIA3 (2), IIIB2 (3), and IIIC4 (4) have been isolated from fruits of Pittosporum tobiraait. and their structures elucidated by spectroscopic and chemical analyses. All the four compounds consist of an acylated pentacyclic triterpenoid aglycone which bears the same oligosaccharide portion. The crude saponin mixture (CIDI) was

  从马铃薯Pittosporum tobira ait的果实中分离出了四个新的三萜酯皂苷，暂定为IIIA 2（1），IIIA 3（2），IIIB 2（3）和IIIC 4（4）。并通过光谱和化学分析阐明了它们的结构。所有四种化合物均由带有相同寡糖部分的酰化五环三萜类糖苷配基组成。发现粗皂苷混合物（CIDI）在不同的人类癌细胞系中显示出显着的体外和体内细胞毒性。
• Five New Cytotoxic Triterpenoid Saponins from the Roots of<i>Symplocos chinensis</i>
  作者：Guang-Miao Fu、Ying-Hong Wang、Song Gao、Mei-Jun Tang、Shi-Shan Yu

  DOI：10.1055/s-2005-871274

  日期：2005.7

  Five new triterpenoid saponins, named symplocososides G-K, were isolated from the roots of Symplocos chinensis. Their structures were elucidated by spectral and chemical methods as symplocososide G, 3beta-O-[beta- D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta- O-[(2 Z)-3,7-dimethyl-2,6-octadienoyl]-22 alpha-O-(2-methylbutanoyl)-R1-barrigenol

  五种新的三萜皂苷，命名为 symplocosososides GK，是从 Symplocos chinensis 的根中分离出来的。它们的结构通过光谱和化学方法阐明为 symplocososide G, 3beta-O-[beta-D-glupyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D -(3-O-乙酰基)-吡喃葡萄糖醛酸}-21β-O-[(2 Z)-3,7-二甲基-2,6-辛二烯酰基]-22 α-O-(2-甲基丁酰基)-R1-barrigenol， symplocososide H, 3beta-O-[beta-D-吡喃葡萄糖基(1-->2)][α-L-阿拉伯呋喃糖基(1-->4)]-β-D-(3-O-乙酰基)-吡喃葡萄糖基}-21beta-O-[(2E)3,7-二甲基-2,6-辛二烯酰基]-22alpha-O-(