玉蕊皂苷元C | 13844-01-4

• 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: 玉蕊皂苷元C
• 英文名称: barringtogenol C
• 英文别名: (3R,4R,4aR,5R,6aS,6bR,12aR)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-3,4,5,10-tetraol；3β,16α,21β,22α,,28-pentahydroxyolean-12-ene；protoaescigenin；olean-12-ene-3β,16α,21β,22α,28-pentaol；(4aR)-3c.4t.5t.10c-Tetrahydroxy-2.2.6at.6bc.9.9.12ac-heptamethyl-4ar-hydroxymethyl-(8atH.12btH.14bcH)-Δ¹⁴-eicosahydro-picen；Oleanen-(12)-pentol-(3β.16α.21β.22α.28)；Theasapogenol B；(3R,4R,4aR,5R,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-3,4,5,10-tetrol
• CAS: 13844-01-4
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: AYDKOFQQBHRXEW-AAUPIIFFSA-N

物化性质

• 熔点：
  315-320 °C (decomp)
• 沸点：
  598.4±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)：
  4.6
• 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：

  玉蕊皂苷元C 在 双氧水 、 溶剂黄146 作用下， 生成 12-Oxo-12,13-dihydro-barringtogenol-C-pentaacetat
  参考文献：
  名称：

  Barua,A.K. et al., Journal of the Indian Chemical Society, 1963, vol. 40, # 6, p. 483 - 485

  摘要：

  DOI：
• 作为产物：
  描述：

  barringtogenol C pentaacetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 玉蕊皂苷元C
  参考文献：
  名称：

  Übertriterpene—XXVI：曙红（Aescin）和死于糖苷泛黄的糖苷

  摘要：

  来自七叶七叶树种子的结晶性主要皂苷“七叶皂苷”是复杂的混合物，其各个成分具有相同的基本原理。存在高度羟基化的三萜衍生物（原七叶皂苷元和巴丁香酚C），其中当归酸/鸟苷酸和乙酸作为酯键合在C-21和C-22处。C-3的OH基与d-葡萄糖醛酸相连，在位置2和4处有两个d-葡萄糖分子，一个d-葡萄糖可部分转化为d-木糖或d-半乳糖。

  DOI：

  10.1016/s0040-4020(01)82635-1

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。
• Triterpenoids—XXIX
  作者：A.K. Barua、S.P. Dutta、B.C. Das

  DOI：10.1016/0040-4020(68)88060-3

  日期：1968.1

  The constitution of barringtogenol B, a new triterpenoid sapogenin isolated from the fruits of Barringtonia acutangula Gaertn has been shown to be 3β, 21β, 22α, 28-tetrahydroxy-16α-angeloyloxy-olean-12-ene

  分离自Barringtonia acutangula Gaertn果实的一种新的三萜类皂甙元Barringtogenol B的组成已显示为3β，21β，22α，28-四羟基-16α-angelyloxy-olean-12-ene
• 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。
• A triterpenoid saponin possessing antileishmanial activity from the leaves of Careya arborea
  作者：Debayan Mandal、Nilendu Panda、Shrabanti Kumar、Sukdeb Banerjee、Nirup B. Mandal、Niranjan P. Sahu

  DOI：10.1016/j.phytochem.2005.10.028

  日期：2006.1

  Bioguided-fractionation of the methanol extract of the leaves of Careya arborea led to isolation of a triterpenoid saponin, designated arborenin, and characterized as 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-2 alpha,3beta-dihydroxy-taraxast-20-en-28-oic acid (1), together with desacylescin III (2). The structures were determined on the basis of extensive 2D NMR spectroscopic analysis

  Careya arborea 叶子的甲醇提取物的生物引导分馏导致三萜皂苷的分离，命名为 arborenin，并表征为 3-O-β-D-吡喃葡萄糖基 (1-->2)-β-D-吡喃葡萄糖基- 2 alpha,3beta-dihydroxy-taraxast-20-en-28-oic 酸 (1)，连同 desacylescin III (2)。结构是在广泛的 2D NMR 光谱分析的基础上确定的。皂苷在体外对杜氏利什曼原虫（菌株 AG 83）显示出抗利什曼原虫活性。
• [EN] PROTOESCIGENIN DERIVATIVE, PROCESS OF ITS PREPARATION, USE OF SAID COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THAT COMPOUND<br/>[FR] DÉRIVÉ DE PROTOESCIGÉNINE, SON PROCÉDÉ DE PRÉPARATION, UTILISATION DUDIT COMPOSÉ ET COMPOSITION PHARMACEUTIQUE LE CONTENANT
  申请人：UNIV WARSZAWSKI MEDYCZNY

  公开号：WO2016135553A1

  公开（公告）日：2016-09-01

  The present invention relates to a protoescigenin derivative of formula (I) having pharmacological properties, process of its preparation, use of such compound as medicament especially for treating vascular disorders, as well as to a pharmaceutical composition comprising such compound.

  本发明涉及具有药理性质的公式（I）的原雌甾醇衍生物，其制备过程，将该化合物用作药物，特别用于治疗血管疾病，以及包含该化合物的药物组合物。