匙羹藤苷元 | 19942-02-0

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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: 匙羹藤苷元
• 中文别名: (3BETA,4ALPHA,16BETA,21BETA)-齐墩果-12-烯-3,16,21,23,28-五醇
• 英文名称: 3β,16β,21β,23,28-pentahydroxyolean-12-ene
• 英文别名: gymnestrogenin；(3β,16β,21β)-olean-12-ene-3,16,21,23,28-pentol；(3S,4aS,5S,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,5,10-triol
• CAS: 19942-02-0
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: SIBYGGBNBRCVQI-DGNDGBPUSA-N

物化性质

• 熔点：
  288-289℃

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  2
• 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

制备方法与用途

生物活性

Gymnestrogenin 是从 Gymnema sylvestre R.Br. 叶片中提取的一种五羟基三萜。它是一种有效的 LXR 拮抗剂，对 LXRα 和 LXRβ 的反式激活具有不同的抑制 IC50 值：2.5 μM 对于 LXRα 和 1.4 μM 对于 LXRβ。此外，Gymnestrogenin 还能直接降低其自身启动子上的 LXR 转录活性，从而减少 mRNA 的表达。

靶点

• IC50: 2.5 μM (LXRα) 和 1.4 μM (LXRβ)

体外研究

Gymnestrogenin 在体外能够减少 SREBP1c 和 ABCA1 的表达，并通过减少 HepG2 细胞中的脂质积累来发挥其生物学作用。

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 匙羹藤苷元 在 吡啶 作用下， 生成 3β,16β,21β,23,28-Penta-O-acetylolean-12-en
  参考文献：
  名称：

  Glochidioside，一种来自Glochidion heynenum的三萜糖苷

  摘要：

  摘要 从Glochidion heynenum 中分离得到了一种新的三萜糖苷glochidioside。其结构已确定为 3β[( O -β- D -吡喃葡萄糖基-(1 → 3)- O -α- L -arabinopyranosyl)oxy]-16β-benzoyloxy-olean-12-ene-21β,23,28-三重奏

  DOI：

  10.1016/s0031-9422(00)84539-2
• 作为产物：
  描述：

  glochidioside 在 盐酸 、 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 匙羹藤苷元
  参考文献：
  名称：

  Glochidioside，一种来自Glochidion heynenum的三萜糖苷

  摘要：

  摘要 从Glochidion heynenum 中分离得到了一种新的三萜糖苷glochidioside。其结构已确定为 3β[( O -β- D -吡喃葡萄糖基-(1 → 3)- O -α- L -arabinopyranosyl)oxy]-16β-benzoyloxy-olean-12-ene-21β,23,28-三重奏

  DOI：

  10.1016/s0031-9422(00)84539-2

文献信息

• Triterpene Saponins from <i>Pleurospermum kamtschaticum</i> and Their Biological Activity
  作者：Il Kyun Lee、Sang Un Choi、Kang Ro Lee

  DOI：10.1248/cpb.c12-00274

  日期：——

  Eleven new triterpene saponins (1–11), together with fourteen known triterpene and triterpene saponins (12–25) were isolated from a MeOH extract of Pleurospermum kamtschaticum HOFFMANN (Umbelliferae). The chemical structures of the new compounds (1–11) were determined by means of MS, 1H-NMR, 13C-NMR, correlated spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), total correlated spectroscopy (TOCSY) and nuclear Overhauser effect spectroscopy (NOESY) to be pleurosaponin A (1)–K (11). The isolated compounds were tested for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, HCT15) in vitro using the sulforhodamine B bioassay (SRB) assay. All compounds showed little cytotoxicity against tested cell lines (IC50 >30 µM).

  从伞形科植物Pleurospermum kamtschaticum HOFFMANN（Pleurospermum kamtschaticum HOFFMANN）的MeOH提取物中分离出11种新的三萜皂苷（1-11）以及14种已知的三萜和三萜皂苷（12-25）。通过质谱、1H-核磁共振、13C-核磁共振、相关光谱（COSY）、异核多键相关光谱（HMBC）、总相关光谱（TOCSY）和核奥弗霍塞尔效应光谱（NOESY）等方法确定了新化合物（1-11）的化学结构为胸腺皂苷 A (1)-K (11)。利用磺基罗丹明 B 生物测定法（SRB）体外测试了分离出的化合物对四种人类肿瘤细胞系（A549、SK-OV-3、SK-MEL-2 和 HCT15）的细胞毒性。所有化合物对受试细胞株的细胞毒性都很小（IC50 >30 µ<小>M）。
• Molecular decodification of gymnemic acids from Gymnema sylvestre. Discovery of a new class of liver X receptor antagonists
  作者：Barbara Renga、Carmen Festa、Simona De Marino、Simone Di Micco、Maria Valeria D’Auria、Giuseppe Bifulco、Stefano Fiorucci、Angela Zampella

  DOI：10.1016/j.steroids.2015.01.024

  日期：2015.4

  The individual chemical components of commercial extract of Gymnema sylvestre, a medicinal plant used in the traditional systems of the Indian medicine for its antidiabetic and hypolipidemic properties, were isolated and evaluated for their capability to act as modulators of nuclear and membrane receptors involved in glucose and lipid homeostasis.The study disclosed for the first time that individual gymnemic acids are potent and selective antagonists for the beta isoform of LXR. Indeed the above activity was shared by the most abundant aglycone gymnemagenin (10) whereas gymnestrogenin (11) was endowed with a dual LXR alpha/beta antagonistic profile. Deep pharmacological investigation demonstrated that gymnestrogenin, reducing the expression of SREBP1c and ABCA1 in vitro, is able to decrease lipid accumulation in HepG2 cells. The results of this study substantiate the use of G. syivestre extract in LXR mediated dislypidemic diseases. (C) 2015 Elsevier Inc. All rights reserved.
• YOSHIKAWA, KAZUKO;AMIMOTO, KAYOKO;ARIHARA, SHIGENOBU;MATSUURA, KOUJI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 852-854
  作者：YOSHIKAWA, KAZUKO、AMIMOTO, KAYOKO、ARIHARA, SHIGENOBU、MATSUURA, KOUJI

  DOI：——

  日期：——
• Compositions and Methods Comprising Zingiber Species
  申请人：Li Dan

  公开号：US20080160116A1

  公开（公告）日：2008-07-03

  An aspect of the present invention relates to compositions comprising a gingerol, for example, compositions comprising gingerol in an amount greater than about 2% by weight. In some aspects of the invention, the composition comprises 6-gingerol, 8-gingerol, 10-gingerol, 6-shagaol, or combinations thereof. Another aspect of the invention relates to a method for extracting a ginger species comprising, sequentially extracting a ginger species plant material to yield an essential oil fraction, a gingerol fraction, a phenolic fraction, and a polysaccharide fraction, wherein the essential oil and gingerol fractions are derived by extracting plant feedstock material by supercritical carbon dioxide extraction, the phenolic fraction is extracted from the plant feedstock material or from the remainder of the essential oil and gingerol extractions by hydroalcoholic extraction, and the polysaccharide fraction is derived by water extraction of the remainder of the phenolic extraction.
• Rice Bran Extracts for Inflammation and Methods of Use Thereof
  申请人：Alberte Randall S.

  公开号：US20090285919A1

  公开（公告）日：2009-11-19

  The present invention relates in part to stabilized rice bran extracts enriched in compounds that have inhibitory activity against certain anti-inflammatory therapeutic endpoints, such as the COX-1, COX-2 and 5-LOX enzymes. Another aspect of the invention relates to pharmaceutical compositions comprising the extracts and to methods of treating inflammatory diseases comprising administering the aforementioned extracts.