升麻醇 | 3779-59-7

• 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 - 类固醇和类固醇衍生物
• 中文名称: 升麻醇
• 英文名称: cimigenol
• 英文别名: (23R,24S)-16,23:16,24-diepoxy-9,19-cyclolanostan-3β,15α,25-triol；(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-22-(2-hydroxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosane-2,9-diol
• CAS: 3779-59-7
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: CNBHUROFMYCHGI-IEUUZZHOSA-N

物化性质

• 熔点：
  227.5-228.5°
• 比旋光度：
  D +38° (c = 0.86 in chloroform)
• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

用途

升麻醇是升麻中的一种活性成分。研究显示，升麻提取物在体内外均表现出良好的抗癌活性。

生物活性

Cimigenol 是升麻属植物的有效成分之一，具有显著的抗肿瘤活性。

反应信息

• 作为产物：
  描述：

  升麻环氧醇苷 在 alpha-L-rhamnosidase 作用下， 反应 72.0h， 以12 mg的产率得到升麻醇
  参考文献：
  名称：

  Bioactivity-Guided Isolation of GABA_A Receptor Modulating Constituents from the Rhizomes of Actaea racemosa

  摘要：

  Black cohosh (Actaea racemosa) is a frequently used herbal remedy for the treatment of mild climacteric symptoms. In the present study, the modulation of gamma-aminobutryic acid (GABA)-induced chloride currents (I-GABA) through GABA type A (GABA(A)) receptors by black cohosh extracts and isolated compounds was investigated. GABA(A) receptors, consisting of alpha(1), beta(2), and gamma(2S) subunits, were expressed in Xenopus laevis oocytes, and potentiation of I-GABA was measured using the two-microelectrode voltage clamp technique. In a bioactivity-guided isolation procedure the positive modulation of I-GABA could be restricted to the plant terpenoid fractions, resulting in the isolation of 11 cycloartane glycosides, of which four significantly (p < 0.05) enhanced I-GABA. The most efficient effect was observed for 23-O-acetylshengmanol 3-O-beta-D-xylopyranoside (4, 100 mu M), enhancing I-GABA by 1692 +/- 201%, while actein (1), cimigenol 3-O-beta-D-xylopyranoside (6), and 25-O-acetylcimigenol 3-O-alpha-L-arabinopyranoside (8) were significantly less active. In the absence of GABA, only 4 induced small (not exceeding 1% of IGABA-max) chloride inward currents through GABA(A) receptors. It is hypothesized that the established positive allosteric modulation of GABA(A) receptors may contribute to beneficial effects of black cohosh extracts in the treatment of climacteric symptoms.

  DOI：

  10.1021/np100479w

文献信息

• Chemical Constituents from Cimicifuga dahurica and Their Anti-Proliferative Effects on MCF-7 Breast Cancer Cells
  作者：Chu Huyen、Bui Luyen、Ghulam Khan、Ha Oanh、Ta Hung、Hui-Jun Li、Ping Li

  DOI：10.3390/molecules23051083

  日期：——

  compounds from natural plants. The 70% ethanolic extract from the rizhomes of Cimicifuga dahurica (Turcz.) Maxim. (Ranunculaceae) was found to possess significant in vitro anti-proliferative effects on MCF-7 breast cancer cells. A phytochemical investigation using assay-guided fractionation of the ethanolic extract of C. dahurica resulted in the isolation of one new phenolic amide glycoside 3, two new lignan

  这项研究旨在从天然植物中寻找新的抗癌化合物。墨西哥大麦（Cimicifuga dahurica（Turcz。）Maxim）的家中的70％乙醇提取物。发现毛R科（毛un科）对MCF-7乳腺癌细胞具有显着的体外抗增殖作用。使用测定引导的达氏梭菌乙醇提取物分级分离进行植物化学研究，结果分离出一个新的酚酰胺糖苷3，两个新的木脂素苷4和7，一个新的9,19-环烷三萜三萜糖苷6和十三种已知的组成1、2、5和8-17。3、4、6和7的结构是使用现代NMR方法及其HRESIMS数据建立的。使用BrdU增殖试剂盒评估了分离出的化合物的抗增殖作用。在17种分离的化合物中，有5种显示出显着的抗增殖作用（p≤0.05），其中化合物7表现出了最显着的抗增殖和细胞周期阻滞作用（p≤0.05），其呈剂量依赖性。蛋白质印迹蛋白表达分析表明c-Myc和细胞周期蛋白D1的表达下调，这进一步阐明了化合物7的抗增殖机制，同时发现
• Studies on the Chinese Crude Drug "Shoma." VIII. Two New Triterpenol Bisdesmosides, 3-Arabinosyl-24-O-acetylhydroshengmanol 15-Glucoside and 3-Xylosyl-24-O-acetylhydroshengmanol 15-Glucoside, from Cimicifuga dahurica.
  作者：Nobuko SAKURAI、Mamoru KOEDA、Takao INOUE、Masahiro NAGAI

  DOI：10.1248/cpb.42.48

  日期：——

  Two new triterpenol glycosides were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae): 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside (1), C43H70O16, mp 222-223 degrees C, [alpha]D +21.0 degrees and 3-xylosyl-24-O-acetylhydroshengmanol 15-glucoside (2), C43H70O16, mp 208-210 degrees C, [alpha]D +9.5 degrees. On acidic hydrolysis, 1 afforded cimigenol (3) as an aglycone, and glucose

  从Cimicifuga dahurica（毛an科）的根茎中分离出两种新的三萜醇糖苷：3-阿拉伯糖基-24-O-乙酰基氢生马酚15-葡糖苷（1），C43H70O16，mp 222-223℃，αD+ 21.0℃和3。 -木糖基-24-O-乙酰基氢圣马酚15-葡糖苷（2）， ，mp 208-210℃，αD+ 9.5℃。在酸性水解下，1得到糖苷三醇（3）为糖苷配基，葡萄糖和阿拉伯糖为糖。在用毛霉菌素进行酶促水解时，1得到24-O-乙酰基氢圣马酚15-O-葡糖苷（4）。根据化学和光谱数据，建议1的结构为（23R，24S）-24-乙酰氧基-3-O-α-L-阿拉伯吡喃糖氧基-16,23-e氧基-9,19-15- O-β-D-吡喃葡萄糖苷。另一个糖苷（2）在其13C-NMR光谱中显示出与1极为相似的化学位移模式。2得到西米可诺尔（3），木糖和葡萄糖。在用毛霉菌素进行酶促水解后，得到2。根
• Cycloartane tetracyclic triterpenoid compound, preparation method therefor and use thereof
  申请人：Hefei Cosource Pharmaceuticals Inc.

  公开号：US10568892B2

  公开（公告）日：2020-02-25

  The present invention relates to the field of natural medicine and pharmaceutical chemistry, and in particular relates to a cycloartane tetracyclic triterpenoid compound (I), a preparation method thereof and the medical use thereof. The pharmacodynamic tests demonstrate that the compound of the present invention has a pharmacodynamic activity on heart and cerebral vessels and can be used to prevent or treat cardiovascular and/or cerebrovascular diseases such as arrhythmia, myocardial infarction, and coronary heart disease or the like.

  本发明涉及天然药物和药物化学领域，尤其涉及一种环木菠萝烷四环三萜类化合物(I)、其制备方法及其医疗用途。 药效学试验证明，本发明化合物对心脑血管具有药效学活性，可用于预防或治疗心律失常、心肌梗塞、冠心病等心脑血管疾病。
• Compositions containing enriched natural crocin and/or crocetin, and their therapeutic or nutraceutical uses
  申请人：Gao Song

  公开号：US10842805B2

  公开（公告）日：2020-11-24

  The invention relates to unique compositions containing enriched and purified natural crocin and/or crocetin for prevention and/or treatment of cancers and other conditions and diseases. Compositions comprise mainly enriched or purified natural crocin or crocetin or combination of both and possible other active phytochemicals. A composition is used as functional food, drink, dietary supplement, or therapeutic dosage to a human orally or through other appropriate way (parenteral, percutaneous, rectal, mucosal, intranasal or topical administration). A method of natural crocin and crocetin enriching and purification is revealed.

  本发明涉及含有富集和纯化的天然羊角霉素和/或羊胎素的独特组合物，用于预防和/或治疗癌症及其他病症和疾病。组合物主要包括富集或纯化的天然巴豆素或巴豆黄素或二者的组合以及可能的其他活性植物化学物质。组合物可作为功能性食品、饮料、膳食补充剂或治疗剂量，口服或通过其他适当方式（肠外、经皮、直肠、粘膜、鼻内或局部给药）给人服用。揭示了一种富集和提纯天然巴豆素和藏红花素的方法。
• Oral care composition
  申请人：——

  公开号：US20020039559A1

  公开（公告）日：2002-04-04

  An oral care composition comprising a Cimicifuga-salt, a coptis, a zanthoxylin, and a filler material is disclosed. The Cimicifuga-salt consists of a salt and a Cimicifuga extract, and an admixture of the Cimicifuga-salt, the coptis and the zanthoxylin accounts for about 1.1% to 80% of the composition by weight and the remaining portion of the composition is the filler material.

  本发明公开了一种口腔护理组合物，该组合物由一种含羞草盐、一种 coptis、一种 zanthoxylin 和一种填充材料组成。含羞草盐由一种盐和一种含羞草提取物组成，含羞草盐、鸦胆子和黄腐素的混合物约占组合物重量的 1.1%至 80%，组合物的剩余部分为填充材料。