西北甘草异黄酮 | 116709-70-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 西北甘草异黄酮
• 英文名称: glycyrrhisoflavone
• 英文别名: 3-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxychromen-4-one
• CAS: 116709-70-7
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: JOQWUUJQWPZLAT-UHFFFAOYSA-N

物化性质

• 沸点：
  631.9±55.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

制备方法与用途

生物活性方面，glycyrrhisoflavone 是一种活性异戊二烯类黄酮化合物，主要来源于甘草（Glycyrrhiza uralensis Fisch.）的根部提取物。研究表明，glycyrrhisoflavone 能抑制α-葡萄糖苷酶（α-glucosidase）。

反应信息

• 作为反应物：
  描述：

  西北甘草异黄酮 生成 Acetic acid 7-acetoxy-3-[3,4-diacetoxy-5-(3-methyl-but-2-enyl)-phenyl]-4-oxo-4H-chromen-5-yl ester
  参考文献：
  名称：

  HATANO, TSUTOMU;KAGAWA, HARUMI;YASUHARA, TAEKO;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 36,(1988) N 6, C. 2090-2097

  摘要：

  DOI：

文献信息

• Phenolic Constituents of Liquorice. VII. A New Chalcone with a Potent Radical Scavenging Activity and Accompanying Phenolics from Liquorice.
  作者：Tsutomu HATANO、Miyuki TAKAGI、Hideyuki ITO、Takashi YOSHIDA

  DOI：10.1248/cpb.45.1485

  日期：——

  Twenty-three phenolics including six new compounds were isolated from a commercial liquorice from North-eastern China. Structures 2-7 were assigned for the new compounds, designated as tetrahydroxy-methoxychalcone, isolicopyranocoumarin, glycyrrhiza-flavonol A, and glycyrrhiza-isoflavones A, B and C, respectively. Compound 2 showed the most potent scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl radical among the tested polyphenols isolated from liquorice. Air-oxidation of 2 in alkaline dimethylsulfoxide solution gave strong ESR signals, indicating the stability of the radical species formed from 2.

  从东北地区的商业甘草中分离出23种酚类化合物，包括6种新化合物。新化合物的结构分别为2-7，分别命名为四羟基甲氧基查尔酮、异吡喃香豆素、甘草黄酮醇A、甘草异黄酮A、B和C。在从甘草中分离出的多酚类化合物中，化合物2对1,1-二苯基-2-苦基肼自由基的清除效果最强。在碱性二甲基亚砜溶液中，化合物2的空气氧化作用产生了强烈的ESR信号，表明由化合物2形成的自由基物种具有稳定性。
• Isoflavonoids and Other Compounds from <i>Psorothamnus </i><i>a</i><i>rborescens </i>with Antiprotozoal Activities
  作者：Manar M. Salem、Karl A. Werbovetz

  DOI：10.1021/np0502600

  日期：2006.1.1

  glycyrrhisoflavone (4a), and calycosin (5), two pterocarpans, maackiain (6) and 4-hydroxymaackiain (7), one triterpene, oleanolic acid (8), and one chalcone, isoliquiritigenin (9). In addition, the structure of the isoflavone fremontin was revised using spectroscopic and chemical methods and was assigned the new structure 3a. The isoflavone 1a and the chalcone 9 displayed leishmanicidal activity with IC50 values of

  生物活性引导的波氏假单胞菌根提取物的分级分离产生新的异黄酮5,7,3'，4'-四羟基-2'-（3,3-二甲基烯丙基）异黄酮（1a）和新的2-芳基苯并呋喃2-（ 2'-羟基-4'，5'-亚甲基二氧苯基）-6-甲氧基苯并呋喃-3-甲醛（2）与7种已知化合物一起，包括3种异黄酮，fremontin（3a），甘草异黄酮（4a）和calycosin（5） ，两种罗汉松，maackiain（6）和4-hydroxymaackiain（7），一种三萜，齐墩果酸（8）和一种查尔酮，异异黄体生成素（9）。此外，异黄酮弗瑞汀的结构使用光谱和化学方法进行了修改，并被赋予了新的结构3a。异黄酮1a和查尔酮9表现出杀菌作用，IC50值分别为13.0和20.7 microM，对抗利什曼原虫多诺万尼的厌食性amastigotes。Calycosin（5）对杜氏布氏锥虫（IC50 12.7 microM）表现出选择性的毒
• Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase.
  作者：Tsutomu HATANO、Taeko YASUHARA、Toshiyuki FUKUDA、Tadataka NORO、Takuo OKUDA

  DOI：10.1248/cpb.37.3005

  日期：——

  An anti-HIV (human immunodeficiency virus) phenolic constituent, licopyranocoumarin (4), and two other new phenolics named licoarylcoumarin (5) and glisoflavone (6) were isolated from Si-pei licorice (a commercial licorice; root and stolon of Glycyrrhiza sp. from the north-western region of China) using droplet countercurrent chromatography and centrifugal partition chromatography, and their structures were assigned based on chemical and spectroscopic data. Kaempferol 3-O-methyl ether (7) and licocoumarone (8) were also isolated from the licorice. The inhibitory effects of ten licorice phenolics on xanthine oxidase were examined. Licohalcone B (1), glycyrrhisoflavone (2), 8 and licochalcone A (19) showed 50% inhibition at the concentration of 1.3-5.6×10<-5>M.

  使用液滴逆流色谱法和离心分离色谱法从Si-pei甘草（一种商业甘草；中国西北地区甘草属植物的根和匍匐茎）中分离出一种抗HIV（人类免疫缺陷病毒）的酚类成分甘草素（4）以及两种新的酚类成分甘草素（5）和甘草黄酮（6），并根据化学和光谱数据确定了其结构。还从甘草中分离出山奈酚3-O-甲醚（7）和甘草黄酮（8）。研究了十种甘草酚类化合物对黄嘌呤氧化酶的抑制作用。甘草黄酮B（1）、甘草黄酮（2）、8和甘草黄酮A（19）在浓度为1.3-5.6×10<-5>M时显示出50%的抑制作用。
• PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR LIGAND AND PROCESS FOR PRODUCING THE SAME
  申请人：MAE Tatsumasa

  公开号：US20090036519A1

  公开（公告）日：2009-02-05

  The present invention easily and efficiently provides a peroxisome proliferator-activated receptor ligand, and a composition for amelioration of insulin resistance or for prevention and/or amelioration of the insulin resistance syndrome containing the same, as an active ingredient. The present invention relates to a peroxisome proliferator-activated receptor ligand which comprises a prenylflavonoid, a chalcone derivative exclusive of prenylflavonoids, a flavonol derivative exclusive of prenylflavonoids, and a salt, a glycoside and/or an esterified substance thereof acceptable as a pharmaceutical preparation or a food or a beverage; a composition containing the above ligand; a plant-derived extract containing the above ligand; and a process for producing the above extract.
• US7524975B2
  申请人：——

  公开号：US7524975B2

  公开（公告）日：2009-04-28