3'-O-甲基香豌豆苷元 | 36190-95-1

• 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: 3'-O-甲基香豌豆苷元
• 英文名称: 3'-O-methylorobol
• 英文别名: 5,7,4'-trihydroxyl-3'-methoxyisoflavone；3'-methoxy-4',5,7-trihydroxyisoflavone；5,7,4'-trihydroxy-3'-methoxyisoflavone；3’-O-methylorobol；3′-O-methylorobol；orobol 3'-methyl ether；5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• CAS: 36190-95-1
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: ZMFBGWWGXBNJAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2914509090
• 储存条件：
  储存条件：2-8℃，干燥，密封保存。

制备方法与用途

3′-O-甲基罗波醇是一种抗氧化剂类黄酮，在2,2-二苯基-1-苦味酸酰肼自由基清除实验中表现出中等的抗氧化活性。

反应信息

• 作为产物：
  描述：

  高圣草酚 在 NADPH disodium salt 、 口服葡萄糖 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 3'-O-甲基香豌豆苷元
  参考文献：
  名称：

  A Versatile Microbial System for Biosynthesis of Novel Polyphenols with Altered Estrogen Receptor Binding Activity

  摘要：

  Isoflavonoids possess enormous potential for human health with potential impact on heart disease and cancer, and some display striking affinities for steroid receptors. Synthesized primarily by legumes, isoflavonoids are present in low and variable abundance within complex mixtures, complicating efforts to assess their clinical potential. To satisfy the need for controlled, efficient, and flexible biosynthesis of isoflavonoids, a three-enzyme system has been constructed in yeast that can convert natural and synthetic flavanones into their corresponding isoflavones in practical quantities. Based on the determination of the substrate requirements of isoflavone synthase, a series of natural and nonnatural isoflavones were prepared and their binding affinities for the human estrogen receptors (ER alpha and ER beta) were determined. Structure activity relationships are suggested based on changes to binding affinities related to small variations on the isoflavone structure.

  DOI：

  10.1016/j.chembiol.2010.03.010

文献信息

• Production and Anti-Melanoma Activity of Methoxyisoflavones from the Biotransformation of Genistein by Two Recombinant Escherichia coli Strains
  作者：Chien-Min Chiang、Yu-Jhe Chang、Jiumn-Yih Wu、Te-Sheng Chang

  DOI：10.3390/molecules22010087

  日期：——

  results showed that two metabolites were produced from the biotransformation, identified as 5,7,4′-trihydroxy-3′-methoxyisoflavone and 5,7,3′-trihydroxy-4′-methoxyisoflavone, respectively, based on their mass and nuclear magnetic resonance spectral data. 5,7,4′-Trihydroxy-3′-methoxyisoflavone showed potent antiproliferative activity toward mouse B16 melanoma cells with an IC50 value of 68.8 μM. In contrast

  使用表达来自巨大芽孢杆菌的酪氨酸酶的重组大肠杆菌通过连续 3'-羟基化，然后使用表达来自 Streptomyces peucetius 的 O-甲基转移酶的另一种重组大肠杆菌进行甲基化，对大豆异黄酮染料木黄酮进行生物转化。结果表明，生物转化产生了两种代谢物，根据它们的质量和核，分别鉴定为 5,7,4'-三羟基-3'-甲氧基异黄酮和 5,7,3'-三羟基-4'-甲氧基异黄酮。磁共振波谱数据。5,7,4'-三羟基-3'-甲氧基异黄酮对小鼠 B16 黑色素瘤细胞显示出有效的抗增殖活性，IC50 值为 68.8 μM。相比之下，即使在 350 μM 浓度下，该化合物对小鼠正常成纤维细胞也没有表现出任何细胞毒性。
• Bioactive fractions and compounds from Dalbergia sissoo for the prevention or treatment of osteo-health related disorders
  申请人：Maurya Rakesh

  公开号：US10292994B2

  公开（公告）日：2019-05-21

  The present invention relates to bioactive fractions and compounds from Dalbergia sissoo for the prevention or treatment of osteo-health related disorders. The present invention relates in the field of pharmaceutical composition that provides new plant extracts, their fractions and pure compound isolated from natural sources that are useful for the prevention and/or treatment of various medical indications associated with estrogen dependent or independent diseases or syndromes or disorders preferably in the prevention or treatment of estrogen dependent or independent diseases or syndromes or disorders caused in humans and animals, and achievement of peak bone mass during skeletal growth and health in humans and animals. Particularly the present invention further relates to the processes for the preparation of biologically active extracts, fractions, and isolation of pure compounds, from Dalbergia sissoo plant from the family Fabaceae their pharmaceutically acceptable salts and compositions of the principal aspect of the present invention.

  本发明涉及用于预防或治疗骨健康相关疾病的 Dalbergia sissoo 的生物活性馏分和化合物。本发明涉及药物组合物领域，提供了新的植物提取物、其馏分和从天然来源分离的纯化合物，这些提取物、馏分和纯化合物可用于预防和/或治疗与雌激素依赖性或独立疾病或综合症或紊乱有关的各种医学指征，优选用于预防或治疗人类和动物引起的雌激素依赖性或独立疾病或综合症或紊乱，以及在人类和动物骨骼生长和健康过程中达到峰值骨量。特别是本发明进一步涉及从豆科植物Dalbergia sissoo中制备生物活性提取物、馏分和分离纯化合物的工艺，它们是本发明主要方面的药学上可接受的盐和组合物。
• Microbial Hydroxylation and Methylation of Genistein by <i>Streptomycetes</i>
  作者：Mohammed Hosny、John P. N. Rosazza

  DOI：10.1021/np9901783

  日期：1999.12.1

  Streptomyces griseus (ATCC 10137) and Streptomyces catenulae (ATCC 23893) were used to convert genistein-5,7,4'-trihydroxyisoflavone (1)-a major isoflavone found in soybeans, into five metabolites, four of which were previously unknown. These were 5,7,3',4'-tetrahydroxy-8-methylisoflavone (5), 5,7,3',4'-tetrahydroxy-8-methylisoflavanone (4), 5,7,4'-trihydroxy-3'-methoxyisoflavone (5), 5,7,8,3',4'-pentahydroxyisoflavone (7), and the known compound, 5,7-dihydroxy-3',4'-dimethoxyisoflavone (6). Identities of these metabolites were established by HRFABMS and 1D and 2D NMR correlation spectroscopy.
• BIOACTIVE FRACTIONS AND COMPOUNDS FROM DALBERGIA SISSOO FOR THE PREVENTION OR TREATMENT OF OSTEO-HEALTH RELATED DISORDERS
  申请人：Council of Scientific and Industrial Research

  公开号：EP2705047A1

  公开（公告）日：2014-03-12
• [EN] BIOACTIVE FRACTIONS AND COMPOUNDS FROM DALBERGIA SISSOO FOR THE PREVENTION OR TREATMENT OF OSTEO-HEALTH RELATED DISORDERS<br/>[FR] FRACTIONS ET COMPOSÉS BIOACTIFS ISSUS DE DALBERGIA SISSOO POUR PRÉVENIR OU TRAITER LES TROUBLES D'ORIGINE OSTÉOPATHIQUE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012147102A1

  公开（公告）日：2012-11-01

  The present invention relates to bioactive fractions and compounds from Dalbergia sissoo for the prevention or treatment of osteo-health related disorders. The present invention relates in the field of pharmaceutical composition that provides new plant extracts, their fractions and pure compound isolated from natural sources that are useful for the prevention and/or treatment of various medical indications^ associated with estrogen dependent or independent diseases or syndromes or disorders preferably in the prevention or treatment of estrogen dependent or independent diseases or syndromes or disorders caused in humans and animals, and achievement of peak bone mass during skeletal growth and health in humans and animals. Particularly the present invention further relates to the processes for the preparation of biologically active extracts, fractions, and isolation of pure compounds, from Dalbergia sissoo plant from the family Fabaceae their pharmaceutically acceptable salts and compositions of the principal aspect of the present invention.