3,3',5,5',7-五羟基-4'-甲氧基黄酮 | 16805-10-0

• 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 - 黄酮类化合物
• 中文名称: 3,3',5,5',7-五羟基-4'-甲氧基黄酮
• 英文名称: 3,5,7-trihydroxy-2-(3,5-dihydroxy-4-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 4'-O-methylmyricetin；mearnsetin；3,5,7,3′,5′-pentahydroxy-4-methoxyflavone；2-(3,5-dihydroxy-4-methoxy-phenyl)-3,5,7-trihydroxy-chromen-4-one；Mearusetin (Myricetin-4'-methylether)；4'-Methylmyricetin；2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxychromen-4-one
• CAS: 16805-10-0
• 化学式: C₁₆H₁₂O₈
• 分子量: 332.266
• InChiKey: HKEQVXVLTOSXLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  699.4±55.0 °C(Predicted)
• 密度：
  1.730±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 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：
  137
• 氢给体数：
  5
• 氢受体数：
  8

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  3,3',5,5',7-五羟基-4'-甲氧基黄酮 在 硼酸 、 sodium carbonate 、 sodium sulfate 作用下， 以 水 为溶剂， 生成 3,5,7,3',5'-pentahydroxy-4'-methoxyflavonol
  参考文献：
  名称：

  鼠李中的黄酮类化合物

  摘要：

  摘要 从鼠李树皮中分离到了一种新的二氢黄酮醇，帕拉西素，以及山奈酚、槲皮素、异鼠李素、鼠李素、芳香树素、圣草酚和紫杉叶素，其结构被阐明为2,3-二氢杨梅素4'-O。

  DOI：

  10.1016/0031-9422(83)80110-1
• 作为产物：
  描述：

  myricetin 4'-methyl ether 3-O-β-D-xylopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 D-吡喃木糖 、 3,3',5,5',7-五羟基-4'-甲氧基黄酮
  参考文献：
  名称：

  One new flavonoid xyloside and one new natural triterpene rhamnoside from the leaves of Syzygium grande

  摘要：

  One new flavonoid glycoside, myricetin 4'-methyl ether 3-O-beta-D-xylopyranoside (1) and one new natural triterpene glycoside, grandoside (2) were isolated from a MeOH extract of the leaves of Syzygium grande, together with thirteen known compounds (3-15). The structures of the new compounds were determined through a combination of spectroscopic and chemical analyses. All of the isolated compounds were evaluated for their antifungal, antibacterial, anti-leishmania, DPPH radical-scavenging and cytotoxic activities by means of MTT assay. (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2014.08.009

文献信息

• Structural Requirements of Flavonoids and Related Compounds for Aldose Reductase Inhibitory Activity.
  作者：Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Masayuki Yoshikawa

  DOI：10.1248/cpb.50.788

  日期：——

  The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2–3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).

  发现，几种天然药材和药用食品的甲醇提取物对大鼠晶状体醛糖还原酶显示抑制作用。在大多数情况下，通过生物测定指导的分离方法，分离得到黄酮类化合物作为活性成分，其中，槲皮苷（IC50=0.15 μM）、愈创木脂苷（0.18 μM）和去甲基芸香糖苷-1（0.082 μM）显示出强的抑制活性。去甲基芸香糖苷-1显示了最强的活性，相当于商品化合成醛糖还原酶抑制剂依帕司他（0.072 μM）的活性。为了阐明黄酮类化合物对醛糖还原酶抑制活性的结构要求，检测了各种黄酮类化合物及相关化合物。结果表明，黄酮类化合物的以下结构要求是：1）具有7-羟基和/或邻苯二酚结构的黄酮和黄酮醇（在B环上的3′,4′-二羟基结构）显示出强的活性；2）5-羟基结构并不影响活性；3）3-羟基和7-O-葡糖基结构降低活性；4）2-3双键增强活性；5）具有邻苯二酚结构的黄酮和黄酮醇显示出比具有连苯三酚结构（3′,4′,5′-三羟基结构）的化合物更强的活性。
• Pharmaceutical compositions and methods for countering chemotherapy induced cardiotoxicity
  申请人：Auransa Inc.

  公开号：US10806716B2

  公开（公告）日：2020-10-20

  This disclosure provides methods and pharmaceutical compositions for reducing or eliminating cardiotoxicity, particularly cardiotoxicity induced by a cancer treatment or other therapy. In some cases, the methods and compositions prevent or reduce cardiotoxicity caused by anthracycline treatment. The methods provided herein often comprise administering a protective agent such as myricetin, tricetin, robinetin, ficetin, vitexin, quercetin, dihydrorobinetin, kaempferol, 7,3′,4′,5′-tetrahydroxyflavone, and myricitrin in conjunction with the administration of a cancer drug or other treatment. They may comprise administering a protective agent in combination with dexrazoxane. The compositions provided herein include co-formulations of a protective agent with a different protective agent or with a cancer treatment (e.g., anthracycline drug).

  本公开提供了减少或消除心脏毒性，特别是由癌症治疗或其他疗法引起的心脏毒性的方法和药物组合物。在某些情况下，这些方法和组合物可以预防或减少蒽环类药物治疗引起的心脏毒性。本文提供的方法通常包括在施用抗癌药物或其他疗法的同时施用一种保护剂，如麦角黄素、三黄素、洋槐黄素、黄荆素、槲皮素、二氢洋槐黄素、山柰酚、7,3′,4′,5′-四羟基黄酮和麦角黄素。它们可以包括将保护剂与右雷佐生联合使用。本文提供的组合物包括一种保护剂与另一种保护剂或与一种癌症治疗药物（如蒽环类药物）的共同制剂。
• KIKUCHI, MASAO;SATO, KENICHI;SHIRAISHI, YOSHIHISA;NAKAYAMA, RYOICHI;WATAN+, YAKUGAKU DZASSI, 110,(1990) N, S. 354-357
  作者：KIKUCHI, MASAO、SATO, KENICHI、SHIRAISHI, YOSHIHISA、NAKAYAMA, RYOICHI、WATAN+

  DOI：——

  日期：——
• Comprehensive nutraceutical agent for treatment/ prevention of Parkinson's disease
  申请人：Mazzio Elizabeth

  公开号：US20070116779A1

  公开（公告）日：2007-05-24

  This invention discloses a comprehensive nutraceutical designed to antagonize major mitigating factors specific to the degenerative process that occurs in Parkinson's disease (PD). The formulation is comprised of pyruvate, succinate and/or oxaloacetate further combined with specific macro/micronutrients, trace elements, amino acids, flavonoids and concentrated plant sources. The formula is based on means to attenuate the loss of ATP/toxicity by PD model toxins: 1-methyl-4-phenylpyridinium and rotenone, scavenge hydrogen peroxide/O 2 , augment antioxidant enzymes, prevent dopamine oxidation to DA-quinone via inhibition of COX, PLA 2 , LOX, xanthine oxidase, tyrosinase, prevent hyperhomocysteinemia, antagonize PARP-1 apoptosis, increase blood flow, glucose and oxygen delivery to the brain, potentiate mitochondrial function, antagonize glia iNOS and MAO or its products, chelate redox-active iron, inhibit hemeoxygenase-1, inhibit alpha-synuclein aggregation, augment ATP storage, mediate anti-inflammatory effects via inhibition. of PDE, MAPK p38/c-Jun NH2-terminal kinase/PGE2, antagonize excitotoxicity and downregulate N-methyltransferase, all of which contribute toward PD pathology.
• Nutraceutical agent for attenuating the neurodegenerative process associated with Parkinson's disease
  申请人：Mazzio Elizabeth

  公开号：US20080292607A1

  公开（公告）日：2008-11-27

  This invention describes a comprehensive nutraceutical designed to antagonize major mitigating factors to the degenerative process associated with Parkinson's disease. The formulation is comprised of a primary base of pyruvate, succinate and/or oxaloacetate, fruit extracts and anthocyanins, further combined with specific macro/micronutrients, trace elements, amino acids, flavonoids and concentrated plant sources. The nutraceutical contains substances that should attenuate the loss of ATP/toxicity by PD model toxins: 1-methyl-4-phenylpyridinium and rotenone, scavenge hydrogen peroxide/O 2 . − , augment antioxidant enzymes, prevent dopamine (DA) oxidation to DA-quinone via inhibition of COX, PLA 2 , LOX, xanthine oxidase, tyrosinase, prevent hyperhomocysteinemia, antagonize PARP-1 apoptosis, increase blood flow, glucose and oxygen delivery to the brain, potentiate mitochondrial function, antagonize glia iNOS and MAO or its products, chelate redox-active iron, inhibit heme oxygenase-1, inhibit alpha-synuclein aggregation, augment ATP storage, mediate anti-inflammatory effects via inhibition of PDE, MAPK p38/c-Jun NH2-terminal kinase/PGE2, antagonize excitotoxicity and downregulate N-methyltransferase, all of which contribute toward PD pathology.

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