5,7-二甲氧基木犀草素 | 90363-40-9

• 物质功能分类: 有机原料
• 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: 5,7-二甲氧基木犀草素
• 英文名称: 5,7-dimethoxyluteolin
• 英文别名: 2-(3,4-Dihydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one；2-(3,4-dihydroxyphenyl)-5,7-dimethoxychromen-4-one
• CAS: 90363-40-9
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: NKGJZNRUAGQIRY-UHFFFAOYSA-N

物化性质

• 沸点：
  584.6±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

5,7-二甲基木犀草素（5,7-Dimethoxyluteolin）是一种多巴胺转运蛋白(DAT)激活剂，其EC50值为3.417 μM。

反应信息

• 作为反应物：
  描述：

  5,7-二甲氧基木犀草素 反应 0.03h， 以1.6%的产率得到木犀草素-5-甲醚
  参考文献：
  名称：

  Geiger, Hans; Casteele, Karel Vande; Sumere, Christiaan F. Van, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 3, p. 393 - 396

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dimethoxy-4H-chromen-4-one 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.0h， 以25%的产率得到5,7-二甲氧基木犀草素
  参考文献：
  名称：

  Discovery and synthesis of novel luteolin derivatives as DAT agonists

  摘要：

  Luteolin, 5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one, has been proposed and proved to be a novel dopamine transporter (DAT) activator. In order to develop this potential of luteolin, a series of novel luteolin derivatives were designed, synthesized, and evaluated for their DAT agonistic activities, utilizing constructed Chinese hamster ovary (CHO) cell lines stably expressing rat DAT. Biological screening results demonstrated that luteolin derivatives 1d, 1e, and 4c carry great DAT agonistic potency (EC(50) = 0.046, 0.869, and 1.375 mu M, respectively) compared with luteolin 8 (EC(50) = 1.45 +/- 0.29 mu M). Luteolin derivative 1d, notably, exhibited a 32-fold-higher DAT agonistic potency than luteolin. These luteolin derivatives represent a novel DAT agonist class, from which lead compounds useful for exploration of additional novel DAT agonists could be drawn. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.049

文献信息

• Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE 2 in LPS-induced RAW 264.7 cells
  作者：Ji-Young An、Hwi-Ho Lee、Ji-Sun Shin、Hyung-Seok Yoo、Jong Seon Park、Seung Hwan Son、Sang Won Kim、Jihyun Yu、Jun Lee、Kyung-Tae Lee、Nam-Jung Kim

  DOI：10.1016/j.bmcl.2017.03.057

  日期：2017.6

  In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound

  为了鉴定新型抗炎化合物，合成了一系列黄酮衍生物，并对其在LPS-中对代表性的促炎性介质一氧化氮（NO）和前列腺素E2（PGE2）产生的抑制作用进行了生物学评估。诱导的RAW 264.7细胞。还研究了它们的构效关系。尤其是，我们发现与木犀草素（一种被称为强效抗炎剂的天然黄酮）相比，化合物3g对PGE2的产生显示出更强的抑制活性，对NO生成具有类似的抑制活性，并且细胞毒性也较弱。
• Biotransformation of 5,7-Methoxyflavones by Selected Entomopathogenic Filamentous Fungi
  作者：Mateusz Łużny、Tomasz Tronina、Ewa Kozłowska、Edyta Kostrzewa-Susłow、Tomasz Janeczko

  DOI：10.1021/acs.jafc.1c00136

  日期：2021.4.7

  transformations. Only in the case of 5,7,3′,4′,5′-pentamethoxyflavone, the strains were able to attach a sugar molecule in place of the methoxy substituent to give 3′-O-β-d-(4″-O-methylglucopyranosyl)-5,7,4′,5′-tetramethoxyflavone. However, we observed the tested strains’ ability to selectively demethylate/hydroxylate the carbon C-3′ and C-4′ of ring B of the substrates used. The structures of four hydroxyl-derivatives

  5,7-二甲氧基黄酮（一种菊花蛋白衍生物）存在于许多植物中，即使在高剂量下也显示出非常低的毒性。基于此现象，我们对通过化学合成获得的一系列菊花，芹菜素和甘油三酸酯的甲氧基衍生物进行了生物转化。我们使用了具有致病性的真菌菌株，证实了它们具有同时黄酮类化合物的羟化/去甲基化和糖基化的能力。甲氧基的数量和连接位置都影响生物转化率和产物的新生量。根据产品和半产品结构，可以得出结论，它们是级联转换的结果。仅在5,7,3'，4'，5'-五甲氧基黄酮的情况下，菌株能够连接糖分子代替甲氧基取代基以产生3'- O-β- d-（4″ -O-甲基吡喃葡萄糖基）-5,7,4'，5'-四甲氧基黄酮。但是，我们观察到了所测试菌株对所用底物B环的碳C-3'和C-4'进行选择性去甲基化/羟化的能力。确定了四种羟基衍生物的结构：4'-羟基-5,7-二甲氧基黄酮，3'-羟基-5,7-二甲氧基黄酮，3'-羟基-5,7,4'，5'-四甲氧基黄酮和5
• Antibacterial and Antioxidant Activity of Synthetic Polyoxygenated Flavonoids
  作者：Mauricio Enrique Osorio-Olivares、Yesseny Vásquez-Martínez、Katy Díaz、Javiera Canelo、Lautaro Taborga、Luis Espinoza-Catalán

  DOI：10.3390/ijms25115999

  日期：——

  Flavonoids are an abundant class of naturally occurring compounds with broad biological activities, but their limited abundance in nature restricts their use in medicines and food additives. Here we present the synthesis and determination of the antibacterial and antioxidant activities of twenty-two structurally related flavonoids (five of which are new) by scientifically validated methods. Flavanones (FV1–FV11) had low inhibitory activity against the bacterial growth of MRSA 97-7. However, FV2 (C5,7,3′,4′ = OH) and FV6 (C5,7 = OH; C4′ = SCH3) had excellent bacterial growth inhibitory activity against Gram-negative E. coli (MIC = 25 µg/mL for both), while Chloramphenicol (MIC = 25 µg/mL) and FV1 (C5,7,3′ = OCH3; 4′ = OH) showed inhibitory activity against Gram-positive L. monocytogenes (MIC = 25 µg/mL). From the flavone series (FO1–FO11), FO2 (C5,7,3′,4′ = OH), FO3 (C5,7,4′ = OH; 3′ = OCH3), and FO5 (C5,7,4′ = OH) showed good inhibitory activity against Gram-positive MRSA 97-7 (MIC = 50, 12, and 50 µg/mL, respectively), with FO3 being more active than the positive control Vancomycin (MIC = 25 µg/mL). FO10 (C5,7= OH; 4′ = OCH3) showed high inhibitory activity against E. coli and L. monocytogenes (MIC = 25 and 15 µg/mL, respectively). These data add significantly to our knowledge of the structural requirements to combat these human pathogens. The positions and number of hydroxyl groups were key to the antibacterial and antioxidant activities.