4'-甲基金圣草黄素 | 4712-12-3

• 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: 4'-甲基金圣草黄素
• 英文名称: 5,7-dihydroxy-3',4'-dimethoxy flavone
• 英文别名: 3',4'-dimethoxyluteolin；luteolin 3',4'-dimethyl ether；luteolin-3′,4′-dimethyl ether；3′,4′-dimethoxy-5,7-dihydroxyflavanone；5,7-Dihydroxy-3',4'-dimethoxyflavone；2-(3,4-dimethoxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 4712-12-3
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: AOLOMULCAJQEIG-UHFFFAOYSA-N

物化性质

• 熔点：
  244 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  538.3±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：20.83 mg/mL (66.28 mM)；水：< 0.1 mg/mL（不溶）
• LogP：
  2.970 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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

• 储存条件：
  -20°C，密闭保存，并保持干燥。

制备方法与用途

生物活性

4'-甲基玉米黄质是有效的细胞色素P450酶（P450）抑制剂，对人P450 1B1依赖的乙氧基烯丙醇-O-脱乙基酶（EROD）的IC50值为19 nM。

靶点

IC50: 19 nM (human P450 1B1-dependent EROD)。

体外研究

4'-甲基玉米黄质（34DM57DHF）是强有力的P450酶抑制剂，特别是针对P450 1B1，其对人P450 1B1依赖的EROD的IC50值为19 nM。

反应信息

• 作为反应物：
  描述：

  4'-甲基金圣草黄素 在 copper(ll) sulfate pentahydrate 、 四丁基溴化铵 、 caesium carbonate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-(((2-(3,4-dimethoxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)methyl)-1H-1,2,3-triazol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  用于海洋防污应用的具有三唑部分的黄酮苷：合成和生物活性评价

  摘要：

  在过去的几十年里，含有杀生物化合物作为活性成分的防污涂料被用来防止生物污垢，并且需要环保的替代品。本课题组前期研究表明，合成得到的多甲氧基查尔酮和糖基化黄酮具有低毒、防污活性。在这项工作中，首次合成了十种新的多甲氧基黄酮和查耳酮，其中八种带有三唑部分。还合成并测试了八种已知的黄酮和查耳酮，以构建这些化合物的定量构效关系（QSAR）模型。发现了三种不同的防污特性：三种化合物（ 1b 、 11a和11b ）对大型污损物种（ Mytilus galloprovincialis ）表现出抗沉降活性，两种化合物（ 6a和6b ）对形成生物膜的海洋细菌Roseobacter litoralis表现出抑制活性，一种化合物 ( 7b ) 对贻贝幼虫和微藻舟形藻均表现出活性。分子的氢键受体能力是对贻贝幼虫抗沉降活性有积极贡献的最重要的描述符，事实上，三唑基糖基化查尔酮 7b 是针对该物种最有效的化合物。最有

  DOI：

  10.3390/md19010005
• 作为产物：
  描述：

  3',4'-dimethoxy-5,7-di[(2-methoxyethoxy)methoxy]flavone 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以86%的产率得到4'-甲基金圣草黄素
  参考文献：
  名称：

  Modulation of human neutrophils' oxidative burst by flavonoids

  摘要：

  Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study, we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ring was evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.019

文献信息

• [EN] 7-CARBOXYMETHYLOXY-3', 4', 5-TRIMETHOXY FLAVONE MONOHYDRATE, THE PREPARATION METHOD AND USES THEREOF<br/>[FR] MONOHYDRATE DE 7-CARBOXYMETHYLOXY-3',4',5-TRIMETHOXY FLAVONE, SON PROCEDE DE PREPARATION ET SON UTILISATION
  申请人：DONG A PHARM CO LTD

  公开号：WO2005023244A1

  公开（公告）日：2005-03-17

  The present invention relates to 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate which is a non hygroscopic product suitable for the preparation of metered dose of 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone having protective activity for gastrointestinal tract including the colon, and a preparation method and uses thereof. 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate of the present invention has advantages such as mucus protecting activity for gastrointestinal tract including the colon, convenience for handling and storage under ordinary humidity owing to its non-hygroscopicity, and ability to contain an active compound consistently for the formulation production of a medicine. In addition, the preparation method of 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate of the present invention reduces long steps of total synthesis and requires mild conditions for the production of a compound because autoclave condition is not necessary for methylation in this case, and makes mass-production possible without any purification process such as recrystallization or column chromatography.

  本发明涉及7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物，这是一种非吸湿性产品，适用于制备具有对胃肠道包括结肠具有保护活性的7-羧甲氧基-3'，4'，5-三甲氧基黄酮的定量剂量，以及其制备方法和用途。本发明的7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物具有诸如对胃肠道包括结肠的黏膜保护活性、由于其非吸湿性而在普通湿度下方便处理和储存的优点，以及能够持续包含活性化合物以便制剂生产药物。此外，本发明的7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物的制备方法减少了总合成的长步骤，并且在这种情况下，对于甲基化不需要高压灭菌条件，因此在生产化合物时需要温和条件，并且可以实现无需任何纯化过程（如重结晶或柱层析）的大规模生产。
• Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance
  作者：Ryuji Tsunekawa、Kazuhiro Katayama、Kengo Hanaya、Shuhei Higashibayashi、Yoshikazu Sugimoto、Takeshi Sugai

  DOI：10.1002/cbic.201800431

  日期：2019.1.18

  Reversal of antitumor agent resistance: Inspired by reported structure– activity studies on reversal effects of flavones on breast cancer resistance protein (BCRP/ABCG2), we site‐selectively synthesized 5‐hydroxy‐3′,4′,7‐trimethoxyflavone (HTMF) and related compounds. HTMF showed reversal of resistance to SN‐38 in K562/BCRP cells (RI50 7.2 nm), suppressed BCRP expression by the cells and inhibited

  抗肿瘤药耐药性的逆转：受报道的关于黄酮对乳腺癌耐药蛋白（BCRP / ABCG2）逆转作用的结构-活性研究的启发，我们定点合成了5-羟基-3'，4'，7-三甲氧基黄酮（HTMF）及相关化合物。HTMF在K562 / BCRP细胞中显示出对SN-38的抗性逆转（RI 50 7.2 n m），抑制了细胞的BCRP表达，并抑制了BCRP底物的流出。
• 크로몬 유도체를 함유하는 미백용 화장료 조성물
  申请人：UNIVERSITY INDUSTRY FOUNDATION, YONSEI UNIVERSITY WONJU CAMPUS 연세대학교 원주산학협력단(120120107738) Corp. No ▼ 141271-0004893BRN ▼224-82-14988

  公开号：KR20160135569A

  公开（公告）日：2016-11-28

  본 발명은 천연물 유래 알로에신과 유사한 구조를 갖는 크로몬(chromone) 유도체를 함유하는 미백용 화장료 조성물에 관한 것으로서, 본 발명에 다른 크로몬 유도체 화합물은 티로시나아제(tyrosinase) 효소의 활성 억제능이 우수하고, 대량 합성이 가능하며, 소량을 적용하여도 현저히 우수한 미백 효과를 나타내고, 피부 미백 성분의 미백 효능을 극대화시켜주며, 천연물로부터 유도된 유도체를 사용하는바 부작용이 적다는 장점을 갖는다.

  本发明涉及一种含有类似于天然植物提取物芦荟素的结构的香豆素衍生物的美白化妆品配方，其中所述发明的香豆素衍生物具有优越的酪氨酸酶活性抑制能力，可进行大规模合成，即使使用少量也能显著展现出优秀的美白效果，并最大程度地增强皮肤美白成分的美白功效，使用从天然植物中提取的衍生物具有较少副作用的优点。
• A New Synthesis for Acacetin, Chrysoeriol, Diosmetin, Tricin and Other Hydroxylated Flavones by Modified Baker-Venkataraman Transformation
  作者：N. Pandurangan

  DOI：10.2174/1570178611999140206115633

  日期：2014.2

  Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses

  Baker-Venkataraman（BV）重排是合成黄酮的选择方法。BV的主要局限性在于它需要对羟基进行广泛的保护和脱保护，这会使该过程冗长且麻烦。在本研究中，使用简单的保护基团和容易获得的原料开发了一种三步有效的方法。描述了新的合成醋氨蝶呤，瓜油酚，薯met皂素，甘油三酸酯和其他羟基黄酮。
• 3',4',5-TRIMETHOXY FLAVONE DERIVATIVES AS STIMULATN OF MUCUS SECRETION, METHOD FOR THE SAME, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
  申请人：Choi Seul-Min

  公开号：US20100130448A1

  公开（公告）日：2010-05-27

  The present invention provides a 3′,4′,5-trimethoxy flavone derivative and a pharmaceutically acceptable salt thereof, preparation thereof, and a pharmaceutical composition for the treatment and prevention of dry eye syndrome comprising the same as an active ingredient. The 3′,4′,5-trimethoxy flavone derivative and its pharmaceutically acceptable salt inhibit corneal damage through excellent stimulatory action on mucus secretion in the conjunctiva and therefore may be effective as a prophylactic or therapeutic agent for dry eye syndrome.

  本发明提供了一种3′,4′,5-三甲氧基黄酮衍生物及其药用可接受的盐，以及其制备方法和一种治疗和预防干眼综合征的药物组合物，其包含作为活性成分的这种衍生物。3′,4′,5-三甲氧基黄酮衍生物及其药用可接受的盐通过在结膜上粘液分泌方面的出色刺激作用抑制角膜损伤，因此可能作为干眼综合征的预防或治疗药物有效。