去甲基姜黄素 | 149732-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 去甲基姜黄素
• 英文名称: 1-(4-hydroxy-3-methoxyphenyl)-7-(3,4-dihydroxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: mono-O-demethylcurcumin；demethoxycurcumin；demethylcurcumin；1-(3,4-dihydroxy-phenyl)-7-(3-methoxy-4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione；Monodemethylcurcumin；(1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• CAS: 149732-51-4
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: FFRFJIZJLZXEJX-YPCIICBESA-N

物化性质

• 熔点：
  183-187°C (dec.)
• 沸点：
  617.5±55.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

ADMET

代谢

O-去甲基姜黄素是姜黄素在人體內的已知代謝物。

O-demethyl curcumin is a known human metabolite of curcumin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  去甲基姜黄素 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到mono-O-demethyltetrahydrocurcumin
  参考文献：
  名称：

  姜黄素衍生物的用途

  摘要：

  本发明提供了姜黄素衍生物的用途。具体提供了式Ⅰ所示姜黄衍生物，或其盐在制备抗炎性疾病的药物和/或COX抑制剂的用途。本发明姜黄素衍生物具有良好COX抑制活性和抗炎活性，可用于制备COX抑制剂和抗炎药物。其中，化合物6和化合物7对于COX‑2抑制活性和抗炎活性的效果最优。可用于制备COX‑2抑制剂和抗炎药物。

  公开号：

  CN110327315A
• 作为产物：
  描述：

  姜黄素 在 Blautia sp. MRG-PMF₁ strain 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 去甲基姜黄素
  参考文献：
  名称：

  Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota

  摘要：

  Curcumin and other curcuminoids from Curcuma longa are important bioactive compounds exhibiting various pharmacological activities. In addition to the known reductive metabolism of curcuminoids, an alternative biotransformation of curcuminoids by human gut microbiota is reported herein. A curcuminoid mixture, composed of curcumin (1), demethoxycurcumin (2), and bisdemethoxycurcumin (3), was metabolized by the human intestinal bacterium Blautia sp. MRG-PMF1. 1 and 2 were converted to new metabolites by the methyl aryl ether cleavage reaction. Two metabolites, demethylcurcumin (4) and bisdemethylcurcumin (5), were sequentially produced from 1, and demethyldemethoxycurcumin (6) was produced from 2. Until now, sequential reduction of the heptadienone backbone of curcuminoids was the only known metabolism to occur in the human intestine. In this study, a new intestinal metabolism of curcuminoids was discovered. Demethylation of curcuminoids produced three new colonic metabolites that were already known as promising synthetic curcumin analogues. The results could explain the observed beneficial effects of turmeric.

  DOI：

  10.1021/acs.jafc.7b00943

文献信息

• Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells
  作者：Jiraporn Tocharus、Sataporn Jamsuwan、Chainarong Tocharus、Chatchawan Changtam、Apichart Suksamrarn

  DOI：10.1007/s11418-011-0599-6

  日期：2012.4

  The chemically modified analogs, the demethylated analogs 4–6, the tetrahydro analogs 7–9 and the hexahydro analogs 10–12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O-demethyldemethoxycurcumin (6) are the two most

  对姜黄素 ( 1 )、脱甲氧基姜黄素( 2 ) 和双脱甲氧基姜黄素 ( 3 )的化学修饰类似物、去甲基化类似物4 – 6、四氢类似物7 – 9和六氢类似物10 – 12对脂多糖活化的抑制活性进行了评估HAPI 小胶质细胞中一氧化氮 (NO) 的产生。Di- O-去甲基姜黄素 ( 5 ) 和O-去甲基去甲氧基姜黄素 ( 6 ) 是抑制 NO 生成的两种最有效的化合物。类似物5和6分别比母体姜黄素1和2 的活性高两倍或几乎两倍。此外，这两种化合物抑制了诱导型 NO 合酶的 mRNA 表达水平。类似物5和6的强大神经保护活性提供了潜在的替代化合物，可作为与活化小胶质细胞相关的神经系统疾病的治疗剂进行开发。
• Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
  作者：Chatchawan Changtam、Poonpilas Hongmanee、Apichart Suksamrarn

  DOI：10.1016/j.ejmech.2010.07.003

  日期：2010.10

  bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was

  姜黄素（1），去甲氧基姜黄素（2）和双去甲氧基姜黄素（3）（药用植物姜黄的姜黄素成分）已在结构上修饰为55个类似物，并已评估了其对结核分枝杆菌的抗分枝杆菌活性。在高活性姜黄素类化合物中，异恶唑类似物是活性最高的基团，单-O-甲基姜黄素异恶唑（53）是活性最高的化合物（MIC 0.09μg/ mL）。它的活性比母体化合物姜黄素（1）高1131倍，分别比标准药物卡那霉素和异烟肼高18倍和2倍。化合物53还显示出对耐多药结核分枝杆菌临床分离株的高活性，MIC值为0.195–3.125μg/ mL。姜黄素类似物表现出抗分枝杆菌活性的结构要求是在异戊基环上存在一个异恶唑环和两个不饱和键。紧密连接于异恶唑环的氮官能团的芳环上合适的对烷氧基的存在和另一个芳环上的游离对羟基的存在增强了生物活性。
• NEW SYNERGISTIC PHYTOCHEMICAL COMPOSITION FOR THE TREATMENT OF OBESITY
  申请人：GOKARAJU Ganga Raju

  公开号：US20100227828A1

  公开（公告）日：2010-09-09

  Synergistic anti-adipogenic and pro-lipolytic compositions for the prevention and amelioration of adipogenesis and lipolysis mediated diseases, comprising at least two extracts selected from enriched demethylated curcuminoids obtained from Curcuma longa, Moringa oleifera and Murraya koenigii . The anti-adipogenic and pro-lipolytic compositions optionally contain one or more anti-obesic agents. These compositions are useful for preventing anti-inflammatory and free radical mediated diseases.

  具有协同抗脂肪生成和促脂肪分解作用的组合物，用于预防和改善由脂肪生成和脂解调节引起的疾病，包括至少选自姜黄，辣木和咖喱叶中富含去甲基化姜黄素的提取物。抗脂肪生成和促脂肪分解组合物可以选择性地包含一个或多个抗肥胖剂。这些组合物有助于预防抗炎和自由基介导的疾病。
• Phosphonate Analogs Of Hiv Integrase Inhibitor Compounds
  申请人：Cai R. Zhenhong

  公开号：US20080076738A1

  公开（公告）日：2008-03-27

  Novel HIV integrase inhibitor compounds having at least one phosphonate group, protected intermediates thereof, and methods for inhibition of HIV-integrase are disclosed.

  本发明公开了至少具有一个膦酸酯基团的新型HIV整合酶抑制剂化合物、其受保护的中间体以及用于抑制HIV整合酶的方法。
• ORALLY ACTIVE CURCUMINOID COMPOUNDS
  申请人：Chaniyilparampu Ramchand Nanappan

  公开号：US20110112190A1

  公开（公告）日：2011-05-12

  The invention discloses a compound of formula (I) wherein, at least one of R 1 , R 2 , R 3 and R 4 is —C(═O)R n and R 1 , R 2 R 3 and R 4 are H or CH 3 and R n is alkyl or alkenyl group. The alkenyl group have one or more number of double bonds either in cis form or trans form or both. In R n , where n is 12 to 30 carbons; and pharmaceutically acceptable salt thereof. The said alkenyl groups are preferably selected from the group consisting of eicosapentaenoic acid (EPA) or DHA (docosahexaenoic acid). This invention further discloses processes for their preparation of compounds of formula I and pharmaceutical compositions that contain these compounds.

  本发明公开了一种化合物，其化学式为(I)，其中，R1，R2，R3和R4中至少一个为—C(═O)Rn，且R1，R2，R3和R4为H或CH3，Rn为烷基或烯基基团。烯基基团具有一个或多个双键，可以是顺式或反式，或两者都有。在Rn中，n为12到30个碳；以及其药学上可接受的盐。所述烯基基团优选选自二十碳五烯酸（EPA）或二十二碳六烯酸（DHA）的群。本发明还公开了制备化合物I的方法和含有这些化合物的药物组合物。