3'-Geranylchalconaringenin | 189299-03-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3'-Geranylchalconaringenin
• 英文别名: 2',4',6',4-tetrahydroxy-3'-geranylchalcone；(E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 189299-03-4
• 化学式: C₂₅H₂₈O₅
• 分子量: 408.494
• InChiKey: GVXVZXDPRNGAOE-ZCFXJLACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

制备方法与用途

AMPK激活剂6（化合物GC）能够降低HepG2和3T3-L1细胞中的脂质含量，并激活AMPK途径。它显著抑制血清中甘油三酯(TG)、总胆固醇(TC)、低密度脂蛋白-C(LDL-C)及其他生化指标的升高。因此，AMPK激活剂6适用于研究非酒精性脂肪肝(NAFLD)和代谢综合征。

反应信息

• 作为反应物：
  描述：

  3'-Geranylchalconaringenin 在 水 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到6-geranylnaringenin
  参考文献：
  名称：

  异戊烯基黄烷酮的简便合成方法：首先完全合成（+/-）-苯二酮A和（+/-）-巯基黄烷酮A。

  摘要：

  已经开发了一种简便而有效的合成C-8和C-6戊烯基黄酮的方法，该方法具有2,4,6-三羟基苯乙酮的高区域选择性烯丙基化和异戊烯化多羟基查耳酮的区域选择性环化的特征。因此，从关键中间体3开始，已经实现了第一个有效的全合成（+/-）-磺基黄烷酮A（1）和（+/-）-苯并二酮A（2），这是两种具有抗菌活性的天然存在的香叶基黄烷酮。通过对geranylated四羟基查耳酮的区域选择性环化4。

  DOI：

  10.1021/np0001124
• 作为产物：
  描述：

  芳樟醇 在 sodium hydroxide 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.5h， 生成 3'-Geranylchalconaringenin
  参考文献：
  名称：

  从啤酒花到啤酒的黄腐酚和相关异戊二烯类黄酮的命运。

  摘要：

  在两个酿造试验中，使用LC / MS-MS从啤酒花（Humulus lupulus L.）到啤酒的LC / MS-MS监测了查尔酮类型的三个烯丙基黄酮类化合物黄腐酚，去甲基黄腐酚和3'-geranylchalconaringenin的命运。在沸腾的麦芽汁中，这三种炔丙基苯甲酮分别被大量转化为其异构体黄烷酮，异黄腐酚，异戊烯基柚皮苷和香叶基柚皮苷。异戊二烯类黄酮的损失是由于发酵过程中从啤酒花到麦芽汁的提取不完全（13-25％），不溶性麦芽蛋白的吸附（18-26％）和酵母细胞的吸附（11-32％）。啤酒贮藏后，以黄腐酚的形式存在，黄腐酚的总产量为啤酒花黄腐酚的22-30％。啤酒花约10％的去甲基黄腐酚完全转化为异戊二烯柚皮苷，留在啤酒中。3'-Geranylchalconaringenin的行为类似于去甲基黄腐酚。溶解度实验表明，（1）麦芽糖与黄腐酚和异黄腐酚形成可溶性复合物，（2）溶解度并不决定成品啤酒的异黄腐酚含量。

  DOI：

  10.1021/jf990101k

文献信息

• Compounds for the prevention and/or treatment of osteoarthrosis
  申请人：Universitätsklinikum Münster

  公开号：EP2392325A1

  公开（公告）日：2011-12-07

  The present invention relates to new compounds which are inter alia derivable from hops for use in the treatment of (for treating)/prevention or healing of a disease which is associated with an excess transport of hyaluronan across a lipid bilayer, in particular a disease which is associated with or characterized by degeneration and/or a destruction of cartilage (and/or for the prevention of aggrecan loss). Food products comprising these compounds for use in the treatment (for treating) a disease which is associated with an excess transport of hyaluronan across a lipid bilayer, in particular a disease which is associated with or characterized by degeneration and/or a destruction of cartilage, are also envisaged.

  本发明涉及可从啤酒花中提取的新化合物，用于治疗（治疗）/预防或治愈与透明质酸在脂质双分子层上的过量转运有关的疾病，特别是与软骨退化和/或软骨破坏有关或以软骨退化和/或软骨破坏为特征的疾病（和/或预防凝集素的损失）。此外，还设想将含有这些化合物的食品用于治疗（治疗）与透明质酸在脂质双分子层上的过度转运有关的疾病，特别是与软骨退化和/或软骨破坏有关或以软骨退化和/或软骨破坏为特征的疾病。
• Treatment of bladder and urinary tract cancers
  申请人：The Regents of the University of California

  公开号：US20040259813A1

  公开（公告）日：2004-12-23

  Compositions of matter and methods wherein chalcone and flavone derivatives are administered to human or veterinary patients for the treatment of bladder or urinary tract cancer. Compounds of the invention include 2′-hydroxy-4,4′,6′-trimethoxychalcone (Flavokawain A).

  向人类或兽类患者施用查尔酮和黄酮衍生物治疗膀胱癌或尿道癌的物质组合物和方法。本发明的化合物包括 2′-羟基-4,4′,6′-三甲氧基查尔酮（Flavokawain A）。
• Novel aromatic prenyltransferases, nucleic acids encoding same and uses therefor
  申请人：Kuzuyama Tomohisa

  公开号：US20060183211A1

  公开（公告）日：2006-08-17

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.

  根据本发明，一种新型芳香族前基转移酶 Orf2 来自于 链霉菌 菌株 CL190 中发现的一种参与萘素生物合成的新型芳香族前基转移酶 Orf2，并阐明了其结构。这种炔基转移酶催化炔基与含有芳香核的化合物之间形成 C-C 键，同时还具有形成 C-O 键的活性。前炔基转移酶的许多晶体结构已得到解决和完善，例如：（1）前炔基转移酶与缓冲分子（TAPS）的复合物；（2）前炔基转移酶与二磷酸香叶酯（GPP）和 Mg 2+ 和 (3) 1,6-二羟基萘（1,6-DHN）或 (4) 黄素（即 2,5,7-三羟基-1,4-萘醌，它是 1,3,6,8-四羟基萘（THN）的氧化产物）的三元复合物。这些结构已分别求解并精炼至 1.5 Å、2.25 Å、1.95 Å 和 2.02 Å。这是首个芳香族预烯基转移酶的结构，显示出一种意想不到的非经典（β/α）桶状结构。与芳香底物和含预烯醇底物及类似物的复合物划定了活性位点，并与所提出的预烯醇基团转移的亲电机制相一致。这些结构还为了解这一结构独特的芳香族前酰基转移酶家族的前酰基链长决定和芳香族共底物识别提供了机理基础。这些结构信息有助于预测蛋白质的芳香族前基转移酶活性。
• Synthesis of natural 3′-Prenylchalconaringenin and biological evaluation of ameliorating non-alcoholic fatty liver disease and metabolic syndrome
  作者：Mengdi Zhang、Zhaoxin Wang、Siyu Hao、Lei Hao、Xinying Zhang、Peng Yu、Hua Sun

  DOI：10.1016/j.ejmech.2020.112649

  日期：2020.11

  Non-alcoholic fatty liver disease (NAFLD) is the most common cause of chronic liver disease and important risk factor for cardiac diseases, diabetes and extrahepatic cancers. Natural 3'-geranylchalconaringenin (GC) and desmethylxanthohumol (DX) from hop were synthesized using a regioselective iodination and the Suzuki coupling reaction as key steps. GC and DX, along with their aglycone naringenin chalcone (NC) were investigated their decreasing the accumulation of cellular lipids. GC reduced lipid content and activated the AMP-activated protein kinase (AMPK) pathway in HepG2 and 3T3-L1 cells. In addition, GC had an obvious therapeutic effect on alleviating NAFLD and metabolic syndrome by activating the AMPK pathway in vivo. In conclusion, GC may be potentially used as a candidate drug and functional food for treating NAFLD and metabolic syndrome. (C) 2020 Elsevier Masson SAS. All rights reserved.
• NOVEL COMPOSITIONS CONTAINING XANTHOHUMOL-CYCLODEXTRIN COMPLEXES
  申请人：Flaxan GmbH & Co. KG

  公开号：EP2249641A1

  公开（公告）日：2010-11-17