4'-O-methylxanthohumol | 123316-63-2

• 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: 4'-O-methylxanthohumol
• 英文别名: (E)-1-[2-hydroxy-4,6-dimethoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 123316-63-2
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: UVBDKJHYMQEAQV-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-O-methylxanthohumol 以 甲醇 、 水 为溶剂， 生成 5,7-di-O-methyl-8-prenylnaringenin
  参考文献：
  名称：

  Prenylflavonoid variation in Humulus lupulus: distribution and taxonomic significance of xanthogalenol and 4′-O-methylxanthohumol

  摘要：

  The resins produced by either lupulin or leaf glands of over 120 plants of Humulus lupulus and one plant of H. japonicus (Cannabinaceae) were analyzed for the presence of prenylated flavonoids. The H. lupulus taxa investigated were H. lupulus var. lupulus from Europe, H. lupulus var. cordifolius from Japan, and H. lupulus From North America. Fifty-two of the plants examined were cultivars of European, American, and Japanese origin, Twenty-two flavonoids were detected in the glandular exudates of. H. lupulus by HPLC-MS-MS. Xanthohumol (3'-prenyl-6'-O-methylchalconaringenin) was the principal prenylflavonoid in all H. lupulus plants and was accompanied by 11 structurally similar chalcones. Ten flavonoids were identified as the flavanone isomers of these chalcones. Three other prenylchalcones were isolated from H. lupulus cv. 'Galena', one of which was identified as 3'-prenyl-4'-O-methylchalconaringenin (named 'xanthogalenol'). The distribution of three 4'-O-methylchalcones, i.e, xanthogalenol, 4'-O-methylxanthohumol, and 4',6'-di-O-methylchalconaringenin, was found to be limited to wild American plants from the Missouri-Mississippi river basin, H. lupulus var. cordifolius, and most of their descendents, These 4'-O-methylchalcones were absent from cultivars of European origin; and from wild hops from Europe and southwestern USA, The flavonoid dichotomy (presence versus absence of 4'-O-methylchalcones) indicates that there are at least two evolutionary lineages within H. lupulus (European and Japanese-American). which is in agreement with morphological, molecular, and phytogeographical evidence. Leaf glands of H. japonicus from eastern Asia did not produce the N. lupulus prenylflavonoids. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00005-4
• 作为产物：
  描述：

  在 盐酸 作用下， 以 甲醇 为溶剂， 以66%的产率得到4'-O-methylxanthohumol
  参考文献：
  名称：

  Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity

  摘要：

  A general strategy for the synthesis of 30-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2 +/- 0.4 mu M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 +/- 0.5 mu M), were more active in comparison to 1 (IC50 9.4 +/- 1.4 mu M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 +/- 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 +/- 2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 +/- 0.6, 3.8 +/- 0.4, and 3.8 +/- 0.5 Trolox equivalents, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.079

文献信息

• Reactivity assessment of chalcones by a kinetic thiol assay
  作者：Sabine Amslinger、Nafisah Al-Rifai、Katrin Winter、Kilian Wörmann、Rebekka Scholz、Paul Baumeister、Martin Wild

  DOI：10.1039/c2ob27163j

  日期：——

  The electrophilic nature of chalcones (1,3-diphenylprop-2-en-1-ones) and many other α,β-unsaturated carbonyl compounds is crucial for their biological activity, which is often based on thiol-mediated regulation processes. To better predict their biological activity a simple screening assay for the assessment of the second-order rate constants (k2) in thia-Michael additions was developed. Hence, a clear structure–activity relationship of 16 differentially decorated hydroxy-alkoxychalcones upon addition of cysteamine could be established. Moreover, amongst other naturally occurring α,β-unsaturated carbonyl compounds k2 values for curcumin and cinnamaldehyde were gained while cinnamic acids or esters gave no or very slow reactions.

  查耳酮（1,3-二苯基丙-2-烯-1-酮）和许多其他α,β-不饱和羰基化合物的亲电性质对其生物活性至关重要，而生物活性通常是基于硫醇介导的调节过程。为了更好地预测它们的生物活性，我们开发了一种简单的筛选方法，用于评估噻-迈克尔加成反应的二阶速率常数（k2）。因此，在添加半胱胺后，16 种不同装饰的羟基烷氧基查耳酮的结构-活性关系得以明确。此外，在其他天然存在的 α、β-不饱和羰基化合物中，姜黄素和肉桂醛的 k2 值得到了提高，而肉桂酸或酯类则没有反应或反应非常缓慢。
• Protein kinase modulation by hops and acacia products cross-reference to related applications
  申请人：Metaproteomics, LLP

  公开号：EP2248532A1

  公开（公告）日：2010-11-10

  An aspect of the invention comprises a composition for modulating the activity of a plurality of disease associated protein kinases in a subject in need thereof, wherein said protein kinase modulation is beneficial to the health of the subject; said composition comprising a therapeutically effective amount of a composition comprising reduced isoalpha acids and a compound or extract derived from acacia.

  本发明的一个方面包括一种组合物，用于调节有需要的受试者体内与疾病相关的多种蛋白激酶的活性，其中所述蛋白激酶的调节对受试者的健康有益；所述组合物包括治疗有效量的组合物，该组合物包含还原型异α酸和从金合欢中提取的化合物或提取物。
• Anti-inflammatory botanical products for the treatment of metabolic syndrome and diabetes
  申请人：Metaproteomics, LLC

  公开号：EP2737897A2

  公开（公告）日：2014-06-04

  The present invention relates to compositions consisting essentially of a therapeutically effective amount of a compound selected from the group consisting of tetrahydro-isohumulone, tetrahydro-isocohumulone, and tetrahydro-isoadhumulone; and metformin, to be used in the treatment of an insulin related disorder, diabetes, obesity, or a cardiovascular disease.

  本发明涉及主要由治疗有效量的选自四氢-异胡麻酮、四氢-异胡麻酮和四氢-异胡麻酮组成的化合物和二甲双胍组成的组合物，用于治疗胰岛素相关疾病、糖尿病、肥胖症或心血管疾病。
• Jain, A. C.; Sinha, S. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 4, p. 317 - 320
  作者：Jain, A. C.、Sinha, S. P.

  DOI：——

  日期：——
• PRENYLFLAVONOID FORMULATIONS
  申请人：Bioactives, Inc.

  公开号：EP1909584A2

  公开（公告）日：2008-04-16