Colupulone | 21621-94-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: Colupulone
• 英文别名: 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(isobutyryl)cyclohexa-2,4-dienone；co-lupulone；colupulon；5-Oxo-2,4,4-tri-(isopenten-(2)-yl)-6-isobutyryl-4,5-dihydroresorcin; Colupulon；3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• CAS: 21621-94-3
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: UNCDMWKTFLUPHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Colupulone 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到5-Hydroxy-2,2-dimethyl-8,8-bis(3-methylbut-2-enyl)-6-(2-methylpropanoyl)chromen-7-one
  参考文献：
  名称：

  Biomimetic Synthesis of Polycyclic Polyprenylated Acylphloroglucinol Natural Products Isolated from Hypericum papuanum

  摘要：

  Biomimetic syntheses of three polycylic polyprenylated acylphloroglucinol natural products isolated from Hypericum papuanum, ialibinone A, ialibinone B, and hyperguinone B, have been accomplished by selective oxidative cyclizations of the proposed biosynthetic precursor 5, which was synthesized from phloroglucinol in three steps.

  DOI：

  10.1021/ol101380a
• 作为产物：
  描述：

  间苯三酚 在 aluminum (III) chloride 、 氨 作用下， 以 乙醚 、 硝基甲烷 、 二氯甲烷 为溶剂， 生成 Colupulone
  参考文献：
  名称：

  The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells

  摘要：

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.11.011

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• [EN] ANTIMICROBIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIMICROBIENS
  申请人：UNIV MICHIGAN

  公开号：WO2013086415A1

  公开（公告）日：2013-06-13

  Provided herein is technology relating to antimicrobial compounds and particularly, but not exclusively, to analogs of rifalazil having increased inhibition of RNA polymerase and decreased induction of human cy-tochrome P450. The compounds have an increased affinity for a bacterial RNA polymerase (e.g., a MTB RNA polymerase) and a decreased affinity for a human pregnane X receptor. Thus, in some embodiments, the steric clash of A or R with residues in the binding pocket of the human pregnane X receptor reduces an affinity of the compound for the human pregnane X receptor. Consequently, in some embodiments the steric clash thus reduces the induction (e.g., an activity) of a cytochrome P450 and/or other related proteins.

  本文提供了与抗菌化合物相关的技术，特别是但不仅限于具有增强RNA聚合酶抑制作用和减少诱导人类细胞色素P450的利法拉唑类似物。这些化合物对细菌RNA聚合酶（例如结核分枝杆菌RNA聚合酶）具有增强亲和力，并对人类孕烷X受体具有降低的亲和力。因此，在某些实施例中，化合物与人类孕烷X受体结合口袋中残基的空间阻碍A或R，降低了化合物对人类孕烷X受体的亲和力。因此，在某些实施例中，这种空间阻碍减少了细胞色素P450和/或其他相关蛋白的诱导（例如活性）。
• COMPOUNDS USEFUL AS MODULATORS OF TRPM8
  申请人：Senomyx, Inc.

  公开号：US20170096418A1

  公开（公告）日：2017-04-06

  The present disclosure relates to compounds which are useful as cooling sensation compounds.

  本公开涉及作为冷感化合物有用的化合物。
• Compositions comprising curcuminoids and either alpha or beta acids for use in the treatment of diabetes
  申请人：Metaproteomics, LLC

  公开号：EP2263663A1

  公开（公告）日：2010-12-22

  The present invention relates to the use of a first component selected from an alpha acid and a beta acid in the manufacture of a medicament for the treatment of diabetes.

  本发明涉及使用从α酸和β酸中选择的第一组分在制造治疗糖尿病药物中的应用。
• Compositions Exhibiting Inhibition Of Cyclooxygenase-2
  申请人：Babish John G.

  公开号：US20090274778A1

  公开（公告）日：2009-11-05

  The invention provides a method of treating diabetes by administering to an individual having diabetes a composition containing a hops extract. In a particular embodiment, an individual having diabetes can be administered a composition comprising a first component selected from the group consisting of alpha acids and beta acids, essential oils, fats and waxed, with the proviso that the first component and second component are not the same compound. The invention additional provides a method of treating diabetes by administering to an individual having diabetes a composition comprising a first component selected from a curcuminoid and a second component selected from an alpha acid and a beta acid.

  本发明提供了一种通过向患有糖尿病的个体给予含啤酒花提取物的组合物来治疗糖尿病的方法。在一个特定的实施例中，可以向患有糖尿病的个体给予一种组合物，其中包括来自阿尔法酸和贝塔酸、精油、脂肪和蜡的第一成分，但第一成分和第二成分不是相同的化合物。本发明还提供了一种通过向患有糖尿病的个体给予包括姜黄素类化合物和阿尔法酸和贝塔酸中的第二成分的组合物来治疗糖尿病的方法。