deoxyhumulone | 4374-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: deoxyhumulone
• 英文别名: 3-methyl-1-[2,4,6-trihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-butan-1-one；3-Methyl-1-[2,4,6-trihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-butan-1-on；{3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone；{3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl)-ketone；3,5-Bis-(3-methyl-2-butenyl)-phloroisovalerophenon；3,5-Diprenyl-phlorisovalerophenon；3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]butan-1-one
• CAS: 4374-93-0
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: NQYBQBZOHCACCR-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  515.1±50.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 保留指数：
  2354;2359

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  deoxyhumulone 在 gland protein extracts from the young cones of the hop cultivars 'Brewer's Gold' 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 律草酮
  参考文献：
  名称：

  脱氧葎草酮转化为啤酒花α-酸葎草酮

  摘要：

  在啤酒花苦酸生物合成的最后一步中，氧化会导致 α-酸的形成。建立了一种在蛋白质存在的情况下分析苦酸的方法，因为发现粗啤酒花提取物中的蛋白质与酚类苦酸相互作用并干扰这些酸的提取和分析。在检测了牛血清白蛋白与啤酒花苦酸的相互作用后，通过冻干浓缩样品并随后通过 HPLC 分析，用于研究脱氧葎草酮向葎草酮的转化。发现在体外发生两种类型的氧化：化学反应和由啤酒花蛋白提取物中的未知因素催化的反应。这项研究的结果表明，这种从啤酒花球果腺毛中分离出来的因子，

  DOI：

  10.1016/s0031-9422(96)00671-1
• 作为产物：
  描述：

  苯异戊二酮 、 1-溴-3-甲基-2-丁烯 生成 deoxyhumulone
  参考文献：
  名称：

  Riedl; Huebner, Chemische Berichte, 1957, vol. 90, p. 2870,2875

  摘要：

  DOI：

文献信息

• CIS 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS
  申请人：Carroll Brian J.

  公开号：US20120108671A1

  公开（公告）日：2012-05-03

  The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (−)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARγ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.

  本申请提供了顺式3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮衍生物及其基本对映纯组合物。这些衍生物包括(+)-(4S,5R)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，(-)-(4R,5S)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，以及它们的盐和晶体。该申请还提供了使用所披露的化合物和组合物来激活PPARγ、激活GPR120、抑制炎症，并治疗对PPARγ调节敏感的病症、对GPR120调节敏感的病症以及代谢紊乱如糖尿病的方法。
• Polyhydroxyphenol derivatives and preventive and therapeutic agents for bone and cartilage diseases containing the same
  申请人：Hoechst Marion Roussel

  公开号：US06177474B1

  公开（公告）日：2001-01-23

  Compounds useful as preventive and therapeutic agents for bone and cartilage diseases; and drug compositions containing the same. The compounds are polyhydroxyphenol derivatives of general formula (I) and quinione analogues derived therefrom (wherein R1 is alkyl, optionally substituted benzyl or optionally substituted aryl; R2 is hydrogen, alkyl, alkenyl or optionally substituted benzyl; R3 is hydrogen, alkyl, alkenyl, optionally substituted benzyl, hydroxyl, alkoxy, alkenyloxy or optionally substituted benzyloxy; R4 is hydrogen, alkyl, alkenyl, optionally substituted benzyl or hydroxyl; and R5 and R6 are each independently hydrogen, alkyl, alkenyl or optionally substituted benzyl). The polyhydroxyphenol derivatives and the quinone analogues exhibit a potent inhibitory activity against bone resorption and are useful as preventive and therapeutic agents for bone and cartilage diseases.

  具有预防和治疗骨骼和软骨疾病作用的化合物；以及含有这些化合物的药物组合物。这些化合物是通式(I)的多羟基酚衍生物和由此衍生的醌类似物（其中R1是烷基、可选择取代的苄基或可选择取代的芳基；R2是氢、烷基、烯烃基或可选择取代的苄基；R3是氢、烷基、烯烃基、可选择取代的苄基、羟基、烷氧基、烯烯氧基或可选择取代的苄氧基；R4是氢、烷基、烯烃基、可选择取代的苄基或羟基；而R5和R6各自独立地是氢、烷基、烯烃基或可选择取代的苄基）。这些多羟基酚衍生物和醌类似物表现出强大的抑制骨吸收活性，并且可用作预防和治疗骨骼和软骨疾病的药物。
• CIS, 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS
  申请人：CARROLL Brian J.

  公开号：US20130018105A1

  公开（公告）日：2013-01-17

  The present application provides cis 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one derivatives and substantially enantiomerically pure compositions thereof. These derivatives include (+)-(4S,5R)—3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, (−)-(4R,5S)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one, and salts and crystals thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, activate GPR120, inhibit inflammation, and treat conditions responsive to PPARγ modulation, conditions responsive to GPR120 modulation, and metabolic disturbances such as diabetes.

  本申请提供了cis 3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮衍生物及其相当对映纯的组合物。这些衍生物包括(+)-(4S,5R)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，(-)-(4R,5S)-3,4-二羟基-2-(3-甲基丁酰基)-5-(3-甲基丁基)-4-(4-甲基戊酰基)环戊-2-烯-1-酮，以及它们的盐和晶体。该申请进一步提供了使用所述化合物和组合物激活PPARγ，激活GPR120，抑制炎症，以及治疗对PPARγ调节敏感的疾病，对GPR120调节敏感的疾病和代谢紊乱，如糖尿病的方法。
• A Heteromeric Membrane-Bound Prenyltransferase Complex from Hop Catalyzes Three Sequential Aromatic Prenylations in the Bitter Acid Pathway
  作者：Haoxun Li、Zhaonan Ban、Hao Qin、Liya Ma、Andrew J. King、Guodong Wang

  DOI：10.1104/pp.114.253682

  日期：2015.3

  Bitter acids (α and β types) account for more than 30% of the fresh weight of hop (Humulus lupulus) glandular trichomes and are well known for their contribution to the bitter taste of beer. These multiprenylated chemicals also show diverse biological activities, some of which have potential benefits to human health. The bitter acid biosynthetic pathway has been investigated extensively, and the genes for the early steps of bitter acid synthesis have been cloned and functionally characterized. However, little is known about the enzyme(s) that catalyze three sequential prenylation steps in the β-bitter acid pathway. Here, we employed a yeast (Saccharomyces cerevisiae) system for the functional identification of aromatic prenyltransferase (PT) genes. Two PT genes (HlPT1L and HlPT2) obtained from a hop trichome-specific complementary DNA library were functionally characterized using this yeast system. Coexpression of codon-optimized PT1L and PT2 in yeast, together with upstream genes, led to the production of bitter acids, but no bitter acids were detected when either of the PT genes was expressed by itself. Stepwise mutation of the aspartate-rich motifs in PT1L and PT2 further revealed the prenylation sequence of these two enzymes in β-bitter acid biosynthesis: PT1L catalyzed only the first prenylation step, and PT2 catalyzed the two subsequent prenylation steps. A metabolon formed through interactions between PT1L and PT2 was demonstrated using a yeast two-hybrid system, reciprocal coimmunoprecipitation, and in vitro biochemical assays. These results provide direct evidence of the involvement of a functional metabolon of membrane-bound prenyltransferases in bitter acid biosynthesis in hop.

  苦酸（α和β型）占啤酒花腺毛重量的30%以上，是啤酒苦味的来源。这些多烯基化合物的生物活性多种多样，其中一些可能对人体健康有益。苦酸的生物合成途径已经过广泛研究，苦酸合成早期步骤的基因也已克隆并确定功能。然而，人们对催化β-苦酸合成途径中三个连续烯基化步骤的酶知之甚少。在此，我们采用酵母（酿酒酵母）系统对芳香烯基转移酶（PT）基因的功能进行了鉴定。利用酵母系统对从啤酒花腺毛特异性互补DNA文库中获得的两个PT基因（HlPT1L和HlPT2）进行了功能鉴定。在酵母中，经过密码子优化的PT1L和PT2与上游基因共表达可产生苦酸，但单独表达任一PT基因时均未检测到苦酸。PT1L和PT2中富含天冬氨酸的基序的逐步突变进一步揭示了β-苦酸生物合成中这两种酶的烯基化序列：PT1L仅催化第一个烯基化步骤，PT2催化随后的两个烯基化步骤。利用酵母双杂交系统、相互共沉淀和体外生化分析，证明了PT1L和PT2之间的相互作用形成的代谢体。这些结果直接证明了膜结合烯基转移酶的功能代谢体参与啤酒花苦酸生物合成。
• Rapid Access to Polyprenylated Phloroglucinols via Alkylative Dearomatization−Annulation:  Total Synthesis of (±)-Clusianone
  作者：Ji Qi、John A. Porco

  DOI：10.1021/ja0762339

  日期：2007.10.1

  A concise approach to the bicyclo[3.3.1]nonane framework of the polyprenylated phloroglucinol natural products utilizing a tandem alkylative dearomatization-annulation sequence is described. Syntheses of (+/-)-clusianone and a complex adamantane framework have been achieved using the developed methodology.