2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone | 54614-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone
• 英文别名: 3-methyl-1-[2,4,6-trihydroxy-3-(3-methyl-but-2-enyl)-phenyl]-butan-1-one；3-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-but-2-enyl)-phenyl]-butan-1-on；{3-(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-methylpropyl) ketone；3-Methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)butan-1-one；3-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl]butan-1-one
• CAS: 54614-64-1
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: LWLGKGHHVBVDKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以91%的产率得到3-methyl-1-(2,4,6-trihydroxy-3-isopentylphenyl)butan-1-one
  参考文献：
  名称：

  Cann, Martin R.; Davis, Anne-Marie; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1984, # 7, p. 1413 - 1421

  摘要：

  DOI：
• 作为产物：
  描述：

  苯异戊二酮 、 1-溴-3-甲基-2-丁烯 在 甲醇 、 乙醚 、 sodium methylate 作用下， 生成 2',4',6'-trihydroxy-3'-(3-methylbut-2-enyl)isovalerophenone
  参考文献：
  名称：

  Riedl, Chemische Berichte, 1952, vol. 85, p. 692,704, 708

  摘要：

  DOI：

文献信息

• HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops
  作者：Yusuke Tsurumaru、Kanako Sasaki、Tatsuya Miyawaki、Yoshihiro Uto、Takayuki Momma、Naoyuki Umemoto、Masaki Momose、Kazufumi Yazaki

  DOI：10.1016/j.bbrc.2011.11.125

  日期：2012.1

  HlPT-1 catalyzed the first transfer of dimethylallyl moiety to phloroglucinol derivatives, phlorisovalerophenone, phlorisobutyrophenone and phlormethylbutanophenone, leading to the formation of humulone and lupulone derivatives. HlPT-1 also recognized naringenin chalcone as a flavonoid substrate to yield xanthohumol, and this broad substrate specificity is a unique character of HlPT-1 that is not seen in

  蛇麻草的雌花（Humulus lupulus L.）发育出大量的称为毛豆蛋白腺的毛状毛，其中包含多种prenylated化合物，例如α-酸和β-酸（分别为humulone和lupulone）以及黄腐酚（chanthohumol），查尔酮衍生物。这些异戊二烯基化的化合物通过异戊二烯基转移酶生物合成，所述异戊二烯基转移酶催化二甲基烯丙基部分向芳族物质的转移。在我们以前的工作中，我们在从富含卢普林的花组织构建的cDNA文库中发现HlPT-1是此类异戊二烯基转移酶的候选基因。在这项研究中，我们使用杆状病毒感染的昆虫细胞中表达的重组蛋白表征了HlPT-1的酶学性质。HlPT-1催化了二甲基烯丙基部分向间苯三酚衍生物苯并异戊二酮的首次转移，苯并异丁苯酮和苯并甲基丁苯酮，导致形成hu草酮和卢普隆衍生物。HlPT-1还认为柚皮素查尔酮为类黄酮底物，可产生黄腐酚，这种广泛的底物特异性是HlPT-1的独特特征
• 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。
• Riedl; Huebner, Chemische Berichte, 1957, vol. 90, p. 2870,2875
  作者：Riedl、Huebner

  DOI：——

  日期：——
• Friedel–Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase
  作者：Kang Zhou、Lena Ludwig、Shu-Ming Li

  DOI：10.1021/np5009784

  日期：2015.4.24

  Naturally occurring prenylated acylphloroglucinol derivatives are plant metabolites with diverse biological and pharmacological activities: Prenylation of acylphloroglucinols plays an important role in the formation of these intriguing natural products and is catalyzed in plants by membrane-bound enzymes. In this study, we demonstrate the prenylation of such compounds by a soluble fungal prenyltransferase AnaPT involved in the biosynthesis of prenylated indole alkaloids. The observed activities of AnaPT toward these substrates are Much higher than that of a microsomal fraction containing an overproduced prenyltransferase from the plant hop.
• <i>gem</i>-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily
  作者：Kang Zhou、Carsten Wunsch、Jungui Dai、Shu-Ming Li

  DOI：10.1021/acs.orglett.6b03594

  日期：2017.1.20

  Aspergillus terreus aromatic prenyltransferase (AtaPT) catalyzes predominantly C-monoprenylation of acylphloroglucinols in the presence of different prenyl diphosphates. With dimethylallyl diphosphate (DMAPP) as prenyl donor, gem-diprenylated products 1D3, 2D3, and 3D3 were also detected. High conversion of 1D1 to 1D3, 2D1 to 2D3, and 3D1 to 3D3 was demonstrated by incubation with AtaPT and DMAPP. The first example of gem-diprenylation by a member of the dimethylallyltryptophan synthase superfamily is provided.