(+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone | 41137-85-3

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone
• 英文别名: (5S)-1,7-bis(4-hydroxyphenyl)5-hydroxyheptan-3-one；5-hydroxy-1,7-bis(4-hydroxyphenyl)-3-heptanone；5-hydroxy-1,7-bis(4-hydroxyphenyl)heptan-3-one；hexahydro(bisdemethoxy)curcumin；hexahydro-bisdemethoxy-curcumin；hexahydrobisdemethoxycurcumin
• CAS: 41137-85-3；93604-01-4；57089-26-6；79120-39-1
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: ZBFSUZGUYFFWGY-UHFFFAOYSA-N

物化性质

• 沸点：
  575.2±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914501900
• 储存条件：
  存储条件：2-8℃，密封保存，干燥环境。

制备方法与用途

Platycophyllonol（Platyphyllon）可以从A. japonica中分离得到。研究表明，它对MCF-7细胞具有细胞毒性作用，其IC50值为46.9 μg/mL。

反应信息

• 作为反应物：
  描述：

  (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 platyphyllenone
  参考文献：
  名称：

  Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species

  摘要：

  The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Tryponosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 mu M, respectively). Among 43 curcuminoid analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in sub-micromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxy-phenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 +/- 0.007 mu M; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 +/- 0.01 mu M). Using a previously characterized diminazene-resistant T. b, brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against 7: b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 +/- 3 and 37 +/- 6 mu M. respectively) while the control drug, pentamidine, displayed an EC50 of 16 +/- 2 mu M. Among the active curcuminoid analogs, four Compounds exhibited EC50 values of less than 5 mu M against Leishmania major promastigotes and four against L mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.035
• 作为产物：
  描述：

  对羟基苯丙酸 在 palladium on activated charcoal 氰基磷酸二乙酯 、 氢氟酸 、 magnesium,2-methylpropane,bromide 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (+/-)-5-hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone
  参考文献：
  名称：

  Kato, Nobuharu; Hamada, Yasumasa; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 3323 - 3326

  摘要：

  DOI：

文献信息

• Biarylheptanoids and other constituents from wood of Alnus japonica
  作者：Masayasu Nomura、Takashi Tokoroyama、Takashi Kubota

  DOI：10.1016/0031-9422(81)83035-x

  日期：1981.1

  Abstract The wood of Alnus japonica has been shown to contain a number of biarylheptanoids as well as other phenolics, including secoisolariciresinol diferulate. The co-occurrence of cyclized biarylheptanoids with their corresponding acyclic biarylheptanoids has been demonstrated and this fact may have biosynthetic significance. The possible chemotaxonomic importance of biarylheptanoids in members

  摘要 桤木 (Alnus japonica) 的木材已被证明含有许多二芳基庚烷类化合物以及其他酚类物质，包括开环异落叶松树脂二铁。环化联芳基庚烷与其相应的无环联芳基庚烷共存已被证明，这一事实可能具有生物合成意义。讨论了双芳基庚烷在桦木科成员中可能的化学分类学重要性。还描述了几种类固醇和三萜类化合物的分离和鉴定。
• Curcuminoids Form Reactive Glucuronides In Vitro
  作者：Erika Pfeiffer、Simone I. Hoehle、Stephan G. Walch、Alexander Riess、Anikó M. Sólyom、Manfred Metzler

  DOI：10.1021/jf0623283

  日期：2007.1.1

  the glucuronic acid moiety at the alcoholic hydroxyl group was formed from the same curcuminoids, but not hexahydro-curcuminoids, by human microsomes. Curcuminoids without a phenolic hydroxyl group gave rise to the aliphatic glucuronide only. The phenolic glucuronides of curcuminoids, but not of hexahydro-curcuminoids, were rather lipophilic and, in part, unstable in aqueous solution, their stability

  由于姜黄素具有抗炎，抗癌和抗阿尔茨海默氏病的活性，因此备受关注，但对其药代动力学和代谢命运知之甚少。因此，目前已经对姜黄素及其主要的I相代谢产物六氢姜黄素以及各种天然和人工类似物的葡糖醛酸苷化进行了体外研究。根据LC-MS / MS分析，由大鼠和人类肝脏微粒体由姜黄素，六氢姜黄素和其他具有酚羟基的类似物产生的主要葡萄糖醛酸苷为酚醛酸葡萄糖苷。然而，由人微粒体由相同的姜黄素而不是六氢姜黄素形成了在醇羟基上带有葡糖醛酸部分的第二葡糖醛酸。没有酚羟基的姜黄素仅产生脂族葡糖醛酸。姜黄素类的酚类葡糖醛酸而不是六氢姜黄素类的酚类葡糖醛酸具有相当的亲脂性，并且在水溶液中部分不稳定，其稳定性在很大程度上取决于芳族取代基的类型。姜黄素及其天然同源物的酚醛葡萄糖醛酸苷，而不是母体化合物，明显抑制了无细胞条件下微管蛋白的组装，暗示了葡糖醛酸苷的化学反应性。姜黄素主要II期代谢产物的这些新颖性质值得进一步研究。它
• Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells
  作者：Jiraporn Tocharus、Sataporn Jamsuwan、Chainarong Tocharus、Chatchawan Changtam、Apichart Suksamrarn

  DOI：10.1007/s11418-011-0599-6

  日期：2012.4

  The chemically modified analogs, the demethylated analogs 4–6, the tetrahydro analogs 7–9 and the hexahydro analogs 10–12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O-demethyldemethoxycurcumin (6) are the two most

  对姜黄素 ( 1 )、脱甲氧基姜黄素( 2 ) 和双脱甲氧基姜黄素 ( 3 )的化学修饰类似物、去甲基化类似物4 – 6、四氢类似物7 – 9和六氢类似物10 – 12对脂多糖活化的抑制活性进行了评估HAPI 小胶质细胞中一氧化氮 (NO) 的产生。Di- O-去甲基姜黄素 ( 5 ) 和O-去甲基去甲氧基姜黄素 ( 6 ) 是抑制 NO 生成的两种最有效的化合物。类似物5和6分别比母体姜黄素1和2 的活性高两倍或几乎两倍。此外，这两种化合物抑制了诱导型 NO 合酶的 mRNA 表达水平。类似物5和6的强大神经保护活性提供了潜在的替代化合物，可作为与活化小胶质细胞相关的神经系统疾病的治疗剂进行开发。
• ——
  作者：Katharina Bratt、Kerstin Sunnerheim

  DOI：10.1023/a:1020847423427

  日期：——

  (+/-)-5-Hydroxy-1,7-bis-(4'-hydroxyphenyl)-3-heptanone (2a), (+/-)-5-hydroxyl-1-(4'-hydroxyphenyl)-7-phenyl-3-heptanone (2b), (+/-)-5-hydroxy-7-(4'-hydroxyphenyl)-1-phenyl-3-heptanone (2c), and (+/-)-5-hydroxy-1,7-bis-(phenyl)-3-heptanone (2d) have been synthesized to study the structure-activity relationship regarding digestibility inhibition in vitro in cow rumen fluid. The activities were compared with the activity of chiral (S)-2a and its glucoside platyphylloside (1), isolated from Betula pendula. Compound 2a was slightly less active, 2b and 2c were more active, and 2d was less active than (S)-2a and platyphylloside.

  (±)-5-羟基-1,7-双-(4'-羟基苯基)-3-庚酮 (2a)、(±)-5-羟基-1-(4'-羟基苯基)-7-苯基-3-庚酮 (2b)、(±)-5-羟基-7-(4'-羟基苯基)-1-苯基-3-庚酮 (2c) 和 (±)-5-羟基-1,7-双-(苯基)-3-庚酮 (2d) 已经被合成，用于研究在牛瘤胃液中体外消化抑制的结构-活性关系。这些化合物的活性与从 Betula pendula 分离出的具有手性 (S)-2a 及其苷 platyphylloside (1) 进行了比较。化合物 2a 的活性略低于 (S)-2a 和 platyphylloside，而 2b 和 2c 的活性更高，2d 的活性则低于 (S)-2a 和 platyphylloside。
• Diarylheptanoids from <i>Dioscorea villosa</i> (Wild Yam)
  作者：Shi-Hui Dong、Dejan Nikolić、Charlotte Simmler、Feng Qiu、Richard B. van Breemen、Djaja D. Soejarto、Guido F. Pauli、Shao-Nong Chen

  DOI：10.1021/np300603z

  日期：2012.12.28

  botanical, wild yam (Dioscorea villosa), makes use of 1D qHNMR and 2D NMR profiles along the preparative fractionation pathway. This quantifiable and structural guidance led to the isolation of 14 diarylheptanoids (1–14), including five new compounds (1–5) with a tetrahydropyrano core skeleton. The structures, including the absolute configurations of both new and previously known diarylheptanoids, were

  一种旨在为广泛使用的植物野山药（Dioscorea villosa）的新植物成分的代谢组学挖掘的分馏方法，利用沿制备分馏途径的 1D qHNMR 和 2D NMR 图谱。导致14二芳基庚（隔离这个量化和结构指导1 - 14，包括五个新化合物（）1 - 5）与四氢吡喃核的骨架。这些结构，包括新的和以前已知的二芳基庚烷类化合物的绝对构型，是通过 HRESIMS、1D 和 2D NMR、1H 迭代全自旋分析 (HiFSA) 和 Mosher 酯法。分离产量与 qHNMR 预测的产量一致，这证实了基于 NMR 的制备型代谢组学挖掘的（半）可量化能力。qHNMR 辅助方法能够从植物提取物的一小部分中识别出新的和潜在重要的化学实体，从而促进了对绒毛草次生代谢组的残留复杂性的表征。不同D. villosa种质的LC-MS 分析进一步证实，二芳基庚烷类化合物代表真正的次生代谢物，可作为D. villosa植物完整性分析的一类新标记。