8-5-cyclic dehydrodiferulic acid | 353455-91-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 8-5-cyclic dehydrodiferulic acid
• 英文别名: 5-(2-Carboxyvinyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid；5-(2-carboxyethenyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
• CAS: 353455-91-1
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: JTHPLBUVRLOJBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-5-cyclic dehydrodiferulic acid 以 二甲基亚砜 为溶剂， 反应 72.0h， 生成 8,5'-diferulic acid
  参考文献：
  名称：

  Structural Transformation of 8–5-Coupled Dehydrodiferulates by Human Intestinal Microbiota

  摘要：

  Ingested dehydrodiferulates (DFAs) are partially released from cereal dietary fiber by human colonic microbiota, but little research has explored the further microbial metabolism of 8-5-coupled DFAs. This study investigated the in vitro microbial metabolism and elucidated major metabolites of free 8-5-DFAs (benzofuran and open forms) and an esterified analogue, 8-5-DFA diethyl ester (benzofuran). Synthesized standard compounds were incubated with fresh human fecal suspensions. Metabolites were isolated and structurally elucidated using high-resolution-LC-time-of-flight-(ToF)-MS, GC-MS, and NMR. Nine metabolite structures were unambiguously characterized with NMR, and four additional metabolites were tentatively identified to reveal structural conversion motifs: propenyl side chain hydrogenation (all substrates), O-demethylation and reductive ring-opening (8-5-DFA diethyl ester and free 8-5-DFA [benzofuran]), and de-esterification (8-5-DFA diethyl ester). A pathway of microbial 8-5-DFA metabolism was proposed based on metabolite formation kinetics. Importantly, deesterification of the 8-5-DFA diethyl ester occurred primarily after and/or concurrently with other metabolism steps. Cleavage to monomers was not observed.

  DOI：

  10.1021/acs.jafc.5b03234
• 作为产物：
  描述：

  阿魏酸 在 laccase from myceliophthora thermophila sp. 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 生成 8-5-cyclic dehydrodiferulic acid
  参考文献：
  名称：

  Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: A green procedure for the synthesis of new compounds

  摘要：

  The enzymatic oxidation of ferulic acid (FA) and ethyl ferulate (EF) with Myceliophthora thermophila laccase, as biocatalyst, was performed in aqueous medium using an eco-friendly procedure to synthesize new active molecules. First, the commercial laccase was ultrafiltrated allowing for the elimination of phenolic contaminants and increasing the specific activity by a factor of 2. Then, kinetic parameters of this laccase were determined for both substrates (FA, EF), indicating a higher substrate affinity for ethyl ferulate. Additionally, enzymatic oxidation led to the synthesis of a FA-major product, exhibiting a molecular mass of 386 g/mol and a EF-major product with a molecular mass of 442 g/mol. Structural analyses by mass spectrometry allowed the identification of dimeric derivatives. The optical properties of the oxidation products showed the increase of red and yellow colours, with FA-products compared to EF-products. Additionally, enzymatic oxidation led to a decrease of antioxidant and cytotoxic activities compared to initial substrates. Consequently, this enzymatic procedure in aqueous medium could provide new compounds presenting optical, antioxidant and cytotoxic interest. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2013.07.119

文献信息

• 10.1021/acs.jafc.4c03713
  作者：Tai, Gangyin、Zhang, Qi、He, Jiangqin、Li, Xiangyang、Gan, Xiuhai

  DOI：10.1021/acs.jafc.4c03713

  日期：——

  A series of ferulic acid dimers were designed, synthesized, and evaluated for anti-TMV activity. Biological assays demonstrated that compounds A6, E3, and E5 displayed excellent inactivating against tobacco mosaic virus (TMV) with EC50 values of 62.8, 94.4, and 85.2 μg mL–1, respectively, which were superior to that of ningnanmycin (108.1 μg mL–1). Microscale thermophoresis indicated that compounds

  设计、合成了一系列阿魏酸二聚体，并评估了其抗 TMV 活性。生物学测定表明，化合物A6 、 E3和E5对烟草花叶病毒（TMV）具有优异的灭活作用，EC 50值分别为62.8、94.4和85.2 μg mL –1 ，优于宁南霉素（108.1 μg mL –1 ）。 –1 ）。微尺度热泳分析表明，化合物A6 、 E3和E5对TMV外壳蛋白具有很强的结合能力，结合亲和力值分别为1.862、3.439和2.926 μM。分子对接和分子动力学模拟表明，化合物A6可以通过氢键和疏水键与TMV外壳蛋白牢固结合。透射电镜和自组装实验表明，化合物A6明显破坏了TMV颗粒的完整性，阻断了病毒感染宿主。这项研究表明， A6可通过抑制 TMV 自组装作为抗病毒药物开发的有前景的先导结构。
• Determination of free diferulic, disinapic and dicoumaric acids in plants and foods
  作者：Jiří Grúz、Jiří Pospíšil、Hana Kozubíková、Tomáš Pospíšil、Karel Doležal、Mirko Bunzel、Miroslav Strnad

  DOI：10.1016/j.foodchem.2014.08.131

  日期：2015.3

  Hydroxycinnamates are common phenolic compounds of plants and plant foods, often found in substantial quantities. Due to their high in vitro antioxidant activity they can easily be oxidized under oxidative conditions. In this study, we found that in vitro oxidation of coumaric, ferulic and sinapic acids resulted mainly in dimeric compounds. We hypothesized that these dimers are present in plants and plant foods not only in their bound form but also as free acids that can be extracted from non-hydrolyzed samples. By applying sensitive UHPLC-MSIMS method, we were able to identify and quantify four free hydroxycinnamic acid dimers for the first time, namely 8-8'-disinapic, 8-5'-diferulic, 8-O-4'-diferulic and 8-3'-dicoumaric acids, in wheat sprouts, Chinese cabbage, millet sprouts, light beer and parsley. Concentrations of dicinnamates in plant tissues ranged from 0.05 to 2.8 mu g g(-1) DW and the monomer:dimer ratio ranged from 2 to 850. (C) 2014 Elsevier Ltd. All rights reserved.
• Laccase-catalyzed dimerization of ferulic acid amplifies antioxidant activity
  作者：Oluyemisi E. Adelakun、Tukayi Kudanga、Ayesha Parker、Ivan R. Green、Marilize le Roes-Hill、Stephanie G. Burton

  DOI：10.1016/j.molcatb.2011.08.010

  日期：2012.1

  Enzymatic modification can be used to enhance the bioactive properties of phenolic compounds. The present study employed laccase from Trametes pubescens to catalyze the modification of ferulic acid in a monophasic or biphasic system, as a way of enhancing its antioxidant capacity. Two dimeric products (m/z 385.1) were purified and characterized as the beta-5 and beta-beta dimers. In the monophasic system, the beta-5 dimer was preferentially formed in dioxane while the beta-beta dimer formation was enriched in ethanol as co-solvent. In the biphasic system, formation of the dimers increased as the concentration of ethyl acetate was increased from 80% to 95%. The beta-5 dimer showed higher antioxidant capacity than the substrate as demonstrated by standard antioxidant assays (DPPH and TEAC). These results demonstrate that alteration of reaction conditions influences the laccase-mediated oxidation of ferulic acid to form dimers with higher antioxidant capacity than the substrate. (C) 2011 Elsevier B.V. All rights reserved.
• Structural Transformation of 8–5-Coupled Dehydrodiferulates by Human Intestinal Microbiota
  作者：Rachel R. Schendel、Cecile Karrer、Diana Bunzel、Melanie Huch、Andreas A. Hildebrand、Sabine E. Kulling、Mirko Bunzel

  DOI：10.1021/acs.jafc.5b03234

  日期：2015.9.16

  Ingested dehydrodiferulates (DFAs) are partially released from cereal dietary fiber by human colonic microbiota, but little research has explored the further microbial metabolism of 8-5-coupled DFAs. This study investigated the in vitro microbial metabolism and elucidated major metabolites of free 8-5-DFAs (benzofuran and open forms) and an esterified analogue, 8-5-DFA diethyl ester (benzofuran). Synthesized standard compounds were incubated with fresh human fecal suspensions. Metabolites were isolated and structurally elucidated using high-resolution-LC-time-of-flight-(ToF)-MS, GC-MS, and NMR. Nine metabolite structures were unambiguously characterized with NMR, and four additional metabolites were tentatively identified to reveal structural conversion motifs: propenyl side chain hydrogenation (all substrates), O-demethylation and reductive ring-opening (8-5-DFA diethyl ester and free 8-5-DFA [benzofuran]), and de-esterification (8-5-DFA diethyl ester). A pathway of microbial 8-5-DFA metabolism was proposed based on metabolite formation kinetics. Importantly, deesterification of the 8-5-DFA diethyl ester occurred primarily after and/or concurrently with other metabolism steps. Cleavage to monomers was not observed.
• Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: A green procedure for the synthesis of new compounds
  作者：Abdulhadi Aljawish、Isabelle Chevalot、Jordane Jasniewski、Cédric Paris、Joël Scher、Lionel Muniglia

  DOI：10.1016/j.foodchem.2013.07.119

  日期：2014.2

  The enzymatic oxidation of ferulic acid (FA) and ethyl ferulate (EF) with Myceliophthora thermophila laccase, as biocatalyst, was performed in aqueous medium using an eco-friendly procedure to synthesize new active molecules. First, the commercial laccase was ultrafiltrated allowing for the elimination of phenolic contaminants and increasing the specific activity by a factor of 2. Then, kinetic parameters of this laccase were determined for both substrates (FA, EF), indicating a higher substrate affinity for ethyl ferulate. Additionally, enzymatic oxidation led to the synthesis of a FA-major product, exhibiting a molecular mass of 386 g/mol and a EF-major product with a molecular mass of 442 g/mol. Structural analyses by mass spectrometry allowed the identification of dimeric derivatives. The optical properties of the oxidation products showed the increase of red and yellow colours, with FA-products compared to EF-products. Additionally, enzymatic oxidation led to a decrease of antioxidant and cytotoxic activities compared to initial substrates. Consequently, this enzymatic procedure in aqueous medium could provide new compounds presenting optical, antioxidant and cytotoxic interest. (C) 2013 Elsevier Ltd. All rights reserved.