似梨木双黄酮-7-O-B-D-吡喃葡萄糖苷 | 50276-96-5

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 似梨木双黄酮-7-O-B-D-吡喃葡萄糖苷
• 中文别名: 金银花双黄酮；似梨木双黄酮-7-O-Β-D-吡喃葡萄糖苷；似梨木双黄酮-7-O-Beta-D-吡喃葡萄糖苷
• 英文名称: Ochnaflavone
• 英文别名: 2-[4-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]phenyl]-5,7-dihydroxychromen-4-one
• CAS: 50276-96-5
• 化学式: C₃₀H₁₈O₁₀
• 分子量: 538.467
• InChiKey: NNPGECDACGBKDH-UHFFFAOYSA-N

物化性质

• 沸点：
  832.1±65.0 °C(Predicted)
• 密度：
  1.622

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 碘 、 三溴化硼 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 、 甲苯 为溶剂， 反应 40.0h， 生成 似梨木双黄酮-7-O-B-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Ochnaflavone 的合成及其对 PGE2 生成的抑制作用

  摘要：

  Ochnaflavone 是一种天然存在的双黄酮类化合物，由通过 COC 键连接的两个芹菜素（5,7,4'-三羟基黄酮）单元组成，首先合成并评估了其对生产的抑制活性。通过改性乌尔曼二芳基醚形成作为关键步骤完成全合成。在不同的反应条件下探索了 4'-卤代黄酮和 3'-羟基-5,7,4'-三甲氧基黄酮的偶联反应。4'-氟-5,7-二甲氧基黄酮 (2c) 和 3'-羟基-5,7,4'-三甲氧基黄酮 (2d) 在 N,N-二甲基乙酰胺中的反应以 58% 的收率得到偶联化合物 3。合成的 ochnaflavone 强烈抑制 LPS 激活的 RAW 264.7 细胞中 PGE2 的产生 ()，这是由于 COX-2 的表达减少。相反，汉黄芩素的抑制机制与茯苓黄酮有些不同，虽然汉黄芩素是一种天然存在的抗炎黄酮类化合物，具有很强的抑制活性，似乎是对COX-2酶的抑制。我们简洁的 ochnaflavone 全

  DOI：

  10.5012/bkcs.2014.35.11.3219

文献信息

• Synthesis of C-3 Coupled Biflavonoids and C-3 Coupled Biflavonoid Analogues
  申请人：Van Der Westhuizen Jan Hendrik

  公开号：US20120289715A1

  公开（公告）日：2012-11-15

  The invention relates to methods for the preparation of an optically inactive and optically active compounds which are selected from the group consisting of C-3 coupled biflavonoids and C-3 coupled biflavonoid analogues from a starting material or intermediate which are respectively selected from the group consisting of optically inactive or optically active flavan-3-ols and optically active flavan-3-ones, the method comprising the steps of (a) providing an optically inactive or active compound having a flavan-3-ol structure or a compound which is a flavan-3-one, (b) if a compound having a flavan-3-ol structure with a hydroxy group on the C-3 carbon is selected as starting material, converting the hydroxy group on the C-3 carbon of the compound having the flavan-3-ol structure to an oxo group to form a flavan-3-one of that compound, (c) providing a compound having a nucleophilic aromatic moiety, which compound is selected from the group of compounds having a nucleophilic aromatic moiety and which have flavonoid base structures and compounds having a nucleophilic aromatic moiety and which do not have a flavonoid base structure, (d) contacting the flavan-3-one provided by step (a) or obtained by step (b) with the compound containing the nucleophilic aromatic moiety in the presence of a Lewis acid; (e) forming a first intermediate compound wherein the oxo group on the C-3 carbon is converted to a hydroxy group by virtue of nucleophilic addition when the compound containing the nucleophilic aromatic moiety is contacted to the C-3 carbon of the flavan-3-one, (f) subjecting the first intermediate compound to dehydration so as to introduce a double bond between the C-3 carbon and C-4 carbon of the intermediate compound with the concomitant removal of the hydroxy group from the C-3 carbon to form an optically active flavene compound which is substituted by the nucleophilic aromatic moiety on the C-3 carbon, (g) optionally subjecting the resultant flavene compound to hydroboration-oxidation hydration thereby removing said double bond between the C-3 carbon and the C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon to form a second intermediate compound, (h) further optionally oxidizing the second intermediate compound of step (g) thereby converting the hydroxy group at the said C-4 carbon to an oxo group, thereby forming a biflavonoid or biflavonoid analogue which is substituted by the selected nucleophilic aromatic moiety on the C-3 carbon, (i) further optionally, and alternatively to step (h), subjecting the resultant flavene compound of step (f) to OsO 4 dihydroxylation thereby removing said double bond between the C-3 carbon and C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon and a hydroxy group at the C-3 carbon to form a third intermediate compound, and (j) subjecting the third intermediate compound to dehydration whereby the hydroxy group at the C-3 carbon is removed and a double bond is introduced between the C-3 carbon and C-4 carbon thereby forming an enol product and allowing such enol product to rearrange spontaneously to form a biflavonoid or biflavonoid analogue having an oxo group at its C-4 carbon and which is substituted by the selected nucleophilic aromatic moiety on its C-3 carbon.

  该发明涉及一种从起始物质或中间体中选择的光学不活性和光学活性化合物的制备方法，所述化合物选自C-3偶联的双黄酮类化合物和C-3偶联的双黄酮类似物，所述起始物质或中间体分别选自光学不活性或光学活性的黄酮-3-醇和光学活性的黄酮-3-酮，所述方法包括以下步骤：(a)提供具有黄酮-3-醇结构或为黄酮-3-酮的化合物，该化合物是光学不活性或活性的；(b)如果选择具有C-3碳上羟基的黄酮-3-醇结构化合物作为起始物质，则将具有黄酮-3-醇结构的化合物的C-3碳上的羟基转化为羟基，形成该化合物的黄酮-3-酮；(c)提供具有亲核芳香基团的化合物，所述化合物选自具有亲核芳香基团的化合物和具有黄酮类基本结构的化合物以及具有亲核芳香基团的化合物和不具有黄酮类基本结构的化合物；(d)在存在Lewis酸的情况下，将步骤(a)提供或步骤(b)获得的黄酮-3-酮与含有亲核芳香基团的化合物接触；(e)形成第一中间化合物，其中通过亲核加成使含有亲核芳香基团的化合物与黄酮-3-酮的C-3碳接触时，C-3碳上的羟基转化为羟基；(f)将第一中间化合物脱水，以在中间化合物的C-3碳和C-4碳之间引入双键，并同时去除C-3碳上的羟基，形成由亲核芳香基团取代C-3碳上的光学活性黄烯化合物；(g)可选地将所得的黄烯化合物经过氢硼氧化水合反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳引入羟基，形成第二中间化合物；(h)可选地进一步氧化步骤(g)中的第二中间化合物，将C-4碳上的羟基转化为羟基，从而形成在C-3碳上由所选亲核芳香基团取代的双黄酮或双黄酮类似物；(i)可选地，作为步骤(h)的替代，将步骤(f)中的所得黄烯化合物经过OsO4二羟基化反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳和C-3碳引入羟基，形成第三中间化合物；(j)将第三中间化合物脱水，从而去除C-3碳上的羟基，并在C-3碳和C-4碳之间引入双键，从而形成烯醇产物，并使该烯醇产物自发重排，形成在其C-4碳上具有羟基的双黄酮或双黄酮类似物，并在其C-3碳上由所选亲核芳香基团取代。
• Total synthesis of ochnaflavone
  作者：Monica M Ndoile、Fanie R van Heerden

  DOI：10.3762/bjoc.9.152

  日期：——

  The first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

  对称双黄酮ochnaflavone的首个全合成已经完成，该化合物由apigenin和luteolin基团组成。同时，2,3,2''，3''-四氢ochnaflavone的四甲氧基醚也被合成。合成ochnaflavone的关键步骤是形成二芳基醚和环化合成链联二聚chalcone以组装两个黄酮核。已建立最佳的实验条件，以进行氧化环化形成ochnaflavone。
• US9155792B2
  申请人：——

  公开号：US9155792B2

  公开（公告）日：2015-10-13
• US9296717B2
  申请人：——

  公开号：US9296717B2

  公开（公告）日：2016-03-29
• [EN] ANTI-WRINKLE COMPOSITION FOR EXTERNAL APPLICATIONS TO THE SKIN CONTAINING BIFLAVONOID DERIVATIVES<br/>[FR] COMPOSITION ANTIRIDES POUR APPLICATION EXTERNE SUR LA PEAU, CONTENANT DES DÉRIVÉS DE BIFLAVONOÏDES
  申请人：AMOREPACIFIC CORP

  公开号：WO2008147022A1

  公开（公告）日：2008-12-04

  [EN] The present invention relates to a cosmetic composition for improving skin wrinkles, which contains biflavonoid derivatives as an active ingredient. The cosmetic composition containing the biflavonoid derivatives of the present invention not only is safe for application on the skin without side-effects but also improves wrinkles caused by UV through procollagen production and MMP-I inhibition.
  [FR] La présente invention concerne une composition cosmétique destinée à améliorer les rides cutanées, qui contient des dérivés de biflavonoïdes en tant qu'ingrédients actifs. La composition cosmétique contenant lesdits dérivés biflavonoïdes de la présente invention peut être appliquée en toute sécurité sur la peau sans provoquer d'effets secondaires. En outre, elle permet également d'améliorer l'état des rides provoquées par les UV, par le biais de la production de procollagène et de l'inhibition de MMP-I.