(+)-catechin 3'-O-β-D-glucopyranoside | 105330-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (+)-catechin 3'-O-β-D-glucopyranoside
• 英文别名: (+)-catechin 3-O-β-D-glucopyranoside；catechin 3'-O-β-D-glucoside；(+)-Catechin-3a(2)-O-I(2)-D-glucoside；(2R,3S)-2-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,4-dihydro-2H-chromene-3,5,7-triol
• CAS: 105330-51-6
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: ZZTOVZGFHZQEAT-FBEISHDNSA-N

物化性质

• 沸点：
  824.0±65.0 °C(Predicted)
• 密度：
  1.670±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+)-catechin 3'-O-β-D-glucopyranoside 在 hesperidinase 作用下， 以 水 为溶剂， 反应 2.0h， 生成 葡萄糖 、 儿茶提取物
  参考文献：
  名称：

  Tannins and related compounds. XLV Rhubarb. 5 Isolation and characterization of flavan-3-ol and procyanidin glucosides.

  摘要：

  通过对优质商品大黄（Choukichio：？(+)-catechin 5-O-β-D-glucopyranoside (1)、(+)-catechin 7-O-β-D-glucopyranoside (2)、procyanidin B-2 8-C-β-D-glucopyranoside (3) 和 procyanidin B-2 6-C-β-D-glucopyranoside (4)。根据化学和光谱证据，前两种化合物被定性为(+)-儿茶素 3'-O-β-D-Glucopyranoside (5)、(+)-catechin 4'-O-β-D-glucopyranoside (6)、(+)-catechin 7, 3'-di-O-β-D-glucopyranoside (7)、(+)-catechin 5, 3'-di-O-β-D-glucopyranoside (8)、(+)-catechin 3'、4'-二-O-β-D-吡喃葡萄糖苷 (9)，(+)-儿茶素 5，4'-二-O-β-D-吡喃葡萄糖苷 (10)，(+)-儿茶素 8-C-β-D-吡喃葡萄糖苷 (11)，(+)-儿茶素 6-C-β-D-吡喃葡萄糖苷 (12)、原花青素 B-3 7-O-β-D-Glucopyranoside (13)、原花青素 B-1 8-C-β-D-Glucopyranoside (14) 和原花青素 B-1 6-C-β-D-Glucopyranoside (15)。

  DOI：

  10.1248/cpb.34.3208
• 作为产物：
  描述：

  (+)-3-O-acetylcatechin 3'-O-β-D-glucoside 在 单宁酶 作用下， 以67%的产率得到(+)-catechin 3'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Catechin Glucosides: Occurrence, Synthesis, and Stability

  摘要：

  Catechins are flavonoids with suggested health benefits, but are unstable during storage, processing and, after ingestion, during gut transit. We hypothesized that catechin glucosides, which occur in various plants, could be more stable than unsubstituted catechin, and additionally be deglucosylated in the gut and so act to deliver catechin in a form able to be absorbed. (+)-Catechin O-glucosides from various sources have been used in the course of this investigation. (+)-Catechin 3'-O-beta-D-glucopyranoside (C3'G), (+)-catechin 5-O-beta-D-glucopyranoside (C5G), and (+)-catechin 3-O-beta-D-glucopyranoside (C3G) were chemically synthesized. (+)-Catechin 4'-O-beta-D-glucopyranoside (C4'G) and (+)-catechin 7-O-beta-D-glucopyranoside (C7G) were prepared enzymically using preparations from lentil and barley. In general, but with some exceptions, the (+)-catechin glucosides were more stable between pH 4 and 8 than (+)-catechin, with C3'G exhibiting greatest stability. The intestinal metabolism of (+)-catechin and all (+)-catechin glucosides in the gut was determined by perfusion of rat intestine in vivo. C3'G and C5G were extensively deglycosylated in the gut, and C3'G showed greatest apparent "absorption" as calculated by the difference between effluent and influent. The results show the potential of catechin glucosides, especially C3'G, as more stable prescursors of catechin.

  DOI：

  10.1021/jf9034095

文献信息

• Potentillanin, a biflavanoid and a procyanidin glycoside from Potentilla viscosa
  作者：Ben Zhang、Gen-ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/0031-9422(88)80042-6

  日期：1988.1

  Abstract An investigation of the root of Potentilla viscosa has led to the isolation and characterization of a novel 6′,8-linked bisflavanoid, potentillanin and a procyanidin B-3 3′- O -glucoside. Furthermore, the occurrence of (+)-catechin and its 3- O -glucoside, procyanidins B-3 and C-2 and afzelechin-(4α→8)-catechin was demonstrated.

  摘要 对 Potentilla viscosa 根的研究导致了一种新型 6',8-连接的双黄酮、potentillanin 和原花青素 B-3 3'-O-葡萄糖苷的分离和表征。此外，还证明了 (+)-儿茶素及其 3-O-葡萄糖苷、原花青素 B-3 和 C-2 以及 afzelechin-(4α→8)-儿茶素的存在。
• METHOD FOR GLYCOSYLATION OF FLAVONOID COMPOUNDS
  申请人：Ochiai Misa

  公开号：US20100256345A1

  公开（公告）日：2010-10-07

  The present invention provides a method for preparing a glycoside of a flavonoid compound, which comprises the step of treating flavonoid and a glycosyl donor with an enzymatic agent having glycosylation activity and being derived from the genus Trichoderma (preferably Trichoderma viride or Trichoderma reesei ). Such a flavonoid compound includes a catechin compound or a methylated derivative thereof, and the glycosyl donor includes a carbohydrate containing a maltotriose residue (preferably maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, dextrin, γ-cyclodextrin or soluble starch). Glycosides obtained by the present invention have higher water solubility, improved taste, and increased stability. The present invention also provides novel glycosides of catechin compounds, which are obtained by the method of the present invention.

  本发明提供了一种制备黄酮类化合物的糖苷的方法，其中包括用具有糖基化活性并来自Trichoderma属（优选为Trichoderma viride或Trichoderma reesei）的酶制剂处理黄酮类化合物和糖基供体。这样的黄酮类化合物包括儿茶素化合物或其甲基化衍生物，糖基供体包括含有麦芽三糖残基的碳水化合物（优选为麦芽三糖、麦芽四糖、麦芽五糖、麦芽六糖、麦芽七糖、糊精或可溶性淀粉）。通过本发明获得的糖苷具有更高的水溶性、改善的口感和增加的稳定性。本发明还提供了通过本发明的方法获得的儿茶素化合物的新型糖苷。
• NOVEL GLYCOSYLTRANSFERASES AND POLYNUCLEOTIDES ENCODING THE SAME
  申请人：Ochiai Misa

  公开号：US20100273154A1

  公开（公告）日：2010-10-28

  The present invention provides novel glycosyltransferase proteins produced by ascomycetous filamentous fungi (preferably species belonging to the genus Trichoderma , more preferably Trichoderma viride ), as well as genes encoding the same. Among novel enzyme proteins provided by the present invention, particularly preferred is an enzyme protein obtained from the culture supernatant of Trichoderma viride strain IAM5141. The novel enzymes of the present invention allow glycosylation of flavonoid compounds to thereby improve their water solubility.

  本发明提供了由子囊菌类丝状真菌（优选属于木霉属，更优选为绿木霉属）产生的新型糖基转移酶蛋白，以及编码其的基因。在本发明提供的新型酶蛋白中，特别优选的是从绿木霉IAM5141菌株的培养上清液中获得的酶蛋白。本发明的新型酶可使黄酮类化合物糖基化，从而提高它们的水溶性。
• METHOD FOR GLYCOSYLATION OF FLAVONOID
  申请人：Suntory Holdings Limited

  公开号：EP2128265A1

  公开（公告）日：2009-12-02

  The present invention provides a method for preparing a glycoside of a flavonoid compound, which comprises the step of treating flavonoid and a glycosyl donor with an enzymatic agent having glycosylation activity and being derived from the genus Trichoderma (preferably Trichoderma viride or Trichoderma reesei). Such a flavonoid compound includes a catechin compound or a methylated derivative thereof, and the glycosyl donor includes a carbohydrate containing a maltotriose residue (preferably maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, dextrin, γ-cyclodextrin or soluble starch). Glycosides obtained by the present invention have higher water solubility, improved taste, and increased stability. The present invention also provides novel glycosides of catechin compounds, which are obtained by the method of the present invention.

  本发明提供了一种制备黄酮类化合物苷的方法，该方法包括用具有糖基化活性的酶制剂处理黄酮类化合物和糖基供体的步骤，该酶制剂来源于毛霉属（最好是病毒毛霉或瑞氏毛霉）。这种类黄酮化合物包括儿茶素化合物或其甲基化衍生物，糖基供体包括含有麦芽三糖残基的碳水化合物（最好是麦芽三糖、麦芽四糖、麦芽五糖、麦芽六糖、麦芽七糖、糊精、γ-环糊精或可溶性淀粉）。通过本发明获得的糖苷具有更高的水溶性、更好的口感和更高的稳定性。本发明还提供了新型儿茶素化合物糖苷，它们是通过本发明的方法获得的。
• NOVEL GLYCOSYLTRANSFERASE AND POLYNUCLEOTIDE ENCODING THE SAME
  申请人：Suntory Holdings Limited

  公开号：EP2130914A1

  公开（公告）日：2009-12-09

  The present invention provides novel glycosyltransferase proteins produced by ascomycetous filamentous fungi (preferably species belonging to the genus Trichoderma, more preferably Trichoderma viride), as well as genes encoding the same. Among novel enzyme proteins provided by the present invention, particularly preferred is an enzyme protein obtained from the culture supernatant of Trichoderma viride strain IAM5141. The novel enzymes of the present invention allow glycosylation of flavonoid compounds to thereby improve their water solubility.

  本发明提供由子囊丝状真菌（最好是属于毛霉属的菌种，更优选病毒毛霉）产生的新型糖基转移酶蛋白，以及编码这些蛋白的基因。在本发明提供的新型酶蛋白中，特别优选的是从病毒毛霉菌株 IAM5141 的培养上清液中获得的酶蛋白。本发明的新型酶可以对黄酮类化合物进行糖基化，从而提高其水溶性。