(2R,3S)-catechin 7-O-β-D-glucopyranoside | 65597-47-9

• 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: (2R,3S)-catechin 7-O-β-D-glucopyranoside
• 英文别名: (+)-catechin-7-O-α-L-arabinofuranoside；(+)-catechin 7-O-β-D-glucopyranoside；(+)-catechin-7-O-β-D-glucopyranoside；(+)-7-β-D-glucopyranosyloxycatechin；catechin 5-O-β-D-glucopyranoside；catechin 7-O-β-D-glucopyranoside；Catechin 7-O-beta-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 65597-47-9
• 化学式: C₂₁H₂₄O₁₁
• 分子量: 452.415
• InChiKey: VLFIBROLAXKPQK-DPRDWZRASA-N

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：

  (2R,3S)-catechin 7-O-β-D-glucopyranoside 在 almond emulsin Wako "standard" 作用下， 反应 24.0h， 以4.20 mg的产率得到儿茶提取物
  参考文献：
  名称：

  Saponin and sapogenol. XXXI. Chemical constituents of the seeds of Vigna angularis (Willd.) Ohwi et Ohashi. (1). Triterpenoidal sapogenols and 3-furanmethanol .BETA.-D-glucopyranoside.

  摘要：

  从赤豆（Vigna angularis (Willd.) Ohwi et Ohashi 豆科）种子中分离得到3-呋喃甲醇β-D-吡喃葡糖苷（1）和（+）-儿茶素7-O-β-D-吡喃葡糖苷（3），并确定了它们的结构。从赤豆中还分离得到了总赤豆皂苷混合物。通过酶解、酸解和光化学降解，从总赤豆皂苷中分离出了4种真正的皂苷元，其中包括3种已知的皂苷元：染料木苷元（7）、大豆苷元B（8）、皂土酸（9）和一个新的皂苷元，命名为赤豆皂苷元（10），并阐明了其结构。作为总赤豆皂苷酸解释放的假皂苷元之一，分离得到了一个新的皂苷元，命名为无水染料木苷元（5），并阐明了其结构。

  DOI：

  10.1248/cpb.31.664
• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-2-(((2R,3R)-4-(benzylthio)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxychroman-7-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 在 Raney-nickel (W-4) 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以1.5 mg的产率得到(2R,3S)-catechin 7-O-β-D-glucopyranoside
  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

文献信息

• New flavanol O-glycosides in grape and wine
  作者：Marie Zerbib、Jean-Paul Mazauric、Emmanuelle Meudec、Christine Le Guernevé、Alexander Lepak、Bernd Nidetzky、Véronique Cheynier、Nancy Terrier、Cédric Saucier

  DOI：10.1016/j.foodchem.2018.06.019

  日期：2018.11

  The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific

  在葡萄和葡萄酒中研究了黄烷-3-醇单己糖单体和二聚体的存在。从葡萄种子和果皮（西拉，梅洛和赤霞珠）中提取多酚提取物，并在三个不同的发育阶段进行采样。还研究了不同的葡萄酒（坦纳特，阿利坎特，西拉，梅洛和歌海娜）。通过UPLC-ESI-IT-MS分析获得的不同样品。通过使用具有特定m / z值的目标分子离子检测到对应于flavan-3-ol己糖苷的特定分子离子：( epi）儿茶素己糖苷为451 ，原花青素二聚体己糖为739。4'- O - β-葡萄糖基-（+）-儿茶素和7- O - β通过使用来自苹果的葡糖基转移酶UGT71A15获得-葡糖基-（+）-儿茶素，并且通过NMR确定它们的结构。这些糖基化的单体和二聚体在所有分析过的葡萄籽和不同阶段的几种皮提取物中以及不同品种的葡萄酒中都得到了鉴定。
• 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。
• Water soluble phenolics derivatives with dermocosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP1867729A1

  公开（公告）日：2007-12-19

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives including (i) protocatechuic acid and its derivatives, (ii) 3,4-dihydroxycinnamic acid with its transisomer or caffeic acid and its derivatives, especially hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its derivatives, especially esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid familly such as taxifolin and fustin (dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhytmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivatives objects of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compound upon time during their usage or by an α-glucosidase (EC 3.2.1.20).

  本发明涉及用酶缩合法制备酚类衍生物，所选酚类包括焦儿茶酚或其衍生物，包括(i) 原儿茶酸及其衍生物，(ii) 3,4-二羟基肉桂酸与其反式异构体或咖啡酸及其衍生物，特别是氢咖啡酸、(iii) 二羟基苯甘醇，以及 (iv) 黄酮家族成员，如 taxifolin 和 fustin（二氢黄酮醇）、fisetin（一种黄酮醇）、eriodictyol（一种黄酮），以及蔗糖的葡萄糖分子。上述酚类衍生物的生产是通过一种葡糖基转移酶（EC 2.4.1.5）实现的，该酶是从白色念珠菌（Leuconostoc species）的培养物中获得的，尤其是从中肠白色念珠菌（Leuconostoc mesenteroides NRRL B-512F）的培养物中获得的。抗高血压、抗缺血、抗心律失常、抗血栓、降胆固醇、抗脂过氧化、保肝、抗炎、抗癌、抗突变、抗肿瘤、抗血栓和血管扩张配方，或任何其他应用领域。此外，本发明的葡糖基化酚类衍生物可被人体天然微生物水解，从而在使用过程中或通过α-葡萄糖苷酶（EC 3.2.1.20）释放出酚类化合物的活性部分。
• 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。
• Flavonoids O-A-glucosylated on the B cycle, method for the production thereof and uses
  申请人：Institut National de la Recherche Agronomique

  公开号：US10647739B2

  公开（公告）日：2020-05-12

  The invention relates to a method for producing derivatives of O-α-glucosylated flavonoid, comprising at least one step of incubating a glucansucrase with a flavonoid and at least one sucrose, the flavonoid being a flavonoid which is monohydroxylated or hydroxylated in a non-vicinal manner on the B cycle. The invention also relates to novel O-α-glucosylated flavonoid derivatives, and to the use thereof.

  本发明涉及一种生产O-α-葡糖基化类黄酮衍生物的方法，该方法至少包括一个步骤，即将葡聚糖琥珀酸酶与类黄酮和至少一种蔗糖孵育，类黄酮是一种在B周期上以非乙烯基方式单羟基化或羟基化的类黄酮。本发明还涉及新型 O-α-葡萄糖基化黄酮衍生物及其用途。