luteolin-3'-O-α-D-glucopyranoside | 5154-41-6

• 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: luteolin-3'-O-α-D-glucopyranoside
• 英文别名: dracocephaloside；3'-O-Glucosylluteolin；5,7-dihydroxy-2-[4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 5154-41-6
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: VNTMXJLNIJFLIF-RQXATKFSSA-N

物化性质

• 熔点：
  243-245 °C
• 沸点：
  812.4±65.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  木犀草素 、 蔗糖 在 二乙二醇二甲醚 、 dextransucrase B-512F 作用下， 以 acetate buffer 为溶剂， 反应 7.0h， 生成 luteolin 4-O-α-D-glucopyranoside 、 luteolin-3'-O-α-D-glucopyranoside
  参考文献：
  名称：

  在水-有机溶剂中通过受体反应合成肠膜十二碳酸葡糖苷酶。

  摘要：

  木犀草素的酶促葡萄糖基化尝试使用两种葡聚糖蔗糖：来自肠膜间叶隐球菌NRRL B-512F的右旋糖核酸酶和来自肠系膜劳森氏菌NRRL B-23192的交替糖蔗糖酶。反应在水性有机溶剂中进行以提高木犀草素的溶解度。在葡聚糖乙酸酯缓冲液（70％）/双（2-甲氧基乙基）醚（30％）的混合物中，由葡聚糖转化酶催化的肠膜肠球菌NRRL B-512F催化反应24小时后，摩尔转化率为44％。通过核磁共振（NMR）光谱表征了两种产物：木犀草素-3'-O-α-d-吡喃葡萄糖苷和木犀草素-4'-O-α-d-吡喃葡萄糖苷。在来自肠膜曼森特罗氏菌NRRL B-23192的交替糖蔗糖酶的存在下，获得了三种另外的产物，其木犀草素转化率为8％。

  DOI：

  10.1016/j.carres.2006.02.008

文献信息

• 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。
• 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。
• Phenolic compounds with cosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP2027279B1

  公开（公告）日：2012-04-18
• WATER SOLUBLE AND ACTIVABLE PHENOLICS DERIVATIVES WITH DERMOCOSMETIC AND THERAPEUTIC APPLICATIONS AND PROCESS FOR PREPARING SAID DERIVATIVES
  申请人：Libragen

  公开号：EP2027279A2

  公开（公告）日：2009-02-25
• NOUVEAUX FLAVONOÏDES O-ALPHA-GLUCOSYLÉS SUR LE CYCLE B, PROCÉDÉ D'OBTENTION ET UTILISATIONS
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：EP3122890A1

  公开（公告）日：2017-02-01