luteolin 4-O-α-D-glucopyranoside

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

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

反应信息

• 作为产物：
  描述：

  木犀草素 、 蔗糖 在 recombinant Deinococcus geothermalis amylosucrase 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 luteolin 4-O-α-D-glucopyranoside
  参考文献：
  名称：

  地热球菌淀粉糖酶经区域选择性转糖基化酶促合成α-黄酮糖苷

  摘要：

  α-黄酮苷具有在制药，化妆品和食品工业中应用的有益特性。然而，它们的化学合成通常受到底物的低效率或稀缺性的限制。在这项研究中，α-黄酮葡萄糖苷是由地热球菌的淀粉酶酶促合成的。（DGAS），分别使用蔗糖和各种黄酮作为葡萄糖基单元和受体的供体。在9种黄酮类物质（芹菜素，chrysin，6,7-二羟基黄酮，高orientinin，7-羟基黄酮，异氟醚草酮，木犀草素，木犀草素3'，7-二葡糖苷和Orientin）中，木犀草素是使用DGAS进行转糖基化反应中最有效的受体。使用2 U DGAS在50 mM Tris-HCl缓冲液（pH 7）中于37°C放置24 h，木犀草素葡萄糖苷的最高产量为86％，供体与受体分子的摩尔比为7：1。合成的木犀草素葡糖苷被鉴定为木犀草素-4'- O -α-D-吡喃葡萄糖苷，其葡萄糖分子通过α-糖苷键与木犀草素B环的C-4'位置相连，由1 H确定和13C核磁共振。该结果清

  DOI：

  10.1371/journal.pone.0207466

文献信息

• Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents
  作者：Anne Bertrand、Sandrine Morel、François Lefoulon、Yves Rolland、Pierre Monsan、Magali Remaud-Simeon

  DOI：10.1016/j.carres.2006.02.008

  日期：2006.5

  attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate buffer (70%)/bis(2-methoxyethyl)

  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％。
• Extending the Structural Diversity of α-Flavonoid Glycosides with Engineered Glucansucrases
  作者：Yannick Malbert、Sandra Pizzut-Serin、Stéphane Massou、Emmanuelle Cambon、Sandrine Laguerre、Pierre Monsan、François Lefoulon、Sandrine Morel、Isabelle André、Magali Remaud-Simeon

  DOI：10.1002/cctc.201402144

  日期：2014.8

  Flavonoids constitute an important class of bioactive molecules, the physicochemical properties of which can be modulated by glucosylation. A structurally guided approach has been used to isolate glucansucrases modified in their acceptor‐binding site and specialized for luteolin glucosylation. Of a small‐size library, we isolate mutants showing up to an 8‐fold increase in flavonoid conversion rate

  类黄酮构成一类重要的生物活性分子，其物理化学性质可通过糖基化来调节。一种结构指导的方法已被用于分离在其受体结合位点修饰并专门用于木犀草素葡萄糖基化的葡聚糖。在一个小型文库中，我们分离出的突变体的类黄酮转化率比亲本酶高出8倍。已经获得了以前从未描述过的二葡萄糖基和三葡萄糖基木犀草素衍生物。它们的水溶性分别增加了282和17 708倍，并且通过糖基化反应可防止氧化。分子对接使您能够洞悉最佳突变体的产品特异性。
• 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