isorhamnetin 3-glucoside | 5041-82-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: isorhamnetin 3-glucoside
• 英文别名: isorhamnetin-3-O-β-D-glucopyranoside；isorhamnetin-3-O-β-glucoside；isorhamnetin-3-O-glucopyranoside；isorhamnetin-3-O-glucopyronoside；isorhamnetin 3-O-D-glucoside；isorhamnetin-3-O-D-glucoside；5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 5041-82-7；6743-92-6；50306-07-5
• 化学式: C₂₂H₂₂O₁₂
• 分子量: 478.409
• InChiKey: CQLRUIIRRZYHHS-YOICORKUSA-N

物化性质

• 熔点：
  155-160°C
• 沸点：
  834.4±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：250 mg/mL（522.58 mM；需要超声波）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• 海关编码：
  29389090
• 储存条件：
  2-8°C

制备方法与用途

生物活性的isorhamnetin-3-O-glucoside 是一种广泛存在于蔬菜和水稻中的天然化合物，经消化后可在肠道菌群中代谢。其化学性质表现为黄色粉末，易溶于氯仿，较难溶于乙醇、丙酮和乙醚，而不溶于石油醚和水，该化合物来源于蒲黄。

用途方面，isorhamnetin-3-O-glucoside 可用于含量测定、鉴定以及药理实验等。此外，其具有显著的降血脂作用。

反应信息

• 作为反应物：
  描述：

  isorhamnetin 3-glucoside 在 盐酸 、 水 作用下， 反应 1.0h， 生成 D-葡萄糖 、 异鼠李素
  参考文献：
  名称：

  Flavonoids of Smyrnium olusatrum from Algeria

  摘要：

  DOI：

  10.1007/s10600-011-0069-0
• 作为产物：
  描述：

  quercetin-3-O-glucoside 在 甲酸 、 1,3-双((三羟甲基)甲基氨基)丙烷 、 Vitis vinifera flavonol and anthocyanin O-methyltransferase 作用下， 以 水 为溶剂， 生成 isorhamnetin 3-glucoside
  参考文献：
  名称：

  Characterization of a Vitis vinifera cv. Cabernet Sauvignon 3′,5′-O-methyltransferase showing strong preference for anthocyanins and glycosylated flavonols

  摘要：

  At ripening initiation in red grapevine (Vitis vinifera) berries, the exocarp turns color from green to red and then to purple due to the accumulation and extent of methylation of anthocyanins. The accumulation of transcripts encoding an O-methyltransferase was recently shown to be closely correlated with the onset of ripening and the degree of blue/purple pigmentation in grapevine berries; however, the biochemical function of this gene has remained uncharacterized. In this study, an O-methyltransferase cDNA that showed a distinct expression pattern when compared to closely related sequences was expressed in Escherichia coli and enzyme assays were carried out with a broad array of anthocyanin and other flavonoid substrates. We demonstrate that this enzyme carries out 3',5'-O-methylation of anthocyanins and flavonol compounds in vitro, which are known to be present in grape berries, with a preference for glycosylated substrates. The highest relative specific activity for the enzyme was found with delphinidin 3-O-glucoside as substrate. The enzyme is not able to methylate flavan type skeletons with chiral centers, such as either catechins or dihydroquercetin. The enzyme showed negligible specific activity for caffeoyl-CoA, compared to flavonol and anthocyanin substrates. Phylogenetic analysis of the O-methyltransferase suggests that it may be a member of a distinct subclass of Type 2 bivalent metal-dependent S-adenosylmethionine O-methyltransferases. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.05.027

文献信息

• Structural aspects of anthocyanin-flavonoid complex formation and its role in plant color
  作者：Lao-Jer Chen、Geza Hrazdina

  DOI：10.1016/0031-9422(81)85111-4

  日期：1981.1

  the complex formation. The presence of a 3-hydroxyl group in the flavonoid molecule has little effect on the complex-forming ability. The nature of the sugar substituent of the complex-forming flavonoid compound has no influence on the reaction. The 5-hydroxyl group of flavonoids is strongly bound by intramolecular hydrogen bond to the 4-carbonyl and does not participate in the complex formation. The

  摘要 黄酮类化合物与花青素形成复合物，导致吸光度增加和后者可见光吸收最大值的红移，主要是基于花青素脱水碱的羰基与花青素的芳香羟基之间形成氢键。形成复合物的类黄酮。类黄酮分子中的羟基数量越多，复合物的形成就越强。类黄酮分子中3-羟基的存在对复合物形成能力影响不大。形成络合物的黄酮类化合物的糖取代基的性质对反应没有影响。黄酮类化合物的 5-羟基通过分子内氢键与 4-羰基强结合，不参与复合物的形成。类黄酮分子中最重要的羟基是位于 7 位的羟基。杂环中C2C3的不饱和度是形成配合物的重要因素。仅类黄酮系统中的芳香羟基不能解释所有的复合物形成能力，表明静电力和构型或空间效应的额外参与。
• Highly Promiscuous Flavonoid 3-<i>O</i>-Glycosyltransferase from <i>Scutellaria baicalensis</i>
  作者：Zilong Wang、Shuang Wang、Zheng Xu、Mingwei Li、Kuan Chen、Yaqun Zhang、Zhimin Hu、Meng Zhang、Zhiyong Zhang、Xue Qiao、Min Ye

  DOI：10.1021/acs.orglett.9b00524

  日期：2019.4.5

  from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could

  从黄cut中发现了一种高度区域特异性和供体混杂的3- O-糖基转移酶Sb3GT1（UGT78B4）。Sb3GT1可以接受五个糖供体（UDP-Glc / -Gal / -GlcNAc / -Xyl / -Ara）催化17种黄酮醇的3- O-糖基化，转化率可以> 98％。通过按比例放大的酶催化作用获得了五种新的糖苷。分子建模和定点诱变表明，G15和P187是供体滥交的关键催化残基。Sb3GT1可能是增加类黄酮3- O-糖苷结构多样性的有前途的催化剂。
• Synthesis of flavonol 3-O-glycoside by UGT78D1
  作者：Guangxiang Ren、Jingli Hou、Qinghong Fang、Hong Sun、Xiaoyan Liu、Lianwen Zhang、Peng George Wang

  DOI：10.1007/s10719-012-9410-5

  日期：2012.8

  notoriously complicated that flavonols such as quercetin, kaempferol and myricetin, are glucosylated regioselectively at the specific position by chemical method. Compared to the chemical method, enzymatic synthesis present several advantages, such as mild reaction condition, high stereo or region selectivity, no protection/deprotection and high yield. UGT78D1 is a flavonol-specific glycosyltransferase, responsible

  糖基化是各种黄酮醇结构修饰的重要方法，与相应的苷元相比，糖苷具有更高的溶解度、稳定性和生物利用度。从生理学的角度来看，植物黄酮的糖基化具有重要意义和意义。然而，众所周知，槲皮素、山奈酚和杨梅素等黄酮醇通过化学方法在特定位置被区域选择性地糖基化是非常复杂的。与化学方法相比，酶法合成具有反应条件温和、立体或区域选择性高、无保护/脱保护和高收率等优点。UGT78D1 是一种黄酮醇特异性糖基转移酶，负责在体外将鼠李糖或葡萄糖转移到 3-OH 位置. 在这项研究中，使用 UDP-葡萄糖作为体外供体核苷测试了 UGT78D1 对 28 种黄酮类受体的活性，发现槲皮素、杨梅素、山奈酚、漆黄素和异鼠李素这 5 种受体在 3-OH 位被糖基化。在此，小规模的 3-O-葡萄糖基化槲皮素、山奈酚和杨梅素由 UGT78D1 合成，其化学结构经1 H 和13 C 核磁共振（NMR）和高分辨率质谱（HRMS）证实。
• Functional characterization of a UDP-glucose:flavonoid 3-O-glucosyltransferase from the seed coat of black soybean (Glycine max (L.) Merr.)
  作者：Nik Kovinich、Ammar Saleem、John T. Arnason、Brian Miki

  DOI：10.1016/j.phytochem.2010.05.009

  日期：2010.8

  The seed coats of black soybean (Glycine max (L.) Merr.) accumulate red (cyanidin-), blue (delphinidin-), purple (petunidin-), and orange (pelargonidin-based) anthocyanins almost exclusively as 3-O-glucosides; however, the responsible enzyme has not been identified. In this study, the full-length cDNA which encodes the enzyme that catalyzes the final step in anthocyanin biosynthesis, namely UDP-glucose:flavonoid 3-O-glucosyltransferase (UGT78K1), was isolated from the seed coat tissue of black soybean using rapid amplification of cDNA ends (RACE). Of the 28 flavonoid substrates tested, the purified recombinant protein glucosylated only anthocyanidins and flavonols, and demonstrated strict 3-OH regiospecificity. Galactose could also be transferred with relatively low activity to the 3-position of cyanidin or delphinidin in vitro. These findings are consistent with previous reports of mainly 3-O-glucosylated and minor amounts of 3-O-galactosylated anthocyanins in the seed coat of black soybean. The recombinant enzyme exhibited pronounced substrate inhibition by cyanidin at 100 mu M acceptor concentration. Transfer of UGT78K1 into the Arabidopsis T-DNA mutant (ugt78d2) deficient in anthocyanidin and flavonol 3-O-glucosyltransferase activity, restored the accumulation of anthocyanins and flavonols, suggesting the in vivo function of the enzyme as a flavonoid 3-O-glucosyltransferase. Genomic and phylogenetic analyses suggest the existence of three additional soybean sequences with high similarity to UGT78K1. RT-PCR confirmed the co-expression of one of these genes (Glyma08g07130) with UGT78K1 in the seed coat of black soybean, suggesting possible functional redundancies in anthocyanin biosynthesis in this tissue. (C) 2010 Elsevier Ltd. All rights reserved.
• Flavonoids of Smyrnium olusatrum from Algeria
  作者：R. Bencheraiet、M. Jay、A. Kabouche、Z. Kabouche

  DOI：10.1007/s10600-011-0069-0

  日期：2011.11