3,5-di-O-β-D-glucopyranoside of malvidin | 47863-30-9

• 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: 3,5-di-O-β-D-glucopyranoside of malvidin
• 英文别名: malvidin 3,5-di-O-β-D-glucopyranoside；malvidin 3-O-glucoside-5-O-glucoside；malvidin-3,5-O-bis-glucoside；malvidin 3,5-diglucoside；malvidin-3,5-diglucoside；malvin；(2S,3R,4S,5S,6R)-2-[7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 47863-30-9
• 化学式: C₂₉H₃₅O₁₇
• 分子量: 655.587
• InChiKey: CILLXFBAACIQNS-BTXJZROQSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -1.83
• 重原子数：
  46
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  259
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3,5-di-O-β-D-glucopyranoside of malvidin 在 氢气 作用下， 以 水 为溶剂， 生成 2-(4-Hydroxy-3,5-dimethoxy-phenyl)-3,5-bis-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-chromen-7-one
  参考文献：
  名称：

  Brouillard, Raymond; Lang, Jacques, Canadian Journal of Chemistry, 1990, vol. 68, # 5, p. 755 - 761

  摘要：

  DOI：
• 作为产物：
  描述：

  以 甲醇 、 phosphate buffer 为溶剂， 生成 3,5-di-O-β-D-glucopyranoside of malvidin
  参考文献：
  名称：

  Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation

  摘要：

  This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

  DOI：

  10.1021/jf071205v

文献信息

• Malonated anthocyanins in malvaceae: Malonylmalvin from Malva sylvestris
  作者：Kosaku Takeda、Shigeki Enoki、Jeffrey B. Harborne、John Eagles

  DOI：10.1016/0031-9422(89)80040-8

  日期：1989.1

  Abstract A new anthocyanin, malvidin 3-(6″-malonylglucoside)-5-glucoside has been characterized in both wild and cultivated forms of Malva sylvestris. Thus the classic source of the anthocyanin, malvin, actually contains the pigment in the flowers in malonated form. Malonated anthocyanins were also detected in Althaea rosea, Lavatera olbia and a Sphaeralcea sp. but they were not present in five other

  摘要 一种新的花青素，锦葵素 3-(6″-丙二酰葡萄糖苷)-5-葡萄糖苷已在野生和栽培的锦葵属植物中得到表征。因此，花青素的经典来源，马尔文，实际上在花中含有丙二酸形式的色素。在 Althaea rosea、Lavatera olbia 和 Sphaeralcea sp. 中也检测到丙二酸化花青素。但它们并不存在于该家族的其他五个物种中。
• Product
  申请人：——

  公开号：US20030091660A1

  公开（公告）日：2003-05-15

  An orally ingestible composition comprising a coated spray-dried material comprising at least four anthocyanins, at least one of which is a monosaccharide and at least one of which is a disaccharide and a process for its production.

  一种可口服的组合物，包含一种由至少四种花青素（其中至少一种是单糖，至少一种是双糖）组成的涂层喷雾干燥材料及其生产工艺。
• Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis
  作者：Fei He、Wei-Kai Chen、Ke-Ji Yu、Xiang-Nan Ji、Chang-Qing Duan、Malcolm J. Reeves、Jun Wang

  DOI：10.1016/j.phytochem.2015.06.023

  日期：2015.9

  Generally, red Vitis vinifera grapes only contain monoglucosidic anthocyanins, whereas most non-vinifera red grapes of the Vitis genus have both monoglucosidic and bis-glucosidic anthocyanins, the latter of which are believed to be more hydrophilic and more stable. Although previous studies have established the biosynthetic mechanism for formation of monoglucosidic anthocyanins, less attention has been paid to that of bis-glucosidic anthocyanins. In the present research, the full-length cDNA of UDP-glucose: anthocyanin 5-0-glucosyltransferase from Vitis amurensis Rupr. cv. 'Zuoshanyi' grape (Va5GT) was cloned. After acquisition and purification of recombinant Va5GT, its enzymatic parameters were systematically analyzed in vitro. Recombinant Va5GT used malvidin-3-O-glucoside as its optimum glycosidic acceptor when UDP-glucose was used as the glycosidic donor. Va5GT-GFP was found to be located in the cytoplasm by analyzing its subcellular localization with a laser-scanning confocal fluorescence microscope, and this result was coincident with its metabolic function of modifying anthocyanins in grape cells. Furthermore, the relationship between the transcriptional expression of Va5GT and the accumulation of anthocyanidin bis-glucosides during berry development suggested that Va5GT is a key enzyme in the biosynthesis of bis-glucosidic anthocyanins in V. amurensis grape berries. (C) 2015 Elsevier Ltd. All rights reserved.
• PROCESS FOR THE PREPARATION OF ANTHOCYANIN-CONTAINING PRODUCTS
  申请人：Medpalett Pharmaceuticals AS

  公开号：EP1443948B1

  公开（公告）日：2005-06-29
• US6967032B2
  申请人：——

  公开号：US6967032B2

  公开（公告）日：2005-11-22