矢车菊素-3-芸香糖苷 | 28338-59-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 矢车菊素-3-芸香糖苷
• 英文名称: cyanidin-3-rutinoside
• 英文别名: cyanidin 3-α-rhamnopyranosyl-(1→6)-β-D-glucopyranoside；cyanidin 3-O-(6''-O-α-rhamnopyranosyl-β-glucopyranoside)；cyanidin 3-O-(6-O-(α-rhamnopyranosyl)-β-glucopyranoside)；cyanidin-3-O-(6''-O-α-rhamnopyranosyl-β-glucopyranoside)；cyanidin-3-rutinosideCyanidin-3-O-rutinoside；cyanidin-(1β->3O)-rutinoside；Keracyanin cation；(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• CAS: 28338-59-2
• 化学式: C₂₇H₃₁O₁₅
• 分子量: 595.534
• InChiKey: USNPULRDBDVJAO-FXCAAIILSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.77
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  240
• 氢给体数：
  10
• 氢受体数：
  14

安全信息

• 储存条件：
  存储条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 矢车菊素-3-芸香糖苷 在 anthocyanin 5-O-glucosyltransferase from Vitis amurensis Rupr. cv. ‘Zuoshanyi’ grape 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.33h， 生成 3-[[6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-吡喃葡萄糖基]氧基]-2-(3,4-二羟基苯基)-5-(beta-D-吡喃葡萄糖基氧基)-7-羟基-1-苯并吡喃鎓
  参考文献：
  名称：

  Molecular and biochemical characterization of the UDP-glucose: Anthocyanin 5-O-glucosyltransferase from Vitis amurensis

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2015.06.023

文献信息

• Unusual anthocyanin reaction with acetone leading to pyranoanthocyanin formation
  作者：Yinrong Lu、L.Yeap Foo

  DOI：10.1016/s0040-4039(00)02246-2

  日期：2001.2

  Anthocyanins undergo unusual facile reactions with acetone to give rise to pyranoanthocyanins, thus showing that the new class of pigments isolated from blackcurrant seeds were a result of solvent participation. This oxidative addition was extended to the successful synthesis of pyranomalvidin or 2-(3,5-dimethoxy-4-hydroxyphenyl)-8-hydroxy-5-methyl-3-O-β-d-glucopyranosyloxypyrano[4,3,2-de]-1-benzopyrylium

  花色素苷与丙酮发生异常的易反应，生成吡喃花色素苷，因此表明从黑加仑子种子中分离出的新型颜料是溶剂参与的结果。这种氧化加成作用扩展到成功合成了吡喃马维丁或2-（3,5-二甲氧基-4-羟基苯基）-8-羟基-5-甲基-3- O -β-d-吡喃葡萄糖基氧基吡喃并[4,3,2-主要葡萄花色苷麦维京素3- O-葡萄糖苷与丙酮的反应生成de ] -1-苯并吡啶鎓。通过2D NMR充分表征了吡喃马维菌素，吡喃花色素B和吡喃德啡肽B的化学结构。
• Influence of cyanidin glycosylation patterns on carboxypyranoanthocyanin formation
  作者：Jacob E. Farr、Gregory T. Sigurdson、M. Mónica Giusti

  DOI：10.1016/j.foodchem.2018.03.117

  日期：2018.9

  enolizable groups to form pyranoanthocyanins. These pigments are less susceptible to degradation and color changes associated with nucleophilic addition common to anthocyanins. This study aimed to evaluate the impact of glycosylation patterns of anthocyanins on carboxypyranoanthocyanin formation. Nine cyanidin derivatives were isolated by semi-preparative HPLC. Pyruvic acid was added to induce pyranoanthocyanin

  花青素可与具有可烯丙基的化合物缩合形成吡喃花青素。这些颜料较不容易降解和变色，这与花色苷常见的亲核加成有关。这项研究旨在评估花色苷的糖基化方式对羧基吡喃花青素形成的影响。通过半制备HPLC分离了九种花色素衍生物。添加丙酮酸以诱导吡喃花青素形成。在25°C下储存31天期间，监测溶液的组成（HPLC-MS / MS），光谱（吸光度380-700 nm）和颜色（CIEL * c * h *）。带有1→6个二糖的氰基-3-糖苷产生最高的吡喃花色素苷产率（〜31％），其次是氰基-3-单糖苷（〜20％）；1→2二糖产生的吡喃花青素比例最低（5-7％）。Cyanidin-3-arabinoside转化为吡喃花色素，但在这些条件下迅速降解（3％产率）。由氰胺丁-3-槐糖苷-5-葡糖苷未形成吡喃花色素苷。糖基键比单独取代的大小更关键，而Cyanidin-3-（葡萄糖基）-（1→6）-（木糖基-（1→2）-半
• 방사선을 이용하여 안토시아닌으로부터 프로토카테큐산 저급 알킬 에스터를 제조하는 방법
  申请人：KOREA ATOMIC ENERGY RESEARCH INSTITUTE 한국원자력연구원(319980077609)

  公开号：KR20150098480A

  公开（公告）日：2015-08-28

  본 발명은 방사선을 이용하여 안토시아닌으로부터 프로토카테큐산 C1 내지 C4 저급 알킬 에스터를 제조하는 방법에 관한 것으로서, 구체적으로 C1 내지 C4 저급 알콜에 녹인 안토시아닌 용액에 방사선을 조사하여 라디칼 소거능이 있는 프로토카테큐산 C1 내지 C4 저급 알킬 에스터를 제조하는 방법에 관한 것이다. 본 발명의 방법에 따라 방사선 조사기술을 이용하여 복잡한 색소 제거 과정 없이 안토시아닌의 분해 반응으로 안토시아닌으로부터 색소를 제거함과 동시에 활성산소 소거 활성이 있는 프로토카테큐산 C1 내지 C4 저급 알킬 에스터를 생성하여 항산화 활성을 방사선 조사 전과 유사하게 유지함으로써 식품, 의약품 및 화장품의 유효성분으로 유용하게 이용될 수 있다.

  本发明涉及一种利用辐射制备从花青素中制备C1至C4低级烷基酯的方法，具体地，本发明涉及一种通过将花青素溶液溶解在C1至C4低级醇中，辐照该溶液以制备具有自由基清除能力的C1至C4低级烷基酯的方法。根据本发明的方法，利用辐射技术通过花青素的分解反应而从花青素中去除色素，同时生成具有抗氧化活性的C1至C4低级烷基酯，从而可以将其作为食品、药品和化妆品的有效成分使用，无需进行复杂的色素去除过程，且保持辐射前后的抗氧化活性类似。
• ADIPONECTIN EXPRESSION PROMOTER
  申请人：SAN-EI GEN F.F.I., INC.

  公开号：EP1602652A1

  公开（公告）日：2005-12-07

  To prevent or alleviate various pathologies caused by lifestyle-related diseases, etc., the present invention provides a substance having an effect of promoting the expression and elevating the expression level of adiponectin, and applications thereof. An adiponectin expression promoting agent containing, as an active ingredient, at least one cyanidin compound selected from the group consisting of cyanidin and cyanidin glycosides can be applied to pharmaceutical or food compositions for use in applications in which the pharmacological effects of adiponectin are utilized.

  为了预防或缓解与生活方式有关的疾病等引起的各种病症，本发明提供了一种具有促进脂肪连通素表达和提高其表达水平效果的物质及其应用。一种含有至少一种选自由青花苷和青花苷糖苷组成的组中的青花苷化合物作为活性成分的促脂肪生成素表达剂可应用于药物或食品组合物中，以用于利用脂肪生成素的药理作用的应用中。
• Glycan therapeutics and related methods thereof
  申请人：KALEIDO BIOSCIENCES, INC.

  公开号：US10314853B2

  公开（公告）日：2019-06-11

  Preparations of glycan therapeutics, pharmaceutical compositions and medical foods thereof, optionally comprising micronutrients, polyphenols, prebiotics, probiotics, or other agents are provided and methods of making same. Also provided are methods of using said gycan therapeutics, e.g. for the modulation of human gastrointestinal microbiota and to treat dysbioses.

  本发明提供了可选择包含微量营养素、多酚、益生元、益生菌或其他制剂的聚糖疗法制剂、药物组合物及其医用食品，以及制造方法。还提供了使用所述糖治疗剂的方法，例如用于调节人类胃肠道微生物群和治疗菌群失调。