cyanidin-3-O-glucoside

• 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: cyanidin-3-O-glucoside
• 英文别名: cyanidin 3-glucoside；C3G；cyanidin 3-D-glucoside；cyanidin 3-glucopyranoside；cyanidin 3-O-β-glucopyranoside；Cyanidin 3-O-beta-D-glucoside；(3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₁H₂₁O₁₁
• 分子量: 449.391
• InChiKey: RKWHWFONKJEUEF-AVPDHNOJSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 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：
  181
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cyanidin-3-O-glucoside 在 盐酸 作用下， 生成 2-(3,4-Dihydroxy-phenyl)-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2H-chromene-2,5,7-triol
  参考文献：
  名称：

  Color and Antioxidant Properties of Cyanidin-Based Anthocyanin Pigments

  摘要：

  A series of cyanidin-based anthocyanin pigments was investigated to determine the effect of structural variation on a number of chemical and physical properties: CIELAB color coordinates, visual detection thresholds, hydration constants (pK(H)), and in vitro antioxidant activities (ORAC). In addition to individual isolated compounds, purified total pigment isolates from blackberry, elderberry, black carrot, red cabbage, and sweet potato were also examined. Acylation with cinnamic acids shifted color tonality (hue angle) to purple, and markedly increased pK(H) and antioxidant activity, but lowered the visual detection threshold. Glycosidic substitution at the 5 position moved tonalities toward purple and decreased pK(H), and tended to lower the ORAC value, but raised the visual detection threshold. Increasing the number of sugar substituents at the 3 position also affected all of these parameters, however, the extent was not predictable. Antioxidant levels of purified anthocyanin extracts were much higher than expected from anthocyanin content indicating synergistic effect of anthocyanin mixtures.

  DOI：

  10.1021/jf0204811
• 作为产物：
  描述：

  2-(3,4-Dihydroxy-phenyl)-3-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2H-chromene-2,5,7-triol 在 盐酸 作用下， 生成 cyanidin-3-O-glucoside
  参考文献：
  名称：

  Color and Antioxidant Properties of Cyanidin-Based Anthocyanin Pigments

  摘要：

  A series of cyanidin-based anthocyanin pigments was investigated to determine the effect of structural variation on a number of chemical and physical properties: CIELAB color coordinates, visual detection thresholds, hydration constants (pK(H)), and in vitro antioxidant activities (ORAC). In addition to individual isolated compounds, purified total pigment isolates from blackberry, elderberry, black carrot, red cabbage, and sweet potato were also examined. Acylation with cinnamic acids shifted color tonality (hue angle) to purple, and markedly increased pK(H) and antioxidant activity, but lowered the visual detection threshold. Glycosidic substitution at the 5 position moved tonalities toward purple and decreased pK(H), and tended to lower the ORAC value, but raised the visual detection threshold. Increasing the number of sugar substituents at the 3 position also affected all of these parameters, however, the extent was not predictable. Antioxidant levels of purified anthocyanin extracts were much higher than expected from anthocyanin content indicating synergistic effect of anthocyanin mixtures.

  DOI：

  10.1021/jf0204811

文献信息

• COMPOSITIONS INCLUDING ANTHOCYANIN OR ANTHOCYANIDIN FOR THE PREVENTION OR TREATMENT OF ARTICULAR CARTILAGE-ASSOCIATED CONDITIONS
  申请人：Johnson Lanny L.

  公开号：US20100196331A1

  公开（公告）日：2010-08-05

  Methods of treating an arthritic joint of a subject, including administering a pharmaceutical composition by injection into the arthritic joint, wherein the composition includes an anthocyanin or anthocyanidin, glucose, and a pharmaceutically acceptable carrier.

  治疗受试者关节炎关节的方法，包括通过注射将药物组合物给药于关节炎关节，其中该组合物包括花青素或花青素苷、葡萄糖和药用可接受载体。
• 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。
• Enzymatic Acylation of Anthocyanin Isolated from Black Rice with Methyl Aromatic Acid Ester as Donor: Stability of the Acylated Derivatives
  作者：Zheng Yan、Chunyang Li、Lixia Zhang、Qin Liu、Shiyi Ou、Xiaoxiong Zeng

  DOI：10.1021/acs.jafc.5b05031

  日期：2016.2.10

  synthesized. This is the first report on the enzymatic acylation of anthocyanin from black rice with methyl aromatic esters as acyl donors and lipase as biocatalyst. Furthermore, the acylation with aromatic carboxylic acids enhanced both the thermostability and light resistivity of anthocyanin. In particular, cyanidin 3-(6″-cinnamoyl)-glucoside was the most stable among the three acylated anthocyanins synthesized

  在减压下，将黑米中的花色苷与芳香族酸甲酯作为酰基供体和南极假丝酵母脂肪酶B进行酶促酰化反应。以苯甲酸甲酯为酰基给体时，最高的转化率为91％。成功合成了花青素3-（6″-苯甲酰基）-葡糖苷，花青素3-（6″-水杨酰基）-葡糖苷和花青素3-（6″-肉桂酰基）-葡糖苷。这是关于黑米中的花色苷以甲基芳族酯为酰基供体，以脂肪酶为生物催化剂进行酶促酰化的首次报道。此外，用芳族羧酸酰化增强了花青素的热稳定性和光电阻率。尤其是，花青素3-（6″-肉桂酰基）-葡糖苷在所合成的三种酰化花色苷中是最稳定的。
• Small Molecule Compound for Enhancing Plant Stress Resistance
  申请人：SHANGHAI INSTITUTES FOR BIOLOGICAL SCIENCES, CHINESE ACADEMY OF SCIENCES

  公开号：US20180360039A1

  公开（公告）日：2018-12-20

  Disclosed are a small molecule compound for enhancing plant stress resistance, a preparation method therefor, and application thereof. Specifically, disclosed are compounds as shown in formula I, salts thereof, optical isomers thereof, racemes thereof, solvates thereof, or precursors thereof. Moreover, the compound of the present invention is a substitute of ABA, can significantly improve the plant stress resistance, and thus has an extremely wide application prospect.

  本文公开了一种用于增强植物抗逆性的小分子化合物，其制备方法以及应用。具体公开了如公式I所示的化合物，其盐，光学异构体，外消旋体，溶剂合物或前体。此外，本发明的化合物是ABA的替代物，可以显著提高植物的抗逆性，因此具有极其广泛的应用前景。
• [EN] CONSTRUCTS AND METHODS FOR BIOSYNTHESIS OF GALANTHAMINE<br/>[FR] CONSTRUCTIONS ET PROCÉDÉS POUR LA BIOSYNTHÈSE DE LA GALANTHAMINE
  申请人：DONALD DANFORTH PLANT SCI CT

  公开号：WO2015196100A1

  公开（公告）日：2015-12-23

  The present disclosure relates generally to the identification of enzymes within the Amaryllidaceae alkaloid biosynthetic pathway as well as to engineering transgenic organisms for the production of galanthamine and/or hemanthamine and/or lycorine. Disclosed herein is the isolation and characterization of cDNAs and encoded norbelladine 4'-0-methyltransferase, CYP96T1-3, and norbelladine synthase/reductase involved in the biosynthesis of galanthamine and haemanthamine. The invention relates to a transgenic plant, comprising within its genome, and expressing, a heterologous nucleotide sequence coding for a class I O-methyltransferase, wherein the O-methyltransferase is norbelladine 4'-0-methyltransferase. In one embodiment, the norbelladine 4'-0-methyltransferase is selected from among NpN40MT1, NpN40MT2, NpN40MT3, NpN40MT4, and NpN40MT5. The invention further contemplates a method of making a transgenic plant.

  本公开涉及总体上识别阿马里利达斯碱生物合成途径中的酶，以及为生产迎春碱和/或血红碱和/或石蒜碱而工程化转基因生物。本公开揭示了所述cDNA的分离和表征，以及编码的norbelladine 4'-0-甲基转移酶、CYP96T1-3和norbelladine合成酶/还原酶，这些酶参与了迎春碱和血红碱的生物合成。该发明涉及一种转基因植物，其基因组中包含并表达了编码I类O-甲基转移酶的异源核苷酸序列，其中O-甲基转移酶是norbelladine 4'-0-甲基转移酶。在一个实施例中，norbelladine 4'-0-甲基转移酶从NpN40MT1、NpN40MT2、NpN40MT3、NpN40MT4和NpN40MT5中选择。该发明进一步考虑了一种制备转基因植物的方法。