2-[(Z)-(3,4-二羟基苯基)亚甲基]-4-羟基-6-(beta-D-吡喃葡萄糖基氧基)-3(2H)-苯并呋喃酮 | 633-15-8

• 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: 2-[(Z)-(3,4-二羟基苯基)亚甲基]-4-羟基-6-(beta-D-吡喃葡萄糖基氧基)-3(2H)-苯并呋喃酮
• 英文名称: aureusidin 6-O-beta-glucoside
• 英文别名: (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-3-one
• CAS: 633-15-8
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.4
• InChiKey: AMJCTDBATIKENQ-YRDFTBLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：

  2',3,4,4',6'-pentahydroxychalcone 4'-O-beta-D-glucoside(1-) 、 氢(+1)阳离子 、 氧气 生成 2-[(Z)-(3,4-二羟基苯基)亚甲基]-4-羟基-6-(beta-D-吡喃葡萄糖基氧基)-3(2H)-苯并呋喃酮 、 水
  参考文献：
  名称：

  Aureusidin Synthase: A Polyphenol Oxidase Homolog Responsible for Flower Coloration

  摘要：

  黄酮类植物素aurones能为一些常见观赏植物的花朵提供黄色。本研究中，我们已经鉴定出一种酶负责在黄色鸢尾花中从类黄酮合成aurone。这种酶（aureusidin synthase）是一种含铜糖蛋白，分子量为39千道尔顿，能催化前体类黄酮2′，4′，6′，4-四羟基查尔酮和2′，4′，6′，3,4-五羟基查尔酮的羟化和/或氧化环化。编码aureusidin synthase的互补DNA在含aurone的品种的花瓣中表达。DNA序列分析表明，aureusidin synthase属于植物多酚氧化酶家族，为植物中多酚氧化酶同源物功能的明确例子，即花色素形成。

  DOI：

  10.1126/science.290.5494.1163

文献信息

• Yellow flowers generated by expression of the aurone biosynthetic pathway
  作者：Eiichiro Ono、Masako Fukuchi-Mizutani、Noriko Nakamura、Yuko Fukui、Keiko Yonekura-Sakakibara、Masaatsu Yamaguchi、Toru Nakayama、Takaharu Tanaka、Takaaki Kusumi、Yoshikazu Tanaka

  DOI：10.1073/pnas.0604246103

  日期：2006.7.18

  Flower color is most often conferred by colored flavonoid pigments. Aurone flavonoids confer a bright yellow color on flowers such as snapdragon (Antirrhinum majus) and dahlia (Dahlia variabilis). A. majus aureusidin synthase (AmAS1) was identified as the key enzyme that catalyzes aurone biosynthesis from chalcones, but transgenic flowers overexpressing AmAS1 gene failed to produce aurones. Here, we

  花的颜色通常是由有色的类黄酮颜料赋予的。淡黄色的黄酮类化合物使花朵如金鱼草（Antirrhinum majus）和大丽花（Dahlia variabilis）呈现亮黄色。Majus aureusidin合酶（AmAS1）被认为是催化从查耳酮中合成生物素的关键酶，但过表达AmAS1基因的转基因花无法产生金质。在这里，我们报告查尔酮4'-O-葡萄糖基转移酶（4'CGT）对于体内的金黄色生物合成和黄色着色是必不可少的。Am4'CGT和AmAS1基因的共表达足以在转基因花（Torenia hybrida）中积累金黄色素6-O-葡萄糖苷。此外，它们的共表达与RNA干扰（RNAi）对花色苷生物合成的下调相结合，产生了黄色的花朵。Am4' CGT-GFP嵌合蛋白位于细胞质中，而AmAS1（N1-60）-RFP嵌合蛋白位于液泡中。因此，我们得出结论，查耳酮在细胞质中被4'-O-糖基化，它们的4'-O-糖苷
• Enzymatic formation of aurones in the extracts of yellow snapdragon flowers
  作者：Takuya Sato、Toru Nakayama、Sanae Kikuchi、Yuko Fukui、Keiko Yonekura-Sakakibara、Takashi Ueda、Tokuzo Nishino、Yoshikazu Tanaka、Takaaki Kusumi

  DOI：10.1016/s0168-9452(00)00385-x

  日期：2001.1

  The yellow coloration of snapdragon (Antirrhinum majus) flowers is mainly provided by the 6-glucosides of aureusidin and bracteatin. However, the biochemical mechanism of aurone biosynthesis is not well understood. In this study, eve have identified aurone-biosynthesizing activity in the extracts of yellow snapdragon flowers. Incubation of 2',4',6',4-tetrahydroxychalcone (THC) with an enzyme preparation in the presence of H2O2 caused the enzymatic formation of a single product, aureusidin, without the formation of a previously proposed 2-(alpha -hydroxybenzyl)coumaranone intermediate. The formation of aureusidin from THC was specifically observed with yellow flowers as well as aurone-accumulating flowers of other colors. The pH optimum for the enzymatic formation of aureusidin was around 5.4. Stoichiometric studies showed that one mole of aureusidin formation was accompanied by the consumption of one mole of oxygen with no detectable consumption of H2O2, which may work as an enzyme activator. The oxidative formation of aureusidin from THC could be explained in terms of the action of a single enzyme, an internal monooxygenase catalyzing the 3-hydroxylation and oxidative cyclization of THC. Incubation of 2',4',6',3,4-pentahydroxychalcone (PHC) with an enzyme yielded both aureusidin and bracteatin at an approximate molar ratio of 6:1. In this case, H2O, was not required for enzyme activity but rather inhibited the reaction. The 4'-glucosides of THC and PHC could also act as substrates for the formation of the 6-glucosides of aurones. These results suggest that aureusidin can be produced from either THC or PHC, whereas bracteatin is not produced through the 5'-hydroxylation of aureusidin but arise solely from PHC. (C) 2001 Elsevier Science Ireland Ltd. All rights reserved.
• Specificity analysis and mechanism of aurone synthesis catalyzed by aureusidin synthase, a polyphenol oxidase homolog responsible for flower coloration
  作者：Toru Nakayama、Takuya Sato、Yuko Fukui、Keiko Yonekura-Sakakibara、Hideyuki Hayashi、Yoshikazu Tanaka、Takaaki Kusumi、Tokuzo Nishino

  DOI：10.1016/s0014-5793(01)02529-7

  日期：2001.6.15

  Aureusidin synthase, which plays a key role in the yellow coloration of snapdragon flowers, is a homolog of plant polyphenol oxidase (PPO). The enzyme specifically acted on chalcones with a 4‐monohydroxy or 3,4‐dihydroxy B‐ring to produce aurones, for whose production the oxidative cyclization of chalcones must be preceded by 3‐oxygenation. However, it exhibited virtually no PPO activity toward non‐chalcone phenolics. The enzyme was competitively inhibited by phenylthiourea, a specific PPO inhibitor. These results led us to propose a mechanism of aurone synthesis by aureusidin synthase on the basis of known PPO‐catalyzed reactions and conclude that the enzyme is a chalcone‐specific PPO specialized for aurone biosynthesis.