4-(β-D-glucopyranosyloxy)hydroxybenzoic acid | 15397-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(β-D-glucopyranosyloxy)hydroxybenzoic acid
• 英文别名: 4-hydroxybenzoic acid 4-O-β-D-glucopyranoside；p-hydroxybenzoic acid 4-O-β-D-glucopyranoside；p-hydroxybenzoic acid-4-O-β-D-glucopyranoside；4-O-β-D-glucopyranosyl-p-hydroxybenzoic acid；4-hydroxybenzoic acid 4-O-β-glucopyranoside；4-O-β-glucopyranosyl-p-hydroxybenzoic acid；4-(beta-D-glucosyloxy)benzoic acid；4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
• CAS: 15397-25-8；15446-51-2
• 化学式: C₁₃H₁₆O₈
• 分子量: 300.265
• InChiKey: XSSDYIMYZONMBL-BZNQNGANSA-N

物化性质

• 熔点：
  211-212 °C
• 沸点：
  590.1±50.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(β-D-glucopyranosyloxy)hydroxybenzoic acid 在 C-terminally His₆-tagged Oryza sativa L. β-glucosidase OsTAGG2 作用下， 以 aq. acetate buffer 为溶剂， 反应 0.17h， 生成 葡萄糖
  参考文献：
  名称：

  Identification of Rice β-Glucosidase with High Hydrolytic Activity towards Salicylic Acid β-D-Glucoside

  摘要：

  beta-Glucosidases (EC 3.2.1.21) split beta-glucosidic linkages at the non-reducing end of glucosides and oligosaccharides to release beta-D-glucose. One of the important functions of plant beta-glucosidase is deglucosylation of inactive glucosides of phytohormones to regulate levels of active hormones. Tuberonic acid is a jasmonate-related compound that shows tuber-inducing activity in the potato. We have identified two enzymes, OsTAGG1 and OsTAGG2, that have hydrolytic activity towards tuberonic acid beta-D-glucoside in rice (Oryza sativa L.). The expression of OsTAGG2 is upregulated by wounding and by methyl jasmonate, suggesting that this isozyme is involved in responses to biotic stresses and wounding, but the physiological substrate of OsTAGG2 remains ambiguous. In this study, we produced recombinant OsTAGG2 in Pichia pastoris (rOsTAGG2P), and investigated its substrate specificity in detail. From 1 L of culture medium, 2.1 mg of purified recombinant enzyme was obtained by ammonium sulfate precipitation and Ni-chelating column chromatography. The specific activity of rOsTAGG2P (182 U/mg) was close to that of the native enzyme (171 U/mg), unlike recombinant OsTAGG2 produced in Escherichia coli, which had approximately 3-fold lower specific activity than the native enzyme. The optimum pH and temperature for rOsTAGG2P were pH 3.4 and 60 degrees C. After pH and heat treatments, the enzyme retained its original activity in a pH range of 3.4-9.8 and below 55 degrees C. Native OsTAGG2 and rOsTAGG2P showed 4.5-4.7-fold higher activities towards salicylic acid beta-D-glucoside, an inactive storage-form of salicylic acid, than towards tuberonic acid beta-D-glucoside (TAG), although OsTAGG2 was originally isolated from rice based on TAG-hydrolytic activity.

  DOI：

  10.1271/bbb.120889
• 作为产物：
  描述：

  对羟基苯甲酸 在 pine pollen 作用下， 生成 4-(β-D-glucopyranosyloxy)hydroxybenzoic acid
  参考文献：
  名称：

  UDP 葡萄糖：来自密花松花粉的 4-(β-d-吡喃葡萄糖基氧基) 苯甲酸葡萄糖基转移酶

  摘要：

  摘要 - 在松树花粉（松花粉）萌发 30 小时期间，外源供应的 4-羟基苯甲酸 (HBA) 被定量转化为 4-(β-d-吡喃葡萄糖基氧基) 苯甲酸 (HBA 葡萄糖苷)。[ 14 C-羧基]HBA([ 14 C]-HBA)也被松花粉转化为[ 14 C]-HBA糖苷。UDP 葡萄糖：通过测量由[ 14 C]-HBA 和UDPG 形成[ 14 C]-HBA 糖苷的速率来测定来自松花粉的4-(β-d-吡喃葡萄糖基氧基)苯甲酸葡萄糖基转移酶。该酶首先从松花粉中部分纯化出来。通过Sephacryl S-300凝胶过滤估计酶的M r 为大约33 000。该酶的最适 pH 值为 7.5，通过添加 3 mM Ca 2+ 和 0.1 mM EDTA，其活性分别增加了约 50% 和 60%。

  DOI：

  10.1016/0031-9422(89)80013-5

文献信息

• 皮膚の老化抑制剤
  申请人：上野製薬株式会社

  公开号：JP2018123118A

  公开（公告）日：2018-08-09

  【課題】 皮膚の老化抑制剤を提供する。【解決手段】 式（１）で表されるヒドロキシ安息香酸およびその誘導体：［式中のＲ１は、水素、メチル基またはグルコシル基を示し、式中のＲ２は、水素、炭素数１から８の直鎖または分岐鎖状の炭化水素基、芳香族炭化水素基、グルコースあるいはソルビトールいずれかの糖残基、からなる群より選択される基を示す］並びにその塩から選択される１以上の化合物を有効成分として含有する皮膚の老化抑制剤を提供する。【選択図】 なし

  【问题】提供皮肤老化抑制剂。 【解决方案】提供一种含有式（1）中所表示的羟基苯甲酸及其衍生物：[其中，R1表示氢、甲基或葡萄糖基，R2表示氢、由1到8个碳原子组成的直链或支链烷基、芳香族烷基、葡萄糖或山梨醇中的任一糖基]以及其盐中的一种或多种化合物作为有效成分的皮肤老化抑制剂。 【选择图】无。
• Glucosylation of phenolic compounds by plant cell cultures
  作者：Mamoru Tabata、Yasuko Umetani、Mitsuko Ooya、Shigeo Tanaka

  DOI：10.1016/0031-9422(88)84097-4

  日期：——

  particular, Datura cultures glucosylated ca 90% of umbelliferone within 24hr after administration. Only Perilla cultures were capable of glucosylating rhein and emodin. The ability of glucosylating isomeric hydroxybenzoic acids varied widely with culture strains. A culture strain of Mallotus transformed p -hydroxybenzoic acid to p - O -β- d -glucosylbenzoic acid and p -hydroxybenzoic acid glucose ester

  摘要 检测了来自 7 种植物的 10 种培养菌株对性感酚类化合物进行葡萄糖基化的能力，包括四种简单酚、四种香豆素、三种黄酮类化合物和三种蒽醌类化合物。曼陀罗、紫草、紫苏和长春花的悬浮培养物能够使间羟基苯甲酸、伞形花酮、七叶亭、瑞香素和甘草素进行葡萄糖基化。特别是，曼陀罗在给药后 24 小时内培养了大约 90% 的伞形酮。只有紫苏培养物能够对大黄酸和大黄素进行葡萄糖基化。对异构羟基苯甲酸进行葡萄糖基化的能力因培养菌株而异。Mallotus的培养菌株将对羟基苯甲酸转化为对-O-β-d-葡萄糖基苯甲酸和对羟基苯甲酸葡萄糖酯，
• Structure of cynanodelphin, a tetra-p-hydroxybenzoated anthocyanin from blue flower of delphinium hybridum
  作者：Tadao Kondo、Kanako Suzuki、Kumi Yoshida、Kaori Oki、Minoru Ueda、Minoru Isobe、Toshio Goto

  DOI：10.1016/0040-4039(91)80173-4

  日期：1991.10

  Structure of cyanodelphin from blue petals of Delphinium hybridum was determined. It contains delphinidin nucleus, four molecules of p-hydroxybenzoic acid and seven molecules of hexoses.

  确定了从翠雀的蓝色花瓣中提取的氰基海豚的结构。它包含飞燕草素核，四个分子的对羟基苯甲酸和七个分子的己糖。
• Tyrosinase Inhibitory Activity of Ethanol Extracts from Medicinal and Edible Plants Cultivated in Okinawa and Identification of a Water-Soluble Inhibitor from the Leaves of<i>Nandina domestica</i>
  作者：Toshiya MASUDA、Nao FUJITA、Yuka ODAKA、Yoshio TAKEDA、Shigetomo YONEMORI、Katsuo NAKAMOTO、Hideki KUNINAGA

  DOI：10.1271/bbb.70249

  日期：2007.9.23

  The tyrosinase inhibitory activity of the extracts of 53 parts of 36 plant species cultivated for edible and medicinal use in Okinawa was investigated. The extract of Nandina domestica showed potent activity among these. The inhibitor in the extract was purified by assay-guided fractionation to give a simple phenol glucoside. Although it was a known compound (4-beta-D-glucopyranosyloxybenzoic acid)

  研究了在冲绳岛种植的用于食用和药用的36种植物中53种植物提取物的酪氨酸酶抑制活性。其中，南天竹的提取物显示出有效的活性。提取物中的抑制剂通过测定指导的分级分离纯化，得到简单的酚葡萄糖苷。尽管它是一种已知的化合物（4-β-D-吡喃葡萄糖基氧基苯甲酸），但这项工作首次揭示了其对酪氨酸酶的抑制活性。
• Glucosylation of isomeric hydroxybenzoic acids by cell suspension cultures of Mallotus japonicus
  作者：Shigeo Tanaka、Keiko Hayakawa、Yasuko Umetani、Mamoru Tabata

  DOI：10.1016/0031-9422(90)80120-6

  日期：1990.1

  Abstract Cultured cells of Mallotus japonicus converted exogenous o -hydroxybenzoic acid into its O -glucoside after a lag period of 8 hr during which time the aglycone was taken up rapidly by the cells, partly excreted and then re-absorbed. The glucosylation of the aglycone into o - O -β- d -glucosylbenzoic acid began almost simultaneously with the induction of glucosyltransferase activity, and ca

  摘要 马蹄莲的培养细胞在8 小时的滞后期后将外源性邻羟基苯甲酸转化为O-葡萄糖苷，在此期间苷元被细胞迅速吸收，部分排泄然后重新吸收。苷元向 o - O -β- d - 葡萄糖基苯甲酸的葡萄糖基化与葡萄糖基转移酶活性的诱导几乎同时开始，并且大约 78% 的苷元在 12 小时内转化为葡萄糖苷。另一方面，间-和对-羟基苯甲酸在给药后立即被葡萄糖基化，后者同时产生其O-葡萄糖苷和葡萄糖酯。抑制剂实验表明 70S 或 80S 核糖体可能参与异构羟基苯甲酸的葡萄糖基化。