tuberonic acid glucoside | 124649-25-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tuberonic acid glucoside
• 英文别名: tuberonic acid-5-O-β-D-glucopyranoside；Cyclopentaneacetic acid, 2-[(2Z)-5-(beta-D-glucopyranosyloxy)-2-penten-1-yl]-3-oxo-, (1R,2S)-；2-[(1R,2S)-3-oxo-2-[(Z)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid
• CAS: 124649-25-8
• 化学式: C₁₈H₂₈O₉
• 分子量: 388.415
• InChiKey: JFDNMLUPLXZXGV-OAIXPKHMSA-N

物化性质

• 沸点：
  650.0±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tuberonic acid glucoside 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：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 2-[(1R,2S)-2-[(Z)-5-羟基戊-2-烯基]-3-氧代环戊基]乙酸 在 Oryza sativa recombinant putative salicylic acid glucosyltransferase 、 magnesium chloride 作用下， 生成 tuberonic acid glucoside
  参考文献：
  名称：

  Purification and cDNA cloning of a wound inducible glucosyltransferase active toward 12-hydroxy jasmonic acid

  摘要：

  Tuberonic acid (12-hydroxy epi-jasmonic acid, TA) and its glucoside (TAG) were isolated from potato leaflets (Solanum tuberosum L.) and shown to have tuber-inducing properties. The metabolism of jasmonic acid (JA) to TAG in plant leaflets, and translocation of the resulting TAG to the distal parts, was demonstrated in a previous study. It is thought that TAG generated from JA transmits a signal from the damaged parts to the undamaged parts by this mechanism. In this report, the metabolism of TA in higher plants was demonstrated using [12-(3) H]TA, and a glucosyltransferase active toward TA was purified from the rice cell cultures. The purified protein was shown to be a putative salicylic acid (SA) glucosyltransferase (OsSGT) by MALDI-TOF-MS analysis. Recombinant OsSGT obtained by overexpression in Escherichia coli was active not only toward TA but also toward SA. The OsSGT characterized in this research was not specific, but this is the first report of a glucosyltransferase active toward TA. mRNA expressional analysis of OsSGT and quantification of TA, TAG, SA and SAG after mechanical wounding indicated that OsSGT is involved in the wounding response. These results demonstrated a crucial role for TAG not only in potato tuber formation, but also in the stress response in plants and that the SA glucosyltransferase can work for TA glucosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.01.004

文献信息

• Synthesis and Bioactivity of Potassium β-<scp>D</scp>-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds
  作者：Yoko NAKAMURA、Ryoji MIYATAKE、Sho INOMATA、Minoru UEDA

  DOI：10.1271/bbb.80338

  日期：2008.11.23

  Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. β-d-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (−)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

  Albizzia saman是一种豆科植物，它在白天气息张开的叶子，夜间则将叶子折叠休息。β-d-葡萄糖吡喃苷12-羟基茉莉酸酯（1）被鉴定为控制这种叶子运动的内源性化学因子。我们开发了一种简洁的合成方法，通过9个步骤从（+）-2合成光学上纯净的（−）-1，总产率为58%。同样，作为结构-活性关系（SAR）研究的类物质1的类似物，如epi-LCF（13）、对映体（14）和半乳糖苷（19）也被合成。SAR研究的结果强烈表明，1的闭叶活性的机制与甲基茉莉酸酯的机制不同，并且还表明涉及了一种不同类型的靶蛋白，该蛋白识别茉莉酸衍生物的反式异构体。
• Identification of a β-glucosidase hydrolyzing tuberonic acid glucoside in rice (Oryza sativa L.)
  作者：Shinji Wakuta、Shigeki Hamada、Hiroyuki Ito、Hideyuki Matsuura、Kensuke Nabeta、Hirokazu Matsui

  DOI：10.1016/j.phytochem.2010.04.025

  日期：2010.8

  Tuberonic acid (TA) and its glucoside (TAG) have been isolated from potato (Solanum tuberosum L) leaflets and shown to exhibit tuber-inducing properties. These compounds were reported to be biosynthesized from jasmonic acid (JA) by hydroxylation and subsequent glycosylation, and to be contained in various plant species. Here we describe the in vivo hydrolytic activity of TAG in rice. In this study, the TA resulting from TAG was not converted into JA. Tuberonic acid glucoside (TAG)-hydrolyzing beta-glucosidase, designated OsTAGG1, was purified from rice by six purification steps with an similar to 4300-fold purification. The purified enzyme migrated as a single band on native PAGE, but as two bands with molecular masses of 42 and 26 kDa on SDS-PAGE. Results from N-terminal sequencing and peptide mass fingerprinting of both polypeptides suggested that both bands were derived from a single polypeptide, which is a member of the glycosyl hydrolase family 1. In the native enzyme, the K-m and V-max values of TAG were 31.7 mu M and 0.25 mu katal/mg protein, OsTAGG1 preferentially hydrolyzed TAG and methyl TAG. Here we report that OsTAGG1 is a specific beta-glucosidase hydrolyzing TAG, which releases the physiologically active TA. (C) 2010 Elsevier Ltd. All rights reserved.
• Identification of Rice β-Glucosidase with High Hydrolytic Activity towards Salicylic Acid β-<scp>D</scp>-Glucoside
  作者：Nami HIMENO、Wataru SABURI、Shinji WAKUTA、Ryosuke TAKEDA、Hideyuki MATSUURA、Kensuke NABETA、Sompong SANSENYA、James R. KETUDAT CAIRNS、Haruhide MORI、Ryozo IMAI、Hirokazu MATSUI

  DOI：10.1271/bbb.120889

  日期：2013.5.23

  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.
• Purification and cDNA cloning of a wound inducible glucosyltransferase active toward 12-hydroxy jasmonic acid
  作者：Yoshiya Seto、Shigeki Hamada、Hideyuki Matsuura、Mana Matsushige、Chizuru Satou、Kosaku Takahashi、Chikara Masuta、Hiroyuki Ito、Hirokazu Matsui、Kensuke Nabeta

  DOI：10.1016/j.phytochem.2009.01.004

  日期：2009.2

  Tuberonic acid (12-hydroxy epi-jasmonic acid, TA) and its glucoside (TAG) were isolated from potato leaflets (Solanum tuberosum L.) and shown to have tuber-inducing properties. The metabolism of jasmonic acid (JA) to TAG in plant leaflets, and translocation of the resulting TAG to the distal parts, was demonstrated in a previous study. It is thought that TAG generated from JA transmits a signal from the damaged parts to the undamaged parts by this mechanism. In this report, the metabolism of TA in higher plants was demonstrated using [12-(3) H]TA, and a glucosyltransferase active toward TA was purified from the rice cell cultures. The purified protein was shown to be a putative salicylic acid (SA) glucosyltransferase (OsSGT) by MALDI-TOF-MS analysis. Recombinant OsSGT obtained by overexpression in Escherichia coli was active not only toward TA but also toward SA. The OsSGT characterized in this research was not specific, but this is the first report of a glucosyltransferase active toward TA. mRNA expressional analysis of OsSGT and quantification of TA, TAG, SA and SAG after mechanical wounding indicated that OsSGT is involved in the wounding response. These results demonstrated a crucial role for TAG not only in potato tuber formation, but also in the stress response in plants and that the SA glucosyltransferase can work for TA glucosylation. (C) 2009 Elsevier Ltd. All rights reserved.