[(1R,2R)-2-{(2Z)-5-[(6,7-二脱氧-β-D-葡萄-七吡喃糖基)氧代]戊-2-烯-1-基}-3-羰基环戊基]乙酸 | 120399-24-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: [(1R,2R)-2-{(2Z)-5-[(6,7-二脱氧-β-D-葡萄-七吡喃糖基)氧代]戊-2-烯-1-基}-3-羰基环戊基]乙酸
• 英文名称: {(1R,2R,2'Z)-2-[5'-(β-D-glucopyranosyloxy)pent-2'-enyl]-3-oxocyclopentane}acetic acid
• 英文别名: (1R,2R)-5'-hydroxyjasmonic acid 5'-O-β-D-glucopyranoside；(-)-(1R,2R)-5-β-D-glucopyranosyloxyjasmonic acid；5′-β-D-glucopyranosyloxyjasmonic acid；12-hydroxyjasmonic acid β-D-glucopyranoside；(-)-5'-β-D-glucopyranosyl-oxyjasmonic acid；(-)-5'-β-D-glucopyranosyloxyjasmonic acid；Tuberonic acid glucoside；2-[(1R,2R)-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: 120399-24-8
• 化学式: C₁₈H₂₈O₉
• 分子量: 388.415
• InChiKey: JFDNMLUPLXZXGV-RKAGECJXSA-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：

  [(1R,2R)-2-{(2Z)-5-[(6,7-二脱氧-β-D-葡萄-七吡喃糖基)氧代]戊-2-烯-1-基}-3-羰基环戊基]乙酸 在 TAG β-glucosidase 作用下， 以 水 为溶剂， 生成 可得然胶 、 12-羟基茉莉酸
  参考文献：
  名称：

  Identification of rice Os4BGlu13 as a β-glucosidase which hydrolyzes gibberellin A4 1-O-β-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides

  摘要：

  Gibberellin 1-O-beta-D-glucose ester hydrolysis activity has been detected in rice seedling extracts, but no enzyme responsible for this activity has ever been purified and identified. Therefore, gibberellin A4 glucosyl ester (GA(4)-GE) beta-D-glucosidase activity was purified from ten-day rice seedling stems and leaves. The family 1 glycoside hydrolase Os4BGlu13 was identified in the final purification fraction. The Os4BGlu13 cDNA was amplified from rice seedlings and expressed as an N-terminal thioredoxin-tagged fusion protein in Escherichia coll. The purified recombinant Os4BGlu13 protein (rOs4BGlu13) had an optimum pH of 4.5, for hydrolysis of p-nitrophenyl beta-D-glucopyranoside (pNPGlc), which was the best substrate identified, with a k(cat)/K-m of 637 mM(-1) s(-1). rOs4BGlu13 hydrolyzed helicin best among natural glycosides tested (K-cat/K-m, of 74.4 mM(-1) s(-1)). Os4BGlu13 was previously designated tuberonic acid glucoside (TAG) beta-glucosidase (TAGG), and here the k(cat)/K-m of rOsBGlu13 for TAG was 6.68 mM(-1) s(-1), while that for GA4-GE was 3.63 mM(-1) s(-1) and for salicylic acid glucoside (SAG) is 0.88 mM(-1) s(-1). rOs4BGlu13 also hydrolyzed oligosaccharides, with preference for short beta-(1 -> 3)-linked over beta-(1 -> 4)linked glucooligosaccharides. The enzymatic data suggests that Os4BGlu13 may contribute to TAG, SAG, oligosaccharide and GA4-GE hydrolysis in the rice plant, although helicin or a similar compound may be its primary target. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2015.07.021
• 作为产物：
  描述：

  methyl (1R,2R)-5'-hydroxyjasmonate 5'-O-β-D-glucopyranoside 在 氢氧化钾 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以100%的产率得到[(1R,2R)-2-{(2Z)-5-[(6,7-二脱氧-β-D-葡萄-七吡喃糖基)氧代]戊-2-烯-1-基}-3-羰基环戊基]乙酸
  参考文献：
  名称：

  Synthesis and Bioactivity of Potassium β-D-Glucopyranosyl 12-Hydroxy Jasmonate and Related Compounds

  摘要：

  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。

  DOI：

  10.1271/bbb.80338

文献信息

• Two Jasmonoid Glucosides and a Phenylvaleric Acid Glucoside from<i>Perilla frutescens</i>
  作者：Tomoyuki Fujita、Kenji Terato、Mitsuru Nakayama

  DOI：10.1271/bbb.60.732

  日期：1996.1

  Three new glucosidic constituents (1–3) were isolated from the methanolie extract of Perilla frutescens. Two of these compounds (t and 2) were jasmonoid glucosides and were determined to be 5’-β-D-glueopyranosyloxyjasmonic acid and 3-β-D-glucopyranosyl-3-epi-2-isocucurbic acid, respectively. The other one (3) was a new glucoside of phenylvaleric acid that was elucidated to be 3-β-D-glucopyranosyloxy-5-phenylvaleric acid. Its aglycone was also found for the first time in nature.

  从紫苏的甲醇提取物中分离出了三种新的糖苷成分（1–3）。其中两种化合物（1和2）是茉莉酸糖苷，分别确定为5'-β-D-葡萄糖吡喃苷氧茉莉酸和3-β-D-葡萄糖吡喃苷-3-表-2-异葫芦酸。另一个（3）是一种新的苯戊酸糖苷，阐明为3-β-D-葡萄糖吡喃苷氧-5-苯戊酸。其配基在自然界中首次被发现。
• Phenolic Glycosides from Berries of <i>Pimenta dioica</i>
  作者：Hiroe Kikuzaki、Yoshiko Miyajima、Nobuji Nakatani

  DOI：10.1021/np0705615

  日期：2008.5.1

  Four new phenolic glycosides, (27hydroxy-3-methoxy-5-allyl)phenyl beta-D-(6-O-E-sinapoyl)glucopyranoside (1), (1'R,5'R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1 -> 6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical - scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.
• 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 rice Os4BGlu13 as a β-glucosidase which hydrolyzes gibberellin A4 1-O-β-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides
  作者：Yanling Hua、Watsamon Ekkhara、Sompong Sansenya、Chantragan Srisomsap、Sittiruk Roytrakul、Wataru Saburi、Ryosuke Takeda、Hideyuki Matsuura、Haruhide Mori、James R. Ketudat Cairns

  DOI：10.1016/j.abb.2015.07.021

  日期：2015.10

  Gibberellin 1-O-beta-D-glucose ester hydrolysis activity has been detected in rice seedling extracts, but no enzyme responsible for this activity has ever been purified and identified. Therefore, gibberellin A4 glucosyl ester (GA(4)-GE) beta-D-glucosidase activity was purified from ten-day rice seedling stems and leaves. The family 1 glycoside hydrolase Os4BGlu13 was identified in the final purification fraction. The Os4BGlu13 cDNA was amplified from rice seedlings and expressed as an N-terminal thioredoxin-tagged fusion protein in Escherichia coll. The purified recombinant Os4BGlu13 protein (rOs4BGlu13) had an optimum pH of 4.5, for hydrolysis of p-nitrophenyl beta-D-glucopyranoside (pNPGlc), which was the best substrate identified, with a k(cat)/K-m of 637 mM(-1) s(-1). rOs4BGlu13 hydrolyzed helicin best among natural glycosides tested (K-cat/K-m, of 74.4 mM(-1) s(-1)). Os4BGlu13 was previously designated tuberonic acid glucoside (TAG) beta-glucosidase (TAGG), and here the k(cat)/K-m of rOsBGlu13 for TAG was 6.68 mM(-1) s(-1), while that for GA4-GE was 3.63 mM(-1) s(-1) and for salicylic acid glucoside (SAG) is 0.88 mM(-1) s(-1). rOs4BGlu13 also hydrolyzed oligosaccharides, with preference for short beta-(1 -> 3)-linked over beta-(1 -> 4)linked glucooligosaccharides. The enzymatic data suggests that Os4BGlu13 may contribute to TAG, SAG, oligosaccharide and GA4-GE hydrolysis in the rice plant, although helicin or a similar compound may be its primary target. (C) 2015 Elsevier Inc. All rights reserved.