methyl (1R,2R)-5'-hydroxyjasmonate 5'-O-β-D-glucopyranoside | 176486-12-7

• 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: methyl (1R,2R)-5'-hydroxyjasmonate 5'-O-β-D-glucopyranoside
• 英文别名: methyl (1R,2S)-2-(5-β-D-glucopyranosyloxy-cis-2-pentenyl)-3-oxo-1-cyclopentaneacetate；(1R,2R)-methyl-5'-hydroxyjasmonate 5'-O-β-D-glucopyranoside；methyl {(1R,2R,2'Z)-2-[5'-(β-D-glucopyranosyloxy)pent-2'-enyl]-3-oxocyclopentane}acetate；(-)-5'-β-D-glucopyranosyloxyjasmonic acid methyl ester；methyl 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]acetate
• CAS: 176486-12-7
• 化学式: C₁₉H₃₀O₉
• 分子量: 402.442
• InChiKey: AJWIFVNLXHFTFD-AHXFZLPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-((1R,2S,3R)-3-hydroxy-2-((Z)-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-enyl)cyclopentyl)ethanoic acid 在 咪唑 、 氢氟酸 、 sodium methylate 、 二甲基氯化铝 、 氰化汞 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.5h， 生成 methyl (1R,2R)-5'-hydroxyjasmonate 5'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer

  摘要：

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00157-x

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。
• 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。
• Synthesis of both the enantiomers of methyl tuberonate, natural methyl β-d-glucopyranosyloxyjasmonate and its epimer
  作者：Munenori Inoue、Takeshi Kitahara

  DOI：10.1016/s0040-4020(99)00157-x

  日期：1999.4

  Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl beta-D-glucopyranosyloxyjasmonate 6, and its epimer, methyl beta-D-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9. (C) 1999 Elsevier Science Ltd. All rights reserved.