12-羟基茉莉酸 | 140631-27-2

• 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: 12-羟基茉莉酸
• 英文名称: (1R,2R,2'Z)-2-(5'-hydroxy-pent-2'-enyl)-3-oxo-cyclopentaneacetic acid
• 英文别名: [(1R,2R,2'Z)-2-(5'-hydroxypent-2'-enyl)-3-oxocyclopentane]acetic acid；(1R,2R)-5'-hydroxyjasmonic acid；(-)-12-hydroxyjasmonic acid；12-hydroxyjasmonic acid；7-epi-tuberonic acid；epi-tuberonic acid；2-[(1R,2R)-2-[(Z)-5-hydroxypent-2-enyl]-3-oxocyclopentyl]acetic acid
• CAS: 140631-27-2
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: RZGFUGXQKMEMOO-BSANDHCLSA-N

物化性质

• 沸点：
  429.5±20.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

制备方法与用途

12-羟基茉莉酸是Samanea saman中的一种非COI1-JAZ依赖性叶片闭合运动激活剂。

反应信息

• 作为产物：
  描述：

  5-(tetrahydropyran-2-yloxy)-3-pentyn-1-ol 在 Lindlar's catalyst 、 对甲苯磺酸 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium hydroxide 、 草酰氯 、 Amberlyst 15 (H+) 、 氰化钠 、 氢气 、 溴 、 三溴化磷 、 lithium carbonate 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 calcium carbonate 、 lithium bromide 作用下， 以 甲醇 、 乙醚 、 水 、 二甲基亚砜 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 75.16h， 生成 12-羟基茉莉酸
  参考文献：
  名称：

  Struktur und synthese von n-(acetoxy)-jasmonoylphenylalaninmethylester aus Praxelis clematidea

  摘要：

  DOI：

  10.1016/s0040-4020(01)83506-7

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。
• Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA
  作者：Hisato Nonaka、Narihito Ogawa、Noriaki Maeda、Yong-Gang Wang、Yuichi Kobayashi

  DOI：10.1039/c0ob00218f

  日期：——

  epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser–Claisen rearrangement, and regioselective Swern oxidation

  表-茉莉酸 （Epi -JA） 和 胡椒酸 （TA）是由关键醛合成的，所有 顺-2-（2-羟基-5-乙烯基环戊基）乙醛（14），其又由（1R）-乙酸的乙酸酯立体选择性地制备。4-环戊烯-1,3-二醇（10）通过用CH 2 CHMgBr进行S N 2型烯丙基取代，然后进行Mitsunobu转化，埃申摩瑟–相应的bis-TES醚（13）的克莱森重排和区域选择性Swern氧化。醛14与[Ph 3 P（CH 2）Me] +的维蒂希反应溴−随后进行氧化Epi -JA（3）对反式异构体的立体选择性。相似地，TA（5）被合成。此外，上述发现已成功地用于提高以前合成的12-氧代PDA（1）。
• Elsholblanosides A−D, Four New Oleuropeic Acid Derivatives Isolated from <i>Elsholtzia blanda</i> and Their Inhibition of NO Production in LPS‐activated RAW264.7 Cells
  作者：Duong Thi Dung、Do Thi Trang、Pham Hai yen、Nguyen Huy Hoang、Bui Huu Tai、Phan Van Kiem

  DOI：10.1002/cbdv.202300785

  日期：2023.8

  afforded four new oleuropeic acid derivatives (1–4), named as elsholblanosides A−D, respectively, together with 11 known compounds (5–15). Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR, and ECD spectra. Compounds 1–4 and 14 showed moderate NO production inhibition in LPS-activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33 μM, compared

  香薷地上部分的植物化学调查。提供了四种新的橄榄酸衍生物 ( 1 – 4 )，分别命名为 elsholblanosides A−D，以及 11 种已知化合物 ( 5 – 15 )。它们的结构是根据 HR-ESI-MS、1D 和 2D NMR 以及 ECD 光谱的广泛分析确定的。化合物1-4和14在LPS激活的RAW264.7细胞中表现出中等程度的NO产生抑制作用，其IC 50值范围为23.2至86.33 μM ，而阳性对照化合物地塞米松的IC 50值为16.9 μM。
• 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.
• 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.