methyl 12-hydroxyjasmonate | 179915-48-1

• 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 12-hydroxyjasmonate
• 英文别名: methyl 2-[(1R,2R)-2-[(Z)-5-hydroxypent-2-enyl]-3-oxocyclopentyl]acetate
• CAS: 179915-48-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: XCZTYYQNVNLGKI-LVUHIJSRSA-N

物化性质

• 沸点：
  363.8±17.0 °C(predicted)
• 密度：
  1.087±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 12-hydroxyjasmonate 在 氢氧化钾 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到12-羟基茉莉酸
  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：

  茉莉酸甲酯 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 methyl 12-hydroxyjasmonate
  参考文献：
  名称：

  Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds

  摘要：

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.092

文献信息

• Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity
  作者：Minoru Ueda、Gangqiang Yang、Yuuki Nukadzuka、Yasuhiro Ishimaru、Satoru Tamura、Yoshiyuki Manabe

  DOI：10.1039/c4ob02106a

  日期：——

  Importance of the d-glycopyranoside structure for the bioactivity and target affinity of jasmonic acid glucoside.

  "

  d-葡萄糖苷结构对茉莉酸葡萄糖苷的生物活性和靶标亲和力的重要性。

  "
• Cardioactive steroid saponins and other constituents from the aerial parts of tribulus cistoides☆
  作者：Hans Achenbach、Harald Hübner、Wolfgang Brandt、Melchior Reiter

  DOI：10.1016/s0031-9422(00)86890-9

  日期：1994.4.19

  From the petrol extract of the aerial parts of Tribulus cistoides three steroid sapogenins and two N-acyltyramines were isolated, whereas the methanolic extract gave nine steroid saponins, among them the cardioactive cistocardin, saponin-3, saponin-4 and saponin-7. Furthermore, a furostanol diglycoside was isolated besides 5'-(hydroxysulphonyloxy) jasmonic acid, D-(+)-pinitol and sucrose. The structures

  从刺蒺藜地上部分的汽油提取物中分离出三种甾体皂苷元和两种 N-酰基酪胺，而甲醇提取物得到九种甾体皂苷，其中有心脏活性的cistocardin、saponin-3、saponin-4和saponin-7。此外，除5'-(羟基磺酰氧基)茉莉酸、D-(+)-松醇和蔗糖外，还分离了呋甾醇二糖苷。这些结构是通过对分离的化合物及其水解产物的光谱研究确定的。5'-(Hydroxysulphonyloxy)茉莉酸已通过部分合成制备。
• 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.
• 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。
• Enantio-differential approach to identify the target cell for glucosyl jasmonate-type leaf-closing factor, by using fluorescence-labeled probe compounds
  作者：Yoko Nakamura、Ryoji Miyatake、Akira Matsubara、Hiromasa Kiyota、Minoru Ueda

  DOI：10.1016/j.tet.2006.06.092

  日期：2006.9

  Potassium beta-D-glucopyranosyl 12-hydroxyjasmonate (1) is a leaf-closing factor of Albizzia plants that induces nyctinastic leaf closure. In this paper, we synthesized probe 3 and its congener 4 by using a pair of enantiomerically pure methyljasmonate that was prepared by using optical resolution, and carried out fluorescence studies using 3 and 4 to identify the target cell of 1. The probe 3 bound to the motor cells of two Albizzia plants, whereas it could not bind to the motor cells of plants belonging to other genus. On the other hand, probe 4 did not bind to the motor cell at all. These results suggested that a specific receptor for I is involved in the motor cell of Albizzia plants. (c) 2006 Elsevier Ltd. All rights reserved.