2-[(1R,2S)-2-[(Z)-5-羟基戊-2-烯基]-3-氧代环戊基]乙酸 | 124649-26-9

• 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: 2-[(1R,2S)-2-[(Z)-5-羟基戊-2-烯基]-3-氧代环戊基]乙酸
• 英文名称: 12-hydroxy-epi-jasmonic acid
• 英文别名: tuberonic acid；TA；2-[(1R,2S)-2-[(Z)-5-hydroxypent-2-enyl]-3-oxocyclopentyl]acetic acid
• CAS: 124649-26-9
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: RZGFUGXQKMEMOO-SZXTZRQCSA-N

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

反应信息

• 作为反应物：
  描述：

  2-[(1R,2S)-2-[(Z)-5-羟基戊-2-烯基]-3-氧代环戊基]乙酸 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以79%的产率得到12-羟基茉莉酸
  参考文献：
  名称：

  表位茉莉酸，胡椒酸和12-氧代PDA的 立体选择性合成†

  摘要：

  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）。

  DOI：

  10.1039/c0ob00218f
• 作为产物：
  描述：

  tuberonic acid glucoside 在 Oryza sativa L. cv. Kitaake tuberonic acid glucoside-hydrolyzing β-glucosidase 、 水 作用下， 反应 0.17h， 生成 2-[(1R,2S)-2-[(Z)-5-羟基戊-2-烯基]-3-氧代环戊基]乙酸
  参考文献：
  名称：

  Identification of a β-glucosidase hydrolyzing tuberonic acid glucoside in rice (Oryza sativa L.)

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2010.04.025

文献信息

• Compositions of Jasmonate Compounds and Methods of Use
  申请人：NanoCare Technologies, Inc.

  公开号：US20130089615A1

  公开（公告）日：2013-04-11

  The disclosure describes nanocarried and/or microcarried jasmonate compounds and their pharmaceutical compositions, as well as use thereof for treating or preventing angiogenesis-related or NF-κB-related disorders. Also disclosed are methods of making the nanocarried and/or microcarried compounds and their compositions.

  该披露描述了纳米载体和/或微米载体的茉莉酸化合物及其制药组合物，以及其用于治疗或预防与血管生成相关或NF-κB相关的疾病的用途。还披露了制备纳米载体和/或微米载体化合物及其组合物的方法。
• COMPOSITIONS OF JASMONATE COMPOUNDS AND METHODS OF USE
  申请人：Nanocare Technologies, Inc.

  公开号：US20150140110A1

  公开（公告）日：2015-05-21

  The disclosure describes nanocarried and/or microcarried jasmonate compounds and their pharmaceutical compositions, as well as use thereof for treating or preventing angiogenesis-related or NF-κB-related disorders. Also disclosed are methods of making the nanocarried and/or microcarried compounds and their compositions.

  该披露描述了纳米载体和/或微米载体茉莉酸化合物及其药物组合物，以及用于治疗或预防与血管生成有关或NF-κB相关的疾病的用途。还披露了制备纳米载体和/或微米载体化合物及其组合物的方法。
• PROCESS FOR PRODUCING TAXANE DITERPENE AND METHOD OF HARVESTING CULTRED CELL CAPABLE OF PRODUCING TAXANE DITERPENE IN HIGH YIELD
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0683232A1

  公开（公告）日：1995-11-22

  A process for producing a taxane diterpene which comprises culturing the tissue or cell of a plant that produces a taxane diterpene in the presence of at least one member selected from the group consisting of jasmonic acids, heavy metal compounds, heavy metal complex ions, heavy metal ions, amines and ethylene-resisting agent; another process for producing a taxane diterpene which comprises culturing the tissue or cell by controlling the condition from the outset such that the oxygen concentration in the gas phase within the culture vessel is lower than the atmospheric oxygen concentration or that the dissolved oxygen concentration in the flowable medium in contact with the tissue or cell is lower than the saturation dissolved oxygen concentration at that temperature; still another process for producing a taxane diterpene which comprises culturing the tissue or cell in a culture tank by flowing into the tank an oxygenic gas containing 0.03-10 % of carbon dioxide; and a method of harvesting a cultured cell capable of producinga taxane diterpene in a high yield which comprises distributing the cells among a number of layers on the basis of a difference in specific gravity, culturing the cells contained in at least one of the layers, and selecting the target cell from among the cells thus cultured. The invention permits industrial production of taxane diterpenes such as taxol useful as a cancer remedy.

  一种生产紫杉烷二萜的工艺，包括在至少一种选自茉莉酸、重金属化合物、重金属络合离子、重金属离子、胺和抗乙烯剂的成员存在下培养产生紫杉烷二萜的植物组织或细胞；另一种生产紫杉烷二萜的工艺，包括在培养组织或细胞时，从一开始就控制 条件，使培养容器内气相中的氧浓度低于大气氧浓度，或使与组织或细胞接 触的可流动介质中的溶解氧浓度低于该温度下的饱和溶解氧浓度； 还有一种生产紫杉烷二萜的工艺，包括在培养槽中培养组织或细胞，向槽中通 入含氧气体，该气体含有 0.03-10%的二氧化碳；以及一种收获能高产生产紫杉烷二萜烯的培养细胞的方法，该方法包括根据比重差将细胞分布在若干层中，培养至少其中一层中的细胞，并从这样培养的细胞中选择目标细胞。本发明允许工业化生产可用于治疗癌症的紫杉烷二萜，如紫杉醇。
• A method of producing a taxane-type diterpene
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0727492A2

  公开（公告）日：1996-08-21

  A method of producing a taxane-type diterpene wherein cells and/or tissue of a plant which produces a taxane-type diterpene is cultured in the presence of at least one substance selected from a coronatine, a bacterium which produces the coronatine, a culture solution or a culture extract of said bacterium, a cyclic polysaccaride, a fatty acid compound, and a compound of formula (X) or (XI): and the taxane-type diterpene is recovered from the resulting culture.

  一种生产紫杉烷型二萜的方法，其中生产紫杉烷型二萜的植物的细胞和/或组织在至少一种物质的存在下进行培养，这些物质选自冠突散囊菌、产生冠突散囊菌的细菌、上述细菌的培养液或培养提取物、环状多羰基化合物、脂肪酸化合物和式(X)或(XI)化合物： 并从所得培养液中回收紫杉烷型二萜。
• A method of producing a taxane-type diterpene and method of obtaining cultured cells which produce the taxane-type diterpene at a high rate
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1063300A2

  公开（公告）日：2000-12-27

  This invention relates to a method of producing a taxane-type diterpene(s) wherein tissues or cells of a plant which produces taxane-type diterpene(s) is cultured in the presence of at least one selected from the group consisting of jasmonic acids, compounds containing a heavy metal, complex ions containing a heavy metal, heavy metal ions, amines and antiethylene agents, a method of producing a taxane-type diterpene wherein the tissues or the cells of the plant are cultured by controlling the oxygen concentration in a gas phase in a culture vessel to less than the oxygen concentration in the atmosphere from the initial stage of the culture, or by controlling the dissolved oxygen concentration in a fluid medium which is in contact with the tissue or the cell to less than the saturated dissolved oxygen concentration at that temperature from the initial stage of the culture, a method of producing a taxane-type diterpene wherein the tissue or the cell of the plant is cultured in a culture vessel, while oxygenic gas containing 0.03 - 10 % of carbon dioxide is used as aeration gas to be introduced to the vessel, and a method of obtaining highly productive cultured cells for the taxane-type diterpene wherein cultured cells of the plant which produces the taxane-type diterpene are separated into a plurality of layers according to the difference in their specific gravities, and the cells contained in at least one layer are cultured, then highly productive cultured cells for the taxane-type diterpene are selected from among those cultured cells. The present invention allows industrial production of a taxane-type diterpene such as taxol which is useful as a therapeutic agent for cancer.

  本发明涉及一种生产紫杉烷型二萜的方法，其中生产紫杉烷型二萜的植物的组织或细胞是在至少一种选自茉莉酸、含重金属的化合物、含重金属的络离子、胺和抗乙烯剂的组中的一种存在下培养的、一种生产紫杉烷类二萜的方法，其中植物组织或细胞的培养是通过控制培养容器中气相中的氧浓度，使其从培养初始阶段起就低于大气中的氧浓度、一种生产紫杉烷类二萜的方法，其中植物的组织或细胞在培养容器中培养，而含氧气体中含有 0.03-10%的二氧化碳作为通气气体引入培养容器中，以及一种获得高产培养细胞的方法，其中将产生萜类二萜的植物的培养细胞根据其比重的差异分成多层，并培养至少一层中所含的细胞，然后从这些培养细胞中选出高产的萜类二萜培养细胞。 本发明可以工业化生产可用作癌症治疗剂的紫杉烷类二萜，如紫杉醇。