茉莉酸甲酯

茉莉酸甲酯
	IUPAC名; Methyl (1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetate
英文名	Methyl jasmonate
识别
CAS号	1211-29-6
PubChem	5281929
ChemSpider	4445210
SMILES	O=C1[C@H](C/C=C\CC)[C@@H](CC(OC)=O)CC1;
InChI	1/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1;
InChIKey	GEWDNTWNSAZUDX-WQMVXFAEBM
EINECS	243-497-1
ChEBI	15929
KEGG	C11512
性质
化学式	C13H20O3
摩尔质量	224.3 g·mol⁻¹
外观	无色液体
熔点	<25℃
沸点	88-90 °C（361-363 K）（当0.1 mmHg）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

茉莉酸甲酯 (缩写 MeJA)是一种挥发性有机物用于植物防卫和许多不同的发育途径如种子发芽、根的生长、开花、果实成熟与植物老化。^[1] 茉莉酸甲酯是来自茉莉酸，该反应由S-腺苷-L-甲硫氨酸:茉莉酸羧基甲基转移酶催化。^[2]

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描述

当植物遭遇生物或非生物胁迫时（特别是食草生物或创伤），植物会产生茉莉铜酸和茉莉酸甲酯堆积在受损的部位，茉莉酸甲酯会向原先植物的防御系统发出信号，也可以通过物理接触或通过空气传播，在未受损的植物中产生防御反应。未受损的植物通过气孔或通过叶细胞的细胞质扩散吸收空气中的茉莉酸甲酯，遭受胁迫时使其产生茉莉酸甲酯，既用于内部防御又是向其他植物的信号传导化合物。^[3]

防御型化学药剂

茉莉酸甲酯可以诱导植物产生多种不同类型的防御化学物质例如植物抗毒素（抗菌素）^[4] 、尼古丁或蛋白酶抑制剂，蛋白酶抑制剂会干扰昆虫的消化过程，阻止昆虫再次食用植物。

茉莉酸甲酯已被用于刺激生产挪威云杉树受损的树脂管（英语：Resin canal）。^[5] 这可以将其作为一种疫苗来抵御许多昆虫的袭击。

实验

在最近的实验中，茉莉酸甲酯喷洒在植物叶片上时，可有效地预防植物中细菌的生长。科学家认为该抗菌作用是来自茉莉酸甲酯诱导的抗性。^[6]

茉莉酸甲酯同时也是一种植物激素，参与卷须（根）的卷曲、开花、种子和果实的成熟。激素的多寡会影响开花时间、花的形态和开花的数量。^[7] 茉莉酸甲酯诱导乙烯控制酶活性，从而将乙烯的量增加至水果成熟所必需的量。^[8]

实验证明植物根部茉莉酸甲酯的多寡会抑制植物其生长。^[9] 据预测，较高数量的茉莉酸甲酯会激活根部先前未激活的基因从而导致生长抑制。^[10]

癌细胞

茉莉酸甲酯诱发癌细胞线粒体中的细胞色素c的释放，导致细胞死亡，但不会损害正常细胞。具体来说，它可能令导致患有B细胞慢性淋巴细胞白血病的人类患者中的细胞死亡，在组织培养物中用茉莉酸甲酯处理时，正常人分离淋巴细胞的治疗时未导致细胞死亡。 ^[11]

参见

茉莉酮
甲基二氢茉莉酮

参考文献

[1]
Cheong, Jong-Joo; Choi, Yang Do. Methyl jasmonate as a vital substance in plants. Trends in Genetics. July 2003, 19 (7): 409–413. doi:10.1016/S0168-9525(03)00138-0.
[2]
Christie, William W. Plant oxylipins: Chemistry and biology, 22 May 2014. Archived from the original on 2015-06-30. Retrieved on 2017-07-11.
[3]
Farmer, E. E.; Ryan, C. A. Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves.. Proceedings of the National Academy of Sciences. 1 October 1990, 87 (19): 7713–7716. PMC 54818 . doi:10.1073/pnas.87.19.7713.
[4]
Stanley, D. Keeping Freshness in Fresh-Cut Produce （页面存档备份，存于互联网档案馆）, Agricultural Research Magazine, United States Department of Agriculture, Feb. 1998. Retrieved on 2010-10-27.
[5]
Martin, D.M., Gershenzon J. and Bohlmann J. Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce （页面存档备份，存于互联网档案馆）, Plant Physiology, 2003. Retrieved on 2016-09-01.
[6]
Luzzatto, T., Yishay, M., Lipsky, A., Ion, A., Belausov, E. and Yedidia, I. Efficient, long-lasting resistance against the soft rot bacterium Pectobacterium carotovorum in calla lily provided by the plant activator methyl jasmonate. Plant Pathology, 56(4):692-701, Aug 2007. doi:10.1111/j.1365-3059.2007.01622.x. Retrieved 2017-07-11.
[7]
Radhika, V., J. Cost, W. Boland, and M. Heil. The role of jasmonates in floral nectar secretion. PLOS ONE. 2010. doi:10.1371/journal.pone.0009265 Retrieved on 2010-10-27.
[8]
Berger, S.; Bell, E.; Mullet, J. E. Two Methyl Jasmonate-Insensitive Mutants Show Altered Expression of AtVsp in Response to Methyl Jasmonate and Wounding. Plant Physiology. 1 June 1996, 111 (2): 525–531. PMC 157863 . doi:10.1104/pp.111.2.525.
[9]
Wasternack, C. Jasmonates: An Update on Biosynthesis, Signal Transduction and Action in Plant Stress Response, Growth and Development （页面存档备份，存于互联网档案馆）. Annals of Botany (2007) 100(4):681-697. doi:10.1093/aob/mcm079. Retrieved on 2010-10-27.
[10]
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC157863/
[11]
Rotem, R., A. Heyfets, O. Fingrut, D. Blickstein, M. Shaklai, and E. Flesher. 2005. Jasmonates: novel anticancer agents acting directly and selectively on human cancer cell mitochondria （页面存档备份，存于互联网档案馆）. Cancer Research 65(5):1984-1993. doi:10.1158/0008-5472.CAN-04-3091. Retrieved on 2010-10-27.

外部链接

General information about methyl jasmonate （页面存档备份，存于互联网档案馆）
Jasmonate: pharmaceutical composition for treatment of cancer. US Patent Issued on October 22, 2002
Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells （页面存档备份，存于互联网档案馆）, Leukemia, Nature, April 2002, Volume 16, Number 4, Pages 608-616
Jasmonates induce nonapoptotic death in high-resistance mutant p53-expressing B-lymphoma cells （页面存档备份，存于互联网档案馆）, British Journal of Pharmacology (2005) 146, 800–808. doi:10.1038/sj.bjp.0706394; published online 19 September 2005

[1] [1]
Cheong, Jong-Joo; Choi, Yang Do. Methyl jasmonate as a vital substance in plants. Trends in Genetics. July 2003, 19 (7): 409–413. doi:10.1016/S0168-9525(03)00138-0.

[2] [2]
Christie, William W. Plant oxylipins: Chemistry and biology, 22 May 2014. Archived from the original on 2015-06-30. Retrieved on 2017-07-11.

[scichina-3] [3]
Farmer, E. E.; Ryan, C. A. Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves.. Proceedings of the National Academy of Sciences. 1 October 1990, 87 (19): 7713–7716. PMC 54818 . doi:10.1073/pnas.87.19.7713.

[4] [4]
Stanley, D. Keeping Freshness in Fresh-Cut Produce （页面存档备份，存于互联网档案馆）, Agricultural Research Magazine, United States Department of Agriculture, Feb. 1998. Retrieved on 2010-10-27.

[5] [5]
Martin, D.M., Gershenzon J. and Bohlmann J. Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce （页面存档备份，存于互联网档案馆）, Plant Physiology, 2003. Retrieved on 2016-09-01.

[6] [6]
Luzzatto, T., Yishay, M., Lipsky, A., Ion, A., Belausov, E. and Yedidia, I. Efficient, long-lasting resistance against the soft rot bacterium Pectobacterium carotovorum in calla lily provided by the plant activator methyl jasmonate. Plant Pathology, 56(4):692-701, Aug 2007. doi:10.1111/j.1365-3059.2007.01622.x. Retrieved 2017-07-11.

[7] [7]
Radhika, V., J. Cost, W. Boland, and M. Heil. The role of jasmonates in floral nectar secretion. PLOS ONE. 2010. doi:10.1371/journal.pone.0009265 Retrieved on 2010-10-27.

[ncbi-8] [8]
Berger, S.; Bell, E.; Mullet, J. E. Two Methyl Jasmonate-Insensitive Mutants Show Altered Expression of AtVsp in Response to Methyl Jasmonate and Wounding. Plant Physiology. 1 June 1996, 111 (2): 525–531. PMC 157863 . doi:10.1104/pp.111.2.525.

[9] [9]
Wasternack, C. Jasmonates: An Update on Biosynthesis, Signal Transduction and Action in Plant Stress Response, Growth and Development （页面存档备份，存于互联网档案馆）. Annals of Botany (2007) 100(4):681-697. doi:10.1093/aob/mcm079. Retrieved on 2010-10-27.

[10] [10]
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC157863/

[11] [11]
Rotem, R., A. Heyfets, O. Fingrut, D. Blickstein, M. Shaklai, and E. Flesher. 2005. Jasmonates: novel anticancer agents acting directly and selectively on human cancer cell mitochondria （页面存档备份，存于互联网档案馆）. Cancer Research 65(5):1984-1993. doi:10.1158/0008-5472.CAN-04-3091. Retrieved on 2010-10-27.

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