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
識別
CAS號	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
性質
化學式	C13H20O3
莫耳質量	224.3 g·mol⁻¹
外觀	無色液體
熔點	<25℃
沸點	88-90 °C（361-363 K）（當0.1 mmHg）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

茉莉酸甲酯 (縮寫 MeJA)是一種揮發性有機物用於植物防衛和許多不同的發育途徑如種子發芽、根的生長、開花、果實成熟與植物老化。^[1] 茉莉酸甲酯是來自茉莉酸，該反應由S-腺苷-L-甲硫氨酸:茉莉酸羧基甲基轉移酶催化。^[2]

描述

當植物遭遇生物或非生物脅迫時（特別是食草生物或創傷），植物會產生茉莉銅酸和茉莉酸甲酯堆積在受損的部位，茉莉酸甲酯會向原先植物的防禦系統發出信號，也可以通過物理接觸或通過空氣傳播，在未受損的植物中產生防禦反應。未受損的植物通過氣孔或通過葉細胞的細胞質擴散吸收空氣中的茉莉酸甲酯，遭受脅迫時使其產生茉莉酸甲酯，既用於內部防禦又是向其他植物的信號傳導化合物。^[3]

防禦型化學藥劑

茉莉酸甲酯可以誘導植物產生多種不同類型的防禦化學物質例如植物抗毒素（抗菌素）^[4] 、尼古丁或蛋白酶抑制劑，蛋白酶抑制劑會干擾昆蟲的消化過程，阻止昆蟲再次食用植物。

茉莉酸甲酯已被用於刺激生產挪威雲杉樹受損的樹脂管（英語：Resin canal）。^[5] 這可以將其作為一種疫苗來抵禦許多昆蟲的襲擊。

實驗

在最近的實驗中，茉莉酸甲酯噴灑在植物葉片上時，可有效地預防植物中細菌的生長。科學家認為該抗菌作用是來自茉莉酸甲酯誘導的抗性。^[6]

茉莉酸甲酯同時也是一種植物激素，參與卷鬚（根）的捲曲、開花、種子和果實的成熟。激素的多寡會影響開花時間、花的形態和開花的數量。^[7] 茉莉酸甲酯誘導乙烯控制酶活性，從而將乙烯的量增加至水果成熟所必需的量。^[8]

實驗證明植物根部茉莉酸甲酯的多寡會抑制植物其生長。^[9] 據預測，較高數量的茉莉酸甲酯會激活根部先前未激活的基因從而導致生長抑制。^[10]

癌細胞

茉莉酸甲酯誘發癌細胞粒線體中的細胞色素c的釋放，導致細胞死亡，但不會損害正常細胞。具體來說，它可能令導致患有B細胞慢性淋巴細胞白血病的人類患者中的細胞死亡，在組織培養物中用茉莉酸甲酯處理時，正常人分離淋巴細胞的治療時未導致細胞死亡。 ^[11]

參見

茉莉酮
甲基二氫茉莉酮

參考文獻

^ 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.
^ Christie, William W. Plant oxylipins: Chemistry and biology, 22 May 2014. Archived from the original on 2015-06-30. Retrieved on 2017-07-11.
^ 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.
^ Stanley, D. Keeping Freshness in Fresh-Cut Produce （頁面存檔備份，存於網際網路檔案館）, Agricultural Research Magazine, United States Department of Agriculture, Feb. 1998. Retrieved on 2010-10-27.
^ Martin, D.M., Gershenzon J. and Bohlmann J. Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce （頁面存檔備份，存於網際網路檔案館）, Plant Physiology, 2003. Retrieved on 2016-09-01.
^ 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.
^ 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.
^ 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.
^ Wasternack, C. Jasmonates: An Update on Biosynthesis, Signal Transduction and Action in Plant Stress Response, Growth and Development （頁面存檔備份，存於網際網路檔案館）. Annals of Botany (2007) 100(4):681-697. doi:10.1093/aob/mcm079. Retrieved on 2010-10-27.
^ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC157863/
^ 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 （頁面存檔備份，存於網際網路檔案館）. Cancer Research 65(5):1984-1993. doi:10.1158/0008-5472.CAN-04-3091. Retrieved on 2010-10-27.

外部連結

General information about methyl jasmonate （頁面存檔備份，存於網際網路檔案館）
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 （頁面存檔備份，存於網際網路檔案館）, Leukemia, Nature, April 2002, Volume 16, Number 4, Pages 608-616
Jasmonates induce nonapoptotic death in high-resistance mutant p53-expressing B-lymphoma cells （頁面存檔備份，存於網際網路檔案館）, British Journal of Pharmacology (2005) 146, 800–808. doi:10.1038/sj.bjp.0706394; published online 19 September 2005

[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.

[scichina-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 （頁面存檔備份，存於網際網路檔案館）, 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 （頁面存檔備份，存於網際網路檔案館）, 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.

[ncbi-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 （頁面存檔備份，存於網際網路檔案館）. Annals of Botany (2007) 100(4):681-697. doi:10.1093/aob/mcm079. Retrieved on 2010-10-27.

[10] ttps://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 （頁面存檔備份，存於網際網路檔案館）. Cancer Research 65(5):1984-1993. doi:10.1158/0008-5472.CAN-04-3091. Retrieved on 2010-10-27.

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茉莉酸甲酯

IUPAC名 Methyl (1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetate
英文名	Methyl jasmonate
識別
CAS號	1211-29-6 ^Y
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
性質
化學式	C₁₃H₂₀O₃
莫耳質量	224.3 g·mol⁻¹
外觀	無色液體
熔點	<25℃
沸點	88-90 °C（361-363 K）（當0.1 mmHg）
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。