cis-12-oxo-Phytodieneoic acid-α-monoglyceride (1) was isolated from Arabidopsis thaliana. The chemical structure of 1 was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the cis-OPDA moiety in 1 was determined by comparison of ¹H NMR spectra and ECD measurements. With respect to the absolute configuration of the β-position of the glycerol backbone, the 2:3 ratio of (S) to (R) was determined by making ester-bonded derivatives with (R)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride and comparing ¹H NMR spectra. Wounding stress did not increase endogenous levels of 1, and it was revealed 1 had an inhibitory effect of A. thaliana post germination growth. Notably, the endogenous amount of 1 was higher than the amounts of (+)-7-iso-jasmonic acid and (+)-cis-OPDA in intact plants. 1 also showed antimicrobial activity against Gram-positive bacteria, but jasmonic acid did not. It was also found that α-linolenic acid-α-monoglyceride was converted into 1 in the A. thaliana plant, which implied α-linolenic acid-α-monoglyceride was a biosynthetic intermediate of 1.

中文翻译：

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拟南芥顺式OPDA-α-单甘油酯的分离及结构测定

顺式-12-氧代-植物二烯酸-α-单甘油酯( 1 )是从拟南芥中分离出来的。1的化学结构是基于详尽的 1D 和 2D NMR 光谱测量并得到 FDMS 和 HRFDMS 数据的支持而阐明的。1中顺式-OPDA 部分的绝对构型通过比较¹ H NMR 谱和 ECD 测量来确定。关于甘油主链β位的绝对构型，通过与( R )-(+)-α-甲氧基-制备酯键衍生物来确定( S )与( R )的2:3比例。 α-三氟甲基苯乙酰氯并比较¹ H NMR 谱。创伤应激不会增加1的内源水平，并且表明1对拟南芥发芽后生长具有抑制作用。值得注意的是，完整植物中1的内源量高于(+)-7-异茉莉酸和(+)-顺式-OPDA的量。 1还表现出对革兰氏阳性菌的抗菌活性，但茉莉酸却没有。还发现α-亚麻酸-α-单甘油酯在拟南芥植物中转化为1，这表明α-亚麻酸-α-单甘油酯是1的生物合成中间体。