Isolation and Structure Determination of -OPDA-α-Monoglyceride from .

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