Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

Abstract

Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(ω5Z)-etherolenoyl-2-O-dinor-(ω5Z)-etherolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-β-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-(7Z,10Z)-hexadecadienoyl-3-O-β-D-galactopyranosyl-sn-glycerol, 1-O-(ω5Z)-etherolenoyl-2-O-α-linolenoyl-3-O-β-D-galactopyranosyl-sn-glycerol, and 1-O-(ω5Z)-etherolenoyl-2-O-palmitoyl-3-O-(α-galactopyranosyl-1-6-β-D-galactopyranosyl)-sn-glycerol. The trivial names “linolipins E, F, G, H and I,” respectively, have been ascribed to these novel complex oxylipins.