title: Isolation and structure elucidation of linolipins C and D, complex oxylipins from flax leaves.
abstract: Two complex oxylipins (linolipins C and D) were isolated from the leaves of flax plants inoculated with phytopathogenic bacteria Pectobacterium atrosepticum. Their structures were elucidated based on UV, MS and NMR spectroscopic data. Both oxylipins were identified as digalactosyldiacylglycerol (DGDG) molecular species. Linolipin C contains one residue of divinyl ether (ω5Z)-etherolenic acid and one α-linolenate residue at sn-1 and sn-2 positions, respectively. Linolipin D possesses two (ω5Z)-etherolenic acid residues at both sn-1 and sn-2 positions. The rapid formation (2-30min) of linolipins C and D alongside with linolipins A and B occurred in the flax leaves upon their damage by freezing-thawing.
authors.affiliation: Kazan Institute of Biochemistry and Biophysics, Russian Academy of Sciences, P.O. Box 30, 420111 Kazan, Russia. Electronic address: chechyotkin@mail.knc.ru.
authors.forename: Ivan R
authors.initials: IR
authors.lastname: Chechetkin
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Blufard
authors.forename: Bulat I
authors.initials: BI
authors.lastname: Khairutdinov
authors.forename: Fakhima K
authors.initials: FK
authors.lastname: Mukhitova
authors.forename: Svetlana S
authors.initials: SS
authors.lastname: Gorina
authors.forename: Andrey Y
authors.initials: AY
authors.lastname: Yarin
authors.forename: Larisa L
authors.initials: LL
authors.lastname: Antsygina
authors.forename: Alexander N
authors.initials: AN
authors.lastname: Grechkin
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D019597:Flax / Q000737:chemistry* / Q000378:metabolism / Q000382:microbiology; D038983:Galactolipids / Q000737:chemistry; D008049:Lipase / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054883:Oxylipins / Q000737:chemistry / Q000302:isolation & purification*; D044043:Pectobacterium / Q000378:metabolism; D018515:Plant Leaves / Q000737:chemistry / Q000382:microbiology; D010940:Plant Proteins / Q000032:analysis / Q000378:metabolism; D013237:Stereoisomerism; D017962:alpha-Linolenic Acid / Q000032:analysis
chemical_list: D038983:Galactolipids; D054883:Oxylipins; D010940:Plant Proteins; C007388:digalactosyldiacylglycerol; C000588945:linolipin C; C000588946:linolipin D; D017962:alpha-Linolenic Acid; D003577:Cytochrome P-450 Enzyme System; C100485:divinyl ether synthase; D008049:Lipase
keywords: (13S)-HPOT; (13S)-hydroperoxy-MGDG; (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid; 1,2-Di-O-[(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoyl]-3-O-β-d-galactopyranosyl-sn-glycerol; DES; Divinyl ether synthase; ESI MS; Etherolenic acid; Flax; Galactolipid; LOX; Linaceae; Linum usitatissimum; Oxylipin; Pectobacterium atrosepticum; SBOCFWSPOCJDHY-NXTVNIMXSA-N; SSSOQCOUWWCQSF-MNNDCQRZSA-N; divinyl ether synthase; electrospray ionization mass spectrometry; lipoxygenase