Gas chromatographic/mass spectrometric and tandem mass spectrometric investigations of synthetic amino acid conjugates of jasmonic acid and endogenously occurring related compounds fromVicia faba L

Abstract

Some partial synthetic amino acid ((S)‐alanine, (S)‐leucine, (S)‐isoleucine, (S)‐aspartic acid, (S)‐glutamic acid, (S)‐phenylalanine, (S)‐ and (R)‐valine) conjugates of the plant growth regulator (‐)‐jasmonic acid (JA) were investigated as methyl esters by capillary gas chromatography/mass spectrometry. By gas chromatographic data (retention indices) as well as by mass spectral behaviour all these substances can be differentiated unequivocally. In addition, the distinction between the leucine and isoleucine JA conjugates was carried out by mass‐analysed ion kinetic energy spectroscopy (tandem mass spectrometry). Based on this some naturally occurring (S)‐isoleucine conjugates of (‐)‐JA, (+)‐7‐iso‐JA and related compounds as well as the (S)‐leucine and (S)‐phenylalanine conjugates of (‐)‐JA could be identified from extracts of the broad bean Vicia faba L.

Amino acid conjugates as metabolites of the plant growth regulator dihydrojasmonic acid in barley (Hordeum vulgare)

“…3). This is in accordance to the principal fragmentation of the JA amino acid conjugates (Kramell et al 1988, Schmidt et al 1990). The fragments b and e comprise the basic structure of DJA, whereas ions of type c, d, (c-C4H8), (e-COOCH3), and Methylated metabolite A2 (A2-Me) shows a molecular ion M + at rrdz 339.…”

“…Contrary, in the leucine conjugate the peak of m/z 131 (88%) shows much higher intensity than that of rvdz 128 (19%). This relationship is in accordance with the MS behavior of the synthetic isoleucine and leucine conjugates of JA, respectively (Schmidt et al 1990). Thus, the metabolite A3 has been identified as N-[9,10-dihydrojasmonoyl]leucine.…”

“…[dihydrojasmonoyl]isoleucine (Cross and Webster 1970), whereas the N-[(-)jasmonoyl]-S-isoleucine is found to occur naturally in apical leaves and young fruits of Vicia faba (Schmidt et al 1990, Schneider et al 1989. However, metabolites conjugated with aromatic amino acids like the N-(12-acetoxyjasmonoyl)phenylalanine methyl ester from Praxelis clematidea (Bohlmann et al 1984) Br~ickner et al 1986, Brfickner et al 1988 could not be detected in barley shoots.…”

Partial purification and characterization of a jasmonic acid conjugate cleaving amidohydrolase from the fungus Botryodiplodia theobromae

“…JA conjugates with isoleucine, leucine and valine were isolated as endogenous compounds from fruits and young leaves of Vicia faba L. [7]. The isoleucine derivative of (-)-jasmonic acid was also reported in pollen of Pinus mugo [8].…”

Transient accumulation of .ALPHA.-ketol linolenic acid (KODA) in immature flower buds of some ornamental plants

“…Flowers of dicotyledonous plants contain high levels of jasmonates, including amino acid conjugates or amides (Miersch et al 1997;Schmidt et al 1990). Hause et al (2000) showed that JA, 12-oxophytodienoic acid (OPDA) and JA isoleucine conjugate were accumulated in flowers of developing plants at much higher concentration (20 nmol/g-tissue) than in leaves.…”