Betaines of Alfalfa

Abstract

Leaf tissue of alfalfa (Medicago sativa L.) was found to contain prolinebetaine, pipecolatebetaine, hydroxyprolinebetaine, and glycinebetaine. As n-butyl esters, these chemical species exhibit molecular cations at mass/charge ratio (m/z) 200, 214, 216, and 174, respectively, when analyzed by fast atom bombardment mass spectrometry. The underivatized betaines exhibit protonated molecular ions at m/z 144, 158, 160, and 118, respectively, when analyzed by desorption chemical ionization mass spectrometry. Extensive (>45-fold) genotypic variation for hydroxyprolinebetaine level was identified in alfalfa. Because a significant inverse correlation between prolinebetaine and hydroxyprolinebetaine levels was observed among 15 alfalfa genotypes evaluated, it is possible that these compounds may be derived from a common intermediate. Birdsfoot trefoil (Lotus corniculatus L.) contained prolinebetaine, but only traces of glycinebetaine, pipecolatebetaine, and hydroxyprolinebetaine. Red clover (TrtfoIium pretense L.) lacked prolinebetaine, pipecolatebetaine, and hydroxyprolinebetaine, but contained appreciable levels of both glycinebetaine and trigonelline. Trigonelline was not detectable in the leaf tissue of any alfalfa genotype or cultivar evaluated.Positive ion FAB-MS2 has been employed to simultaneously quantify the levels and determine the stable isotope abundance of quaternary ammonium compounds such as glycinebetaine (3,4,9,10,12,13,16) and its precursors (e.g. betaine aldehyde) (3, 10, 13) in plants. Desorption ionization mass spectrometry methods, including FAB-MS, are particularly suited to analysis of complex mixtures of preformed ionic species which exhibit surface activity in liquid sample matrices (13).

Stress metabolism. IX. Effect of salt stress on trigonelline accumulation in tomato

“…Trigonelline, but not choline, accumulated in response to salt stress, imposed either abruptly or progressively and also under prolonged salt stress. A similar observation has been made in alfalfa (Parameshwara 1984;Wood et al 1991), Populus trichocarpa × P. deltoides (Bray et al 1992), drought stressed Medicago spp. (Naidu et al 1992), salt marsh grass, Sporobolus virginicus (Marchum and Murdoch 1992), members of South American Moraceae (Shrestha and Brissels 1991), Leymus sabulosus (Gorham et al 1984) and in salt-stressed legumes (Tramontano and Jowe 1997).…”

Application of Capillary Electrophoresis to the Simultaneous Determination of Betaines in Plants

“…Neither AB nor HPB was detected in the present samples. Wood et al 24 analyzed the betaine levels, such as GB, PB, HPB and pipecolate betaine, in a variety of alfalfa cultivar and some other plants, like red clover and trefoil by FAB-MS. The betaine levels in these plants deviate very widely in level from 10 -6 to 10 -3 mol/kg FW.…”

Proline Betaine Accumulation and Metabolism in Alfalfa Plants under Sodium Chloride Stress. Exploring Its Compartmentalization in Nodules

“…This betaine is found mainly in some species of Plumbaginaceae, Capparidaceae, Rutaceae, Labiatae, Compositae, and Leguminosae (Wyn Jones and Storey, 1981;Rhodes and Hanson, 1993;Hanson et al, 1994). In alfalfa (Medicago sativa), Pro betaine is the major betaine (Robertson and Marion, 1960;Wyn Jones and Storey, 1981), but other betaines, such as pipecolate betaine (homostachydrine), trigonelline, hydroxyproline betaine, and Gly betaine, have also been identified in various alfalfa genotypes (Wood et al, 1991). In addition to alfalfa, other Medicago species, such as Medicago truncatula, Medicago littoralis, Medicago rugosa, and Medicago polymorpha, produce Pro betaine with significant genotypic variations (Wood et al, 1991;Naidu et al, 1992).…”

“…In alfalfa (Medicago sativa), Pro betaine is the major betaine (Robertson and Marion, 1960;Wyn Jones and Storey, 1981), but other betaines, such as pipecolate betaine (homostachydrine), trigonelline, hydroxyproline betaine, and Gly betaine, have also been identified in various alfalfa genotypes (Wood et al, 1991). In addition to alfalfa, other Medicago species, such as Medicago truncatula, Medicago littoralis, Medicago rugosa, and Medicago polymorpha, produce Pro betaine with significant genotypic variations (Wood et al, 1991;Naidu et al, 1992). Pro betaine, which is released by alfalfa seeds during germination (Phillips et al, 1995), is an inducer of nodulation (nod) genes in Sinorhizobium meliloti, the alfalfa-symbiotic species (Phillips et al, 1992).…”