4-Hydroxypipecolic Acid and Pipecolic Acid in Acacia Species:  Their Determination by High-Performance Liquid Chromatography, Its Application to Leguminous Plants, and Configuration of 4-Hydroxypipecolic Acid

Abstract

A new method for the determination of naturally occurring imino acids in plants was devised. This method comprises the formation of dinitrophenyl derivatives and their measurement by HPLC. The determination limits were 100 pmol for 4-hydroxypipecolic acid (HPA) and proline (Pro) and 10 pmol for pipecolic acid (Pip). The recoveries of HPA, Pro, and Pip from leaf homogenate of an Acacia species were 95.9 ± 2.8, 100.5 ± 1.7, and 101.1 ± 2.3%, respectively. HPA was found in leaves, seeds, and roots of five kinds of Acacia but not in leaves of other members of the legume family. The HPA content of Acacia dealbata link leaves was much higher in winter than in summer. From X-ray analysis, HPA was found to be hydrated by two water molecules that are situated in a vacant channel formed by the molecular arrangement of HPA. HPA had no remarkable physiological or pharmaceutical activities. Keywords: 4-Hydroxypipecolic acid; pipecolic acid; Acacia species; leguminous plants; determination

l‐lysine metabolism to N‐hydroxypipecolic acid: an integral immune‐activating pathway in plants

“…Schenk and Schütte, ; Kristensen et al ., ; Hatanaka and Kaneko, ; Romeo et al ., ; Kite et al ., ). For example, trans ‐4‐hydroxypipecolic acid was detected in Acacia species, and radiolabeling experiments suggest that the compound is derived from the direct hydroxylation of Pip (Fowden, ; Kunii et al ., ). While the biochemical bases of C ‐hydroxylation reactions within the piperidine ring of Pip in plants are not clear yet, fungal 2‐oxoglutarate‐dependent dioxygenases with regio‐ and stereoselective l ‐Pip 4‐hydroxylase activity have been characterized (Hibi et al ., ).…”

The genus Acacia as invader: the characteristic case of Acacia dealbata Link in Europe

“…The production of allelochemicals by A. dealbata in the introduced range is well documented (Carballeira and Reigosa, 1999;Lorenzo et al, 2008). Although we do not know the chemical composition of the exudates and leachates of A. dealbata well, the presence of sterols, p-hydroxycinnamic acids, chalcone glycosides, iminoacids and triterpenes has been published (Freire et al, 2005;Freire et al, 2007;Imperato, 1982;Kunii et al, 1996;Pereira et al, 1996), some of them well known as allelochemicals.…”

“…However, there are also some harmful substances (Seigler, 2002), among them complex phenolic compounds (Seigler, 2003). In A. dealbata there can be found iminoacids (Kunii et al, 1996), chalcone glycosides (Imperato, 1982), triterpenes (Pereira et al, 1996), sterols (Freire et al, 2005) and p-Hydroxycinnamic acids (especially caffeic acid esters with long-chain fatty alcohols, Freire et al, 2007), some of which can act as allelochemicals . When A. dealbata was introduced into NW Spain, it brought "novel weapons" (Callaway and Aschehoug, 2000) that interfere with native species (Carballeira and Reigosa, 1999;Lorenzo et al, 2008).…”

Metabolic Trajectories Following Contrasting Prudent and Western Diets from Food Provisions: Robust Biomarkers of Short-Term Changes in Habitual Diet

“…Similarly, urinary OH-PCA was found to have a moderate correlation with fiber and fruit & vegetable intake, and inversely related to total fat. This data indicates that higher excretion of OH-PCA in urine is likely derived from intake of leguminous plants [49] and citrus fruits [50] when following a Prudent diet, but represents an endogenous lysine metabolite [51] also produced by gut microbiota [52]. Indeed, urinary OH-PCA or its ratio to sodium (OH-PCA/Na) discriminated between DIGEST participants from two diet treatment arms ( Figure S10) with good accuracy (AUC ≈ 0.83 to 0.88, p < 3.0 E-4), as well as sensitivity and specificity (≈ 90%).…”