Phytoalexins of the crucifer Barbarea vulgaris: Structural profile and correlation with glucosinolate turnover
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Phytoalexins of the crucifer Barbarea vulgaris : Structural profile and correlation with glucosinolate turnover. / Cárdenas, Pablo D.; Landtved, Jonas P.; Larsen, Signe H.; Lindegaard, Nicolai; Wøhlk, Sebastian; Jensen, Karen R.; Pattison, David I.; Burow, Meike; Bak, Søren; Crocoll, Christoph; Agerbirk, Niels.
In: Phytochemistry, Vol. 213, 113742, 2023.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Phytoalexins of the crucifer Barbarea vulgaris
T2 - Structural profile and correlation with glucosinolate turnover
AU - Cárdenas, Pablo D.
AU - Landtved, Jonas P.
AU - Larsen, Signe H.
AU - Lindegaard, Nicolai
AU - Wøhlk, Sebastian
AU - Jensen, Karen R.
AU - Pattison, David I.
AU - Burow, Meike
AU - Bak, Søren
AU - Crocoll, Christoph
AU - Agerbirk, Niels
N1 - Funding Information: We thank Prof. M.S.C. Pedras for generously sharing standards and suggestions, including detailed comments to earlier versions of the manuscript, MSc E. Ciepiel for assisting with biological experiments, Dr. T. Yang for carrying out chiral HPLC of kjaerin, Dr. T.P. Hauser for constructive discussions, Torben og Alice Frimodts Fond for financial support, and three anonymous reviewers for constructive comments which improved the manuscript. Publisher Copyright: © 2023 The Authors
PY - 2023
Y1 - 2023
N2 - Phytoalexins are antimicrobial plant metabolites elicited by microbial attack or abiotic stress. We investigated phytoalexin profiles after foliar abiotic elicitation in the crucifer Barbarea vulgaris and interactions with the glucosinolate-myrosinase system. The treatment for abiotic elicitation was a foliar spray with CuCl2 solution, a usual eliciting agent, and three independent experiments were carried out. Two genotypes of B. vulgaris (G-type and P-type) accumulated the same three major phytoalexins in rosette leaves after treatment: phenyl-containing nasturlexin D and indole-containing cyclonasturlexin and cyclobrassinin. Phytoalexin levels were investigated daily by UHPLC-QToF MS and tended to differ among plant types and individual phytoalexins. In roots, phytoalexins were low or not detected. In treated leaves, typical total phytoalexin levels were in the range 1–10 nmol/g fresh wt. during three days after treatment while typical total glucosinolate (GSL) levels were three orders of magnitude higher. Levels of some minor GSLs responded to the treatment: phenethylGSL (PE) and 4-substituted indole GSLs. Levels of PE, a suggested nasturlexin D precursor, were lower in treated plants than controls. Another suggested precursor GSL, 3-hydroxyPE, was not detected, suggesting PE hydrolysis to be a key biosynthetic step. Levels of 4-substituted indole GSLs differed markedly between treated and control plants in most experiments, but not in a consistent way. The dominant GSLs, glucobarbarins, are not believed to be phytoalexin precursors. We observed statistically significant linear correlations between total major phytoalexins and the glucobarbarin products barbarin and resedine, suggesting that GSL turnover for phytoalexin biosynthesis was unspecific. In contrast, we did not find correlations between total major phytoalexins and raphanusamic acid or total glucobarbarins and barbarin. In conclusion, two groups of phytoalexins were detected in B. vulgaris, apparently derived from the GSLs PE and indol-3-ylmethylGSL. Phytoalexin biosynthesis was accompanied by depletion of the precursor PE and by turnover of major non-precursor GSLs to resedine. This work paves the way for identifying and characterizing genes and enzymes in the biosyntheses of phytoalexins and resedine.
AB - Phytoalexins are antimicrobial plant metabolites elicited by microbial attack or abiotic stress. We investigated phytoalexin profiles after foliar abiotic elicitation in the crucifer Barbarea vulgaris and interactions with the glucosinolate-myrosinase system. The treatment for abiotic elicitation was a foliar spray with CuCl2 solution, a usual eliciting agent, and three independent experiments were carried out. Two genotypes of B. vulgaris (G-type and P-type) accumulated the same three major phytoalexins in rosette leaves after treatment: phenyl-containing nasturlexin D and indole-containing cyclonasturlexin and cyclobrassinin. Phytoalexin levels were investigated daily by UHPLC-QToF MS and tended to differ among plant types and individual phytoalexins. In roots, phytoalexins were low or not detected. In treated leaves, typical total phytoalexin levels were in the range 1–10 nmol/g fresh wt. during three days after treatment while typical total glucosinolate (GSL) levels were three orders of magnitude higher. Levels of some minor GSLs responded to the treatment: phenethylGSL (PE) and 4-substituted indole GSLs. Levels of PE, a suggested nasturlexin D precursor, were lower in treated plants than controls. Another suggested precursor GSL, 3-hydroxyPE, was not detected, suggesting PE hydrolysis to be a key biosynthetic step. Levels of 4-substituted indole GSLs differed markedly between treated and control plants in most experiments, but not in a consistent way. The dominant GSLs, glucobarbarins, are not believed to be phytoalexin precursors. We observed statistically significant linear correlations between total major phytoalexins and the glucobarbarin products barbarin and resedine, suggesting that GSL turnover for phytoalexin biosynthesis was unspecific. In contrast, we did not find correlations between total major phytoalexins and raphanusamic acid or total glucobarbarins and barbarin. In conclusion, two groups of phytoalexins were detected in B. vulgaris, apparently derived from the GSLs PE and indol-3-ylmethylGSL. Phytoalexin biosynthesis was accompanied by depletion of the precursor PE and by turnover of major non-precursor GSLs to resedine. This work paves the way for identifying and characterizing genes and enzymes in the biosyntheses of phytoalexins and resedine.
KW - 2-Phenylethylglucosinolate
KW - Aromatic glucosinolates
KW - Benzenic glucosinolates
KW - Brassicaceae
KW - Copper chloride
KW - Elicitation
KW - Gluconasturtiin
KW - Glucosinolate hydrolysis
KW - Indole glucosinolates
KW - Indole phytoalexins
KW - Induction
KW - Myrosinase
KW - Phytoalexin biosynthesis
KW - Tribe cardamineae
U2 - 10.1016/j.phytochem.2023.113742
DO - 10.1016/j.phytochem.2023.113742
M3 - Journal article
C2 - 37269935
AN - SCOPUS:85161698023
VL - 213
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
M1 - 113742
ER -
ID: 357379411