Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa)

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Abstract

Avenanthramides are amides, with a phenylalkenoic acid (PA) and an anthranilic acid (AA) subunit, which are secondary metabolites of oat. Oat seeds were germinated, extracted, and the avenanthramides analysed by a combination of UHPLC with ion trap and high resolution ESI-MS. Typical fragmentation pathways with corresponding diagnostic fragments belonging to the PA and AA subunits were identified and summarised in a decision guideline. Based on these findings 28 unique avenanthramides were annotated in the oat seed(ling) extracts, including the new avenanthramide 6f (with a 4/5-methoxy AA subunit). Avenanthramide content increased by 25 times from seed to seedling. Avenanthramides 2p, 2c, and 2f, which are commonly described as the major avenanthramides, represented less than 20% of the total content in the seedlings. Future quantitative analyses should, therefore, include a wider range of avenanthramides to avoid underestimation of the total avenanthramide content.

LanguageEnglish
Pages682-690
JournalFood Chemistry
Volume277
DOIs
Publication statusPublished - 30 Mar 2019

Fingerprint

Avena sativa
Germination
oats
germination
anthranilic acid
Seed
Seeds
Seedlings
seeds
avenanthramides
avenanthramide-2C
Avena
Acids
seedlings
acids
Metabolites
amides
Amides
secondary metabolites
traps

Keywords

  • Avena sativa
  • Avenanthramides
  • Cereal grain
  • Germination
  • LC-MS
  • Phytoalexin
  • Plant defence
  • Poaceae

Cite this

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title = "Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa)",
abstract = "Avenanthramides are amides, with a phenylalkenoic acid (PA) and an anthranilic acid (AA) subunit, which are secondary metabolites of oat. Oat seeds were germinated, extracted, and the avenanthramides analysed by a combination of UHPLC with ion trap and high resolution ESI-MS. Typical fragmentation pathways with corresponding diagnostic fragments belonging to the PA and AA subunits were identified and summarised in a decision guideline. Based on these findings 28 unique avenanthramides were annotated in the oat seed(ling) extracts, including the new avenanthramide 6f (with a 4/5-methoxy AA subunit). Avenanthramide content increased by 25 times from seed to seedling. Avenanthramides 2p, 2c, and 2f, which are commonly described as the major avenanthramides, represented less than 20{\%} of the total content in the seedlings. Future quantitative analyses should, therefore, include a wider range of avenanthramides to avoid underestimation of the total avenanthramide content.",
keywords = "Avena sativa, Avenanthramides, Cereal grain, Germination, LC-MS, Phytoalexin, Plant defence, Poaceae",
author = "{de Bruijn}, {Wouter J.C.} and {van Dinteren}, Sarah and Harry Gruppen and Vincken, {Jean Paul}",
year = "2019",
month = "3",
day = "30",
doi = "10.1016/j.foodchem.2018.11.013",
language = "English",
volume = "277",
pages = "682--690",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier",

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TY - JOUR

T1 - Mass spectrometric characterisation of avenanthramides and enhancing their production by germination of oat (Avena sativa)

AU - de Bruijn, Wouter J.C.

AU - van Dinteren, Sarah

AU - Gruppen, Harry

AU - Vincken, Jean Paul

PY - 2019/3/30

Y1 - 2019/3/30

N2 - Avenanthramides are amides, with a phenylalkenoic acid (PA) and an anthranilic acid (AA) subunit, which are secondary metabolites of oat. Oat seeds were germinated, extracted, and the avenanthramides analysed by a combination of UHPLC with ion trap and high resolution ESI-MS. Typical fragmentation pathways with corresponding diagnostic fragments belonging to the PA and AA subunits were identified and summarised in a decision guideline. Based on these findings 28 unique avenanthramides were annotated in the oat seed(ling) extracts, including the new avenanthramide 6f (with a 4/5-methoxy AA subunit). Avenanthramide content increased by 25 times from seed to seedling. Avenanthramides 2p, 2c, and 2f, which are commonly described as the major avenanthramides, represented less than 20% of the total content in the seedlings. Future quantitative analyses should, therefore, include a wider range of avenanthramides to avoid underestimation of the total avenanthramide content.

AB - Avenanthramides are amides, with a phenylalkenoic acid (PA) and an anthranilic acid (AA) subunit, which are secondary metabolites of oat. Oat seeds were germinated, extracted, and the avenanthramides analysed by a combination of UHPLC with ion trap and high resolution ESI-MS. Typical fragmentation pathways with corresponding diagnostic fragments belonging to the PA and AA subunits were identified and summarised in a decision guideline. Based on these findings 28 unique avenanthramides were annotated in the oat seed(ling) extracts, including the new avenanthramide 6f (with a 4/5-methoxy AA subunit). Avenanthramide content increased by 25 times from seed to seedling. Avenanthramides 2p, 2c, and 2f, which are commonly described as the major avenanthramides, represented less than 20% of the total content in the seedlings. Future quantitative analyses should, therefore, include a wider range of avenanthramides to avoid underestimation of the total avenanthramide content.

KW - Avena sativa

KW - Avenanthramides

KW - Cereal grain

KW - Germination

KW - LC-MS

KW - Phytoalexin

KW - Plant defence

KW - Poaceae

U2 - 10.1016/j.foodchem.2018.11.013

DO - 10.1016/j.foodchem.2018.11.013

M3 - Article

VL - 277

SP - 682

EP - 690

JO - Food Chemistry

T2 - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

ER -