Characterization of yellow pigments formed on reaction of 2-(1H-pyrrolyl)carboxylic acids with pyruvic acid in garlic greening model systems

Hu, Dan; Zhang, Jian; Zhang, Tuo; Dong, Jing; Leng, Xiaojing; Zhao, Guanghua

doi:10.1016/j.foodres.2009.12.009

Cited by 14 publications

(5 citation statements)

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“…No color species with a methine bridge, abundantly formed during onion/leek pinking, were detected in the present model systems. Furthermore, we did not observe the presence of any pyrrole-based compounds containing a four carbon bridge reported previously. − …”

Section: Resultscontrasting

confidence: 56%

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Allium Discoloration: Color Compounds Formed during Greening of Processed Garlic

Kubec

Curko

Urajová

et al. 2017

J. Agric. Food Chem.

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Structures and formation pathways of compounds responsible for blue-green discoloration of processed garlic were studied in model systems. A procedure was developed for isolation of the color compounds and their tentative identification by high-performance liquid chromatography coupled to a diode array detector and tandem mass spectrometry. It was found that the pigment is a mixture of numerous pyrrole-based purple/blue and yellow species. Experiments with isotope-labeled precursors revealed that two molecules of an amino acid are involved in the formation of each color compound. In the purple/blue species (λ = 565-600 nm), both amino acid molecules are incorporated into two 3,4-dimethylpyrrole-derived rings linked together by a propenylidine bridge. On the other hand, the yellow compounds (λ = 420-450 nm) contain only one N-substituted 3,4-dimethylpyrrole ring, to which the second amino acid is bound via a propenylidine side chain.

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Section: Resultscontrasting

confidence: 56%

“…On the other hand, a series of yellow species (λ max = 401–437 nm) generated in various model systems were identified only tentatively on the basis of MS data (Figure ). − …”

Section: Introductionmentioning

confidence: 99%

Allium Discoloration: Color Compounds Formed during Greening of Processed Garlic

Kubec

Curko

Urajová

et al. 2017

J. Agric. Food Chem.

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“…In another study with hydrophobic amino acids, it was hypothesized that the intensity of garlic greening could be related to the dimension of the amino acid R group, namely, the smaller the size of the R group, the larger the color intensity (Wang et al, 2008b). Nevertheless, this hypothesis was not confirmed for hydrophilicamino acids as, in a following study, glutamic acid yielded a more intense green color compared to asparagine, which has a bigger R-group (Hu et al, 2010).…”

Section: Formation Of Pigmentsmentioning

confidence: 81%

Garlic greening: Pigments biosynthesis and control strategies

et al. 2021

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Greening is a major problem for garlic’s quality. This phenomenon leads to discoloration of the product and is directly related to the alliinase-catalyzed conversion of isoalliin into 1-propenyl-containing thiosulfates. Garlic crushing, refrigeration, and storage in normal atmosphere, as well as in the presence of monocarboxylic acids, are established the main factors that promote its greening. In last decades, the study of biochemical pathway of this phenomenon has allowed to effectively understand the main steps and key enzymes involved, and to identify optimum conditions for chemical and enzymatic reactions leading to discoloration. These findings have, in some cases, determined the development of new tools for the control of garlic greening on large scale. After providing an updated description of the biochemistry of green pigments produced in garlic, this review reports an overview on the strategies for controlling discoloration of garlic at industrial level.

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“…The unstable blue pigment will be slowly decomposed into yellow pigment. The reaction of pyruvic acid with PP [2-(1H-pyrrolyl) carboxylic acids] might serve as another pathway for forming the yellow pigment ( 8 ), which is mixed with the undecomposed blue pigment to form the green pigment as the fourth step ( 5 ).…”

Section: Introductionmentioning

confidence: 99%

Transcriptome in Combination Proteome Unveils the Phenylpropane Pathway Involved in Garlic (Allium sativum) Greening

Niu

et al. 2021

Front. Nutr.

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Garlic (Allium sativum) is an important vegetable crop that is widely used in cooking and medicine. The greening phenomenon of garlic severely decreases the quality of garlic and hinders garlic processing. To study the mechanism of garlic greening, comprehensive full-length transcript sets were constructed. We detected the differences in greening between Pizhou (PZ) garlic and Laiwu (LW) garlic that were both stored at −2.5°C and protected from light at the same time. The results showed that 60,087 unigenes were respectively annotated to the NR, KEGG, GO, Pfam, eggNOG and Swiss Prot databases, and a total of 30,082 unigenes were annotated. The analysis of differential genes and differential proteins showed that PZ garlic and LW garlic had 923 differentially expressed genes (DEGs), of which 529 genes were up regulated and 394 genes were downregulated. Through KEGG and GO enrichment analysis, it was found that the most significant way of enriching DEGs was the phenylpropane metabolic pathway. Proteomics analysis found that there were 188 differentially expressed proteins (DAPs), 162 up-regulated proteins, and 26 down-regulated proteins between PZ garlic and LW garlic. The content of 10 proteins related to phenylpropanoid biosynthesis in PZ garlic was significantly higher than that of LW garlic. This study explored the mechanisms of garlic greening at a molecular level and further discovered that the formation of garlic green pigment was affected significantly by the phenylpropanoid metabolic pathway. This work provided a theoretical basis for the maintenance of garlic quality during garlic processing and the future development of the garlic processing industries.

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Characterization of yellow pigments formed on reaction of 2-(1H-pyrrolyl)carboxylic acids with pyruvic acid in garlic greening model systems

Cited by 14 publications

References 14 publications

Allium Discoloration: Color Compounds Formed during Greening of Processed Garlic

Allium Discoloration: Color Compounds Formed during Greening of Processed Garlic

Garlic greening: Pigments biosynthesis and control strategies

Transcriptome in Combination Proteome Unveils the Phenylpropane Pathway Involved in Garlic (Allium sativum) Greening

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