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פותח על ידי קלירמאש פתרונות בע"מ -
Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase
Year:
2019
Source of publication :
Phytochemistry
Authors :
אבדאח, מוופק
;
.
יאהיה, מוסעב
;
.
נוואדה, בגווט
;
.
Volume :
159
Co-Authors:

Berim, A., Institute of Biological Chemistry, Washington State University, P. O. Box 646340, Pullman, WA  99164-6340, United States; Ibdah, M., Sakhnin College Academic College for Teacher Education, Sakhnin, Israel; Dudareva, N., Purdue University, Department of Biochemistry, 175 S. University Street, West Lafayette, IN  47907-2063, United States

Facilitators :
From page:
179
To page:
189
(
Total pages:
11
)
Abstract:

Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce considerable amounts of the phenylpropenes methyleugenol and methylisoeugenol. Notably, methyleugenol is most abundant in young leaves, while methylisoeugenol is the dominant phenylpropene in mature leaf tissue. The goal of the present study was to shed light on the biochemistry and molecular biology of these compounds’ biosynthesis and accumulation. Using the available genomic and transcriptomic data, we isolated a cDNA encoding eugenol/isoeugenol synthase (DcE(I)GS1), an NADPH-dependent enzyme that converts coniferyl acetate to eugenol. This enzyme exhibits dual product specificity and yields propenylphenol isoeugenol alongside allylphenol eugenol. Furthermore, we identified a cDNA encoding S-adenosyl-L-methionine:eugenol/isoeugenol O-methyltransferase 1 (DcE(I)OMT1) that produces methyleugenol and methylisoeugenol via methylation of the para-OH-group of their respective precursors. Both DcE(I)GS1 and DcE(I)OMT1 were expressed in seeds, roots, young and mature leaves, and the DcE(I)OMT1 transcript levels were the highest in leaves. The DcE(I)GS1 protein is 67% identical to anise t-anol/isoeugenol synthase and displays an apparent Km of 247 μM for coniferyl acetate. The catalytic efficiency of DcEOMT1 with eugenol is more than five-fold higher than that with isoeugenol, with Km values of 40 μM for eugenol, and of 115 μM for isoeugenol. This work expands the current knowledge of the enzymes involved in phenylpropene biosynthesis and would enable studies into structural elements defining the regioselectivity of phenylpropene synthases. © 2018

Note:
Related Files :
Apiaceae
Daucus carota
Eugenol synthase
Methylisoeugenol
O-Methyltransferase
O-methyltransferase (OMT)
עוד תגיות
תוכן קשור
More details
DOI :
10.1016/j.phytochem.2018.12.020
Article number:
0
Affiliations:
Database:
סקופוס
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
38977
Last updated date:
02/03/2022 17:27
Creation date:
15/01/2019 12:33
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Scientific Publication
Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase
159

Berim, A., Institute of Biological Chemistry, Washington State University, P. O. Box 646340, Pullman, WA  99164-6340, United States; Ibdah, M., Sakhnin College Academic College for Teacher Education, Sakhnin, Israel; Dudareva, N., Purdue University, Department of Biochemistry, 175 S. University Street, West Lafayette, IN  47907-2063, United States

Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase

Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce considerable amounts of the phenylpropenes methyleugenol and methylisoeugenol. Notably, methyleugenol is most abundant in young leaves, while methylisoeugenol is the dominant phenylpropene in mature leaf tissue. The goal of the present study was to shed light on the biochemistry and molecular biology of these compounds’ biosynthesis and accumulation. Using the available genomic and transcriptomic data, we isolated a cDNA encoding eugenol/isoeugenol synthase (DcE(I)GS1), an NADPH-dependent enzyme that converts coniferyl acetate to eugenol. This enzyme exhibits dual product specificity and yields propenylphenol isoeugenol alongside allylphenol eugenol. Furthermore, we identified a cDNA encoding S-adenosyl-L-methionine:eugenol/isoeugenol O-methyltransferase 1 (DcE(I)OMT1) that produces methyleugenol and methylisoeugenol via methylation of the para-OH-group of their respective precursors. Both DcE(I)GS1 and DcE(I)OMT1 were expressed in seeds, roots, young and mature leaves, and the DcE(I)OMT1 transcript levels were the highest in leaves. The DcE(I)GS1 protein is 67% identical to anise t-anol/isoeugenol synthase and displays an apparent Km of 247 μM for coniferyl acetate. The catalytic efficiency of DcEOMT1 with eugenol is more than five-fold higher than that with isoeugenol, with Km values of 40 μM for eugenol, and of 115 μM for isoeugenol. This work expands the current knowledge of the enzymes involved in phenylpropene biosynthesis and would enable studies into structural elements defining the regioselectivity of phenylpropene synthases. © 2018

Scientific Publication
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