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Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities
Year:
2000
Source of publication :
Plant Science
Authors :
דודאי, נתיב
;
.
זיו-רז, איריס
;
.
חיימוביץ', דוד
;
.
לוינסון, אפרים
;
.
לסטוצ'קין, אלנה
;
.
לרקוב, אולגה
;
.
פוטיבסקי, אליהו
;
.
רביד, עוזי
;
.
תדמור, יעקב
;
.
Volume :
160
Co-Authors:
Lewinsohn, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Ziv-Raz, I., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel, Department of Food Engineering and Biotechnology, Technion-Israel Institute of Technology, Haifa 32000, Israel
Dudai, N., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Tadmor, Y., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Lastochkin, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Larkov, O., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Chaimovitsh, D., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Ravid, U., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Putievsky, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Pichersky, E., Department of Biology, University of Michigan, Ann Arbor, MI 48109-1048, United States
Shoham, Y., Department of Food Engineering and Biotechnology, Technion-Israel Institute of Technology, Haifa 32000, Israel
Facilitators :
From page:
27
To page:
35
(
Total pages:
9
)
Abstract:
Sweet basil (Ocimum basilicum L., Lamiaceae) is a common herb, used for culinary and medicinal purposes. The essential oils of different sweet basil chemotypes contain various proportions of the allyl phenol derivatives estragole (methyl chavicol), eugenol, and methyl eugenol, as well as the monoterpene alcohol linalool. To monitor the developmental regulation of estragole biosynthesis in sweet basil, an enzymatic assay for S-adenosyl-L-methionine (SAM):chavicol O-methyltransferase activity was developed. Young leaves display high levels of chavicol O-methyltransferase activity, but the activity was negligible in older leaves, indicating that the O-methylation of chavicol primarily occurs early during leaf development. The O-methyltransferase activities detected in different sweet basil genotypes differed in their substrate specificities towards the methyl acceptor substrate. In the high-estragole-containing chemotype R3, the O-methyltransferase activity was highly specific for chavicol, while eugenol was virtually not O-methylated. In contrast, chemotype 147/97, that contains equal levels of estragole and methyl eugenol, displayed O-methyltransferase activities that accepted both chavicol and eugenol as substrates, generating estragole and methyl eugenol, respectively. Chemotype SW that contains high levels of eugenol, but lacks both estragole and methyl eugenol, had apparently no allylphenol dependent O-methyltransferase activities. These results indicate the presence of at least two types of allylphenol-specific O-methyltransferase activities in sweet basil chemotypes, one highly specific for chavicol; and a different one that can accept eugenol as a substrate. The relative availability and substrate specificities of these O-methyltransferase activities biochemically rationalizes the variation in the composition of the essential oils of these chemotypes. © 2000 Elsevier Science Ireland Ltd.
Note:
Related Files :
allylphenol o methyltransferase
essential oils
Eugenol
Methyl eugenol
Ocimum basilicum
Phytochemistry
unclassified drug
עוד תגיות
תוכן קשור
More details
DOI :
10.1016/S0168-9452(00)00357-5
Article number:
Affiliations:
Database:
סקופוס
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
25818
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:17
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Scientific Publication
Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities
160
Lewinsohn, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Ziv-Raz, I., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel, Department of Food Engineering and Biotechnology, Technion-Israel Institute of Technology, Haifa 32000, Israel
Dudai, N., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Tadmor, Y., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Lastochkin, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Larkov, O., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Chaimovitsh, D., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Ravid, U., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Putievsky, E., Newe ya'Ar Research Center, Agricultural Research Organization, P.O. Box 1021, Ramat Yishay 30095, Israel
Pichersky, E., Department of Biology, University of Michigan, Ann Arbor, MI 48109-1048, United States
Shoham, Y., Department of Food Engineering and Biotechnology, Technion-Israel Institute of Technology, Haifa 32000, Israel
Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities
Sweet basil (Ocimum basilicum L., Lamiaceae) is a common herb, used for culinary and medicinal purposes. The essential oils of different sweet basil chemotypes contain various proportions of the allyl phenol derivatives estragole (methyl chavicol), eugenol, and methyl eugenol, as well as the monoterpene alcohol linalool. To monitor the developmental regulation of estragole biosynthesis in sweet basil, an enzymatic assay for S-adenosyl-L-methionine (SAM):chavicol O-methyltransferase activity was developed. Young leaves display high levels of chavicol O-methyltransferase activity, but the activity was negligible in older leaves, indicating that the O-methylation of chavicol primarily occurs early during leaf development. The O-methyltransferase activities detected in different sweet basil genotypes differed in their substrate specificities towards the methyl acceptor substrate. In the high-estragole-containing chemotype R3, the O-methyltransferase activity was highly specific for chavicol, while eugenol was virtually not O-methylated. In contrast, chemotype 147/97, that contains equal levels of estragole and methyl eugenol, displayed O-methyltransferase activities that accepted both chavicol and eugenol as substrates, generating estragole and methyl eugenol, respectively. Chemotype SW that contains high levels of eugenol, but lacks both estragole and methyl eugenol, had apparently no allylphenol dependent O-methyltransferase activities. These results indicate the presence of at least two types of allylphenol-specific O-methyltransferase activities in sweet basil chemotypes, one highly specific for chavicol; and a different one that can accept eugenol as a substrate. The relative availability and substrate specificities of these O-methyltransferase activities biochemically rationalizes the variation in the composition of the essential oils of these chemotypes. © 2000 Elsevier Science Ireland Ltd.
Scientific Publication
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