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קהילה:
אסיף מאגר המחקר החקלאי
פותח על ידי קלירמאש פתרונות בע"מ -
Naturally occurring norephedrine oxazolidine derivatives in khat (Catha edulis)
Year:
2012
Source of publication :
Planta Medica
Authors :
בר, עינת
;
.
דודאי, נתיב
;
.
לוי, אסף
;
.
לוינסון, אפרים
;
.
קריזבסקי, רז
;
.
Volume :
78
Co-Authors:
Krizevski, R., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel, Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Beer-Sheva, Israel
Bar, E., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Dudai, N., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Levy, A., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Lewinsohn, E., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Sitrit, Y., Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Beer-Sheva, Israel
Ben-Shabat, S., Department of Pharmacology, Faculty of Health Sciences, Ben-Gurion University of the Negev, P. O. Box 653, Beer-Sheva 84105, Israel
Facilitators :
From page:
838
To page:
842
(
Total pages:
5
)
Abstract:
Khat (Catha edulis Forsk.) is a perennial shrub whose young leaves are chewed for their psychostimulating and anorectic properties. The main active principles of khat are believed to be the phenylpropylamino alkaloids, primarily ()-cathinone [(S)-α-aminopropiophenone], (+)-cathine [(1S)(2S)- norpseudoephedrine], and ()-norephedrine [(1R)(2S)-norephedrine]. GC-MS analyses of young leaf extracts indicated the presence of two oxazolidine derivatives, 2,4-dimethyl-5-phenyloxazolidine and 4-methyl-2-(trans-1-pentenyl)-5- phenyloxazolidine. To ascertain the chemical identity of these compounds, we synthesized the putative compounds by condensation of norephedrine and acetaldehyde or trans-2-hexenal, respectively. Spectroscopic analyses (GC-MS, NMR) of the structures of these synthetic compounds showed them to have identical retention indexes and mass spectra characteristic to 2,4-dimethyl-5-phenyloxazolidine and 4-methyl-2-(trans-1-pentenyl)-5- phenyloxazolidine. Marked differences in the ratios between each of these two norephedrine oxazolidine derivatives and total phenylpropylamino alkaloids were found among thirteen different khat accessions further indicating polymorphism in alkaloid ratios and content in C. edulis. © Georg Thieme Verlag KG Stuttgart · New York.
Note:
Related Files :
1 phenyl 1,2 propanedione
Catha edulis
cathinone
Gas Chromatography
phenyloxazolidine alkaloids
Phytochemistry
עוד תגיות
תוכן קשור
More details
DOI :
10.1055/s-0031-1298430
Article number:
0
Affiliations:
Database:
סקופוס
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
24740
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:09
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Scientific Publication
Naturally occurring norephedrine oxazolidine derivatives in khat (Catha edulis)
78
Krizevski, R., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel, Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Beer-Sheva, Israel
Bar, E., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Dudai, N., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Levy, A., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Lewinsohn, E., Department of Aromatic Medicinal and Spice Crops, Newe Yaar Research Center, Agricultural Research Organization, Ramat Yishay, Israel
Sitrit, Y., Jacob Blaustein Institutes for Desert Research, Ben-Gurion University of the Negev, Beer-Sheva, Israel
Ben-Shabat, S., Department of Pharmacology, Faculty of Health Sciences, Ben-Gurion University of the Negev, P. O. Box 653, Beer-Sheva 84105, Israel
Naturally occurring norephedrine oxazolidine derivatives in khat (Catha edulis)
Khat (Catha edulis Forsk.) is a perennial shrub whose young leaves are chewed for their psychostimulating and anorectic properties. The main active principles of khat are believed to be the phenylpropylamino alkaloids, primarily ()-cathinone [(S)-α-aminopropiophenone], (+)-cathine [(1S)(2S)- norpseudoephedrine], and ()-norephedrine [(1R)(2S)-norephedrine]. GC-MS analyses of young leaf extracts indicated the presence of two oxazolidine derivatives, 2,4-dimethyl-5-phenyloxazolidine and 4-methyl-2-(trans-1-pentenyl)-5- phenyloxazolidine. To ascertain the chemical identity of these compounds, we synthesized the putative compounds by condensation of norephedrine and acetaldehyde or trans-2-hexenal, respectively. Spectroscopic analyses (GC-MS, NMR) of the structures of these synthetic compounds showed them to have identical retention indexes and mass spectra characteristic to 2,4-dimethyl-5-phenyloxazolidine and 4-methyl-2-(trans-1-pentenyl)-5- phenyloxazolidine. Marked differences in the ratios between each of these two norephedrine oxazolidine derivatives and total phenylpropylamino alkaloids were found among thirteen different khat accessions further indicating polymorphism in alkaloid ratios and content in C. edulis. © Georg Thieme Verlag KG Stuttgart · New York.
Scientific Publication
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