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The withanolides of Withania somnifera chemotypes I and II
Year:
1975
Source of publication :
Phytochemistry
Authors :
Abraham, Arieh
;
.
Volume :
14
Co-Authors:
Abraham, A., Agricultural Research Organization, Volcani Center, Bet Dagon, Israel
Kirson, I., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Lavie, D., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Glotte, E., The Hebrew University of Jerusalem, Faculty of Agriculture, Rehovot, Israel
Facilitators :
From page:
189
To page:
194
(
Total pages:
6
)
Abstract:
Seven steroidal lactones of the withanolide series have been isolated as minor constituents of the leaves of Withania somnifera Dun. (Solanaceae) chemotype I, along with the major component withaferin A. Structures have been assigned to the new compounds: withanolide N (17α,27-dihydroxy-1-oxo-20R,22R-witha-2,5,14,24-tetraenolide) (6a) and withanolide O (4β,17α-dihydroxy-1-oxo-20R,22R-witha-2,5,8(14),24-tetraenolide) (7a). Similarly the leaves of W. somnifera chemotype II afforded three new withanolides along with the major component withanolide D (9a) and trace amounts of withanolide G (10). The new compounds are: 27-hydroxywithanolide D(4β,20α,27-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (11a), 14α-hydroxywithanolide D (4β,14α,20α-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (12a) and 17α-hydroxywithanolide D (4β,17β,20α-trihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolide) (13a). Whereas all the withanolides of chemotype I are unsubstituted at C-20 (20α-H), those of chemotype II possess an OH at this position (20α-OH). © 1975.
Note:
Related Files :
Solanaceae
steroidal lactones
structure determination and correlation.
Withania somnifera
Withanolides
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More details
DOI :
10.1016/0031-9422(75)85035-7
Article number:
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
31791
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 01:05
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Scientific Publication
The withanolides of Withania somnifera chemotypes I and II
14
Abraham, A., Agricultural Research Organization, Volcani Center, Bet Dagon, Israel
Kirson, I., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Lavie, D., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Glotte, E., The Hebrew University of Jerusalem, Faculty of Agriculture, Rehovot, Israel
The withanolides of Withania somnifera chemotypes I and II
Seven steroidal lactones of the withanolide series have been isolated as minor constituents of the leaves of Withania somnifera Dun. (Solanaceae) chemotype I, along with the major component withaferin A. Structures have been assigned to the new compounds: withanolide N (17α,27-dihydroxy-1-oxo-20R,22R-witha-2,5,14,24-tetraenolide) (6a) and withanolide O (4β,17α-dihydroxy-1-oxo-20R,22R-witha-2,5,8(14),24-tetraenolide) (7a). Similarly the leaves of W. somnifera chemotype II afforded three new withanolides along with the major component withanolide D (9a) and trace amounts of withanolide G (10). The new compounds are: 27-hydroxywithanolide D(4β,20α,27-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (11a), 14α-hydroxywithanolide D (4β,14α,20α-trihydroxy-1-oxo-5β,6β-epoxy-20R,22R-witha-2,24-dienolide) (12a) and 17α-hydroxywithanolide D (4β,17β,20α-trihydroxy-1-oxo-5β,6β-epoxy-20S,22R-witha-2,24-dienolide) (13a). Whereas all the withanolides of chemotype I are unsubstituted at C-20 (20α-H), those of chemotype II possess an OH at this position (20α-OH). © 1975.
Scientific Publication
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