Biosynthesis of phytosterols in Calendula officinalis flowers from (2R)- and (2RS)-[2-14C, 2-3H]-mevalonic acid. The incorporation of a 15α-tritium atom into sitosterol

Author(s):  
Jacek K. Sliwowski ◽  
Eliahu Caspi
1969 ◽  
Vol 114 (4) ◽  
pp. 885-892 ◽  
Author(s):  
L J Goad ◽  
G. F. Gibbons ◽  
Loretta M. Bolger ◽  
H H Rees ◽  
T W Goodwin

1. Incubation of a rat liver homogenate with 3R-[2−14C,(5R)-5−3H1]mevalonic acid gave cholesterol with 3H/14C atomic ratio 6:5. 2. Conversion of the labelled cholesterol into 3β-acetoxy-6-nitrocholest-5-ene or cholest-4-ene-3,6-dione resulted in the loss of one tritium atom from C-6. 3. These results show that during cholesterol biosynthesis the 6α-hydrogen atom of a precursor sterol is eliminated during formation of the C-5–C-6 double bond. 4. Incorporation of 3R-[2−14C,(5R)-5−3H1]mevalonic acid into the sterols of larch (Larix decidua) leaves gave labelled cycloartenol and β-sitosterol with 3H/14C atomic ratios 6:6 and 6:5 respectively. 5. One tritium atom was lost from C-6 on conversion of the labelled β-sitosterol into either 3β-acetoxy-6-nitrostigmast-5-ene or stigmast-4-ene-3,6-dione, demonstrating that formation of the C-5–C-6 double bond of phytosterols also involves the elimination of the 6α-hydrogen atom of a precursor sterol. 6. The 3R-[2−14C,(5R)-5−3H1]mevalonic acid was also incorporated by larch (L. decidua) leaves into a sterol that co-chromatographed with 28-isofucosterol. Confirmation that the radioactivity was associated with 28-isofucosterol was obtained by co-crystallization with carrier 28-isofucosterol and ozonolysis of the acetate to give radioactively labelled 24-oxocholesteryl acetate. 7. The significance of these results to phytosterol biosynthesis is discussed.


Planta Medica ◽  
2015 ◽  
Vol 81 (16) ◽  
Author(s):  
C Nicolaus ◽  
A Sievers-Engler ◽  
R Murillo ◽  
M Lämmerhofer ◽  
I Merfort

Planta Medica ◽  
2016 ◽  
Vol 82 (05) ◽  
Author(s):  
H Rafiee ◽  
H Naghdi Badi ◽  
A Mehrafarin ◽  
M Taghi Khosravi ◽  
M Tamjidi

2018 ◽  
Vol 72 (4) ◽  
pp. 37-46
Author(s):  
Arkadiusz Telesiński ◽  
Mirosław Onyszko ◽  
Martyna Śnioszek ◽  
Maciej Płatkowski ◽  
Michał Stręk

2012 ◽  
Vol 11 (9) ◽  
pp. 1721-1724
Author(s):  
Roxana Vatavu ◽  
Constantin Leonte ◽  
Teodor Robu. ◽  
Catalina Slabu-Pascal

2018 ◽  
Vol 18 (14) ◽  
pp. 1167-1174 ◽  
Author(s):  
Petra Lovecka ◽  
Jan Lipov ◽  
Kamila Thumova ◽  
Anna Macurkova

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