Plant sterol biosynthesis: 7-oxo-obtusifoliol (cas 16910-32-0) analogues as potential selective inhibitors of cytochrome P-450 dependent obtusifoliol (cas 16910-32-0) 14α-demethylase

Add time:08/07/2019    Source:sciencedirect.com

A series of 7-oxo-obtusifoliol (cas 16910-32-0) analogues have been synthetized and investigated as potential inhibitors of cytochrome P-450 dependent obtusifoliol 14α-demethylase (P-450OBT.14DM) from higher plant microsomes. 7-Oxo-24ξ(24')-dihydro-obtusifoliol and 7-oxo-24(25)-dihydro-29-nor-lanosterol were potent competitive inhibitors for P-450OBT.14DM, binding 125–200 times more tightly than the substrates obtusifoliol and 24(25)-dihydro-29-nor-lanosterol. Inhibition of P-450OBT14DM by these analogues showed strict structural requirements including the 8-en-7-one system which was compulsory for binding. 7-Oxo-24(25)-dihydro-lanosterol possessing an additional 4β-methyl substituent, did not have such inhibitory effects. Treatment of cultures of suspended bramble cells with 7-oxo-24(25)-dihydro-29-nor-lanosterol resulted in a strong decrease of [14C]acetate incorporation into the demethyl-sterols fraction and in an accumulation of [14C]obtusifoliol. This confirms that P-450OBT14DM is the main in vivo target of 7-oxo-24(25)-dihydro-29-nor-lanosterol in the sterol-biosynthetic pathway.

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