Abstract
25-Azacycloartanol (I), 2-aza-2-dihydrosqualene (II) and Tridemorph (2,6-dimethyl-N-tridecylmorpholine) (III) are potent inhibitors of higher plant sterol biosynthesis. The first two molecules have been designed using rational enzymological concepts. I, II and III were shown to inhibit the S-adenosyl-L-methionine: cycloartenol C-24-methyltransferase, the 2,3-oxidosqualene: beta-amyrin-cyclase and the cycloeucalenol: obtusifoliol isomerase, respectively. Inhibition was demonstrated either in vivo on bramble cell suspensions or in vitro on microsomes from maize seedlings. Each inhibitor has been shown to have a high affinity for its presumed enzymic target and only negligible inhibitory action on the other two enzymes. The applications of these results to further physiological studies are discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Chemical Phenomena
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Chemistry
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Fabaceae
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Fungicides, Industrial / pharmacology
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Intramolecular Transferases*
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Isomerases / antagonists & inhibitors*
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Methyltransferases / antagonists & inhibitors*
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Morpholines / pharmacology
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Phytosterols / pharmacology
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Plants / enzymology*
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Plants, Medicinal
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Squalene / analogs & derivatives
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Squalene / pharmacology
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Steroid Isomerases / antagonists & inhibitors*
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Structure-Activity Relationship
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Zea mays
Substances
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Fungicides, Industrial
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Morpholines
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Phytosterols
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tridemorph
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25-azacycloartanol
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Squalene
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2-aza-2-dihydrosqualene
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Methyltransferases
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S-adenosyl-L-methionine-cycloartenol methyltransferase
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Isomerases
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Steroid Isomerases
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cycloeucalenol-obtusifol isomerase
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Intramolecular Transferases
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2,3-oxidosqualene-beta-amyrin-cyclase