The absolute configuration of precocene I dihydrodiols produced by metabolism of precocene I by corpora allata of Locusta migratoria, in vitro.
The corpora allata from adult female Locusta migratoria metabolize precocene I (7-methoxy-2,2-dimethyl-2H-benzo [b]pyran to cis- & trans-precocene I dihydrodiols (3,4-dihydro-7-methoxy-2,2-dimethyl-2H-benzo [b]pyran-3,4-diol). Derivatization of the dihydrodiols with (-)menthoxy acetyl chloride allowed complete resolution of all four optical isomers. When [4-3H]-precocene I was incubated in vitro with Locusta migratoria corpora allata, it was metabolized stereospecifically to (-)trans-(3R,4S) and (+)cis-(3R,4R) dihydrodiols. Approximately half the precosyl residues bound to cellular macromolecules were discharged by heating to 95 degrees C at neutral pH, as dihydrodiols of the same stereochemistry.
D001578:Benzopyrans / Q000096:biosynthesis / Q000378:metabolism*; D006110:Grasshoppers / Q000378:metabolism*; D007605:Juvenile Hormones / Q000037:antagonists & inhibitors*; D009924:Organ Culture Techniques; D013237:Stereoisomerism; D014316:Tritium
D001578:Benzopyrans; D007605:Juvenile Hormones; D014316:Tritium; C019539:precocene I; C038507:3,4-dihydro-7-methoxy-2,2-dimethyl-2H-1-benzopyran-3,4-diol