Phytochemistry p. 1041 - 1044 (1988)
Update date:2022-08-28
Topics:
Suga, Takayuki
Hirata, Toshifumi
Hamada, Hiroki
Murakami, Satoru
The biotransformation of (1R)-(+)-p-menth-4(8)-en-3-one and (1R,4S)-(-)- and (1R,4R)-(+)-p-menth-3-ones with a suspension of cultured cells of Nicotiana tabacum was investigated.It was found that (i) the cultured cells regio- and stereoselectively hydroxylated the 4-position of (1R,4S)- and (1R,4R)-p-menth-3-ones to give (1R,4R)- and (1R,4S)-4-hydroxy-p-menth-3-ones, respectively and (ii) the cultured cells stereoselectively reduced the C-C double bond of the p-menth-4(8)-en-3-one from the si-face at C-4 and then the carbonyl group from the re-face.Key Word Index: Nicotiana tabacum; Solanaceae; tissue culture; biotransformation; hydroxylation; reduction; stereoselectivity; 3-oxo-p-menthanes.
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