Many isoprenylated flavonoids have been isolated from Japanese mulberry tree (Moraceae). Among them, kuwanons G (
1) and H (
2) were the first isolated active substances exhibiting a hypotensive effect. These compounds are considered to be formed through an enzymatic Diels-Alder type reaction between an isoprenyl portion of an isoprenylphenol as the diene and an α, β-double bond of chalcone as the dienophile. The absolute configurations of these Diels-Alder type adducts were confirmed by three different methods. The stereochemistries of the adducts were consistent with those of ones in the Diels-Alder reaction involving
exo- and
endo-addition. Some strains of
Morus alba callus tissues have a high productivity of mulberry Diels-Alder type adducts, such as chalcomoracin (
3) and kuwanon J (
4). The biosynthetic studies of the mulberry Diels-Alder type adducts have been carried out with the aid of the cell strain. Chalcomoracin (
3) and kuwanon J (
4) were proved to be enzymatic Diels-Alder type reaction products by the administration experiments with
O-methylchalcone derivatives. Furthermore, for the isoprenoid biosynthesis of prenylflavonoids in
Morus alba callus tissues by administration of [1,3-
13C
2]- and [2-
13C]-glycerol, a novel way through the junction of glycolysis and pentose-phosphate cycle was proved. Two independent isoprenoid biosynthetic pathways, that for sterols and that for isoprenoid-phenols, operate in the
Morus alba cell cultures. The former is susceptible to compactin (ML-236) and the latter resists to compactin in the cell cultures, respectively.
(Communicated by Shoji SHIBATA, M.J.A.)
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