Biosynthetic Studies of Natural Products and Their Application

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(1) Metabolic pathways for rishitin, a phytoalexin of potato were clarified, and hydrogen peroxide was identified as an endogeneous elicitor of this phytoalexin. (2) The absolute stereochemistry of new prenyltransferase reactions were established. (3) Essential activation factors for undecaprenyl diphosphate synthase were isolated and identified. (4) The two essential protein components of hexaprenyl diphosphate synthase were purified and their functions were characterized. (5) Bacterial squalene synthetase was first isolated. (6) Phosphoryl derivatives of ecdysteroids were identified as conjugates in Bombyx ovaries. (7) Biosynthesis of ursolic acid from aceatate in tissue cultures of Rabdasia japonica Hara was elucidated with ^<13>C,^2H-double labeled precursors. (8) A complex consisting of luciferase and luciferin derived pigment was isolated from Cypridina. (9) Stereo- and regeo-controlled reactions with NAD(P)H models were developed. (10) Stereoselective reductions by yeast were used to prepare useful chiral synthons. (11) Acromelic acids, agelasines, and bayunol were synthesized by effective methods. (12) New terpenoids with novel strucures were isolated from marine organisms. (13) New synthetic reactions useful for biosynthetic study were developed.Information was effectively exchanged among the members of this project to promote their research activities.