Tryptophol Metabolism by a Species of Arthrobacter |
| |
Authors: | Yôsuke Mino |
| |
Affiliation: | Division of Entomology and Plant Physiology, Obihiro Zootechnical University, Obihiro, Japan |
| |
Abstract: | The stereochemistry of some dihydrofurano-isoflavones previously isolated from white lupin roots, or obtained following fungal metabolism of prenylated isoflavones, was investigated using CD spectroscopy. The osmate ester/pyridine complex of dextrorotatory lupinisoflavone A (1) exhibited a positive CD Cotton effect at 480 nm, indicating a side-structure configuration (S at C- 2″), opposite to that of natural rotenone (9), which afforded a negative Cotton effect at 474 nm (R- configuration at C-2′ on the side structure [ring E]). The stereochemistry of the laevorotatory luteone metabolite BC-1 (2) and lupinisoflavone D (4) (both ^-configuration at C-2″) was similarly determined after converting to the corresponding dehydrate (10) or trimethyl-dehydrate (1b, 10a). |
| |
Keywords: | Fischer glycosidation protective group TMSCl acid catalyst |
|
|