Aromadendrane transformations by Curvularia lunata ATCC 12017
| Autor: | William F. Reynolds, Paul B. Reese, Dwight O Collins |
|---|---|
| Rok vydání: | 2002 |
| Předmět: |
Curvularia lunata
Magnetic Resonance Spectroscopy Ketone Stereochemistry Plant Science Horticulture Hydroxylation Sesquiterpene Biochemistry chemistry.chemical_compound Biotransformation Hyptis verticillata Molecular Biology Squamulosone chemistry.chemical_classification Molecular Structure biology Fungi General Medicine Fungi imperfecti biology.organism_classification Culture Media chemistry Oxidation-Reduction Sesquiterpenes |
| Zdroj: | Phytochemistry. 60:475-481 |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/s0031-9422(02)00136-x |
| Popis: | The naturally occurring sesquiterpene squamulosone ( 1 ), isolated from Hyptis verticillata (Labiatae), was synthetically reduced to five analogues that were identified as (1 S ,10 S )-9α-hydroxy- allo -aromadendrane ( 2 ), (1 R ,10 R )-9β-hydroxyaromadendrane ( 3 ), (1 S ,10 S )- allo -aromadendran-9-one ( 4 ), (1 R ,10 R )-aromadendran-9-one ( 5 ) and aromadendra-1,9-diene ( 6 ). Each congener was incubated with the fungus Curvularia lunata ATCC 12017 in two different growth media. All the substrates except the deoxy compound 6 underwent a simple redox reaction. Ketone 5 additionally experienced remote hydroxylation while analogue 6 , possessing a conjugated diene system, was most extensively metabolised. The substrates and products presented here, but one, are all novel. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect