| Autor: |
Kerr RG; Department of Chemistry and Biochemistry, and Center of Excellence in Biomedical and Marine Biotechnology, Florida Atlantic University, Boca Raton, FL 33431, USA. rkerr@fau.edu, Kohl AC, Ferns TA |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of industrial microbiology & biotechnology [J Ind Microbiol Biotechnol] 2006 Jul; Vol. 33 (7), pp. 532-8. Date of Electronic Publication: 2006 Mar 23. |
| DOI: |
10.1007/s10295-006-0106-3 |
| Abstrakt: |
The pseudopterosins are a family of diterpene glycosides isolated from the gorgonian coral Pseudopterogorgia elisabethae. These metabolites exhibit potent anti-inflammatory activity, and this review describes our efforts to elucidate their biosynthetic origin. A radioactivity-guided isolation was used to identify the terpene cyclase product. In addition, a detailed NMR-guided search for potential biosynthetic intermediates identified metabolites which were tested by incubating 3H-labeled analogues with a cell-free extract of the coral. All labeled metabolites were generated biosynthetically, and radiochemical purity was established by a combination of HPLC purification and derivatization. In summary, pseudopterosins are produced by a cyclization of geranylgeranyl diphosphate to elisabethatriene, aromatization to erogorgiaene, two successive oxidations to 7,8-dihydroxyerogorgiaene and a glycosylation to afford a seco-pseudopterosin as a key intermediate. A dehydrogenation leads to amphilectosins which undergo ring closures to yield the pseudopterosins. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
|
