Elucidation of the biosynthetic origin of the ...
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| Title | Elucidation of the biosynthetic origin of the anti-inflammatory pseudopterosins |
| Author(s) | R. Kerr, A. Kohl, T. Ferns |
| Journal | Journal of industrial microbiology & biotechnology |
| Date | 2006 |
| Volume | 33 |
| Issue | 7 |
| Start page | 532 |
| End page | 538 |
| Abstract | 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. |
| DOI | 10.1007/s10295-006-0106-3 |
| ISSN | 1367-5435 |
Using APA 6th Edition citation style.
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