Kerr Russell G, Kohl Amber C, Ferns Tyrone A
Department of Chemistry and Biochemistry, and Center of Excellence in Biomedical and Marine Biotechnology, Florida Atlantic University, Boca Raton, FL 33431, USA.
J Ind Microbiol Biotechnol. 2006 Jul;33(7):532-8. doi: 10.1007/s10295-006-0106-3. Epub 2006 Mar 23.
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.
伪蕨素是从柳珊瑚Pseudopterogorgia elisabethae中分离得到的一类二萜糖苷。这些代谢产物具有强大的抗炎活性，本综述描述了我们为阐明其生物合成起源所做的努力。采用放射性导向分离法鉴定萜类环化酶产物。此外，通过详细的核磁共振导向搜索潜在的生物合成中间体，鉴定出了一些代谢产物，这些代谢产物通过将3H标记的类似物与珊瑚的无细胞提取物一起孵育来进行测试。所有标记的代谢产物都是通过生物合成产生的，其放射化学纯度通过高效液相色谱纯化和衍生化相结合的方法确定。总之，伪蕨素是由香叶基香叶基二磷酸环化生成伊丽莎白三烯，芳构化生成埃罗戈烯，连续两次氧化生成7,8-二羟基埃罗戈烯，然后糖基化生成一种裂环伪蕨素作为关键中间体。脱氢反应生成两性霉素，两性霉素经过环化反应生成伪蕨素。
