Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
J Nat Prod. 2013 Jul 26;76(7):1238-41. doi: 10.1021/np400355h. Epub 2013 Jun 26.
The dimeric diazofluorenes known as the lomaiviticins are produced by the marine bacterium Salinispora pacifica DPJ-0019. Investigation of the fermentation broth of DPJ-0019 has yielded the first monomeric benzo[b]fluorene isolated from this species, (-)-homoseongomycin (13). (-)-Homoseongomycin (13) is related to the known natural product seongomycin (10), which is co-produced with the monomeric diazofluorenes known as the kinamycins. We describe the synthesis of the isotopically labeled derivative homoseongomycin-d5 (14), via the intermediacy of the diazofluorene "prelomaiviticin-d5" (12). Our studies establish that (-)-homoseongomycin (13) may be derived from prelomaiviticin (11) and suggest that 13 and 10 are shunt or detoxification metabolites in lomaiviticin and kinamycin biosynthesis, respectively.
已知二聚体二氮菲类化合物洛马维辛由海洋细菌盐单胞菌 DPJ-0019 产生。对 DPJ-0019 的发酵液进行研究，从该种中分离得到了第一个单体苯并[b]芴，（-）-同宗霉素（13）。（-）-同宗霉素（13）与已知天然产物色宗霉素（10）有关，色宗霉素与已知的单体二氮菲类化合物金霉素共同产生。我们通过中间产物二氮菲“前洛马维辛-d5”（12）描述了同位素标记衍生物同宗霉素-d5（14）的合成。我们的研究表明，（-）-同宗霉素（13）可能来源于前洛马维辛（11），并表明 13 和 10 分别是洛马维辛和金霉素生物合成中的支路或解毒代谢物。
