Brevianamide F Explained

Brevianamide F , also known as cyclo-(L-Trp-L-Pro), belongs to a class of naturally occurring 2,5-diketopiperazines.^[1] It is the simplest member and the biosynthetic precursor of a large family of biologically active prenylated tryptophan-proline 2,5-diketopiperazines that are produced by the fungi A. fumigatus^[2] and Aspergillus sp.^[3] It has been isolated from the bacterium Streptomyces sp. strain TN58 and shown to possess activity against the Gram-positive bacteria S. aureus and Micrococcus luteus.^[4] It has also been isolated from Bacillus cereus associated with the entomopathogenic nematode Rhabditis (Oscheius) sp. and shown to have antifungal activity against T. rubrum, C. neoformans, and C. albicans, better than amphotericin B.^[5] Although the proline 2,5-diketopiperazines are the most abundant and structurally diverse 2,5-diketopiperazines found in food, cyclo(L-Trp-L-Pro) has only been found as a minor 2,5-diketopiperazine (8.2 ppm) in autolyzed yeast extract.^[6] Initially, cyclo(L-Trp-L-Pro) and its DL, LD, and DD isomers showed potential for use in the treatment of cardiovascular dysfunction,^[7] but they were later shown to be hepatotoxic.^[8]

See also

• Brevianamide

Notes and References

1. Borthwick . Alan D. . 2012 . 2,5-Diketopiperazines: Synthesis, reactions, medicinal chemistry, and bioactive natural products . Chemical Reviews . 112 . 7 . 3641–3716 . 10.1021/cr200398y . 22575049 . 12893829.
2. Nierman . William C. . Pain . Arnab . Anderson . Michael J. . Wortman . Jennifer R. . Kim . H. Stanley . Arroyo . Javier . Berriman . Matthew . Abe . Keietsu . Archer . David B. . Bermejo . Clara . Bennett . Joan . Bowyer . Paul . Chen . Dan . Collins . Matthew . Coulsen . Richard . Davies . Robert . Dyer . Paul S. . Farman . Mark . Fedorova . Nadia . Fedorova . Natalie . etal . 2005 . Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus . Nature . 438 . 7071 . 1151–1156 . 10.1038/nature04332 . free . 16372009 . 4338031 . free. 10261/71531 . free .
3. Ding . Yousong . de Wet . Jeffrey R. . Cavalcoli . James . Li . Shengying . Greshock . Thomas J. . Miller . Kenneth A. . Finefield . Jennifer M. . Sunderhaus . James D. . McAfoos . Timothy J. . Tsukamoto . Sachiko . Williams . Robert M. . Sherman . David H. . 2010 . Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp. . Journal of the American Chemical Society . 132 . 36 . 12733–12740 . 10.1021/ja1049302 . 2941195 . 20722388 . 13058643.
4. Ben Ameur Mehdi . Raoudha . Shaaban . Khaled A. . Rebai . Ines Karray . Smaoui . Slim . Bejar . Samir . Mellouli . Lotfi . 2009 . Five naturally bioactive molecules including two rhamnopyranoside derivatives isolated from the Streptomyces sp. strain TN58 . Natural Product Research . 23 . 12 . 1095–1107 . 10.1080/14786410802362352 . 19662574 . 30343010.
5. Nishanth Kumar . S. . Nath . Vishnu Sukumari . Pratap Chandran . R. . Nambisan . Bala . 2014 . Cyclic dipeptides from rhabditid entomopathogenic nematode-associated Bacillus cereus have antimicrobial activities . World Journal of Microbiology and Biotechnology . 30 . 2 . 439–449 . 10.1007/s11274-013-1461-7 . 23979826 . 6079944.
6. Borthwick . Alan D. . Da Costa . Neil C. . 2017 . 2,5-Diketopiperazines in food and beverages: Taste and bioactivity . Critical Reviews in Food Science and Nutrition . 57 . 4 . 718–742 . 10.1080/10408398.2014.911142 . 25629623 . 1334464.
7. Jamie . Hajierah . Kilian . Gareth . Dyason . Karin . Milne . Pieter J. . 2002 . The effect of the isomers of cyclo(Trp-Pro) on heart and ion-channel activity . Journal of Pharmacy and Pharmacology . 54 . 12 . 1659–1665 . 10.1211/002235702252 . free . 12542896 . 12453892 . free.
8. Jamie . H. . Kilian . G. . Milne . P. J. . 2002 . Hepatotoxicity of the isomers of cyclo(Trp-Pro) . Die Pharmazie . 57 . 9 . 638–642 . 12369454 . 23942810.