Brevianamide F , also known as cyclo-(
L-Trp-
L-Pro), belongs to a class of naturally occurring
2,5-diketopiperazines. 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'' and ''Aspergillus'' sp. 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''. It has also been isolated from ''Bacillus cereus'' associated with the
entomopathogenic nematode
Entomopathogenic nematodes (EPN) are a group of nematodes (thread worms), that cause death to insects. The term ''entomopathogenic'' has a Greek origin, with ''entomon'', meaning ''insect'', and ''pathogenic'', which means ''causing disease''. T ...
''Rhabditis'' (''Oscheius'') sp. and shown to have antifungal activity against ''T. rubrum'', ''C. neoformans'', and ''C. albicans'', better than
amphotericin B
Amphotericin B is an antifungal medication used for serious fungal infections and leishmaniasis. The fungal infections it is used to treat include mucormycosis, aspergillosis, blastomycosis, candidiasis, coccidioidomycosis, and cryptococ ...
. 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. Initially, cyclo(
L-Trp-
L-Pro) and its
DL,
LD, and
DD isomers showed potential for use in the treatment of cardiovascular dysfunction, but they were later shown to be hepatotoxic.
See also
*
Brevianamide
References
{{reflist
Diketopiperazines