Brevianamide F

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.fumigates [2] and Aspergillus sp. [3] It has been isolated from the bacterium Streptomyces sp. strain TN58 and shown to possess activity against two Gram-positive bacteria, S.aureus and Micrococcus luteus, [4] and 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 (8.2ppm) 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] however they were later shown to be hepatoxic.[8]

Brevianamide F
Names
IUPAC name
(3S,8aS)-3-(1H-Indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Other names
Cyclo-(L-Trp-L-Pro)
Identifiers
3D model (JSmol)
ChemSpider
Properties
C16H17N3O2
Molar mass 283.331 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  2. Nierman WC, Pain A, Anderson MJ, Wortman JR, Kim HS, Arroyo J, Berriman M, Abe K, Archer DB, Bermejo C, Bennett J (December 2005). "Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus". Nature. 438 (7071): 1151–1156. doi:10.1038/nature04332. PMID 16372009.
  3. Ding Y, Wet JR, Cavalcoli J, Li S, Greshock TJ, Miller KA, Finefield JM, Sunderhaus JD, McAfoos TJ, Tsukamoto S, Williams RM, Sherman DH (August 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. doi:10.1021/ja1049302. PMC 2941195. PMID 20722388.
  4. Ben Ameur Mehdi R, Shaaban KA, Rebai IK, Smaoui S, Bejar S, Mellouli L (August 2009). "Five naturally bioactive molecules including two rhamnopyranoside derivatives isolated from the Streptomyces sp. strain TN58". Natural Product Research. 23 (12): 1095–1107. doi:10.1080/14786410802362352.
  5. Kumar SN, Nath VS, Chandran RP, Nambisan B (February 2014). "Cyclic dipeptides from rhabditid entomopathogenic nematode-associated Bacillus cereus have antimicrobial activities". World Journal of Microbiology and Biotechnology. 30 (2): 439–449. doi:10.1007/s11274-013-1461-7. PMID 23979826.
  6. Borthwick AD, Da Costa NC (2017). "2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity". Critical Reviews in Food Science and Nutrition. 57 (4): 718–742. doi:10.1080/10408398.2014.911142. PMID 25629623.
  7. Jamie H, Kilian G, Dyason K, Milne PJ (December 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. doi:10.1211/002235702252. PMID 12542896.
  8. Jamie H, Kilian G, Milne PJ (September 2002). "Hepatotoxicity of the isomers of cyclo (Trp-Pro)". Die Pharmazie. 57 (9): 638–642. PMID 12369454.
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