Chemistry:Brevianamide F
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| Names | |
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| Preferred IUPAC name
(3S,8aS)-3-[(1H-Indol-3-yl)methyl]hexahydropyrido[1,2-a]pyrazine-1,4-dione | |
| Other names
Cyclo-(L-Trp-L-Pro)
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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 | |
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
References
- ↑ Borthwick, Alan D. (2012). "2,5-Diketopiperazines: Synthesis, reactions, medicinal chemistry, and bioactive natural products". Chemical Reviews 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
- ↑ Nierman, William C. et al. (2005). "Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus". Nature 438 (7071): 1151–1156. doi:10.1038/nature04332. PMID 16372009.
- ↑ Ding, Yousong; de Wet, Jeffrey R.; Cavalcoli, James; Li, Shengying; Greshock, Thomas J.; Miller, Kenneth A.; Finefield, Jennifer M.; Sunderhaus, James D. et al. (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. PMID 20722388.
- ↑ 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. doi:10.1080/14786410802362352. PMID 19662574.
- ↑ 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. doi:10.1007/s11274-013-1461-7. PMID 23979826.
- ↑ 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. doi:10.1080/10408398.2014.911142. PMID 25629623.
- ↑ 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. doi:10.1211/002235702252. PMID 12542896.
- ↑ Jamie, H.; Kilian, G.; Milne, P. J. (2002). "Hepatotoxicity of the isomers of cyclo(Trp-Pro)". Die Pharmazie 57 (9): 638–642. PMID 12369454.
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