Brevianamide F

Brevianamide F
Names
	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)
Identifiers
CAS Number	38136-70-8;
3D model (JSmol)	Interactive image;
ChemSpider	157941;
PubChem CID	181567;
UNII	76XZ426FPP ;
CompTox Dashboard (EPA)	DTXSID10959075 ;
	InChI InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14-/m0/s1 Key: RYFZBPVMVYTEKZ-KBPBESRZSA-N;
	SMILES [H][C@@]12CCCN1C(=O)[C@H](Cc1c[nH]c3ccccc13)NC2=O;
Properties
Chemical formula	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]

References[edit]

^ 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. S2CID 12893829.
^ 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; et al. (2005). "Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus". Nature. 438 (7071): 1151–1156. doi:10.1038/nature04332. hdl:10261/71531. PMID 16372009. S2CID 4338031.
^ 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. doi:10.1021/ja1049302. PMC 2941195. PMID 20722388. S2CID 13058643.
^ 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. S2CID 30343010.
^ 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. S2CID 6079944.
^ 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. S2CID 1334464.
^ 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. S2CID 12453892.
^ Jamie, H.; Kilian, G.; Milne, P. J. (2002). "Hepatotoxicity of the isomers of cyclo(Trp-Pro)". Die Pharmazie. 57 (9): 638–642. PMID 12369454. S2CID 23942810.

[1] 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. S2CID 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; et al. (2005). "Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus". Nature. 438 (7071): 1151–1156. doi:10.1038/nature04332. hdl:10261/71531. PMID 16372009. S2CID 4338031.

[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. doi:10.1021/ja1049302. PMC 2941195. PMID 20722388. S2CID 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. doi:10.1080/14786410802362352. PMID 19662574. S2CID 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. doi:10.1007/s11274-013-1461-7. PMID 23979826. S2CID 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. doi:10.1080/10408398.2014.911142. PMID 25629623. S2CID 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. doi:10.1211/002235702252. PMID 12542896. S2CID 12453892.

[8] Jamie, H.; Kilian, G.; Milne, P. J. (2002). "Hepatotoxicity of the isomers of cyclo(Trp-Pro)". Die Pharmazie. 57 (9): 638–642. PMID 12369454. S2CID 23942810.

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