Beauvericin

Beauvericin

Names
IUPAC name (3S,6R,9S,12R,15S,18R)-3,9,15-Tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Identifiers
CAS Number	26048-05-5  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3000  Y
ChEMBL	ChEMBL373872  N
ChemSpider	2277520  Y
KEGG	C11590  N
PubChem CID	3007984
UNII	26S048LS2R  Y
CompTox Dashboard (EPA)	DTXSID00891834
InChI InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1 Y Key: GYSCAQFHASJXRS-FFCOJMSVSA-N Y InChI=1/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1 Key: GYSCAQFHASJXRS-FFCOJMSVBB
SMILES O=C1N(C)[C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H]1C(C)C)Cc2ccccc2)C)C(C)C)Cc3ccccc3)C)C(C)C)Cc4ccccc4
Properties
Chemical formula	C45H57N3O9
Molar mass	783.963 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Beauvericin is a depsipeptide with antibiotic and insecticidal effects belonging to the enniatin family. It was isolated from the fungus Beauveria bassiana , but is also produced by several other fungi, including several Fusarium species; ^{[1] [2]} it may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. ^{[2] [3] [4]} Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals. ^[2]

Chemically, beauvericin is a cyclic hexadepsipeptide with alternating N-methyl-phenylalanyl and D-hydroxy-iso-valeryl residues. Its ion-complexing capability allows beauvericin to transport alkaline earth metal and alkali metal ions across cell membranes.^{[ citation needed ]}

Beauvericin has in vitro fungicidal effects on Candida parapsilosis when used in combination with the antifungal drug ketoconazole at dosages of 0.1 μg/ml. Increased survivability rates and low cytotoxicity were also observed in mouse models. ^[5]

References

1. Hamill RL, Higgens CE, Boaz HE, Gorman M (1969). "The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina". Tetrahedron Letters. 10 (49): 4255–4258. doi:10.1016/S0040-4039(01)88668-8.
2. Logrieco A, Moretti A, Castella G, et al. (1998). "Beauvericin Production by Fusarium Species". Appl Environ Microbiol. 64 (8): 3084–8. Bibcode:1998ApEnM..64.3084L. doi:10.1128/AEM.64.8.3084-3088.1998. PMC   106821 . PMID   9687479.
3. Logrieco A, Rizzo A, Ferracane R, Ritieni A (2002). "Occurrence of Beauvericin and Enniatins in Wheat Affected by Fusarium avenaceum Head Blight". Appl Environ Microbiol. 68 (1): 82–5. Bibcode:2002ApEnM..68...82L. doi:10.1128/AEM.68.1.82-85.2002. PMC   126553 . PMID   11772612.
4. Jestoi M, Rokka M, Yli-Mattila T, Parikka P, Rizzo A, Peltonen K (2004). "Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples". Food Additives and Contaminants. 21 (8): 794–802. doi:10.1080/02652030410001713906. PMID   15370831. S2CID   19565366.
5. Zhang L; Yan K; Zhang Y; Huang R; Bian J; Zheng C; Sun H; Chen Z; Sun N; An R; Min F; Zhao W; Zhuo Y; You J; Song Y; Yu Z; Liu Z; Yang K; Gao H; Dai H; Zhang X; Wang J; Fu C; Pei G; Liu J; Zhang S; Goodfellow M; Jiang Y; Kuai J; Zhou G; Chen X.K (2007). "High-throughput synergy screening identifies microbial metabolites as combination agents for the treatment of fungal infections". Proc Natl Acad Sci U S A. 104 (11): 4606–11. Bibcode:2007PNAS..104.4606Z. doi: 10.1073/pnas.0609370104 . PMC   1838648 . PMID   17360571.