Blasticidin A

Blasticidin A
Names
	IUPAC name 1-methyl-3-[1,8,9,11,13,15,17,19,21,23,25,26,27,28,29-pentadecahydroxy-2,4,6,10,14,16-hexamethyl-30-[3,4,5,6-tetrahydroxy-6-(2-hydroxydodecyl)oxan-2-yl]triacont-2-enylidene]pyrrolidine-2,4-dione
Identifiers
CAS Number	100513-53-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	68004077 ;
PubChem CID	76169554;
	InChI InChI=1S/C58H107NO23/c1-9-10-11-12-13-14-15-16-17-35(60)27-58(81)56(79)55(78)53(76)46(82-58)26-44(69)52(75)54(77)51(74)43(68)24-38(63)22-36(61)21-37(62)23-39(64)32(5)49(72)33(6)40(65)25-41(66)34(7)50(73)42(67)20-30(3)18-29(2)19-31(4)48(71)47-45(70)28-59(8)57(47)80/h19,29-30,32-44,46,49-56,60-69,71-79,81H,9-18,20-28H2,1-8H3 Key: VVBSMETZVCGSHB-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCC(CC1(C(C(C(C(O1)CC(C(C(C(C(CC(CC(CC(CC(C(C)C(C(C)C(CC(C(C)C(C(CC(C)CC(C)/C=C(\C)/C(=C/2\C(=O)CN(C2=O)C)/O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O;
Properties
Chemical formula	C58H107NO23
Molar mass	1186.463 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Blasticidin A is an antibiotic produced by Streptomyces sp. that has antifungal^[1] and antibacterial^[2] activity. First synthesized in 1955, it was initially identified as a potential antifungal treatment for Magnaporthe grisea. Further research after discovery demonstrated in-vivo effectiveness against Pyricularia oryzae (the causative agent of Magnaporthe grisea) and Penicillium chrysogenum (the fungus which produces Penicillin)^[1]^[3] A later study found it to have fairly wide antifungal effect, demonstrating the ability to kill members of the Alternaria, Botrytis, Corticium, Gloeosporium, Glomerella, Macrosporium, Ophiobolus, and Piricularia genera with relatively low doses. The same study showed efficacy against some strains of Candida albicans and Rodotorula, and a narrower spectrum of antibacterial function; effective against Bacillus subtilis, Corynebacterium xerosis (a causative agent of several opportunistic infections), Pseudomonas solanacearam, Proteus vulgaris (a causative agents for Urinary tract infections), Shigella sonnei (one of the causative agents of Shigellosis) and Staphylococcus aureus.^[2]

Despite fairly wide efficacy, it is a poor candidate for human or vetrinary use due to the high toxcicity of similar coumpounds including Blasticidin S.^[4]

References

1 2 Fukunaga, Kazuo; Misato, Tomomasa; Ishii, Itaru; Asakawa, Masaru (1955-07-01). "Blasticidin, A New Anti-Phytopathogenic Fungal Substance. Part I". Bulletin of the Agricultural Chemical Society of Japan. 19 (3): 181–188. doi:10.1080/03758397.1955.10857286. ISSN 0375-8397.
1 2 Kono, Yoshiki; Takeuchi, Setsuo; Yonehara, Hiroshi (1968). "STUDIES ON BLASTICIDIN A". The Journal of Antibiotics. 21 (7): 433–438. doi:10.7164/antibiotics.21.433. ISSN 0021-8820.
↑ Biologically Active Natural Products: Argochemicals. Cutler G. G., Cutler S. J.; p 193-198. (1999)
↑ Yang, C. C.; Deng, J. F. (April 1996). "Clinical experience in poisonings following exposure to blasticidin S, a curiously strong fungicide". Veterinary and Human Toxicology. 38 (2): 107–112. ISSN 0145-6296. PMID 8693684.

[:0-1] 1 2 Fukunaga, Kazuo; Misato, Tomomasa; Ishii, Itaru; Asakawa, Masaru (1955-07-01). "Blasticidin, A New Anti-Phytopathogenic Fungal Substance. Part I". Bulletin of the Agricultural Chemical Society of Japan. 19 (3): 181–188. doi:10.1080/03758397.1955.10857286. ISSN 0375-8397.

[:1-2] 1 2 Kono, Yoshiki; Takeuchi, Setsuo; Yonehara, Hiroshi (1968). "STUDIES ON BLASTICIDIN A". The Journal of Antibiotics. 21 (7): 433–438. doi:10.7164/antibiotics.21.433. ISSN 0021-8820.

[3] Biologically Active Natural Products: Argochemicals. Cutler G. G., Cutler S. J.; p 193-198. (1999)

[4] Yang, C. C.; Deng, J. F. (April 1996). "Clinical experience in poisonings following exposure to blasticidin S, a curiously strong fungicide". Veterinary and Human Toxicology. 38 (2): 107–112. ISSN 0145-6296. PMID 8693684.

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