Roquefortin C , or simply Roquefortin , is an indole alkaloid , mycotoxin , produced by a number of species of the genus Penicillium , in particular Penicillium roqueforti .
| Rockfortin | |
|---|---|
 | |
| Are common | |
| Systematic name | (3E, 5aS, 10bR, 11aS) -3- (1H-imidazol-4-ylmethylene) -10b- (2-methyl-3-buten-2-yl) -6,10b, 11,11a-tetrahydro-2H- pyrazino [1 ', 2': 1,5] pyrrolo [2,3-b] indole-1,4 (3H, 5aH) -dione |
| Chem. formula | C 22 H 23 N 5 O 2 |
| Physical properties | |
| Molar mass | 389.45 g / mol |
| Thermal properties | |
| T. melt. | 203 ° C |
| Classification | |
| Reg. CAS number | 58735-64-1 |
| PubChem | |
| Smiles | |
| Inchi | |
| ChemSpider | |
Nerve toxin contained in small quantities in cheese produced using roquefort penicillium cultures.
Content
Properties
Upon extraction with methanol, it crystallizes with the formation of colorless needle crystals with a melting point of 202–205 ° C.
Ultraviolet absorption maxima are at 323, 238, 210 nm.
An intermediate product of the synthesis of another mycotoxin oxalin species Penicillium oxalicum .
Rockfortin LD 50 for male mice is 15–159 mg / kg with intraperitoneal administration.
History
It was first isolated and characterized in 1976 by P.M. Scott, M.-A. Merrien and J. Polonsky as the main metabolite of Penicillium roqueforti .
The biological origin of the toxin in cheese made using roquefort penicillin was experimentally confirmed in 1983.
Notes
Literature
- Weidenbörner M. Encyclopedia of Food Mycotoxins. - 2001. - P. 220-221.
- Scott PM, Merrien M.-A., Polonsky J. Roquefortine and isofumigaclavine A, metabolites from Penicillium roqueforti // Experientia. - 1976. - Vol. 32 (2). - P. 140-142. - DOI : 10.1007 / BF01937728 .
- Wagener RE, Davis ND, Diener UL Penitrem A and Roquefortine Production by Penicillium commune // Applied and Environmental Microbiology. - 1980. - Vol. 39 (4). - P. 882–887.