Hercynine

L-Hercynine is a precursor of L-(+)-Ergothioneine (E600000); a natural molecule isolated from the rye ergot fungus and later identified in rat erythrocytes and liver and in numerous other animal tissues. Its antioxidizing properties may afford the compound therapeutic potential or it may be used as a food additive or in cosmetics.

ChEBI: N(alpha),N(alpha),N(alpha)-trimethyl-L-histidine is an amino-acid betaine and a member of N(alpha)-methyl-L-histidines. It is a conjugate base of a N(alpha),N(alpha),N(alpha)-trimethyl-L-histidinium(1+).

Hercynine is an intermediate (precursor) in ERGO biosynthesis; thus, fungi and mycobacteria can synthesize hercynine, but animals cannot. A human study showed that hercynine was detected in whole blood, plasma, urine, and saliva, and another clinical study showed that the levels of hercynine correlated with those of ERGO in whole blood, which suggested that hercynine is a metabolite of ERGO. However, the levels of hercynine were lower than those of ERGO, which presented the possibility that hercynine was further oxidized.

A method for producing hercynine on an industrial scale comprises the steps of:

1. reacting L-histidine, in a polar solvent or a mixture of polar solvents, with a methylating agent, MeX, at room temperature under controlled pH conditions;

2. separating the organic products from the inorganic salts formed during the reaction by electrodialysis; and the electrodialysis is carried out on a reaction medium adjusted to a pH between 8.5 to 9.5;

3. recrystallization of L-histidine betaine (hercynine) to eliminate organic impurities.