Mercurialis perennis

An interesting process of C-C bond formation is represented by the autooxidation of Mercurialis perennis L. plant alkaloid hermidin. The reaction proceeds through the formation of a transient blue anion-radical, which dimerizes with the transfer of the reaction center to give, eventually, chryso-hermidin as a dimeric hexaketone (Wasserman et al. 1993 Scheme 7.59). 

Methylamine is produced in small quantities in the decomposition of nitrogenous organic matter, and is one of the products of the distillation of animal matter and of wood. It occurs in herring brine along with dimethylamine and trimethylamine, and in Mercurialis perennis. 

Amination of aldehydes by an amino acid aldehyde aminotransferase from Mercurialis perennis was inhibited strongly by pyruvate, oxaloacetate, and oxoglutarate, and this inhibition was suspected to be competitive (Hartmann et al., 1972). Formation of coniceine by an alanine 5-keto-octanal aminotransferase was inhibited competitively by pyruvate and uncompetitively by glyoxylate (Roberts, 1978). With the L-ornithine 2-oxoacid aminotransferase from Cucurbita pepo, severe inhibition by valine, leucine, and isoleucine could be observed, but there was no inhibition by lysine or proline (Lu and Mazelis, 1975). Cucurbita maxima ornithine aminotransferase, however, was reported to be inhibited by proline (Splittstoesser and Fowden, 1973), as well as by canavanine and diaminobutyrate. 

Although methylamine is widespread in plants, it is probably produced as an artifact of isolation in many cases. Other simple amines arise from transamination. An enz)mie system from Mercurialis perennis (Euphorbiaceae) was capable of producing a series of amines from ethylamine to undecylam-ine in the presence of the corresponding aldehydes and alanine (Fig. 28.2) (Smith, 1980). 

Swan, G.A. Isolation, Structure, and Synthesis of Hermidin, a Chromogen from Mercurialis perennis L. J. Chem. Soc. (London) Perkin Trans I 1985, 1757. 

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