Two novel macamides from the roots of 'Maca' (Lepidium meyenii Walpers)

CHAIN, FERNANDO EZEQUIEL; GRAU, ALFREDO; MARTINS, JOSÉ C.; CATALÁN, CESAR ATILIO NAZARENO

Blankenberge

Simposio; 12th Edition of the Young Belgium Magnetic Resonance Scientist; 2013

Lepidium meyenii Walpers, most commonly known as ?Maca?, is an edible crop of economic importance. Its energizing and aphrodisiac properties led to regard this crop as a mild alternative to Viagra®. Its modern significance stems not only in its caloric value but in its therapeutics properties, as a general stimulant, dietary supplement and for the treatment of different sexual dysfunctions. Nowadays there are several enterprises in the USA, Europe and Asia that commercialize dietary supplements with maca extracts as principal constituent. Among the wide variety of secondary metabolites found in maca, the macamides group arises for its importance. These amides, derived from the condensation of benzylamine with saturated and unsaturated fatty acids, are not found in other Lepidium species or in any other genera, thus they are true chemical markers for the specie. It has been proposed that this group of biologically active compounds is responsible for the improvement in the sexual activity that maca consumption provides; in addition, some of the properties attributed to Maca have been validated experimentally using laboratory animals and some of its active principles have been isolated. However, there is no conclusive evidence regarding its pharmacological effects, thus more in-depth studies are needed. In the present work, 2 new macamides have been characterized from the roots of L. meyenii Walpers. The hexanic extract of the root was analysed by LC-MS and subsequently subjected to HPLC-UV. This allowed to isolate N-(3,4-dimethoxybenzyl)-hexadecanamide and N-benzyltetracosanamide. The structure of these novel compounds was unambiguously established by 1D and 2D NMR spectroscopy.