New natural lignanamides from hempseed cakes (Cannabis sativa L.)

Industrial hemp (Cannabis sativa L.) is cultivated in many countries for textile and nutritional interest. Hempseed is an excellent source of healthy unsaturated fatty acids and therefore is used for the production of oil. Hempseed cakes, the byproducts of this industry, are not currently considered as having high economic added value. But hempseed and its residue is a source of amides compounds derived from caffeic acid [1]. Recently, it has been shown that two of these compounds, N-trans-caffeoyltyramine and cannabisin B, possess predominant radical scavenging activity [2]. Thus hempseed cakes constitute a real interesting crude material for the extraction of biologically active compounds. Arginase, a metalloenzyme involved in urea cycle and in the biosynthesis of polyamines, utilizes L-arginine, the same substrate as nitric oxide synthase (NOS) that produces nitric oxide (NO). Work over the last decades revealed that arginase inhibitors might be a valuable strategy for the treatment of various diseases associated to increased polyamines production and/or decreased NO production [3]. Considering that caffeoyl compounds, especially nitrogen derivatives, could have a potential activity as inhibitor of arginase, we performed a phytochemical study of hempseed cakes with the goal to isolate interesting compounds for biological evaluation. We report here the first results of our work with the isolation and structural elucidation of two new natural lignanamides, among them 1 was previously obtained by semisynthesis [4]. The next step will be the evaluation of these compounds for arginase inhibition activity, using a test with purified bovine arginase, developed in our unit research.

Acknowledgements: We thank Michel Charreyron, oil producer, manager of “La goutte d'Or du Plateau” (Le Fied, Fanche-Comté, Jura) for the supply of hempseed cakes.

Keywords: Hempseed cakes; Cannabis sativa L.; lignanamides; arginase inhibitors

References:

1. Sakakibara I. et al. (1995) Phytochemistry 38: 1003 – 1007. 2. Chen, T. et al. (2012) Food Chemistry 134: 1030 – 1037. 3. Pernow, J. and Jung, C. (2013) Cardiovasc. Res. 98: 334 – 343. 4. Sakakibara I. et al. (1991) Phytochemistry 30: 3013 – 3016.