Constituents of Lepidium meyenii‘‘Maca’’

National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University MS 38677, USA.
Phytochemistry (Impact Factor: 3.35). 02/2002; 59(1):105-10. DOI: 10.1016/S0031-9422(01)00395-8
Source: PubMed

ABSTRACT The tubers of Lepidium meyenii contain the benzylated derivative of 1,2-dihydro-N-hydroxypyridine, named macaridine, together with the benzylated alkamides (macamides), N-benzyl-5-oxo-6E,8E-octadecadienamide and N-benzylhexadecanamide, as well as the acyclic keto acid, 5-oxo-6E,8E-octadecadienoic acid. The structure elucidation of the isolated compounds was based primarily on 1D and 2D NMR spectroscopic analyses, including 1H-1H COSY, 1H-13C HMQC, 1H-13C HMBC and 1H-1H NOESY experiments, as well as from 1H-15N NMR HMBC correlations for macaridine and N-benzylhexadecanamide.

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Available from: Jianping Zhao, Aug 20, 2015
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    • "Macamides are bioactive secondary benzylalkylamides reported in L. meyenii hypocotyls (Ganzera et al., 2002; McCollom et al., 2005; Zhao et al., 2005; Muhammad et al., 2002). Although the material used for analysis in these publications consisted of dried hypocotyls or commercially available products obtained from them, it has been assumed that the macamides were present also in fresh hypocotyls as is the case with other species reported to contain alkamides (Martin-Tanguy et al., 1978; Greger, 1984; Molina-Torres et al., 1999; Clifford et al., 2002). "
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    ABSTRACT: Maca, Lepidium meyenii Walpers (Brassicaceae), is an annual herbaceous plant native to the high plateaus of the Peruvian central Andes. Its underground storage hypocotyls have been a traditional medicinal agent and dietary staple since pre-Columbian times. Reported properties include energizing and fertility-enhancing effects. Published reports have focused on the benzylalkamides (macamides) present in dry hypocotyls as one of the main bioactive components. Macamides are secondary amides formed by benzylamine and a fatty acid moiety, with varying hydrocarbon chain lengths and degree of unsaturation. Although it has been assumed that they are usually present in fresh undamaged tissues, analyses show them to be essentially absent from them. However, hypocotyls dried by traditional Andean postharvest practices or industrial oven drying contain up to 800μgg(-1) dry wt (2.3μmolg(-1) dry wt) of macamides. In this study, the generation of macamides and their putative precursors were studied during nine-week traditional drying trials at 4200m altitude and in ovens under laboratory conditions. Freeze-thaw cycles in the open field during drying result in tissue maceration and release of free fatty acids from storage and membrane lipids up to levels of 1200μgg(-1) dry wt (4.3μmolg(-1) dry wt). Endogenous metabolism of the isothiocyanates generated from glucosinolate hydrolysis during drying results in maximal benzylamine values of 4300μgg(-1) dry wt (40.2μmolg(-1) dry wt). Pearson correlation coefficients of the accumulation profiles of benzylamine and free fatty acid to that of macamides showed good values of 0.898 and 0.934, respectively, suggesting that both provide sufficient substrate for amide synthesis during the drying process. Copyright © 2015 The Authors. Published by Elsevier Ltd.. All rights reserved.
    Phytochemistry 03/2015; DOI:10.1016/j.phytochem.2015.02.030 · 3.35 Impact Factor
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    • "These spectroscopic data are in close correlation with that reported in the literature about macamides (Wang et al., 2007; McCollom et al., 2005; Muhammad et al., 2002; Zhao et al., 2005) but to our knowledge this is the first report of compounds 1 and 2 from a natural source. It should be noted that 1 is the first macamide found in Lepidium meyenii Walp. "
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    ABSTRACT: The non-polar extract of the tubers of Lepidium meyenii Walpers yielded two benzylated alkamides (macamides), N-(3,4-dimethoxybenzyl)-hexadecanamide (1) and N- benzyltetracosanamide (2). The structure elucidation of the compounds was based on 1D and 2D NMR spectroscopic analyses, including H-1-H-1 COSY, H-1-C-13 HSQC, H-1-C-13 HMBC, H-1-N-15 HSQC and HMBC experiments. (c) 2014 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
    Phytochemistry Letters 05/2014; 8. DOI:10.1016/j.phytol.2014.03.005 · 1.54 Impact Factor
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    • "Indeed, folk medicines are often valid sources of bioactive substances that are potentially useful in the treatment of many diseases, as demonstrated by the search for new medicinal agents for the treatment of trypanosomiasis, leishmaniasis and other diseases (Braña et al. 2005). In fact, a broad range of plant families and species contain active trypanocidal and leishmanicidal substances (Muhammad et al. 2002, Cui et al. 2003, Takahashi et al. 2004, González et al. 2005, Tasdemir et al. 2006, Corrêa et al. 2011). For example, diterpene resin acids, which are found in conifers , are known to be a potent defence against herbivores and pathogens (Martin et al. 2002). "
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    ABSTRACT: The activity of five (1-5) abietane phenol derivatives against Leishmania infantum and Leishmania braziliensis was studied using promastigotes and axenic and intracellular amastigotes. Infectivity and cytotoxicity tests were performed with J774.2 macrophage cells using Glucantime as a reference drug. The mechanisms of action were analysed by performing metabolite excretion and transmission electron microscopy ultrastructural studies. Compounds 1-5 were more active and less toxic than Glucantime. The infection rates and mean number of parasites per cell observed in amastigote experiments showed that derivatives 2, 4 and 5 were the most effective against both L. infantum and L. braziliensis. The ultrastructural changes observed in the treated promastigote forms confirmed that the greatest cell damage was caused by the most active compound (4). Only compound 5 caused changes in the nature and amounts of catabolites excreted by the parasites, as measured by ¹H nuclear magnetic resonance spectroscopy. All of the assayed compounds were active against the two Leishmania species in vitro and were less toxic in mammalian cells than the reference drug.
    Memórias do Instituto Oswaldo Cruz 05/2012; 107(3):370-6. DOI:10.1590/S0074-02762012000300012 · 1.57 Impact Factor
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