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: 2.55). 02/2002; 59(1):105-10. DOI: 10.1016/S0031-9422(01)00395-8
Source: PubMed


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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    • "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 · 2.55 Impact Factor
    • "Carbohydrate, lipid, protein, fiber, inorganic salt, amino acid, fatty acid, and sterol content of the hypocotyls of L. meyenii have been described.[13] Additionally, it also contains alkaloids, steroids, macaene and macamide, while some investigators suggest that L. meyenii exerts hormonal balancing effect through Maca alkaloids, which act on the hypothalamus-pituitary axis and the adrenals,[14] but, there is no supporting evidence. Further experiments are needed to assess which compound, of the several Maca's components, is responsible of the observed in vivo effects. "
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    ABSTRACT: Objective: To evaluate the effect of long-term ethanol extract of Lepidium meyenii (Maca) on serum hormone levels in ovariectomized (OVX) rats and compare them with the effect of diethylstilbestrol. Materials and Methods: Fifty female Sprague-Dawley rats were ovariectomized or sham operated. Both sham and OVX control groups (n = 10, respectively) received the vehicle. The remaining OVX rats were oral administrated with ethanol extract of Maca (0.096, or 0.24g/kg; n = 10, respectively) and diethylstilbestrol (0.05 mg/kg; n = 10). The treatment continued for 28 weeks. At week 12 and week 28, the blood of rats was collected and serum hormone levels, including estradiol (E2), testosterone (T) and follicle-stimulating hormone (FSH) were measured by radioimmunoassay. Results: At week 12, the levels of serum E2 were slightly higher in Maca groups than that in OVX group; T levels were significantly decreased; and FSH levels were advanced slightly in Maca groups than that in sham group. After 28 weeks administration, serum E2 levels in Maca-treated animals did not differ significantly from sham control, the low dose of Maca increased serum E2 levels, and Maca prevented increase in serum FSH levels compared with OVX group. Conclusions: Long-term Maca supply modulates endocrine hormone balance in OVX rats, especially it decreases enhanced FSH levels. It is proposed that Maca may become a potential choice for postmenopausal women.
    Indian Journal of Pharmacology 07/2014; 46(4):416-9. DOI:10.4103/0253-7613.135955 · 0.69 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(1). DOI:10.1016/j.phytol.2014.03.005 · 1.45 Impact Factor
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