Bioactive Maca (Lepidium meyenii) alkamides are a result of traditional Andean postharvest drying practices

Phytochemistry

Volumn 116, Issue 1, 2015, Pages 138-148

  Esparza, Eliana ^a   Hadzich, Antonella ^a   Kofer, Waltraud ^a   Mithöfer, Axel ^b   Cosio, Eric G ^a  

^a PONTIFICIA UNIVERSIDAD CATÓLICA DEL PERÚ   (Peru)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

Alkamides; Benzylamine; Benzylisothiocyanate; Brassicaceae; Fatty acid amide hydrolase; Glucosinolates; Lepidium meyenii; Maca; Macamides; Post harvest processing

Indexed keywords

BRASSICACEAE; LEPIDIUM MEYENII;

AMIDE; PLANT EXTRACT;

CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; HYPOCOTYL; ISOLATION AND PURIFICATION; LEPIDIUM; NUCLEAR MAGNETIC RESONANCE; PERU; PHYTOTHERAPY;

HUMANS; HYPOCOTYL; LEPIDIUM; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PERU; PHYTOTHERAPY; PLANT EXTRACTS; POLYUNSATURATED ALKAMIDES;

EID: 84934889883     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.02.030     Document Type: Article

References (44)

1. Bednarek, P., Pislewska-Bednarek, M., Svatos, A., Schneider, B., Doubsky, J., Mansurova, M., Humphry, M., Consonni, C., Panstruga, R., Sanchez-Vallet, A., Molina, A., Schulze-Lefert, P., 2009. A glucosinolate metabolism pathway in living plant cells mediates broad-spectrum antifungal defense. Science 323, 101-106.
2. Bones, A. M., Rossiter, J. T., 2006. The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67, 1053-1067.
3. Brown, P. D., Tokuhisa, J. G., Reichelt, M., Gershenzon, J., 2003. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62, 471-481.
4. Canales, M., Aguilar, J., Prada, A., Marcelo, A., Huamán, C., Carbajal, L., 2000. Nutritional evaluation of Lepidium meyenii (Maca) in albino mice and their descendants. Arch. Latinoam. Nutr. 50, 126-133.
5. Cheng, D. L., Hashimoto, K., Uda, Y., 2004. In vitro digestion of sinigrin and glucotropaeolin by single strain of Bifidobacterium and identification of the digestive products. Food Chem. Toxicol. 42, 351-357.
6. Clément, C., Diaz, D., Manrique, I., Avula, B., Khan, I. A., Ponce Aguirre, D. D., Kunz, C., Mayer, A. C., Kreuzer, M., 2010. Secondary metabolites in maca as affected by hypocotyl color, cultivation history, and site. Agron. J. 102, 431-439.
7. Clifford, L. J., Nair, M. G., Rana, J., Dewitt, D. L., 2002. Bioactivity of alkamides isolated from Echinacea purpurea (L.) Moench. Phytomedicine 9, 249-253.
8. Devane, W. A., Axelrod, J., 1994. Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid, by brain membranes. Proc. Natl. Acad. Sci. USA 91, 6698-6701.
9. Dini, A., Migliuolo, G., Rastrelli, L., Saturnino, P., Schettino, O., 1994. Chemical composition of Lepidium meyenii. Food Chem. 49, 347-349.
10. Ganzera, M., Zhao, J., Muhammad, I., Khan, I. A., 2002. Chemical profiling and standardization of Lepidium meyenii (maca) by reversed phase high performance liquid chromatography. Chem. Pharm. Bull. (Tokyo) 50, 988-991.
11. Gimsing, A. L., Poulsen, J. L., Pedersen, H. L., Hansen, H. C., 2007. Formation and degradation kinetics of the biofumigant benzyl isothiocyanate in soil. Environ. Sci. Technol. 41, 4271-4276.
12. Gonzales, G. F., Miranda, S., Nieto, J., Fernandez, G., Yucra, S., Rubio, J., Yi, P., Gasco, M., 2005. Red maca (Lepidium meyenii) reduce prostate size in rats. Reprod. Biol. Endocrinol. 3, 1-16.
13. Gonzales, G. F., Nieto, J., Rubio, J., Gasco, M., 2006. Effect of black maca (Lepidium meyenii) on one spermatogenic cycle in rats. Andrologia 38, 166-172.
14. Goosen, T. C., Mills, D. E., Hollenberg, P. F., 2001. Effects of benzyl isothiocyanate on rat and human cytochromes P450: identification of metabolites formed by P450 2B1. J. Pharmacol. Exp. Ther. 296, 198-206.
15. Greger, H., 1984. Alkamides: structural relationships, distribution and biological activity. Planta Med. 50, 366-375.
16. Högestätt, E. D., Jönsson, B. A., Ermund, A., Andersson, D. A., Björk, H., Alexander, J. P., Cravatt, B. F., Basbaum, A. I., Zygmunt, P. M., 2005. Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolasedependent arachidonic acid conjugation in the nervous system. J. Biol. Chem. 280, 31405-31412.
17. Kataoka, K., Shiota, T., Takeyasu, T., Minoshima, T., Watanabe, K., Tanaka, H., Mochizuki, T., Taneda, K., Ota, M., Tanabe, H., Yamaguchi, H., 1996. Potent Inhibitors of acyl-CoA: cholesterol acyltransferase. 2. Structure-activity relationships of novel N-(2, 2-dimethyl-2, 3-dihydrobenzofuran-7-yl) amides. J. Med. Chem. 39, 1262-1270.
18. Kruszka, K. K., Gross, R. W., 1994. The ATP- and CoA-independent synthesis of arachidonoylethanolamide. A novel mechanism underlying the synthesis of the endogenous ligandofthe cannabinoid receptor. J. Biol. Chem. 269, 14346-14348.
19. Li, G., Ammerman, U., Quiroz, C. F., 2001. Glucosinolate contents in maca (Lepidium peruvianum, Chacón) seeds, sprouts, mature plants and several derived commercial products. Econ. Bot. 55, 255-262.
20. Martin-Tanguy, J., Cabanne, F., Perdrizet, E., Martin, C., 1978. The distribution of hydroxycinnamic acid amides in flowering plants. Phytochemistry 17, 1927-1928.
21. Matthäus, B., Luftmann, H., 2000. Glucosinolates in members of the family Brassicaceae: separation and identification by LC/ESI-MS-MS. J. Agric. Food Chem. 48, 2234-2239.
22. McCollom, M. M., Villinski, J. R., McPhail, K. L., Craker, L. E., Gafner, S., 2005. Analysis of macamides in samples of maca (Lepidium meyenii) by HPLC-UV-MS/MS. Phytochem. Anal. 16, 463-469.
23. Mewis, I., Schreiner, M., Nguyen, C. N., Krumbein, A., Ulrichs, C., Lohse, M., Zrenner, R., 2012. UV-B irradiation changes specifically the secondary metabolite profile in broccoli sprouts: induced signaling overlaps with defense response to biotic stressors. Plant Cell Physiol. 53, 1546-1560.
24. Møldrup, M. E., Geu-Flores, F., Olsen, C. E., Halkier, B. A., 2011. Modulation of sulfur metabolism enables efficient glucosinolate engineering. BMC Biotechnol. 11, 1-8.
25. Molina-Torres, J., Garćia-Chávez, A., Ramírez-Chávez, E., 1999. Antimicrobial properties of alkamides present in flavouring plants traditionally used in Mesoamerica: affinin and capsaicin. J. Ethnopharmacol. 64, 241-248.
26. Montalbetti, C. A. G. N., Falque, V., 2005. Amide bond formation and peptide coupling. Tetrahedron 61, 10827-10852.
27. Muhammad, I., Zhao, J., Dunbar, C., Khan, I. A., 2002. Constituents of Lepidium meyenii "Maca". Phytochemistry 59, 105-110.
28. National Research Council (USA). Advisory Committee on Technology Innovation, 1989. Maca. In Lost crops of the Incas: little-known plants of the Andes with promise for worldwide cultivation. National Academy Press, Washington D. C., pp. 57-65.
29. Olsen, O., Sørensen, H., 1980. Glucosinolates and amines in Reseda media. Phytochemistry 19, 1783-1787.
30. Piacente, S., Carbone, V., Plaza, A., Zampelli, A., Pizza, C., 2002. Investigation of tuber constituents of maca (Lepidium meyenii Walp.). J. Agric. Food Chem. 50, 5621-5625.
31. Pino-Figueroa, A., Vu, H., Kelley, C. J., Maher, T. J., 2011. Mechanism of action of Lepidium meyenii (Maca): an explanation for its neuroprotective activity. Am. J. Neuroprot. Neuroregen. 3, 87-92.
32. Rubio, J., Dang, H., Gong, M., Liu, X., Chen, S., Gonzales, G. F., 2007. Aqueous and hydroalcoholic extracts of black maca (Lepidium meyenii) improve scopolamineinduced memory impairment in mice. Food Chem. Toxicol. 45, 1882-1890.
33. Rubio, J., Riqueros, M. I., Gasco, M., Yucra, S., Miranda, S., Gonzales, G. F., 2006. Lepidium meyenii (Maca) reversed the lead acetate induced-damage on reproductive function in male rats. Food Chem. Toxicol. 44, 1114-1122.
34. Ruiz-Luna, A. C., Salazar, S., Aspajo, N. J., Rubio, J., Gasco, M., Gonzales, G. F., 2005. Lepidium meyenii (maca) increases litter size in normal adult female mice. Reprod. Biol. Endocrinol. 3, 16.
35. SCIICEX, 2013. Evolución de las exportaciones del producto maca. Sistema Integrado de Información de Comercio Exterior, Peru. http://www.siicex.gob.pe/siicex/apb/ReporteResumen. aspx?psector=1025&preporte=prodresu&pvalor=1934.
36. Sendker, J., Nahrstedt, A., 2008. Generation of primary amide glucosides from cyanogenic glucosides. Phytochemistry 70, 388-393.
37. Shrestha, R., Noordermeer, M. A., van der Stelt, M., Veldink, G. A., Chapman, K. D., 2002. N-acylethanolamines are metabolized by lipoxygenase and amidohydrolase in competing pathways during cottonseed imbibition. Plant Physiol. 130, 391-401.
38. Tang, C. S., Bhothipaksa, K., Frank, H. A., 1972. Bacterial degradation of benzyl isothiocyanate. Appl. Microbiol. 23, 1145-1148.
39. Ueda, N., Kurahashi, Y., Yamamoto, S., Tokunaga, T., 1995. Partial purification and characterization of porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270, 23823-23827.
40. Wang, Y., Wang, Y., McNeil, B., Harvey, L. M., 2007. Maca: an Andean crop with multi-pharmacological functions. Food Res. Intern. 40, 783-792.
41. Williams, D. J., Critchley, C., Pun, S., Chaliha, M., O'Hare, T. J., 2009. Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds. Phytochemistry 70, 1401-1409.
42. Xing-Hao, T., Hua, Z., Hong, Z., Ying, F., Jin, G., Wen-Wen, Z., 2014. Experimental study on fluidized bed drying process of Maca (Lepidium meyenii Walp.) tuber. J. Chem. Pharm. Res. 6, 1185-1193.
43. Yábar, E., Pedreschi, R., Chirinos, R., Campos, D., 2011. Glucosinolate content and myrosinase activity evolution in three maca (Lepidium meyenii Walp.) ecotypes during preharvest, harvest and postharvest drying. Food Chem. 127, 1576-1583.
44. Zhao, J., Muhammad, I., Dunbar, D. C., Mustafa, J., Khan, I. A., 2005. New alkamides from maca (Lepidium meyenii). J. Agric. Food Chem. 53, 690-693.