Journal of Agricultural Science and Engineering
Articles Information
Journal of Agricultural Science and Engineering, Vol.7, No.4, Dec. 2021, Pub. Date: Nov. 22, 2021
N-Benzylated Alkamides Isolated from Maca Planted in China
Pages: 75-86 Views: 484 Downloads: 83
Authors
[01] Jing Gan, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China; Jiangsu Hope-pharm Co., Ltd, Changzhou, P. R. China.
[02] Chuan He, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China.
[03] Qiulu Chen, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China.
[04] Yalin Liu, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China.
[05] Hang Hu, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China.
[06] Xiaoqiang Sun, Key Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou, P. R. China.
[07] Defeng Xu, National & Local Joint Engineering Research Center for High-efficiency Refining and High-quality Utilization of Biomass, School of Pharmacy, Changzhou University, Changzhou, P. R. China; Jiangsu Hope-pharm Co., Ltd, Changzhou, P. R. China.
Abstract
Lepidium meyenii (maca) is an edible herbaceous biennial plant of the Brassicaceae family that is native to South America and has been marketed for its traditional medicinal effects. N-benzylated alkamides, commonly known as “macamides”, have been found in maca and are considered as functional component of maca. Macamides could significantly enhance the libido and sexual potency of normal mice, improve anti-fatigue and anti-oxidant status in rats, and function as fatty acid amide hydrolase inhibitors to provide analgesic, anti-inflammatory, and neuroprotective effects. Maca was introduced into China in 2002. Now, China has become an important producer of maca in the world. However, chemical investigations of maca planted in China were rarely reported. Here, seventeen N-benzylated alkamides (macamides) in maca from Wenbi Mountain were identified by liquid chromatography mass spectrometry (LC-MS) and four of them were successfully isolated, namely N-3-methoxybenzyl-9Z-octadecenamide (1), N-benzyl-9Z-octadecenamide (2), N-(3-methoxybenzyl)-hexadecanamide (3), and N-benzyl-hexadecanamide (4). The chemical structure of these four compounds were established by spectroscopic and spectrometric methods including 1H nuclear magnetic resonance (NMR), 13C NMR, 2D NMR, electrospray ionization-high resolution mass spectrometry (ESI-HRMS), ultraviolet–visible spectroscopy (UV-Vis), and fourier transform infrared spectroscopy (FT-IR). These compounds are useful marker compounds for the quality control of Lepidium meyenii planted in China.
Keywords
Maca, Lepidium meyenii, N-benzylated Alkamides, Macamides, Isolation
References
[01] Lim, T. K. (2015). Lepidium meyenii, in: Edible Medicinal and Non Medicinal Plants. Springer International Publishing AG., Dordrecht, Netherland, pp. 801-828.
[02] Lee, M. S.; Lee, H. W.; You, S. K.; Ha, T. (2016). The use of maca (Lepidium meyenii) to improve semen quality: A systematic review. Maturitas, 92: 64-69.
[03] Liu, H.; Jin, W. W.; Fu, C. H.; Dai, P. F.; Yu, Y. T.; Huo, Q.; Yu, L. J. (2015). Discovering anti-osteoporosis constituents of maca (Lepidium meyenii) by combined virtual screening and activity verification. Food Res. Int., 77: 215-220.
[04] Wang, Y. L.; Wang, Y. C.; Mcneil, B.; Harvey, L. M. (2007). Maca: An Andean crop with multi-pharmacological functions. Food Res. Int., 40: 783-792.
[05] Zhang, S. Z.; Yang, F.; Shao, J. L.; Pu, H. M.; Ruan, Z. Y.; Yang, W. L. and Li, H. (2020). The metabolic formation profiles of macamides accompanied by the conversion of glucosinolates in maca (Lepidium meyenii) during natural air drying. Int. J. Food Sci. Technol., 55: 2428-2440.
[06] Xia, C.; Deng, J.; Pan, Y.; Lin, C.; Zhu, Y.; Xiang, Z.; Li, W.; Chen, J.; Zhang, Y.; Zhu, B.; Huang, Q. (2021). Comprehensive Profiling of Macamides and Fatty Acid Derivatives in Maca with Different Postharvest Drying Processes Using UPLC-QTOF-MS. ACS Omega, 6: 24484–24492.
[07] Peng, X.; Huang, Y.; Liu, J.; Zhang, R.; Li, Z.; Zhou, L.; Qiu, M. (2021). 1H qNMR-based quantitative analysis of total macamides in five maca (Lepidium meyenii Walp.) dried naturally. J. Food Compos. Anal., 100: 103917.
[08] Zheng, B. L.; He, K. C.; Kim, H.; Rogers, L.; Shao, Y.; Huang, Z. Y.; Lu, Y.; Yan, S. J.; QIEN, L. C.; Zheng, Q. Y. (2000). Effect of a lipidic extract from Lepidium meyenii on sexual behavior in mice and rats. Urology, 55: 598-602.
[09] Choi, E. H.; Kang, J. I.; Cho, J. Y.; Lee, S. H.; Kim, T. S.; Yeo, I. H.; Chun, H. S. (2012). Supplementation of standardized lipid-soluble extract from maca (Lepidium meyenii) increases swimming endurance capacity in rats. J. Funct. Foods, 4: 568-573.
[10] Almukadi, H.; Wu, H.; Böhlke, M.; Kelley, C. J.; Maher, T. J.; Pino-Figueroa, A. (2013). The macamide N-3-methoxybenzyl-linoleamide is a time-dependent fatty acid amide hydrolase (FAAH) inhibitor. Mol. Neurobiol., 48: 333-339.
[11] Gugnani, K. S.; Vu, N.; Rondón-Orti, A. N.; Böhlke, M.; Maher, T. J.; Pino-Figueroa, A. J. (2018). Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells. Toxicol. Appl. Pharma., 340: 67-76.
[12] Wu, H.; Kelley, C. J.; Pino-Figueroa, A.; Vu, H. D.; Maher, T. J. (2013). Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition. Bioorgan. Med. Chem., 21: 5188-5197.
[13] Chain, F. E.; Grau, A.; Martins, J. C.; Catalán, C. A. N. (2014). Macamides from wild ‘Maca’, Lepidium meyenii Walpers (Brassicaceae). Phytochem. Lett., 8: 145-148.
[14] Hajdu, Z. Nicolussi, S.; Rau, M.; Lorántfy, L.; Forgo, P.; Hohmann, J.; Csupor, D.; Gertsch, J. (2014). Identification of endocannabinoid system-modulating N-alkylamides from Heliopsis helianthoides var. scabra and Lepidium meyenii. J. Nat. Prod., 77: 1663-1669.
[15] Zheng, B. L.; Kim, C. H.; Wolthoff, S.; He, K.; Rogers, L.; Shao, Y.; Zheng, Q. Y. (2001). Extract of Lepidium meyenii roots for pharmaceutical applications. US Patent 6,267,995 B1.
[16] Gao, D. F. and Zhang, Z. S. (2013). Functional Constituents Identification in Maca, a Novel Food, by UPLC-MS/MS. J. Anhui Agri. Sci., 41: 830-832.
[17] Wan, W. T.; Zhang, Z. P.; Tan, X. L.; Yi, F.; Xiao, W.; Xu, L. J.; Xiao, P. G. (2015). The investigation of industrial development of Maca (Lepidium meyenii Walp.) in Yunnan Province. Mod. Chinese Med., 17: 726-729.
600 ATLANTIC AVE, BOSTON,
MA 02210, USA
+001-6179630233
AIS is an academia-oriented and non-commercial institute aiming at providing users with a way to quickly and easily get the academic and scientific information.
Copyright © 2014 - American Institute of Science except certain content provided by third parties.