Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities

• Published in: Journal of agricultural and food chemistry Vol. 63; no. 49; pp. 10611 - 10619
• Main Authors: Yan, Xiaoli, Tang, Jiajing, dos Santos Passos, Carolina, Nurisso, Alessandra, Simões-Pires, Claudia Avello, Ji, Mei, Lou, Hongxiang, Fan, Peihong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.12.2015; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Antioxidants - pharmacology; Cannabis - chemistry; Chemistry; Chemistry, Applied; Cholinesterase Inhibitors - pharmacology; Ethanol; Food Science & Technology; Life Sciences & Biomedicine; Models, Molecular; Molecular Structure; Phenols - chemistry; Phenols - pharmacology; Physical Sciences; Plant Extracts - chemistry; Pyrrolidines - chemistry; Pyrrolidines - pharmacokinetics; Science & Technology; Seeds - chemistry; acetylcholinesterase inhibitor; antioxidant; hemp seed; lignanamides; cannabisin; FRUITS; PROTEIN; PHENOLIC-COMPOUNDS; LYCIUM-CHINENSE; FREE-RADICALS; PRODUCTS; ROOT BARK; GROSSAMIDE; SOLANACEAE PLANTS; CONSTITUENTS
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.5b05282

Hemp seed is known for its content of fatty acids, proteins, and fiber, which contribute to its nutritional value. Here we studied the secondary metabolites of hemp seed aiming at identifying bioactive compounds that could contribute to its health benefits. This investigation led to the isolation of 4 new lignanamides, cannabisin M (2), cannabisin N (5), cannabisin O (8), and 3,3′-demethyl-heliotropamide (10), together with 10 known lignanamides, among which 4 was identified for the first time from hemp seed. Structures were established on the basis of NMR, HR-MS, UV, and IR as well as by comparison with the literature data. Lignanamides 2, 7, and 9–14 showed good antioxidant activity, among which 7, 10, and 13 also inhibited acetylcholinesterase in vitro. The newly identified compounds in this study add to the diversity of hemp seed composition, and the bioassays implied that hemp seed, with lignanamides as nutrients, may be a good source of bioactive and protective compounds.