title: Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities.
abstract: 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.
authors.affiliation: Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
authors.forename: Xiaoli
authors.initials: X
authors.lastname: Yan
authors.affiliation: Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
authors.forename: Jiajing
authors.initials: J
authors.lastname: Tang
authors.affiliation: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Carolina
authors.initials: C
authors.lastname: dos Santos Passos
authors.affiliation: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Nurisso
authors.affiliation: School of Pharmaceutical Sciences, University of Geneva, University of Lausanne , Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Claudia Avello
authors.initials: CA
authors.lastname: Simões-Pires
authors.affiliation: Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
authors.forename: Mei
authors.initials: M
authors.lastname: Ji
authors.affiliation: Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
authors.forename: Hongxiang
authors.initials: H
authors.lastname: Lou
authors.affiliation: Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
authors.forename: Peihong
authors.initials: P
authors.lastname: Fan
mesh_terms: D000975:Antioxidants / Q000494:pharmacology*; D002188:Cannabis / Q000737:chemistry*; D002800:Cholinesterase Inhibitors / Q000494:pharmacology*; D000431:Ethanol; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry / Q000493:pharmacokinetics; D012639:Seeds / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D002800:Cholinesterase Inhibitors; D010636:Phenols; D010936:Plant Extracts; D011759:Pyrrolidines; C482753:heliotropamide; D000431:Ethanol
keywords: acetylcholinesterase inhibitor; antioxidant; cannabisin; hemp seed; lignanamides