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.
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Among Cannabis hydroxycinnamic acid amides are N-trans-coumaroyl-tyramine in roots, and N-trans-feruloyltyramine and N-trans-caffeoyltyramine in flowers, seeds, and roots.
“Among these are the hydroxycinnamic acid amides (HCAAs) N-trans-coumaroyl-tyramine in roots, and N-trans-feruloyltyramine and N-trans-caffeoyltyramine in flowers, seeds, and roots.”
Fifteen phenolic amides and lignanamides have been identified in Cannabis.
“Additionally, fifteen phenolic amides and lignanamides have been identified in Cannabis (Figure 1 and Figure 2).”
Other Cannabis metabolites include cannabisins A to G, cannabisins M, N and O, 3,3′-demethylheliotropamide, and grossamide, with cannabisins B and G present in roots.
“Other metabolites include cannabisins A to G, as well as cannabisins M, N and O, 3,3′-demethylheliotropamide, and grossamide, with cannabisins B and G present in the roots [12,14,29,30,41].”
Cannabisin A and D are among the most effective lignanamides in DPPH (IC50 = 32.9 and 23.9 μM), ABTS (6.6 and 0.5 μM), and ORAC (7.3 and 73.0 μM) assays, compared with quercetin (25.5, 0.4, and 9.2 μM).
“They found that cannabisin A and D were among the most effective lignanamides tested in DPPH (IC50 = 32.9 μM and 23.9 μM), ABTS (IC50 = 6.6 μM and 0.5 μM), and ORAC (IC50 = 7.3 μM and 73.0 μM) assays, against the positive control quercetin (IC50 = 25.5 μM, 0.4 μM, and 9.2 μM) [41].”
C. sativa lignanamides with anticholinesterase activity are 3,3′-demethyl-heliotropamide (IC50 = 46.2 μM) and 3,3′ demethyl-grossamide (IC50 = 38.7 μM), compared with galanthamine (IC50 = 2.8 μM).
“C. sativa lignanamides presenting anticholinesterase activity are 3,3′-demethyl-heliotropamide (IC50 = 46.2 μM) and 3,3′ demethyl-grossamide (IC50 = 38.7 μM), against the positive control galanthamine (IC50 = 2.8 μM).”
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- Authors
- Yan, X., Tang, J., dos Santos Passos, C., Nurisso, A., Simões-Pires, C. A., Ji, M., Lou, H., & Fan, P.
- Affiliations
- Shandong University (CN)
- School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland
- University of Geneva (CH)
- Department of Natural Product Chemistry, Key Laboratory of Chemical Biology of Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China
- Corresponding author
- Fan, Peihong
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-12-02
- Volume
- 63
- Issue
- 49
- Pages
- 10611-10619
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2238286371
- Cited by
- 160
- References
- 5
- Citations by year
- 2026: 9 · 2025: 14 · 2024: 16 · 2023: 22 · 2022: 22 · 2021: 25 · 2020: 18 · 2019: 12 · 2018: 9 · 2017: 10 · 2016: 3
- FWCI
- 3.19
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Agricultural and Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Shandong Province (2015GSF119025)
- National Natural Science Foundation of China (81473323)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant-derived Lignans Synthesis and Bioactivity
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Phytochemistry and Biological Activities
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Keywords
- lignanamides, hemp seeds, Cannabis sativa, secondary metabolites, antioxidant activity, acetylcholinesterase inhibition, structure elucidation, bioactive compounds
- MeSH terms
- Ethanol, Antioxidants, Cannabis, Cholinesterase Inhibitors, Models, Molecular, Phenols, Plant Extracts, Pyrrolidines, Seeds, Molecular Structure
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