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Characterization of Lignanamides from Hemp (Cannabis sativa L.) Seed and Their Antioxidant and Acetylcholinesterase Inhibitory Activities
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 (<b>2</b>), cannabisin N (<b>5</b>), cannabisin O (<b>8</b>),
and 3,3′-demethyl-heliotropamide (<b>10</b>), together
with 10 known lignanamides, among which <b>4</b> 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 <b>2</b>, <b>7</b>,
and <b>9</b>–<b>14</b> showed good antioxidant
activity, among which <b>7</b>, <b>10</b>, and <b>13</b> 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