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

Marsupellins A–F, <i>ent</i>-Longipinane-Type Sesquiterpenoids from the Chinese Liverwort <i>Marsupella alpine</i> with Acetylcholinesterase Inhibitory Activity

Acetylcholinesterase (AChE) inhibitory activity-guided fractionation of the Chinese liverwort <i>Marsupella alpine</i> afforded six new [marsupellins A–F (<b>1</b>–<b>6</b>)] and three known (<b>7</b>–<b>9</b>) <i>ent</i>-longipinane-type sesquiterpenoids. The structures were determined from MS and NMR spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Compounds <b>1</b>–<b>9</b> exhibited moderate to weak AChE inhibitory activity

Hapmnioides A–C, Rearranged Labdane-Type Diterpenoids from the Chinese Liverwort <i>Haplomitrium mnioides</i>

Many exceptional labdane-type diterpenoids have been exclusively found in liverworts, which serve as taxonomic molecules or play important ecological roles in interactions among organisms. Three unprecedented labdane-type diterpenoids hapmnioides A (<b>1</b>), B (<b>2</b>), and C (<b>3</b>) formed through cascade rearrangement from the Chinese liverwort <i>Haplomitrium mnioides</i> are reported. Their structures were established by comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction, and their anti-inflammatory activities were also preliminarily tested