Abstract
The weak but noteworthy presence of (poly)phenols in hemp seeds has been long overshadowed by the essential polyunsaturated fatty acids and digestible proteins, considered responsible for their high nutritional benefits. Instead, lignanamides and their biosynthetic precursors, phenylamides, seem to display interesting and diverse biological activities only partially clarified in the last decades. Herein, negative mode HR-MS/MS techniques were applied to the chemical investigation of a (poly)phenol-rich fraction, obtained from hemp seeds after extraction/fractionation steps. This extract contained phenylpropanoid amides and their random oxidative coupling derivatives, lignanamides, which were the most abundant compounds and showed a high chemical diversity, deeply unraveled through high resolution tandem mass spectrometry (HR-MS/MS) tools. The effect of different doses of the lignanamides-rich extract (LnHS) on U-87 glioblastoma cell line and non-tumorigenic human fibroblasts was evaluated. Thus, cell proliferation, genomic DNA damage, colony forming and wound repair capabilities were assessed, as well as LnHS outcome on the expression levels of pro-inflammatory cytokines. LnHS significantly inhibited U-87 cancer cell proliferation, but not that of fibroblasts, and was able to reduce U-87 cell migration, inducing further DNA damage. No modification in cytokines’ expression level was found. Data acquired suggested that LnHS acted in U-87 cells by inducing the apoptosis machinery and suppressing the autophagic cell death.
Highlights
Plant foods, thanks to the functionality of their bioactive secondary metabolites, are considered to be both safe and able to promote good health [1], explaining some important targeted effects in humans, and preventing affluence diseases, such as cardiovascular diseases and cancers [2]
The interest in the polyphenols contained in hemp seed was for a long time obscured by its high content in essential polyunsaturated fatty acids, mainly linoleic and α-linolenic acids, though different flavonoid glycosides were identified in cold-pressing hemp seed oil [24,25]
The recovery of bioactive compounds from hempseed meal could be the driving force for developing new hemp seed-based goods, in which the processing of hemp fruits waste is valuable for fully exploiting the innumerable advantages of this crop [59,60]
Summary
Thanks to the functionality of their bioactive secondary metabolites, are considered to be both safe and able to promote good health [1], explaining some important targeted effects in humans, and preventing affluence diseases, such as cardiovascular diseases and cancers [2]. Bioactive compounds are in ancient crops, whose actual recovery further renewed the phytochemical research into the discovery of beneficial substances, which could be present, after food processing, in the daily meals or be exceptionally lost in produced waste and by-products [3]. Molecules 2020, 25, 1049 chemically characterized by a phenylpropanoid core, which are reported to exert numerous biological effects in mammals, including antitumor and antioxidant activities [4]. They act as phytoestrogens and are converted by intestinal microflora into mammalian lignans or enterolignan compounds [5]. Flaxseed (Linum usitatissimum L.) is reported to contain about 75–800 times more lignans than cereal grains, legumes, fruits and vegetables, together with antioxidant flavonols and hydroxycinnamic acids [7], and lariciresinol was one of the main constituents of pumpkin seeds (Cucurbita pepo L.) [8]
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