Chemical constituents of hemp (Cannabis sativa L.) seed with potential anti-neuroinflammatory activity

Zhou, Yuefang; Wang, Shanshan; Lou, Hongxiang; Fan, Peihong

doi:10.1016/j.phytol.2017.11.013

Cited by 76 publications

(57 citation statements)

References 28 publications

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“…The ion at m/z 145.0293 confirmed coumaroyl moiety, as well as the fragment ion at m/z 160.0408, which could be from the cleavage at the N-Cα bond and the following 1,4 nucleophilic addition on the β'-carbon of the phenylpropanoid side chain. The presence of the coumaroyl moiety was further revealed through the UV-DAD spectrum of the compound, which is was similar to that previously reported for this hydroxycinnamoyl amide (HAA) [26] and it was consistent with the loss of catechol group as highlighted by the blue shift of the absorption band detectable at 324 nm in compound 1 ( Figure S3).…”

Section: Hr-ms Analysis: Phenylamidessupporting

confidence: 87%

“…This latter could be also obtained from the base peak due to 163.06 Da loss. UV-DAD spectrum of peak 16 was fully comparable to that previously reported for the pure reference compound [26]. In fact, UV-DAD spectrum exhibited a characteristic strong maximum at 256 nm and only small peaks between 280 and 350 nm.…”

Section: Hr-ms Analysis: Lignanamidessupporting

confidence: 83%

“…Indeed, after oil recovery, hemp seed meal yet represents an important food polyphenol source. Several phenylamides and lignanamides were previously isolated and structurally identified mainly by means of nuclear magnetic resonance (NMR) spectroscopic tools [20,26]. Herein, in order to get insight into the chemical composition of commercial hempseeds, ultrasound assisted maceration was applied on seeds first ground with a knife mill and crushed into liquid N 2 to better preserve the integrity of the fruit's constituents.…”

Section: Resultsmentioning

confidence: 99%

“…The occurrence of a phenylcoumaran lignandiamide with 2,3-dihydrobenzofuran nucleus was supposed, and it could be derived through the 8-5 coupling of two caffeoyl alcohols [41]. The comparison of the UV-DAD spectrum with that reported in literature allowed us to putatively further identify the compound [26]. Finally, the [M − H] − ion of compound under peak 32, which fragmented into the base peak at m/z 298.1083, and minor fragment ions at m/z 178.0503 and 135.0444, could be attributable to 3,3 -demethyl-heliotropamide, an oxopyrrolidine-3-carboxamide, previously isolated from hemp fruits [20], whereas the benzodioxanes-type lignandiamides, cannabisin M and cannabisin Q, were tentatively identified from TOF-MS/MS spectra of compounds 36 and 38 ( Figure S10).…”

Section: Hr-ms Analysis: Lignanamidesmentioning

confidence: 91%

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Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells

et al. 2020

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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.

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Section: Hr-ms Analysis: Phenylamidessupporting

confidence: 87%

Section: Hr-ms Analysis: Lignanamidessupporting

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Hr-ms Analysis: Lignanamidesmentioning

confidence: 91%

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Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells

et al. 2020

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“…To date, a total of 567 natural constituents covering several chemical classes have been identified from C. sativa [1, 2]. The most important classes are the cannabinoids, terpenoids, nitrogenous compounds, noncannabinoid phenols, flavonoids, and steroids [3].…”

Section: Introductionmentioning

confidence: 99%

Chemical and Biological Studies of <b><i>Cannabis sativa</i></b> Roots

Elhendawy

Wanas

Radwan

et al. 2018

Med Cannabis Cannabinoids

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The chemical study of Cannabis sativa roots led to the isolation and identification of 10 compounds. Their chemical structures were unambiguously established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry as friedelan-3-one (1), epifriedelanol (2), β-sitosterol (3), ergost-5-en-3-ol (4), methyl hexadecanoate (5), pentadecanoic acid (6), 10E-hexadecenoic acid (7), 4-hydroxy-3-methoxybenzaldehyde (8), β-sitosterol-β-D-glucoside (9) and p-coumaroyltyramine (10). Compounds 5–9 were reported for the first time from C. sativa roots. All the isolated compounds were tested for their antimicrobial activity. Compound 4 showed modest activity against Cryptococcus neoformans with an IC₅₀ value of 13.7 μg/mL, while compound 10 displayed potent activity against Escherichia coli with an IC₅₀ value of 0.8 μg/mL. A high-performance liquid chromatography method was developed and validated for the detection and quantification of p-coumaroyltyramine (10) in the extracts of different varieties of C. sativa roots.

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Hemp (Cannabis sativaL.) Agronomic Practices, Engineering Properties, Bioactive Compounds and Utilization in Food Processing Industry

Mittal

Panghal

Gupta

2023

Harvesting Food From Weeds

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Chemical constituents of hemp (Cannabis sativa L.) seed with potential anti-neuroinflammatory activity

Cited by 76 publications

References 28 publications

Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells

Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells

Chemical and Biological Studies of <b><i>Cannabis sativa</i></b> Roots

Hemp (Cannabis sativaL.) Agronomic Practices, Engineering Properties, Bioactive Compounds and Utilization in Food Processing Industry

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