The isolation and identification of two compounds with predominant radical scavenging activity in hempseed (seed of Cannabis sativa L.)

Chen, Tianpeng; He, Jinfeng; Zhang, Jianchun; Li, Xiaohui; Zhang, Hua; Hao, Jianxiong; Li-te, LI

doi:10.1016/j.foodchem.2012.03.009

Cited by 131 publications

(133 citation statements)

References 16 publications

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“…N-trans-caffeoyltyramine (UV λ max in MeOH 220, 294, 318 nm) and cannabisin B (UV λ max in MeOH 220, 245, 283, 335 nm) were identified on the basis of their spectral characteristics, as they were previously isolated and identified as phenolic compounds with predominant radical-scavenging activity in hemp seed. 35 The identification of N-trans-caffeoyltyramine and cannabisin B within the present research, solely based on UV spectral characteristics, has been only tentative. However, the presence of previously known and new lignanamides and cannabisins was recently reported by Lesma et al, 6 who performed a thorough investigation of the metabolic content of hemp seeds in various cultivars, making an important contribution to their NMR spectroscopic characterization.…”

Section: Physical Characteristics Of Hemp Meal Fractionsmentioning

confidence: 63%

Characterization of Byproducts Originating from Hemp Oil Processing

Pojić

Mišan

Sakač

et al. 2014

J. Agric. Food Chem.

129

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Valorization of hemp seed meal, a byproduct of hemp oil processing, was performed by measuring the distribution of nutritional and antinutritional compounds in different hemp seed meal fractions. According to chemical composition, two cotyledon-containing fractions (>180 and <180 μm) were significantly richer in protein (p < 0.05) (41.2% ± 0.04% and 44.4% ± 0.02%, respectively), lipid (15.1% ± 0.02% and 18.6% ± 0.04%, respectively), and sugar content (4.96% ± 0.11% and 3.46% ± 0.08%, respectively) in comparison to the hull-containing fractions (>350 and >250 μm), which were significantly richer in crude fiber content (29.5% ± 0.04% and 21.3% ± 0.03%, respectively). The free radical scavenging capacity (IC50) of fraction extracts increased (p < 0.05) with increasing mean particle size (from 17.18 ± 0.59 to 5.29 ± 0.30 mg/mL). Cannabisin B and N-trans-caffeoyltyramine were the most abundant phenolic compounds in the hull fractions (from 267 ± 15.9 to 287 ± 23.1 mg/kg), while cotyledon fractions had higher content of catechin (from 313 ± 12.4 to 744 ± 22.2 mg/kg) and p-hydroxybenzoic acid (from 124 ± 6.47 to 129 ± 8.56 mg/kg (P < 0.05). Well-balanced ω-6 to ω-3 fatty acid ratio (3:1) was determined in all fractions. Antinutrients (trypsin inhibitors, phytic acid, glucosinolates, and condensed tannins) were mostly located in the cotyledon fractions. These findings indicate that the separation of hemp seed meal into different fractions could be used to concentrate valuable target compounds and consequently facilitate their recovery.

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Section: Physical Characteristics Of Hemp Meal Fractionsmentioning

confidence: 63%

Characterization of Byproducts Originating from Hemp Oil Processing

Pojić

Mišan

Sakač

et al. 2014

J. Agric. Food Chem.

129

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“…Chromatograms were acquired at 219, 257, 320, and 335 nm, and data from triplicate samples were analyzed using the Chromeleon software (Version 7.2 SR4, Thermo Fisher Scientific, Waltham, MA USA). For the external standard calibration curves and linearity verification, caffeic acid and catechin were chosen and generated at 320 and 219 nm, respectively (Chen et al, ). External standard calibration curves were obtained from a series of solutions in 80% (v/v) aqueous acetone from 1.0 to 100 μg mL −1 ( n = 11), with R 2 = 0.9998 for caffeic acid and 0.9994 for catechin.…”

Section: Extraction Of Phenolic Compounds From Hempseed Cakesmentioning

confidence: 99%

“…Cannabis phenolics possess anti‐inflammatory properties: They inhibit prostaglandin E2 production by cultured rheumatoid synovial cells (Barrett et al, ). They have recently been shown to demonstrate antimicrobial as well as antileishmanial activity in addition to exhibiting strong antioxidative scavenging activity and anticancer efficacy (Carvalho et al, ; Chen et al, ).…”

Section: Introductionmentioning

confidence: 99%

“…Cannabisin A is a naturally occurring lignanamide with an arylnaphthalene skeleton. Chen et al () isolated N ‐ trans ‐caffeoyltyramine and cannabisin B from hempseed hulls using 60% ethanol. Heat pretreatments, in addition to the type of solvent used for extraction, are also known to increase the amount of phenolic compounds in oilseed cake and meal (Spielmeyer et al, ; Zago et al, ).…”

Section: Introductionmentioning

confidence: 99%

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Effect of Solvent, Preheating Temperature, and Time on the Ultrasonic Extraction of Phenolic Compounds from Cold‐Pressed Hempseed Cake

Liang

Zago

Nandasiri

et al. 2018

J Americ Oil Chem Soc

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The effect of different solvents (aqueous methanol [70%, v/v], aqueous acetone [80%, v/v], and a solvent mixture [MA] of aqueous methanol [70%, v/v] and aqueous acetone [70%, v/v] in a ratio of 1:1 [v/v]), preheating temperatures (140, 160, and 180 C), and times of exposure (5, 15, and 30 min) on the ultrasonic extraction of the main phenolic compounds from hempseed cake (Cannabis sativa) was investigated. A simplified new high-performance liquid chromatography (HPLC) method was developed to identify and quantify the main phenolics (namely, N-transcaffeoyltyramine and cannabisin B) in the extracts. Two other main compounds, numbered 3 and 4, were also detected. The results showed that the nature of the extracting solvent had a significant (P < 0.05) impact on the ultrasonic extraction of phenolic compounds. The acetone extracts exhibited the highest total phenolic content (TPC), followed by MA and methanol. The preheating temperature and time of exposure enhanced the TPC for all solvents examined. The main phenolics, N-trans-caffeoyltyramine, cannabisin B, and compound 3, were positively affected by the temperature and time of exposure, irrespective of the solvents used. In sharp contrast, compound 4 appeared to be thermally sensitive: increasing preheating time and temperature decreased the yields of this compound. This study demonstrated that acetone was the most effective extracting solvent and that preheating enhanced the yield of the main phenolics.

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“…In comparison with other materials, these extracts contained lower condensed tannin than those obtained from Artemisia herba-alba (5.47 ±0.09 mg CE/g DW), Ruta chalpensis (4.73 ±0.14 mg CE/g DW) and Peganum hamala (2.03 ±0.06 mg CE/g DW) (Khlifi et al, 2013). Generally, the extraction effi ciency of bioactive compounds is largely depending on the solvent used (Leblanc et al, 2009;Xi et al, 2009;Chen et al, 2012). The present study shows that among all the solvent; ethyl acetate and water were better solvents for effective extraction of tannins as compared to other solvents like n-hexane and methanol.…”

Section: Total Phenolic Content In Diff Erent Extracts (Tpc)mentioning

confidence: 87%

Effect of extraction solvents on the biomolecules and antioxidant properties of Scorzonera undulata (Asteraceae): Application of factorial design optimization phenolic extraction

Athmouni

Belghith

Bellassouad

et al. 2015

Acta Sci Pol Technol Aliment

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Background. Phenolic compounds were extracted and isolated from S. undulata roots. Methods. Sample of roots from E. hirta was tested for phenolic compounds, and in vitro antioxidant activity by diphenyl-1-picrylhydrazyl (DPPH) assay, ABTS, FRAP and reducing power was measured using cyanoferrate method. Results. The methanolic fraction exhibited the highest total phenol content (6.12 ±0.11 mg AGE/g DW). On the other hand, the highest fl avonoids concentration was observed in ethyl acetate fraction (2.90 ±0.05 mg CE/g DW) in addition to anthocyanins (28.56 ±3.96 mg/l). Besides, the highest level of tannins content was measured in the polar aprotic solvent ethyl acetate extract (3.25 ±0.06 mg CE/g DW). The different extracts of S. undulata were evaluated for their radical scavenging activities by means of the DPPH assay. The strongest scavenging activity was observed in methanolic fraction scavenged radicals effectively with IC 50 values of 0.14 ±0.02 mg/ml. Similarly, the potassium ferricyanide reduction (FRAP) and ABTS•+ of methanol extract. On the other hand, the total reducing power of ethyl acetate extract was found higher than of other extracts. This paper presents the application of the design-of experiment method for optimizing the extraction of phenolic content using methanol solvent. The resulting regression model has shown that the effect of temperature is not statistically signifi cant (with >95% certainty), while that of agitation speed is. The two main effects are contributed by the solvent concentration and the maceration period. Conclusion. Our results clearly showed that the extraction of phenolic compounds and their antioxidant capacity is signifi cantly affected by solvent combinations. S. undulata presented the highest total phenolic content, total fl avonoids content and antioxidant capacity values. The resulting regression model has shown that the effect of temperature is not statistically signifi cant (with >95% certainty), while that of agitation speed is.

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The isolation and identification of two compounds with predominant radical scavenging activity in hempseed (seed of Cannabis sativa L.)

Cited by 131 publications

References 16 publications

Characterization of Byproducts Originating from Hemp Oil Processing

Characterization of Byproducts Originating from Hemp Oil Processing

Effect of Solvent, Preheating Temperature, and Time on the Ultrasonic Extraction of Phenolic Compounds from Cold‐Pressed Hempseed Cake

Effect of extraction solvents on the biomolecules and antioxidant properties of Scorzonera undulata (Asteraceae): Application of factorial design optimization phenolic extraction

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