N-trans-ρ-caffeoyl tyramine isolated from Tribulus terrestris exerts anti-inflammatory effects in lipopolysaccharide-stimulated RAW 264.7 cells

Ko, Han‐Jik; Ahn, Eun‐Kyung; Oh, Joa Sub

doi:10.3892/ijmm.2015.2301

Cited by 34 publications

(16 citation statements)

References 26 publications

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“…This compound was tentatively identified as cannabisin B by comparison with the literature data (Sakakibara et al, ), and its molecular formula was reported as C 34 H 32 N 2 O 8 (Chen et al, ). Cannabisin B is highly regarded for its antioxidant activity as it inhibited arginase in in vitro assays (Bourjot et al, ) and exhibited anti‐inflammatory effects (Ko et al, ). Chen et al () provided evidence that hempseed hull, a by‐product that is usually discarded after the oil extraction process, could be used as a source of natural antioxidants.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

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 eluent fractions G46-51-1-13 were obtained from this initial liquid chromatographic separation. The fractions were examined to an in vitro assay to assess their inhibitory effect on NO production ( 24 ).…”

Section: Methodsmentioning

confidence: 99%

Anti-inflammatory effect of tribulusamide D isolated from Tribulus terrestris in lipopolysaccharide-stimulated RAW264.7 macrophages

Lee

Ahn

Hong

et al. 2017

Molecular Medicine Reports

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Tribulus terrestris (T. terrestris) has been used as a traditional medicine for the treatment of a variety of diseases, including inflammation, edema and hypertension. The aqueous and ethanol extracts of T. terrestris contain alkaloids, flavonoids, tannins, quinines and phenolic compounds. Tribulusamide D is a compound that has been isolated from the ethanol extract of T. terrestris. The present study investigated the anti-inflammatory effect of tribulusamide D on lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Tribulusamide D inhibited the production of LPS-induced nitric oxide and prostaglandin E2, by reducing the expression of inducible nitric oxide synthase and cyclooxygenase-2 expression, respectively. The expression of these genes associated with inflammation was determined using reverse transcription-polymerase chain reaction and western blot analysis. Furthermore, tribulusamide D reduced the expression of LPS-induced inflammatory cytokines, including interleukin (IL)-6, IL-10 and tumor necrosis factor-α. They were quantified using an enzyme-linked immunosorbent assay. In addition, the present study confirmed that the inhibitory effects of tribulusamide D on the inflammatory response were mediated through inactivation of mitogen-activated protein kinase p38 and inhibition of nuclear localization of nuclear factor-B, which were also determined by western blot analysis. To the best of our knowledge, the current study is the first to demonstrate that tribulusamide D exerts anti-inflammatory activity by altering the expression of inflammatory mediators and cytokines, indicating that tribulusamide D could be developed as a potential therapeutic agent for the treatment of inflammatory disorders.

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“…A constitutional isomer of the previous compound was N-caffeoyltyramine, which was found to inhibit macrophage-mediated inflammatory responses through the suppression of the production of NO and pro-inflammatory cytokines [31]. This compound was tentatively identified under peak 5.…”

Section: Hr-ms Analysis: Phenylamidesmentioning

confidence: 97%

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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N-trans-ρ-caffeoyl tyramine isolated from Tribulus terrestris exerts anti-inflammatory effects in lipopolysaccharide-stimulated RAW 264.7 cells

Cited by 34 publications

References 26 publications

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

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

Anti-inflammatory effect of tribulusamide D isolated from Tribulus terrestris in lipopolysaccharide-stimulated RAW264.7 macrophages

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

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