N-trans-caffeoyltyramine

UHPLC-DPPH method reveals antioxidant tyramine and octopamine derivatives in Celtis occidentalis.[Pubmed:32980795]

J Pharm Biomed Anal. 2020 Nov 30;191:113612.

Celtis occidentalis L. (common Hackberry, Cannabaceae) has been applied in the traditional medicine for a long time as a remedy for sore throat, aid during menstruation and for treating jaundice. Nevertheless, the phytochemical exploration of the plant is still incomplete, literature data is limited to flavonoid derivatives isolated from the leaves. The present study reports screening approaches for bioactive compounds in C. occidentalis by fast and simple UHPLC-coupled assays. The UHPLC-DPPH method revealed six constituents in the methanolic extract of the twigs that had not been reported in C. occidentalis before. The antioxidant compounds were isolated by the means of flash chromatography and semi-preparative HPLC and identified by Orbitrap(R) MS and NMR spectroscopy as N-trans-p-coumaroyloctopamine (1), N-trans-feruloyloctopamine (2), N-trans-caffeoyltyramine (3), 2-trans-3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2-oxoethyl] prop-2-enamide (4), N-trans-p-coumaroyltryramine (5) and N-trans-feruloyltyramine (6). Despite the high antioxidant activity measured in the present study and literature data suggesting potential positive effects of the compounds in the central nervous system, the PAMPA-BBB assay performed with the Celtis extract revealed that none of the aforementioned compounds are able to penetrate across the blood-brain barrier via transcellular passive diffusion.

Hydroxycinnamic acid derivatives isolated from hempseed and their effects on central nervous system enzymes.[Pubmed:32664762]

Int J Food Sci Nutr. 2020 Jul 14:1-11.

New neuroprotective treatments of natural origin are being investigated. Both, plant extracts and isolated compounds have shown bioactive effects. Hempseed is known for its composition of fatty acids, proteins, fibre, vitamins, as well as a large number of phytochemical compounds. After a defatting process of the seeds, hydroxycinnamic acids and its amine derivatives are the majoritarian compounds in an ethyl acetate fraction (EAF). In the present study, we investigated in vitro effect on neuronal enzymes: MAO-A, MAO-B, tyrosinase and acetylcholinesterase. Besides, the effect of EAF on striatal biogenic amines in mice was evaluated. Both, EAF and isolated compounds (N-trans-caffeoyltyramine and N-trans-coumaroyltyramine), showed inhibitory action on MAO-A, MAO-B and tyrosinase. Furthermore, an increasing of biogenic amines was observed in the corpus striatum of the mice, after administration of EAF. These findings show that EAF and the hydroxycinnamic acid derivatives may represent a potential treatment in degenerative neuronal diseases.

Characterization of bioactive compounds in defatted hempseed (Cannabis sativa L.) by UHPLC-HRMS/MS and anti-inflammatory activity in primary human monocytes.[Pubmed:32329481]

Food Funct. 2020 May 1;11(5):4057-4066.

Hempseed (Cannabis sativa L.) has beneficial impact on human health mainly because of its wide variability of bioactive compounds. However, many of them are not fully characterized yet. In this work, hempseed was defatted and through a bio-guided studied, two fractions (F03 and F05) with the highest content of phenols, flavonoids and antioxidant capacity were selected. Fractions were chemically analyzed by UHPLC HRMS/MS. The anti-inflammatory capacities of these compounds were evaluated on human monocytes using flow cytometry, RT-qPCR and Elisa procedures. A high amount of phenolic compounds were identified, with the major compound being: N-trans-caffeoyltyramine (6.36 mg g(-1) in F05 and 1.28 mg g(-1) in F03). Both, F03 and F05 significantly reduced the inflammatory competence of LPS-treated human primary monocytes, decreasing TNF-alpha and IL-6 gene expression and secretion. These findings indicate that in the defatted fraction of the hempseed there are a wide number of compounds with beneficial potential to prevent and treat inflammatory disorders, as well as other processes caused by oxidative stress.

Antiproliferative and antioxidant effect of polar hemp extracts (Cannabis sativa L., Fedora cv.) in human colorectal cell lines.[Pubmed:31544542]

Int J Food Sci Nutr. 2020 Jun;71(4):410-423.

Total phenolic content and antioxidant activity of polar extracts of edible resources from Fedora hemp cultivar (Cannabis sativa L.), namely seed, flour and oil, were evaluated. The main components in the polar extracts were identified using HPLC-DAD and HPLC-ESI-MS/MS. As expected, the molecular profile of components from seeds and flour was strictly similar, dominated by N-trans-caffeoyltyramine. The profile of oil polar extracts contained hydroxycinnamic acid derivatives and cannabinoids at lower extent. While the extracts from hemp seed and flour did not interfere with growth of Caco-2 and HT-29 cell, the one from oil (150 microg/mL) significantly reduced cell viability after 24 h of treatment. This effect was associated with the activation of apoptotic cell death and was independent from the antioxidant capacity of the oil polar extract. Notably, HT-29 cells differentiated with sodium butyrate were not sensitive to the cytotoxic effect of the oil extract.

Isolation of Cinnamic Acid Derivatives from the Bulbs of Allium tripedale.[Pubmed:29862209]

Adv Biomed Res. 2018 Apr 24;7:60.

Background: Allium genus with 750 species is the most diverse genus in the Amaryllidaceae family. Historically, Allium species have been used as medicinal plants, especially for prevention and treatment of cardiovascular diseases and considered as valuable sources of phytonutrients. Phytochemical investigation of Allium tripedale, locally called "Anashq," which is an edible plant of the "Zagros" region (west of Iran) was conducted in the present study. Materials and Methods: Air-dried bulbs of the plant were extracted in a four-step extraction method with increasing polarity using hexane, chloroform, chloroform-methanol (9:1), and methanol. Chloroform-methanol (9:1) extract was fractionated by medium-pressure liquid chromatography on a RP-18 column using a linear gradient solvent system of H2O to MeOH. Phenolic-rich fractions were subjected to the final isolation and purification of the constituents by reversed-phase high-performance liquid chromatography method. Structure elucidation of the compounds was performed through comprehensive methods including 1D-and 2D-NMR and mass spectroscopy. Results: Two cinnamic acid derivatives were isolated from the bulbs of A. tripedale; using spectroscopic methods, their chemical structures were determined as 6,7-dimethoxy N-trans-caffeoyltyramine (1) and N-trans-feruloyltyramine (2). Conclusion: Cinnamic acid derivatives are pharmacologically active phenolic compounds, which have been isolated from different Allium species. Isolation of these compounds from A. tripedale is reported for the first time in this study and could be used as a chemical basis for explanation of the plant biological and pharmacological activities.

Phenolics, acyl galactopyranosyl glycerol, and lignan amides from Tetragonia tetragonioides (Pall.) Kuntze.[Pubmed:30263405]

Food Sci Biotechnol. 2016 Oct 31;25(5):1275-1281.

Eleven antioxidative compounds, including five lignin amides, were isolated from the aerial part of Tetragonia tetragonioides (New Zealand spinach) using 1,1-diphenyl-2-picrylhydrazyl radicalscavenging assay-guided purification. The structures were determined by nuclear magnetic resonance and electrospray ionization-mass spectroscopy. These compounds were identified as methyl linoleate (1), methyl coumarate (2), methyl ferulate (3), 1-O-stearoyl-3-O-beta-D-galactopyranosyl-sn-glycerol (4), 1-O-caffeoyl-beta-D-glucopyranoside (5), N-trans-caffeoyltyramine (6), cannabisin B (7), cannabisin A (8), Ntrans-feruloyltyramine (9), N-cis-feruloyltyramine (10), and N-trans-sinapoyltyramine (11). Compounds 1, 2, 4, 5, and 8-11 were isolated for the first time from this plant.

Characterization of byproducts originating from hemp oil processing.[Pubmed:25426777]

J Agric Food Chem. 2014 Dec 24;62(51):12436-42.

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 mum) 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 mum), 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 omega-6 to omega-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.

The isolation and identification of two compounds with predominant radical scavenging activity in hempseed (seed of Cannabis sativa L.).[Pubmed:23107724]

Food Chem. 2012 Sep 15;134(2):1030-7.

Forty samples were extracted from defatted kernels and hulls of two varieties of hempseed (Bama and Yunma No. 1) using 10 different polar solvent systems. The radical scavenging capacity of the extracts was evaluated using 2,2-diphenyl-1-pikrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays and the total phenolic content was determined by Folin-Ciocalteu's phenol reagent. The correlation analysis indicated that the antioxidants in hempseed belonged to phenolic and DPPH() assay was suitable for evaluating the radical scavenging activity. Two compounds, with predominant antiradical activity, were isolated in 60% ethanol extract of hempseed hull using macroporous resin absorption, LH-20 gel chromatography, and high performance liquid chromatography methods, which were identified as N-trans-caffeoyltyramine and cannabisin B by high-resolution mass spectra, nuclear magnetic resonance spectra, and ultraviolet data. The two compounds exhibited significant high DPPH() scavenging activity and protective effect against in vitro oxidation of human low-density lipoprotein compared with extracts from flaxseed, grape seed, and soybean. This suggests that hempseed hull extract is a potential source of natural antioxidants, which could be added to dietary supplements to help prevent oxidative stress.

Cinnamoylphenethyl amides from Polygonum hyrcanicum possess anti-trypanosomal activity.[Pubmed:22816300]

Nat Prod Commun. 2012 Jun;7(6):753-5.

A methanolic extract from aerial parts of Polygonum hyrcanicum (Polygonaceae) showed high activity against Trypanosoma brucei rhodesiense (IC50 = 3.7 microg/mL). Bioassay-guided fractionation of the extract resulted in isolation of cinnamoylphenethyl amides, including N-trans-caffeoyltyramine (1), N-trans-p-coumaroyltyramine (7), and N-trans-feruloyltyramine (8) as the main active constituents (IC50s ranging from 2.2 to 13.3 microM). Some structurally related, but less active compounds, such as cannabisin B (2), tyrosol (3), p-coumaric acid (4), ferulic acid (5), and N-cis-feruloyltyramine (6) were also identified, along with N-trans-3,4-dimethoxycinnamoyldopamine (9). Cytotoxicity of the active compounds in L6 cells was determined, and selectivity indices (SI) of 7.9 to 33.4 were calculated.

Amides from the stem of Capsicum annuum.[Pubmed:21425680]

Nat Prod Commun. 2011 Feb;6(2):227-9.

7'-(4'-hydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (1), 7'-(3',4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (2), N-p-trans-coumaroyltyramine (3), N-trans-caffeoyltyramine (4), beta-sitostenone (5), ferulic acid (6), hydroferulic acid (7), 5-hydroxy-3,4-dimethoxycinnamic acid (8), veratic acid (9), vanillic acid (10), isovanillic acid (11), syringic acid (12), (+)-syringaresinol (13), and pheophorbide a (14) were isolated from the stems of Capsicum annuum (Solanaceae). Among them, 1 is a new amide compound. The structures of these compounds were characterized and identified by spectral analyses.

One new cinnamic imide dervative from the fruits of Tribulus terrestris.[Pubmed:18629718]

Nat Prod Res. 2008;22(11):1007-1010.

One new cinnamic imide derivative, named tribulusimide C (1), was isolated from the fruits of Tribulus terrestris, together with three known compounds, N-p-coumaroyltyramine (2), terrestriamide (3), N-trans-caffeoyltyramine (4). The structure of 1 was elucidated based on chemical analysis and spectral methods (IR, 1D and 2D NMR, HR-FAB-MS, EI-MS).

[Studies on the chemical constituents from Caragana intermedia].[Pubmed:16722312]

Zhong Yao Cai. 2006 Jan;29(1):19-21.

OBJECTIVE: To study the chemical constituents from Caragana intermedia. METHODS: The compounds were separated by chromatography methods. Their structures were identified by spectral analysis. RESULTS: Eight compounds were isolated and identified as 7,5'-dihydroxy-3 '-methoxyisoflavone-7-O-beta-D-glucoside (1), isorhamnetin 7-O-alpha-L-rhamnoside (2), 3, 4-dihydroxybenzoic acid (3), N-trans-caffeoyltyramine (4), D-3-O-methyl-inositol (5),7alpha-hydroxy-beta-sitosterol (6),7beta-hydroxy-beta-sitosterol (7) and stearic acid (8). CONCLUSION: All these compounds were obtained from this plant for the first time.

Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship.[Pubmed:11804514]

J Agric Food Chem. 2002 Jan 30;50(3):468-72.

The structure-activity relationships of synthetic caffeic acid amide and ester analogues as potential antioxidants and free radical scavengers have been investigated. The 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) scavenging activity of the test compounds was N-trans-caffeoyl-L-cysteine methyl ester (5) > N-trans-caffeoyldopamine (4) > N-trans-caffeoyltyramine (3) > N-trans-caffeoyl-beta-phenethylamine (2) > Trolox C (8) > caffeic acid phenethyl ester (1) > caffeic acid (6) > ferulic acid (7). This established that the radical scavenging activity of the compounds increased with increasing numbers of hydroxyl groups or catechol moieties and also with the presence of other hydrogen-donating groups (-NH, -SH). The antioxidative activity of the compounds was also investigated in an emulsified linoleic acid oxidation system accelerated by 2,2'-azobis(2-amidinopropane) dihydrochloride. The order was 1 > 2 > 4 > 3 > or = 5 > 6 > 8 > 7. Therefore, in the emulsion system, the antioxidative activity of the test compounds depends not only on the hydroxyl groups or catechol rings but also on the partition coefficient (log P) or hydrophobicity of the compounds. This supports the concept that hydrophobic antioxidants tend to exhibit better antioxidative activity in an emulsion system.

Anti-herpes simplex virus type-1 flavonoids and a new flavanone from the root of Limonium sinense.[Pubmed:10865449]

Planta Med. 2000 May;66(4):333-6.

From the root of Limonium sinense (Girard) Ktze a new (2R,3S)-3,5,7,4'-tetrahydroxy-3',5'-dimethoxyflavanone was isolated and named isodihydrosyringetin (3), together with nine other known compounds, (-)-epigallocatechin 3-O-gallate (1), samarangenin B (2), myricetin (4), myricetin 3-O-alpha-rhamnopyranoside (5), quercetin 3-O-alpha-rhamnopyranoside (6), (-)-epigallocatechin (7), gallic acid (8), N-trans-caffeoyltyramine (9), and N-trans-feruloyltyramine (10). All of them were examined for their inhibitory effects on herpes simplex virus type-1 (HSV-1) replication in Vero cells. Both compounds 1 and 2 exhibited potent inhibitory activities in HSV-1 replication. Comparison of the IC50 values indicated that compounds 1 and 2 had higher inhibitory activities than the positive control acyclovir (38.6 +/- 2.6 vs. 55.4 +/- 5.3 microM, P < 0.001; 11.4 +/- 0.9 vs. 55.4 +/- 5.3 microM, P < 0.0005). Cytotoxicity was unlikely involved because no cell deaths were observable in the Vero cells following 5 day treatments with compound 1 or 2.

Grossamide and N-trans-caffeoyltyramine from Annona crassiflora seeds.[Pubmed:17252415]

Planta Med. 1996 Feb;62(1):76.

Grossamide, and N-trans-caffeoyltyramine, were isolated for the first time from the seeds of Annona crassiflora Mart, and in the Annonaceae family.