Cannabisin B

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.

Cannabisin B induces autophagic cell death by inhibiting the AKT/mTOR pathway and S phase cell cycle arrest in HepG2 cells.[Pubmed:23411211]

Food Chem. 2013 Jun 1;138(2-3):1034-41.

This study investigates the anticancer properties of Cannabisin B, purified from hempseed hull, in HepG2 human hepatoblastoma cells. The results indicate that Cannabisin B significantly inhibited cell proliferation by inducing autophagic cell death rather than typical apoptosis. Cell viability transiently increased upon the addition of a low concentration of Cannabisin B but decreased upon the addition of high concentrations. Cannabisin B-induced changes in cell viability were completely inhibited by pre-treatment with 3-methyladenine (3-MA), indicating that the induction of autophagy by Cannabisin B caused cell death. Additionally, Cannabisin B induced S phase cell cycle arrest in a dose-dependent manner. Moreover, Cannabisin B was found to inhibit survival signaling by blocking the activation of AKT and down-stream targets of the mammalian target of rapamycin (mTOR). These findings suggest that Cannabisin B possesses considerable antiproliferative activity and that it may be utilised as a promising chemopreventive agent against hepatoblastoma disease.

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.