Also described are substantially pure preparations of various cannabinoids and cannabinoid acids, and also extracts enriched in cannabinoids and cannabinoid acids. Historically, cannabis was regarded by many physicians as unique; having the ability to counteract pain resistant to opioid analgesics, in conditions such as spinal cord injury, and other forms of neuropathic pain including pain and spasm in multiple sclerosis. The use of cannabis continued until the middle of the twentieth century, when the recreational use of cannabis prompted legislation which resulted in the prohibition of its use.
Next Section Abstract Exposure of cells to a wide variety of chemoprotective compounds confers resistance to a broad set of carcinogens.
For a subset of the chemoprotective compounds, protection is generated by an increase in the abundance of the protective phase II detoxification enzymes, such as glutathione S-transferase GST.
We have recently developed a cell culture system, using rat liver epithelial RL 34 cells, that potently responds to the phenolic antioxidants resulting in the induction of GST activity Kawamoto, Y. In the present study, we investigated the phase II-inducing potency of an isothiocyanate compound in vitro and in vivo and examined a possible induction mechanism.
Based on an extensive screening of vegetable extracts for GST inducer activity in RL34 cells, we found Japanese horseradish, wasabi Wasabia japonica, syn. Eutrema wasabias the richest source and identified 6-methylsulfinylhexyl isothiocyanate 6-HITCan analogue of sulforaphane 4-methylsulfinylbutyl isothiocyanate isolated from broccoli, as the major GST inducer in wasabi.
In animal experiments, we found that 6-MSHI was rapidly absorbed into the body and induced hepatic phase II detoxification enzymes more potently than sulforaphane.
Xenobiotic metabolizing enzymes play a major role in regulating the toxic, oxidative damaging, mutagenic, and neoplastic effects of chemical carcinogens. Mounting evidence has indicated that the induction of phase II detoxification enzymes, such as glutathioneS-transferases GSTs ,1 results in protection against toxicity and chemical carcinogenesis, especially during the initiation phase.
The GSTs are a family of enzymes that catalyze the nucleophilic addition of the thiol of reduced glutathione GSH to a variety of electrophiles for a review, see Ref.
In addition, the GSTs bind with varying affinities to a variety of aromatic hydrophobic compounds. It is now generally accepted that the GSTs are encoded by at least five different gene families.
It has been shown that the induction of GST is associated with the reduced incidence and multiplicity of tumors 23. Recently, two transgenic rodent studies clearly demonstrated that one of the GST isozymes can profoundly alter the susceptibility to chemical carcinogenesis in mouse skin 4 and rat liver 5.
Thus, the induction of GSTs is regarded as one of the most important determinants in cancer susceptibility and that its elevated synthesis is required to prevent toxic compounds from accumulating in the cells.
The induction of phase II enzymes, such as GSTs, is reported to be evoked by an extraordinary variety of chemical agents, including Michael reaction acceptors, diphenols, quinones, isothiocyanates, peroxides, vicinal dimercaptans, and others With few exceptions, these agents are electrophiles, and accordingly, many of these inducers are substrates for phase II detoxification enzymes.
Epidemiologic studies have found that persons who consume a high proportion of green and yellow vegetables in their diet have a decreased risk of developing some types of cancer 9 Subsequent laboratory work has led to the isolation of various phase II inducers from fruits and vegetables that reduce the incidence of experimental carcinogenesis in animal models.
Later, as an approach for the detection of novel phase II inducing cancer chemoprotective agents, Talalay and his colleagues developed an in vitro assay system using cultured Hepa 1c1c7 murine hepatoma cells They then used this assay to demonstrate that Brassica vegetables are particularly rich sources of phase II inducers and to identify sulforaphane 4-methylsulfinylbutyl isothiocyanate as the principal phase II inducer in broccoli extracts They also have demonstrated that sulforaphane is a dose-related inhibitor of carcinogen-induced mammary tumorigenesis in rats In the present study, using the RL34 cells, we determined the GST induction potencies of food plants and found that the wasabi extracts induce GST activity with great potency.
We provided an analysis of the wasabi extracts that demonstrate an isothiocyanate compound as a principal inducer of phase II enzymes. Moreover, we have investigated the phase II inducing potency of this compound in vitro and in vivo and examined a possible induction mechanism.
The 6-HITC-related compounds were synthesized in our laboratory. Wasabi Wasabia japonica, syn. Ultraviolet absorption spectra were measured with a Hitachi U-Best spectrophotometer, and fluorescence spectra were recorded with a Hitachi F spectrometer.
The wasabi roots 1. The homogenates were then sequentially extracted with ethyl acetate, 2 litersn-butanol 2 liters and water 1 liters. Detection was carried out at nm.
Identification of the active compound was done by spectroscopic analyses The spectral data of 6-HITC were as follows: The CH2Cl2 was carefully removed under atmospheric pressure in a N2 stream on the ice bath.
The residue was redissolved with an adequate amount of CH2Cl2. Each peak was identified by the retention time of each authentic or synthetic sample and the gas-liquid chromatography-mass spectrometry analysis using a JEOL MStation MS mass spectrometer linked to a Hewlett-Packard column, DB-1, 0.
These analyses were repeated three times.
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Cytochrome PA1-mediated ethoxyresorufin O-deethylase activity was measured using the procedures of Kennedy et al. The protein concentration was determined using the bicinchoninic acid protein assay Pierce.
Western Blot Analysis The homogenates prepared from the cells or animal tissues were treated with SDS-sample buffer without dye or 2-mercaptoethanol and immediately boiled for 5 min. The protein concentrations were determined using the BCA protein assay kit Pierce. Satoh of Hirosaki University School of Medicine.
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