- Research Article
- Published:
Cannabinoid-like anti-inflammatory compounds from flax fiber
Cellular & Molecular Biology Letters volume 17, pages 479–499 (2012)
Abstract
Flax is a valuable source of fibers, linseed and oil. The compounds of the latter two products have already been widely examined and have been proven to possess many health-beneficial properties. In the course of analysis of fibers extract from previously generated transgenic plants overproducing phenylpropanoids a new terpenoid compound was discovered.
The UV spectra and the retention time in UPLC analysis of this new compound reveal similarity to a cannabinoid-like compound, probably cannabidiol (CBD). This was confirmed by finding two ions at m/z 174.1 and 231.2 in mass spectra analysis. Further confirmation of the nature of the compound was based on a biological activity assay. It was found that the compound affects the expression of genes involved in inflammatory processes in mouse and human fibroblasts and likely the CBD from Cannabis sativa activates the specific peripheral cannabinoid receptor 2 (CB2) gene expression. Besides fibers, the compound was also found in all other flax tissues. It should be pointed out that the industrial process of fabric production does not affect CBD activity.
The presented data suggest for the first time that flax products can be a source of biologically active cannabinoid-like compounds that are able to influence the cell immunological response. These findings might open up many new applications for medical flax products, especially for the fabric as a material for wound dressing with anti-inflammatory properties.
Abbreviations
- ALA:
-
α-linoleic acid
- CB1:
-
cannabinoid receptor 1
- CB2:
-
cannabinoid receptor 2
- CBC:
-
cannabichromene
- CBCA:
-
cannabichromenic acid
- CBD:
-
cannabidiol
- CBDA:
-
cannabidiolic acid
- CBGA:
-
cannabigerolic acid
- CBN:
-
cannabinol
- CHI:
-
chalcone isomerise
- CHS:
-
chalcone synthase
- CREB:
-
cAMP response element-binding
- DEG:
-
differentially expressed genes
- DFR:
-
dihydroflavonol reductase
- DMEM:
-
Dulbecco’s Modified Eagle Medium
- EDTA:
-
ethylenediaminetetraacetate
- GAPDH:
-
glyceraldehyde-3-phosphate dehydrogenase
- GC-MS:
-
gas chromatography-mass spectrometry
- GPP:
-
geranyl pyrophosphate
- HPLC:
-
high-performance liquid chromatography
- IL1β:
-
interleukin 1β
- IL6:
-
interleukin 6
- IL8:
-
interleukin 8
- IFN-γ:
-
interferon γ
- IPP:
-
isopentenyl diphosphate
- LPS:
-
lipopolysacharide
- MCP-1:
-
monocyte chemotactic protein 1
- NFκB:
-
nuclear factor κB
- NHDF:
-
normal human dermal fibroblasts
- OLA:
-
olivetolic acid
- PBS:
-
phosphate buffered saline
- PKA:
-
protein kinase A
- PUFA:
-
polyunsaturated fatty acids
- RQ:
-
relative quantification
- RT PCR:
-
real-time polymerase chain reaction
- SD:
-
standard deviation
- SDG:
-
secoisolariciresinol diglucoside
- SE:
-
standard error
- SOCS-1:
-
suppressor of cytokine signaling 1
- TFA:
-
trifluoroacetic acid
- THC:
-
tetrahydrocannabinol
- THCA:
-
Δ9-tetrahydrocannabinolic acid
- TLR4:
-
Toll-like receptor 4
- TNF-α:
-
tumor necrosis factor α
- TNFR:
-
TNF receptor
- UPLC:
-
ultra performance liquid chromatography
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Styrczewska, M., Kulma, A., Ratajczak, K. et al. Cannabinoid-like anti-inflammatory compounds from flax fiber. Cell Mol Biol Lett 17, 479–499 (2012). https://doi.org/10.2478/s11658-012-0023-6
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DOI: https://doi.org/10.2478/s11658-012-0023-6