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Biomolecules Oct 2020Amygdalin is a natural cyanogenic compound that plants produce in the fight against insects and herbivores. Excessive amounts of amygdalin by animals and humans can...
Amygdalin is a natural cyanogenic compound that plants produce in the fight against insects and herbivores. Excessive amounts of amygdalin by animals and humans can potentially lead to fatal intoxication. However, studies confirm that amygdalin has antitumor properties, including the ability to inhibit the proliferation of cancer cells and to induce their apoptosis. The analysis of amygdalin in various matrices is an important analytical problem today. The publication presents the methodology of direct determination of amygdalin in water, sewage, and biological materials using electrospray ionization mass spectrometry (ESI-MS) and a new analytical method using flowing atmospheric-pressure afterglow mass spectrometry (FAPA-MS). The methods of analyte pre-concentration using a magnetic, molecularly imprinted polymer (mag-MIP) and the influence of interferents on the recorded spectra were discussed. Analytical parameters in ESI-MS and FAPA-MS methods were established. The linearity range was 4.5 µg L-45 mg L in positive mode ESI-MS and FAPA-MS. The limit of detection (LOD) for ESI-MS was 0.101 ± 0.003 µg L and the limit of quantification (LOQ) was 0.303 ± 0.009 µg L. In FAPA-MS, the LOD was 0.050 ± 0.002 µg L and the LOQ was 0.150 ± 0.006 µg L. The content of amygdalin in various matrices was determined.
Topics: Amygdalin; Animals; Antineoplastic Agents; Apoptosis; Atmospheric Pressure; Cell Proliferation; Chromatography, High Pressure Liquid; Humans; Limit of Detection; Neoplasms; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry
PubMed: 33086630
DOI: 10.3390/biom10101459 -
Proceedings of the National Academy of... Oct 1981Amygdalin, the gentiobioside derivative of mandelonitrile commonly referred to as Laetrile, is presently under intensive investigation as a potential cancer...
Amygdalin, the gentiobioside derivative of mandelonitrile commonly referred to as Laetrile, is presently under intensive investigation as a potential cancer chemotherapeutic agent. Because of this interest, we investigated the activity of beta-glucosidases that cleave glucose from amygdalin and from prunasin (mandelonitrile monoglucoside) in tissues from germ-free rats and in normal and neoplastic human tissues. Rat and human small intestinal mucosa contain high levels of activity of glucosidases that act on both of these cyanogenic glucosides. Release of glucose from these compounds was not detected in any of the human neoplastic tissues examined in the present study. These observations are consistent with reports of cyanide toxicity through the oral use of amygdalin or prunasin and pose serious questions concerning the alleged tumoricidal effect of amygdalin.
Topics: Amygdalin; Animals; Female; Germ-Free Life; Glucosidases; Glucosides; Glycosides; Humans; Intestinal Mucosa; Intestines; Neoplasms; Nitriles; Rats; Substrate Specificity; Tissue Distribution; beta-Glucosidase
PubMed: 6796962
DOI: 10.1073/pnas.78.10.6513 -
Biomolecules & Therapeutics Jan 2016Amygdalin, D-mandelonitrile-β-D-glucoside-6-β-glucoside, belongs to aromatic cyanogenic glycoside group derived from rosaceous plant seed. Mounting evidence has...
Amygdalin, D-mandelonitrile-β-D-glucoside-6-β-glucoside, belongs to aromatic cyanogenic glycoside group derived from rosaceous plant seed. Mounting evidence has supported the anti-cancer effects of amygdalin. However, whether amygdalin indeed acts as an anti-tumor agent against breast cancer cells is not clear. The present study aimed to investigate the effect of amygdalin on the proliferation of human breast cancer cells. Here, we show that amygdalin exerted cytotoxic activities on estrogen receptors (ER)-positive MCF7 cells, and MDA-MB-231 and Hs578T triple-negative breast cancer (TNBC) cells. Amygdalin induced apoptosis of Hs578T TNBC cells. Amygdalin downregulated B-cell lymphoma 2 (Bcl-2), upregulated Bcl-2-associated X protein (Bax), activated of caspase-3 and cleaved poly ADP-ribose polymerase (PARP). Amygdalin activated a pro-apoptotic signaling molecule p38 mitogen-activated protein kinases (p38 MAPK) in Hs578T cells. Treatment of amygdalin significantly inhibited the adhesion of Hs578T cells, in which integrin α5 may be involved. Taken together, this study demonstrates that amygdalin induces apoptosis and inhibits adhesion of breast cancer cells. The results suggest a potential application of amygdalin as a chemopreventive agent to prevent or alleviate progression of breast cancer, especially TNBC.
PubMed: 26759703
DOI: 10.4062/biomolther.2015.172 -
Molecules (Basel, Switzerland) Oct 2021The inflammatory reaction accompanies in part or in full any disease process in the vascularized metazoan. This complicated reaction is controlled by regulatory... (Review)
Review
The inflammatory reaction accompanies in part or in full any disease process in the vascularized metazoan. This complicated reaction is controlled by regulatory mechanisms, some of which produce unpleasant symptomatic manifestations of inflammation. Therefore, there has been an effort to develop selective drugs aimed at removing pain, fever, or swelling. Gradually, however, serious adverse side effects of such inhibitors became apparent. Scientific research has therefore continued to explore new possibilities, including naturally available substances. Amygdalin is a cyanogenic glycoside present, e.g., in bitter almonds. This glycoside has already sparked many discussions among scientists, especially about its anticancer potential and related toxic cyanides. However, toxicity at different doses made it generally unacceptable. Although amygdalin given at the correct oral dose may not lead to poisoning, it has not yet been accurately quantified, as its action is often affected by different intestinal microbial consortia. Its pharmacological activities have been studied, but its effects on the body's inflammatory response are lacking. This review discusses the chemical structure, toxicity, and current knowledge of the molecular mechanism of amygdalin activity on immune functions, including the anti-inflammatory effect, but also discusses inflammation as such, its mediators with diverse functions, which are usually targeted by drugs.
Topics: Amygdalin; Animals; Anti-Inflammatory Agents, Non-Steroidal; Cyclooxygenase 1; Cyclooxygenase 2; Cytokines; Humans; Inflammation; Inflammation Mediators
PubMed: 34641516
DOI: 10.3390/molecules26195972 -
International Archives of Allergy and... 2021Cough-variant asthma (CVA) is a special type of asthma, solely manifesting with coughing. Studies suggest that airway inflammation is associated with CVA pathogenesis....
Amygdalin Attenuates Airway Epithelium Apoptosis, Inflammation, and Epithelial-Mesenchymal Transition through Restraining the TLR4/NF-κB Signaling Pathway on LPS-Treated BEAS-2B Bronchial Epithelial Cells.
BACKGROUND
Cough-variant asthma (CVA) is a special type of asthma, solely manifesting with coughing. Studies suggest that airway inflammation is associated with CVA pathogenesis. Amygdalin is found to have an anti-inflammatory potential, while how it affects CVA remains unexplored.
METHODS
Cytotoxicity delivered by various concentrations of LPS and amygdalin on BEAS-2B cells was determined by Cell Counting Kit-8 assay. CVA in vitro models were established via LPS exposure on BEAS-2B cells which underwent amygdalin pretreatment. Cell apoptosis was determined by flow cytometry. Production of tumor necrosis factor (TNF)-α, interleukin (IL)-6, IL-8, and mucin 5AC (MUC5AC) in BEAS-2B cells was measured by ELISA and qRT-PCR. Expressions of TLR4, E-cadherin, N-cadherin, α-smooth muscle actin (SMA), vimentin, phosphorylated-p65 (p-p65), p65, phosphorylated-IκBα (p-IκBα), and IκBα in BEAS-2B cells were measured by qRT-PCR or Western blot.
RESULTS
LPS and high concentrations of amygdalin (over 600 μg/mL) decreased BEAS-2B cell toxicity. Exposure to LPS inhibited toxicity, enhanced apoptosis; and promoted production of TNF-α, IL-6, IL-8, and MUC5AC, increased the levels of N-Cadherin, α-SMA, vimentin, p-p65, and p-IκBα, and decreased the levels of E-cadherin and IκBα in BEAS-2B cells. Amygdalin pretreatment counteracted the effects of LPS on BEAS-2B cells. Overexpressing TLR4 reversed amygdalin-exerted effects in LPS-exposed BEAS-2B cells.
CONCLUSION
Amygdalin attenuated airway epithelium apoptosis, inflammation and epithelial-mesenchymal transition through restraining the TLR4/NF-κB signaling pathway in CVA.
Topics: Amygdalin; Anti-Inflammatory Agents; Apoptosis; Cell Line; Cytokines; Epithelial-Mesenchymal Transition; Humans; Lipopolysaccharides; NF-kappa B; Respiratory Mucosa; Signal Transduction; Toll-Like Receptor 4
PubMed: 34428767
DOI: 10.1159/000514209 -
International Journal of Environmental... Jun 2011Recently, considerable attention has been focused on dietary and medicinal phytochemicals that inhibit, reverse or retard diseases caused by oxidative and inflammatory... (Review)
Review
Recently, considerable attention has been focused on dietary and medicinal phytochemicals that inhibit, reverse or retard diseases caused by oxidative and inflammatory processes. Vernonia amygdalina is a perennial herb belonging to the Asteraceae family. Extracts of the plant have been used in various folk medicines as remedies against helminthic, protozoal and bacterial infections with scientific support for these claims. Phytochemicals such as saponins and alkaloids, terpenes, steroids, coumarins, flavonoids, phenolic acids, lignans, xanthones, anthraquinones, edotides and sesquiterpenes have been extracted and isolated from Vernonia amygdalina. These compounds elicit various biological effects including cancer chemoprevention. Garcinia kola (Guttiferae) seed, known as "bitter kola", plays an important role in African ethnomedicine and traditional hospitality. It is used locally to treat illnesses like colds, bronchitis, bacterial and viral infections and liver diseases. A number of useful phytochemicals have been isolated from the seed and the most prominent of them is the Garcinia bioflavonoids mixture called kolaviron. It has well-defined structure and an array of biological activities including antioxidant, antidiabetic, antigenotoxic and hepatoprotective properties. The chemopreventive properties of Vernonia amygdalina and Garcinia biflavonoids have been attributed to their abilities to scavenge free radicals, induce detoxification, inhibit stress response proteins and interfere with DNA binding activities of some transcription factors.
Topics: Amygdalin; Antioxidants; Biflavonoids; Chemoprevention; Humans; Vernonia
PubMed: 21776245
DOI: 10.3390/ijerph8062533 -
Frontiers in Plant Science 2021Amygdalin, a naturally occurring compound, is one of the main active ingredients of the Chinese raw bitter almond. The variation in amygdalin composition of seed kernels...
Amygdalin, a naturally occurring compound, is one of the main active ingredients of the Chinese raw bitter almond. The variation in amygdalin composition of seed kernels among the six almond species was determined, and relationships with geoenvironmental factors were analyzed. The amygdalin content exhibited great diversity, ranging from 0.0004 to 9.73 g/100 g. The highest level of amygdalin was detected in Tangut almond, with 5.45-9.73 g/100 g. The other kernels showed a range from 3.14 to 6.80 g/100 g in wild almond and from 3.00 to 4.22 g/100 g in longstalk almond. Amygdalin in common almond was almost undetectable. Factor analysis showed that amygdalin content in spp. kernels increased with altitude and decreased with the degree of aspect. Many environmental factors were closely related to amygdalin content, including annual precipitation (Bio12), UV intensity, and topsoil base saturation (T_BS), which all had a significant effect on amygdalin content. The amygdalin content is closely related to rainfall indicators, especially annual precipitation (Bio12), with the highest factor analysis value (3.63). Water regulates amygdalin in diverse ways. Since amygdalin is water-soluble, water can reduce the inhibitory effect of amygdalin on germination and regulate the synthesis of amygdalin at the late stage of germination by activating the amygdalin synthesis genes and . This study expands the understanding of amygdalin in almond resources and provides the direction for the regulation of amygdalin.
PubMed: 35154172
DOI: 10.3389/fpls.2021.753151 -
Acta Biochimica Et Biophysica Sinica Sep 2022Mounting evidence supports that long-term exposure to fine particle pollutants (PM2.5) is closely implicated in cardiovascular diseases, especially atherosclerosis....
Mounting evidence supports that long-term exposure to fine particle pollutants (PM2.5) is closely implicated in cardiovascular diseases, especially atherosclerosis. Amygdalin is reported to attenuate external stimuli-induced cardiovascular diseases. However, the underlying mechanisms are still not understood. In this study, we aim to explore the protective effects of amygdalin on PM2.5-induced human umbilical vein endothelial cell (HUVEC) injury and unravel the specific mechanisms by MTT, DCFH-DA, biochemical, immunofluorescence, ELISA, RT-qPCR, flow cytometry, TUNEL and western blot analysis. The results reveal that amygdalin reverses PM2.5-induced cytotoxicity and attenuates intracellular ROS production. Moreover, amygdalin increases the levels of SOD and GSH and alleviates the MDA content. Additionally, amygdalin causes a decline of IL-6, IL-1β, TNF-α and COX-2 levels. Moreover, amygdalin inhibits NF-κB p50 and TLR4 protein expressions and NF-κB p65 nuclear translocation. Concomitantly, a decline of phospho-NF-κB p65/NF-κB p65 and phospho-IκB-α/IκB-α is detected. Meanwhile, amygdalin pretreatment reduces HUVEC apoptosis. In addition, amygdalin triggers an upregulation of Bcl-2 and a downregulation of Bax after stimulation with PM2.5. Collectively, these results suggest that amygdalin suppresses PM2.5-induced HUVEC injury by regulating the TLR4/NF-κB and Bcl-2/Bax signaling pathways, indicating that amygdalin may be a novel target for atherosclerosis treatments.
Topics: Humans; NF-kappa B; Amygdalin; bcl-2-Associated X Protein; NF-KappaB Inhibitor alpha; Human Umbilical Vein Endothelial Cells; Toll-Like Receptor 4; Cardiovascular Diseases; Signal Transduction; Particulate Matter
PubMed: 36178164
DOI: 10.3724/abbs.2022136 -
PloS One 2014The cyanogenic diglucoside amygdalin, derived from Rosaceae kernels, is employed by many patients as an alternative anti-cancer treatment. However, whether amygdalin...
The cyanogenic diglucoside amygdalin, derived from Rosaceae kernels, is employed by many patients as an alternative anti-cancer treatment. However, whether amygdalin indeed acts as an anti-tumor agent is not clear. Metastasis blocking properties of amygdalin on bladder cancer cell lines was, therefore, investigated. Amygdalin (10 mg/ml) was applied to UMUC-3, TCCSUP or RT112 bladder cancer cells for 24 h or for 2 weeks. Tumor cell adhesion to vascular endothelium or to immobilized collagen as well as tumor cell migration was examined. Effects of drug treatment on integrin α and β subtypes, on integrin-linked kinase (ILK) and total and activated focal adhesion kinase (FAK) were also determined. Integrin knock-down was carried out to evaluate integrin influence on migration and adhesion. A 24 h or 2 week amygdalin application distinctly reduced tumor cell adhesion and migration of UMUC-3 and RT112 cells. TCCSUP adhesion was also reduced, but migration was elevated under amygdalin. Integrin subtype expression was significantly and specifically altered by amygdalin depending on the cell line. ILK was moderately, and activated FAK strongly, lost in all tumor cell lines in the presence of amygdalin. Knock down of β1 integrin caused a significant decrease in both adhesion and migration of UMUC-3 cells, but a significant increase in TCCSUP adhesion. Knock down of β4 integrin caused a significant decrease in migration of RT112 cells. Since the different actions of amygdalin on the different cell lines was mirrored by β1 or β4 knock down, it is postulated that amygdalin influences adhesion and migratory properties of bladder cancer cells by modulating β1 or β4 integrin expression. The amygdalin induced increase in TCCSUP migratory behavior indicates that any anti-tumor benefits from amygdalin (seen with the other two cell lines) may depend upon the cancer cell type.
Topics: Amygdalin; Antineoplastic Agents; Cell Adhesion; Cell Line, Tumor; Cell Membrane; Cell Movement; Chemotaxis; Endothelial Cells; Flow Cytometry; Gene Expression; Gene Knockdown Techniques; Humans; Integrins; RNA, Small Interfering; Urinary Bladder Neoplasms
PubMed: 25333694
DOI: 10.1371/journal.pone.0110244 -
Journal of Applied Microbiology Feb 2015Cyanogenic glycosides are phytotoxic secondary metabolites produced by some crop plants. The aim of this study was to identify lactic acid bacteria (LAB) capable of...
AIMS
Cyanogenic glycosides are phytotoxic secondary metabolites produced by some crop plants. The aim of this study was to identify lactic acid bacteria (LAB) capable of catabolizing amygdalin, a model cyanogenic glycoside, for use in the biodetoxification of amygdalin-containing foods and feeds.
METHODS AND RESULTS
Amygdalin-catabolizing lactobacilli were characterized using a combination of cultivation-dependent and molecular assays. Lactobacillus paraplantarum and Lactobacillus plantarum grew robustly on amygdalin (Amg(+)), while other LAB species typically failed to catabolize amygdalin (Amg(-)). Interestingly, high concentrations of amygdalin and two of its metabolic derivatives (mandelonitrile and benzaldehyde) inhibited the growth of Lact. plantarum RENO 0093. The differential regulation of genes tentatively involved in cyanohydrin metabolism illustrated that the metabolism of amygdalin- and glucose-grown cultures also differed significantly.
CONCLUSIONS
Amygdalin fermentation was a relatively uncommon phenotype among the LAB and generally limited to strains from the Lact. plantarum group. Phenotype microarrays (PM) enabled strain-level discrimination between closely related strains within a species and suggested that phenotypic differences might affect niche specialization.
SIGNIFICANCE AND IMPACT OF THE STUDY
Amygdalin-degrading lactobacilli with practical application in the biodetoxification of amygdalin were characterized. These strains show potential for use as starter cultures to improve the safety of foods and feeds.
Topics: Amygdalin; Fermentation; Gene Expression Regulation, Bacterial; Lactobacillus; Lactobacillus plantarum; Nitriles; Phenotype
PubMed: 25421573
DOI: 10.1111/jam.12704