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Thursday, 31 October 2013

Phytochemicals in Foods - 13 Health Benefits of Dithiolthiones (isothiocyanates)

Dithiolthiones are phytochemicals in the class of Organosulfides, found abundantly in cruciferous vegetables, garden sorrel, horseradish, etc.

Health Benefits
1. Anti acetaminophen hepatotoxicity
In the investigation of Anethol dithiolthione (ADT), usually prescribed as a choleretic drug, given orally 1 hour prior to acetaminophen (AAP) (450 mg/kg intraperitoneally) in Swiss female mice, found that ADT exhibited an hepatoprotective potency at doses as low as 10 mg/kg relative to serum aminotransferase activities and hepatic glutathione related enzyme system (glutathione reductase, peroxidase, transferase), according to "Protective effect of anethol dithiolthione against acetaminophen hepatotoxicity in mice" by Warnet JM, Christen MO, Thevenin M, Biard D, Jacqueson A, Claude JR.(1)

2. Chemopreventive efficacy
in the observation of two exposure regimens used to compare the efficacies of early (Regimen-A) versus late (Regimen-B) intervention in prevention of lung tumorigenesis in A/J mice, indicated that Evaluation of lung tumor multiplicity following exposure to oltipraz showed that oltipraz inhibited the tumor development in a dose-dependent manner (10-100 mg/m(3)) with inhibition ranging from 37 to 53% in Regimen A and 51% in Regimen B, when compared with the B[a]P group. Analysis of the tumor incidence showed that 81.5% of the animals had 10 or more tumors in the B[a]P group, whereas, in oltipraz exposure groups, there was a significant decrease in Regimen A (24-36%) and in Regimen B (42%), according to "The chemopreventive efficacy of inhaled oltipraz particulates in the B[a]P-induced A/J mouse lung adenoma model" by Sharma S, Gao P, Steele VE.(2)

3. Detoxication of xenobiotics
In the testing The dithiolthiones, oltipraz, ADT, 116L and 129L, in mice and in rats, oltipraz. Intragastric administration of dithiolthiones (oltipraz, ADT or 116L; two doses each of 1 g/kg body weight) found that Dithiolthiones present in cabbage may play a role in the protective actions of diets high in vegetables against the toxic actions of xenobiotics, according to "Biochemical effects of dithiolthiones' by Ansher SS, Dolan P, Bueding E.(3)

4. Antioxidants
In the examination of the role of glutathione (GSH) in the regulation of this adhesion phenomenon and in the increased tyrosine phosphorylation induced by ROS, found that ADT reduced both PMN adhesion to ROS-stimulated human umbilical vein endothelial cells (HUVEC) and tyrosine phosphorylation of p125FAK and paxillin. ADT increased redox status by increasing intracellular GSH content in oxidized cells. These results show that GSH can reverse the effect of oxidation on tyrosine kinase activation and phosphorylation, and thus plays an important role in cell signaling. They also confirm the antioxidant activity of ADT, according to "Anethole dithiolethione regulates oxidant-induced tyrosine kinase activation in endothelial cells" by Ben-Mahdi MH, Gozin A, Driss F, Andrieu V, Christen MO, Pasquier C.(4)

5. Aflatoxin B1 contamination
In the study of the influence of oltipraz and a second dithiolthione, (1,2) dithiolo (4,3-c)-1,2-dithiole-3,6 dithione (DDD) on bovine hepatic aflatoxin B1 biotransformation, found that Oltipraz inhibited aflatoxin B1 metabolism as no aflatoxin M1 and no aflatoxin B1-dihydrodiol, the second metabolite found in bovine hepatocytes, was formed. DDD did not significantly inhibit aflatoxin B1 metabolism. It could be demonstrated that the inhibition of aflatoxin B1 metabolism was due to the inhibition of several cytochrome P450 enzyme activities by oltipraz. In contrast, DDD inhibited only ethoxyresorufin O-deethylation activity, according to "Inhibition of aflatoxin M1 production by bovine hepatocytes after intervention with oltipraz" by Kuilman ME, Maas RF, Woutersen-van Nijnanten FM, Fink-Gremmels J.(5)

6. Cancer prevention
In the investigation of The critical role of the glutathione S-transferase (GST) and their importance in cancer prevention and susceptibility, clinical studies revealed that the GST activity of blood lymphocytes from individuals with either a personal or family history of colorectal cancer or a personal history of colon polyps was decreased significantly when compared to that of healthy controls. Phase 1 clinical evaluation of oltipraz has demonstrated its ability to induce GST activity as well as the level of transcripts encoding gamma-glutamylcysteine synthetase (gamma-GCS) and DT-diaphorase in the colon mucosa of individuals at increased risk for colorectal cancer. The observed correlation between the posttreatment response in blood lymphocytes and colon mucosa suggested that blood lymphocytes may be used in future trials as a surrogate biomarker of the responsiveness of colon tissue to chemopreventive regimens, according to "Glutathione S-transferases--biomarkers of cancer risk and chemopreventive response" by Clapper ML, Szarka CE.(6)

7. Anti nephrotoxicity
in the determination of s the effects of ADT on hexachloro-1,3-butadiene (HCBD)-induced nephrotoxicity in the rat and the mechanism of its action, found that ADT protects rats against HCBD-induced nephrotoxicity by a mechanism that does not involve the modulation of HCBD conjugation with liver GSH, nor the modulation of the kidney NPSH level and beta-lyase activity. The mechanism of protection conferred to rats by an ADT pretreatment against HCBD-induced nephrotoxicity appears to take place in the kidney at a step beyond the generation of ultimate toxic metabolites derived from PCBC, according to 'Assessment of the role of glutathione conjugation in the protection afforded by anethol dithiolthione against hexachloro-1,3-butadiene-induced nephrotoxicity" by Bouthillier L, Charbonneau M, Brodeur J.(7)

8. Inhibition of platelet aggregation
in the investigation of Anethole dithiolthione (ADT) (10 mumol/l) inhibition of platelet aggregation and the formation of thromboxane (Tx)B2 in plasma in response to adenosine diphosphate (ADP), epinephrine and arachidonic acid (AA), indicated that ADT had no additive effect on the inhibition of thrombin-induced platelet aggregation by acetylsalicylic acid. ADT was a more effective inhibitor of AA-induced platelet aggregation than butylated hydroxytoluene. ADT inhibited the release of 3H-AA from platelet phospholipids in response to ADP and collagen. It is suggested that ADT inhibits platelet aggregation by inhibiting thromboxane synthesis and preventing AA release, according to "Effect of anethole dithiolthione on human platelet aggregation" by Selley ML, McGuiness JA, Bartlett MR, Ardlie NG.(8)

9. Early colon carcinogenesis
in the study of the effect of dietary oltipraz on liver and colonic mucosal enzymes and DNA adducts in evaluating the modulating role of this agent during the early period of azoxymethane (AOM)-induced carcinogenesis, showed that dietary oltipraz enhances the colonic and liver glutathione S-transferase activity and reduced the formation of DNA adducts. In addition, dietary oltipraz modulates liver and colonic ODC and TPK activities that have been shown to play a role in tumor promotion, according to "Effect of oltipraz [5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione] on azoxymethane-induced biochemical changes related to early colon carcinogenesis in male F344 rats" by Rao CV, Nayini J, Reddy BS.(9)

10. Lipid peroxidation
in the observation of the drug anisyldithiolthione (ADT) acted as a good inhibitor of lipid peroxidation induced in rat liver microsomes either chemically by FeSO4 and reducing agents (cysteine or ascorbate) or enzymatically by NADPH and CC14, showed that at doses as low as 5 mg per kg it completely suppressed ethane exhalation by acetaminophen-intoxicated mice and also protected them very efficiently against mortality caused by acetaminophen overdose. The inhibitory effect of ADT toward lipid peroxidation seems to be linked to the presence of its dithiolthione function, according to "A new potent inhibitor of lipid peroxidation in vitro and in vivo, the hepatoprotective drug anisyldithiolthione" by Mansuy D, Sassi A, Dansette PM, Plat M.(10)

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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/2780509
(2) http://carcin.oxfordjournals.org/content/27/8/1721.abstract
(3) http://www.ncbi.nlm.nih.gov/pubmed/3744194
(4) http://www.ncbi.nlm.nih.gov/pubmed/11213483
(5) http://www.ncbi.nlm.nih.gov/pubmed/10682385
(6) http://www.ncbi.nlm.nih.gov/pubmed/9679568
(7) http://www.ncbi.nlm.nih.gov/pubmed/8685901
(8) http://www.ncbi.nlm.nih.gov/pubmed/1497692
(9) http://www.ncbi.nlm.nih.gov/pubmed/2020672
(10) http://www.ncbi.nlm.nih.gov/pubmed/3964266

Phytochemicals in Foods - 11 Health Benefits of Sulphoraphane

Sulphoraphane are phytochemicals in the class of Dithiolthiones, belonging to group of Organosulfides, found abundantly in broccoli, Brussels sprouts or cabbages, etc.

Health Benefits
1. Prostate cancer
In the investigation of the effects of Sulforaphane (SFN) on DNA methylation status of cyclin D2 promoter, and how alteration in promoter methylation impacts cyclin D2 gene expression in LnCap cells, found that SFN significantly decreased the expression of DNA methyltransferases (DNMTs), especially DNMT1 and DNMT3b. Furthermore, SFN significantly decreased methylation in cyclin D2 promoter regions containing c-Myc and multiple Sp1 binding sites. Reduced methlyation of cyclin D2 promoter corresponded to an increase in cyclin D2 transcript levels, suggesting that SFN may de-repress methylation-silenced cyclin D2 by impacting epigenetic pathways, according to "Promoter de-methylation of cyclin D2 by sulforaphane in prostate cancer cells" by Hsu A, Wong CP, Yu Z, Williams DE, Dashwood RH, Ho E.(1)

2. Breast cancer
In the evaluation of sulforaphane, a natural compound derived from broccoli/broccoli sprouts, for its efficacy to inhibit breast CSCs and its potential mechanism, found that Sulforaphane inhibits breast CSCs and downregulates the Wnt/beta-catenin self-renewal pathway. These findings support the use of sulforaphane for the chemoprevention of breast cancer stem cells and warrant further clinical evaluation, according to "Sulforaphane, a dietary component of broccoli/broccoli sprouts, inhibits breast cancer stem cells" by Li Y, Zhang T, Korkaya H, Liu S, Lee HF, Newman B, Yu Y, Clouthier SG, Schwartz SJ, Wicha MS, Sun D.(2)

3. Aging and aging related diseases
In the elucidating the modulatory role of nutrition in aging and age-related disease development, indicated that nutrients can act as the source of epigenetic modifications and can regulate the placement of these modifications. Nutrients involved in one-carbon metabolism, namely folate, vitamin B12, vitamin B6, riboflavin, methionine, choline and betaine, are involved in DNA methylation by regulating levels of the universal methyl donor S-adenosylmethionine and methyltransferase inhibitor S-adenosylhomocysteine. Other nutrients and bioactive food components such as retinoic acid, resveratrol, curcumin, sulforaphane and tea polyphenols can modulate epigenetic patterns by altering the levels of S-adenosylmethionine and S-adenosylhomocysteine or directing the enzymes that catalyse DNA methylation and histone modifications, according to "Nutritional influences on epigenetics and age-related disease" by Park LK, Friso S, Choi SW.(3)

4. Human brain microvascular endothelial cells (HBMECs)
In the delineation of a unique brain endothelial phenotype in that MMP-9 secretion is increased upon phorbol 12-myristate 13-acetate (PMA) treatment of HBMEC, indicated that Sulforaphane (SFN), an isothiocyanate present in broccoli which exhibits chemopreventive properties, selectively inhibited the secretion of MMP-9 but not that of MMP-2. The decrease in MMP-9 gene expression correlated with a decrease in the expression of the mRNA stabilizing factor HuR protein triggered by SFN. PMA-induced HBMEC migration was also antagonized by SFN. Silencing of the MMP-9 gene inhibited PMA-induced MMP-9 secretion, cell migration, and in vitro tubulogenesis on Matrigel. While SFN inhibited the chemoattractive abilities of brain tumor-derived growth factors, it failed to inhibit PMA-induced tubulogenesis, according to "The diet-derived sulforaphane inhibits matrix metalloproteinase-9-activated human brain microvascular endothelial cell migration and tubulogenesis" by Annabi B, Rojas-Sutterlin S, Laroche M, Lachambre MP, Moumdjian R, Béliveau R.(4)

5. Oxidative stress
In the investigation of anti oxidative stress of Sulforaphane [1-isothiocyanate-(4R)-(methylsulfinyl)butane] is a natural dietary isothiocyanate produced by the enzymatic action of the myrosinase on glucopharanin, a 4-methylsulfinylbutyl glucosinolate contained in cruciferous vegetables of the genus Brassica such as broccoli, brussel sprouts, and cabbage, found that Sulforaphane is considered an indirect antioxidant; this compound is able to induce many cytoprotective proteins, including antioxidant enzymes, through the Nrf2-antioxidant response element pathway. Heme oxygenase-1, NAD(P)H: quinone oxidoreductase, glutathione-S-transferase, gamma-glutamyl cysteine ligase, and glutathione reductase are among the cytoprotective proteins induced by sulforaphane. In conclusion, sulforaphane is a promising antioxidant agent that is effective to attenuate oxidative stress and tissue/cell damage in different in vivo and in vitro experimental paradigms, according to "Protective effect of sulforaphane against oxidative stress: Recent advances" by Guerrero-Beltrán CE, Calderón-Oliver M, Pedraza-Chaverri J, Chirino YI.(5)

6. Anti nephrotoxicity
In the evaluation of whether SFN induces a cytoprotective effect on the CDDP-induced nephrotoxicity, found that The renoprotective effect of SFN on CDDP-induced nephrotoxicity was associated with the attenuation in oxidative/nitrosative stress and the preservation of antioxidant enzymes, according to "Sulforaphane protects against cisplatin-induced nephrotoxicity" by Guerrero-Beltrán CE, Calderón-Oliver M, Tapia E, Medina-Campos ON, Sánchez-González DJ, Martínez-Martínez CM, Ortiz-Vega KM, Franco M, Pedraza-Chaverri J.(6)

7. Liver protection
In the investigation of the effect of sulforaphane (SFN) on regulation of NF-E2-related factor-2 (Nrf2)-antioxidant response element (ARE) pathway in liver injury induced by intestinal ischemia/reperfusion (I/R), showed that SFN pretreatment attenuates liver injury induced by intestinal I/R in rats, attributable to the antioxidant effect through Nrf2-ARE pathway, according to "Sulforaphane protects liver injury induced by intestinal ischemia reperfusion through Nrf2-ARE pathway" by Zhao HD, Zhang F, Shen G, Li YB, Li YH, Jing HR, Ma LF, Yao JH, Tian XF.(7)

8. Antibacterial Effects
In the evaluation of the effects of various glucosinolate-derived hydrolysis products (HP) as antibacterial compounds against Enterobacteriaceae and Enterococcaceae isolated from intestinal segments of healthy pigs collected directly from slaughter-houses in the North of Portugal, found that the glucosinolates-derived HPs were very effective in vitro inhibitors of bacterial growth. The natural products, and specifically the isothiocyanates, should be evaluated as potential alternative control agents for potentially pathogenic bacteria (e.g., dietary amendment of pig foods with glucosinolate-containing plants), according to "Antibacterial Effects of Glucosinolate-Derived Hydrolysis Products Against Enterobacteriaceae and Enterococci Isolated from Pig Ileum Segments" by Saavedra MJ, Dias CS, Martinez-Murcia A, Bennett RN, Aires A, Rosa EA.(8)

9. Anti-inflammatory Effects
In the investigation of the anti-inflammatory effects of two dietary compounds, nobiletin (NBN) and sulforaphane (SFN), in combination. Noncytotoxic concentrations of NBN, SFN, and their combinations were studied in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells, indicated that low doses of NBN and SFN in combination significantly suppressed LPS-induced upregulation of IL-1 mRNA levels and synergistically increased HO-1 mRNA levels. Overall, our results demonstrated that NBN and SFN in combination produced synergistic effects in inhibiting LPS-induced inflammation in RAW 264.7 cells, according to "Synergistic Anti-inflammatory Effects of Nobiletin and Sulforaphane in Lipopolysaccharide-Stimulated RAW 264.7 Cells" by Guo S, Qiu P, Xu G, Wu X, Dong P, Yang G, Zheng J, McClements DJ, Xiao H.(9)

10. Hypertension
In the determination of whether the metabolite of glucoraphanin, sulforaphane, was responsible for this improved blood pressure and whether this is associated with normalization of renal methylated DNA, showed that Sulforaphane administration rectified pathological abnormalities in SHRSP kidneys and significantly improved blood pressure. This was associated with normalization of global kidney DNA methylation suggesting that DNA methylation could be associated with hypertension, according to "The dietary phase 2 protein inducer sulforaphane can normalize the kidney epigenome and improve blood pressure in hypertensive rats" by Senanayake GV, Banigesh A, Wu L, Lee P, Juurlink BH.(10)

11. Diabetic symptoms
In the determination of whether dietary compounds targeting NFE2-related factor 2 (Nrf2) activation used to attenuate renal damage and preserve renal function during the course of streptozotocin (STZ)-induced diabetic nephropathy, showed that SF or CA significantly attenuated common metabolic disorder symptoms associated with diabetes in Nrf2(+/+) but not in Nrf2(-/-) mice, indicating SF and CA function through specific activation of the Nrf2 pathway. Furthermore, SF or CA improved renal performance and minimized pathological alterations in the glomerulus of STZ-Nrf2(+/+) mice. Nrf2 activation reduced oxidative damage and suppressed the expression of TGF-β1, extracellular matrix proteins and p21 both in vivo and in HRMCs. In addition, Nrf2 activation reverted p21-mediated growth inhibition and hypertrophy of HRMCs under hyperglycemic conditions, according to "Therapeutic potential of Nrf2 activators in streptozotocin-induced diabetic nephropathy" by Zheng H, Whitman SA, Wu W, Wondrak GT, Wong PK, Fang D, Zhang DD.(11)

12. Etc.
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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/22303414
(2) http://www.ncbi.nlm.nih.gov/pubmed/20388854
(3) http://www.ncbi.nlm.nih.gov/pubmed/22051144
(4) http://www.ncbi.nlm.nih.gov/pubmed/18435488
(5) http://www.ncbi.nlm.nih.gov/pubmed/21129940
(6) http://www.ncbi.nlm.nih.gov/pubmed/19913604
(7) http://www.ncbi.nlm.nih.gov/pubmed/20572303
(8) http://www.ncbi.nlm.nih.gov/pubmed/22356572
(9) http://www.ncbi.nlm.nih.gov/pubmed/22335189
(10) http://www.ncbi.nlm.nih.gov/pubmed/22052072
(11) http://www.ncbi.nlm.nih.gov/pubmed/22025779

Phytochemicals in Foods - 9 Health Benefits of Polysulfides

Polysulfides are phytochemicals in a class of chemical compounds containing chains of sulfur atoms, belonging to the group of Organosulfides found abundantly in ioxidized product, including beer, wine, whiskey, garlic oil, etc.

Health Benefits
1.
Colon cancer
In the searching new drugs with anticancer activities, by combining coumarins with polysulfides in the form of di-coumarin polysulfides, found that the novel coumarin compounds regulated the phosphatase activity of the cell cycle regulating cdc25 family members, indicating that these phosphatases are implicated in the induction of cell cycle arrest and possibly in apoptosis induction as well. In addition, coumarin polysulfides also down-regulated the level of cdc25C, which also contributed to the arrest in the G(2)-phase of the cell cycle, according to "Coumarin polysulfides inhibit cell growth and induce apoptosis in HCT116 colon cancer cells" by Saidu NE, Valente S, Bana E, Kirsch G, Bagrel D, Montenarh M.(1)

2. Anti cancers
In the determination of the influence of highly pure diallylsulfides with a chain of 1-4 sulphur atoms agents on cell viability, cell cycle arrest and induction of apoptosis in HCT116 human colon cancer cells, found that the induction of apoptosis was indeed dependent on the redox-state of the cell, with anti-oxidants being able to prevent sulfide-induced apoptosis. Furthermore, using HCT116 cells which were either positive or negative for p53 revealed that p53 is clearly dispensable for induction of apoptosis. Growth arrest and induction of apoptosis is associated with a considerable reduction of the level of cdc25C, according to "Diallylpolysulfides induce growth arrest and apoptosis" by Busch C, Jacob C, Anwar A, Burkholz T, Aicha Ba L, Cerella C, Diederich M, Brandt W, Wessjohann L, Montenarh M.(2)

3. Harmful and beneficial effects of organic monosulfides, disulfides, and polysulfides
In the investigation of the harmful and Beneficial effects of many organic sulfides (mono-, di-, and polysulfides) presented in our environment, showed that Some sulfides are toxic, and there is evidence that such toxicity is caused by the ability of these substances to generate reactive oxygen species. Some sulfides, however, have been shown to protect against toxicants and carcinogens. These beneficial effects are believed to involve, at least in part, the ability of sulfides to inhibit the enzymatic activation of pro-toxicants and to increase tissue activities of enzymes that protect against electrophiles. Some sulfides also have potential as cancer chemotherapeutics, according to "Harmful and beneficial effects of organic monosulfides, disulfides, and polysulfides in animals and humans" by Munday R.(3)

4. Antiproliferative effect
In the determination of in vitro and in vivo studies reported that organosulfur compounds (OSCs), naturally found in Allium vegetables, are able to suppress the proliferation of various tumor cells, showed that Diallyl- and dipropyltetrasulfides have emerged as interesting irreversible inhibitors of the Cdc25 isoforms A and C in vitro. Furthermore, growth of both sensitive (MCF-7) and resistant (Vcr-R) human breast carcinoma cells was significantly decreased by these tetrasulfides. The observed antiproliferative effect appeared to be associated with a G2-M cell cycle arrest, according to 'Antiproliferative effect of natural tetrasulfides in human breast cancer cells is mediated through the inhibition of the cell division cycle 25 phosphatases" by Viry E, Anwar A, Kirsch G, Jacob C, Diederich M, Bagrel D.(4)

5. Cardiovascular diseases
found that stimulation of nitric oxide generation in endothelial cells seems to be the critical preventive mechanism. Garlic may promote an anti-inflammatory environment by cytokine modulation in human blood. Cardioprotective effects of dietary garlic are mediated in large part via the generation of hydrogen sulfide (H2S). Garlic-derived organic polysulfides are converted by erythrocytes into hydrogen sulfide which relaxes vascular smooth muscle, induces vasodilation of blood vessels, and significantly reduces blood pressure, according to "Garlic (Allium sativum L.) and cardiovascular diseases" by Ginter E, Simko V.(5)

6. Liver cancer
In the investigation of the effect of allyl sulfides from garlic: monosulfide, disulfide and trisulfide on cell proliferation and viability, caspase 3 activity and hydrogen peroxide (H(2) O(2) ) production in HepG2 cells, showed that Among the compounds under study, diallyl trisulfide (DATS), a sulfane sulfur-containing compound, showed the highest biological activity in HepG2 cells. This compound increased the H(2) O(2) formation, lowered the thiol level and produced the strongest inhibition of cell proliferation and the greatest induction of caspase 3 activity in HepG2 cells, according to "The effects of garlic-derived sulfur compounds on cell proliferation, caspase 3 activity, thiol levels and anaerobic sulfur metabolism in human hepatoblastoma HepG2 cells" by Iciek M, Kwiecień I, Chwatko G, Sokołowska-Jeżewicz M, Kowalczyk-Pachel D, Rokita H.(6)

7. Antibacterial effects
Fourier transform infrared (FT-IR) spectroscopy and Raman spectroscopy used in a study of the cell injury and inactivation of Campylobacter jejuni from exposure to antioxidants from garlic,
confirmed that organosulfur compounds are responsible for the substantial antimicrobial activity of garlic, much greater than those of garlic phenolic compounds, as indicated by changes in the spectral features of proteins, lipids, and polysaccharides in the bacterial cell membranes, according to "Investigating antibacterial effects of garlic (Allium sativum) concentrate and garlic-derived organosulfur compounds on Campylobacter jejuni by using Fourier transform infrared spectroscopy, Raman spectroscopy, and electron microscopy" by Lu X, Rasco BA, Jabal JM, Aston DE, Lin M, Konkel ME.(7)

8. Gastric cancer
In the determination of Allylmercapto glutathione S-conjugate, S-allylmercapto-L-cysteine (SAMC), biotransformed from allyl sulfides and from naturally occurring water-soluble garlic derivatives, for its inhibition of tumorigenesis, found that SAMC inhibited tumor growth rate by 31.36% and 37.78% at doses of 100 and 300 mg/kg, respectively. Apoptosis in the implanted tumor cells was manifested by apoptotic characteristics, including morphological changes of chromatin crescent, cell shrinkage and membrane blebbing. The apoptosis index of 100 mg/kg and 300 mg/kg of SAMC was 20.74 ± 2.50% and 30.61 ± 2.42%, respectively, by terminal deoxy-nucleotidyl transferase-mediated deoxyuridine triphosphate (dUTP) nick-end labeling (TUNEL) staining, according to "Anticancer activity of S-allylmercapto-L-cysteine on implanted tumor of human gastric cancer cell" by Lee Y, Kim H, Lee J, Kim K.(8)

9. Anti fungal activities
In the evaluation of the effect of diallyldisulphide (DADS), an important organosulphur compound found in garlic (Allium sativum), on antioxidant systems in Candida species, showed that a significant decrease in superoxide dismutase, glutathione-S-transferase, and glutathione peroxidase activities but an increase in catalase activity were observed. Increased levels of lipid peroxidation and decreased levels of glutathione were observed in treated cells. Activity of glucose-6-phosphate dehydrogenase decreased significantly following DADS treatment and could be correlated with a decrease in glutathione concentration in both Candida species, according to "Effect of diallyldisulphide on an antioxidant enzyme system in Candida species" by Yousuf S, Ahmad A, Khan A, Manzoor N, Khan LA.(10)

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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/22264758
(2) http://www.ncbi.nlm.nih.gov/pubmed/20126995
(3) http://www.ncbi.nlm.nih.gov/pubmed/22004350
(4) http://www.ncbi.nlm.nih.gov/pubmed/21253673
(5) http://www.ncbi.nlm.nih.gov/pubmed/21033626
(6) http://www.ncbi.nlm.nih.gov/pubmed/22095390
(7) http://www.ncbi.nlm.nih.gov/pubmed/21642409
(8) http://www.ncbi.nlm.nih.gov/pubmed/21532156
(9) http://www.ncbi.nlm.nih.gov/pubmed/20962904

Phytochemicals in Foods - 8 Health Benefits of Sulfides

Sulfides are phytochemicals in a class of chemical compounds containing anion of sulfur in its lowest oxidation state of 2s, belonging to the group of Organosulfides found abundantly in Beer, cocktail mixes, wine, fresh potatoes, garlic oil, etc.

Health Benefits
1. Colon cancer
In the investigation of diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS) are presented in the Alliaceae family particularly in garlic and their effects on chemo-resistance of human cancer cells, a major obstacle in the treatment and management of malignant cancers, found that DADS and DATS induced Mdr1 and MRP1 gene expression (p<0.05). DADS promoted MRP3 gene expression (p<0.05) as well as DADS and DATS increased MRP4 and MRP6 gene expression (p<0.05) in the colo 205 xenograft mice. Based on our in vitro and in vivo results, diallyl polysulfides (DAS, DADS and DATS) affected the gene expression of the multidrug resistance in colo 205 human colon cancer cells in vitro and in vivo, according to 'Diallyl sulfide, diallyl disulfide and diallyl trisulfide affect drug resistant gene expression in colo 205 human colon cancer cells in vitro and in vivo" by Lai KC, Kuo CL, Ho HC, Yang JS, Ma CY, Lu HF, Huang HY, Chueh FS, Yu CC, Chung JG.(1)

2. Skin cancer
In the investigation of Diallyl sulfide (DAS), diallyl disulfide (DADS), and diallyl trisulfide (DATS), extracted from crushed garlic by steam-distillation and it anticancer activity in several cancer types, found that DATS revealed better growth inhibition of A375 and BCC cells than DADS and DAS did. Further demonstrated that DATS increased intracellular reactive oxygen species (ROS) generation, induced cytosolic Ca(2+) mobilization, and decreased mitochondrial membrane potential (DeltaPsim). Western blot results showed the concordance for the expression of molecules involved in G(2)/M arrest and apoptosis observed by cell cycle and cell viability analysis, according to "Allyl sulfides inhibit cell growth of skin cancer cells through induction of DNA damage mediated G2/M arrest and apoptosis" by
Wang HC, Yang JH, Hsieh SC, Sheen LY.(2)

3. Lung adenocarcinoma
In the valuation of the anticarcinogenic and antimutagenic effectsfrom DAS (diallyl sulfide), DADS (diallyl disulfide), and DATS (diallyl trisulfide), major oil-soluble allyl sulfides (OAS) represent major garlic constituents, found that OASs DADS and DATS induce significant apoptosis in human lung adenocarcinoma A549 cells, whereas DAS does not. Differential modulation of reactive oxygen intermediates (ROI) and mitochondria membrane potential (MMP) may account for the apoptotic effects of DADS and DAT, according to "Apoptosis induction in human lung adenocarcinoma cells by oil-soluble allyl sulfides: triggers, pathways, and modulators" by Wu XJ, Hu Y, Lamy E, Mersch-Sundermann V.(3)

4. Cervical cancer
In the investigation of Diallyl sulfide (DAS), one of the main active constituents of garlic, for it inhibition of cancer cells in vitro and promotion of immune responses in vivo, found that DAS induced G0/G1 cell cycle arrest and apoptosis in HeLa cells through caspase- and mitochondria and p53 pathways providing further understanding of the molecular mechanisms of DAS action in cervical cancer, according to "Diallyl sulfide induces cell cycle arrest and apoptosis in HeLa human cervical cancer cells through the p53, caspase- and mitochondria-dependent pathways" by Wu PP, Chung HW, Liu KC, Wu RS, Yang JS, Tang NY, Lo C, Hsia TC, Yu CC, Chueh FS, Lin SS, Chung JG.(4)

5. Thyroid cancer
In the investigation of whetherDAS could induce growth inhibition and apoptosis in ATC cells. In MTT assay, DAS treatment inhibited the proliferation of ARO cells in a dose-dependent manner, showed that DAS-induced apoptosis was associated with a decrease in the level of Bcl-2 expression and an increase in the level of Bax expression, and cytochrome c was remarkably released from mitochondrial into the cytosol by DAS. Furthermore, caspase-9 and caspase-3 were activated by DAS, and DAS cleaved PARP. Taken together, DAS decreased cell proliferation and induced apoptosis via mitochondrial signaling pathway in ATC cells, according to "Diallyl sulfide induces growth inhibition and apoptosis of anaplastic thyroid cancer cells by mitochondrial signaling pathway" by Shin HA, Cha YY, Park MS, Kim JM, Lim YC.(5)

6. Antioxidants and inhibits inflammation
in the elucidation of the role of a transcription factor, Nuclear factor E2-related factor 2 (Nrf2) in inducing antioxidants and phase II enzymes during gentamicin toxicity in Wistar rats, showed that DAS enhances antioxidants and suppresses inflammatory cytokines through the activation of Nrf2, thereby protecting the cell against oxidative stress induced by gentamicin, according to "Diallyl sulfide enhances antioxidants and inhibits inflammation through the activation of Nrf2 against gentamicin-induced nephrotoxicity in Wistar rats.' by Kalayarasan S, Prabhu PN, Sriram N, Manikandan R, Arumugam M, Sudhandiran G.(6)

7. Joint inflammation
Investigation of the effects of diallyl sulfide (DAS), a garlic sulfur compound, on joint tissue inflammatory responses induced by monosodium urate (MSU) crystals and interleukin-1beta (IL-1beta), found that DAS prevents IL-1beta and MSU crystal induced COX-2 upregulation in synovial cells and chondrocytes and ameliorates crystal induced synovitis potentially through a mechanism involving NF-kappaB. Anti-inflammatory actions of DAS may be of value in treatment of joint inflammation, according to "Inhibition of cyclooxygenase 2 expression by diallyl sulfide on joint inflammation induced by urate crystal and IL-1beta' by Lee HS, Lee CH, Tsai HC, Salter DM.(7)

8. Neuroprotective effects
In the investigation of Diallyl sulfide (DAS), the main organosulfur component of garlic neuroprotective effects against ischemia/reperfusion injury, showed that for animals with induced ischemia/reperfusion, those pretreated with 200 mg/kg DAS showed an infarct volume (22.36 ± 0.67%) significantly lower than that of the non-treated ischemia/reperfusion group (38.23 ± 0.72%), and the percentage of terminal dUTP nick-end labeling-positive cells (23.46 ± 1.02%) of the DAS-pretreated group was also significantly decreased compared to non-treated (36.41 ± 1.58%). Fluorescence immunohistochemistry staining and western blot analysis indicated that DAS reduced caspase-3 expression and increased Bcl-2 expression, according to "Neuroprotective effects of diallyl sulfide against transient focal cerebral ischemia via anti-apoptosis in rats" by Lin X, Yu S, Chen Y, Wu J, Zhao J, Zhao Y.(8)

9. Etc.

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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/22397993
(2) http://www.ncbi.nlm.nih.gov/pubmed/20459099
(3) http://www.ncbi.nlm.nih.gov/pubmed/19197990
(4) http://www.ncbi.nlm.nih.gov/pubmed/21424116
(5) http://www.ncbi.nlm.nih.gov/pubmed/20219414
(6) http://www.ncbi.nlm.nih.gov/pubmed/19374873
(7) http://www.ncbi.nlm.nih.gov/pubmed/18573668
(8) http://www.ncbi.nlm.nih.gov/pubmed/22196859

Phytochemicals in Foods - 10 Health Benefits of Indole-3-carbinol

Indole-3-carbinol is a phytochemical in the class of Indoles, found abundantly in cabbage, kale, brussels sprouts, rutabaga, mustard greens, broccoli, etc.

Health Benefits
1. Breast cancer
In the investigation of
treatment of highly tumorigenic MDA-MB-231 human breast cancer cells with indole-3-carbinol (I3C) directly inhibited the extracellular elastase-dependent cleavage of membrane-associated CD40, showed that I3C directly inhibits the elastase-mediated proteolytic processing of CD40, which alters downstream signaling to disrupt NF-kappaB-induced cell survival and proliferative responses. Furthermore, the establish of a new I3C-mediated antiproliferative cascade has significant therapeutic potential for treatment of human cancers associated with high levels of elastase and its CD40 membrane substrate, according to "Direct inhibition of elastase activity by indole-3-carbinol triggers a CD40-TRAF regulatory cascade that disrupts NF-kappaB transcriptional activity in human breast cancer cells" by Aronchik I, Bjeldanes LF, Firestone GL.(1)

2. Lung cancer
In the examination of the inhibitory effects of N-acetyl-S-(N-2-phenethylthiocarbamoyl)-l-cysteine (PEITC-NAC), myo-inositol (MI) and indole-3-carbinol (I3C) or 3,3'-diindolylmethane (DIM), alone and in combination, on 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) plus benzo[a]pyrene (BaP)-induced A/J mouse lung tumorigenesis and proliferation of A549 cells and human bronchial epithelial cells (HBECs) and relevant potential mechanisms, found that the assessment of the anti-proliferative effects of the individual agents or their combinations showed significant reductions in the proliferation of cigarette smoke condensate (CSC)-pretreated HBEC (reduction by 30-41% at 48 h and 41-58% at 72 h) and A549 cells (30-43% at 48 h and 40-59% at 72 h), but not in dimethyl sulfoxide-pretreated HBEC. Combinatorial treatment with the agents also caused marked reductions in the activation of Akt, extracellular signal-regulated kinase and nuclear factor-kappaB in lung tumor tissues, CSC-pretreated HBEC and A549 cells, according to "Inhibition of lung carcinogenesis and critical cancer-related signaling pathways by N-acetyl-S-(N-2-phenethylthiocarbamoyl)-l-cysteine, indole-3-carbinol and myo-inositol, alone and in combination" by Kassie F, Melkamu T, Endalew A, Upadhyaya P, Luo X, Hecht SS.(2)

3. Pancreatic cell lines
In the examination of the possible mechanism of I3C-enhanced efficacy on pancreatic cell lines (BxPC-3, Mia Paca-2, PL-45, AsPC-1 and PANC-1) for modulation of human equilibrative nucleoside transporter 1 (hENT1) expression, showed that Gemcitabine alone showed no effect on hENT1 expression. However, combining gemcitabine with I3C further increased hENT1 expression. Cell viability assays revealed no effect of I3C on normal cells, hTERT-HPNE. hENT1-specific inhibitor, nitrobenzylthioinosine, significantly abrogated I3C-induced gemcitabine cytotoxicity, further demonstrating its specificity, according to "Enhanced efficacy of gemcitabine by indole-3-carbinol in pancreatic cell lines: the role of human equilibrative nucleoside transporter 1" by Wang H, Word BR, Lyn-Cook BD.(3)

4. Prostate cancer
In the examination of the chemopreventive effects and the molecular mechanism of I3C, particularly the anti-oxidative stress pathway regulated by nuclear erythroid related factor 2 (Nrf2), found that treatments of transgenic adenocarcinoma of mouse prostate, TRAMP C1 cells with I3C also resulted in the induction of Nrf2-mediated genes. I3C significantly suppressed the incidence of palpable tumor and reduced the genitourinary weight in TRAMP mice. Western blots and qPCR analyses of prostate tissues showed that I3C induced the expression of Nrf2, NAD(P)H quinine oxidoreductase 1 (NQO-1) as well as cell cycle and apoptosis related biomarkers in I3C-fed TRAMP mice, according to "In vivo pharmacodynamics of indole-3-carbinol in the inhibition of prostate cancer in transgenic adenocarcinoma of mouse prostate (TRAMP) mice: Involvement of Nrf2 and cell cycle/apoptosis signaling pathways" by Wu TY, Saw CL, Khor TO, Pung D, Boyanapalli SS, Kong AN.(4)

5. Vulval intraepithelial neoplasia
In the evaluation of the effectiveness and safety of medical interventions for high grade Vulval intraepithelial neoplasia (VIN), a pre-malignant condition of the vulval skin, associated with infection with human papilloma virus (HPV) infection, indicated that four trials met our inclusion criteria: three assessed the effectiveness of topical imiquimod versus placebo in women with high grade VIN; one examined low versus high dose indole-3-carbinol in similar women. Meta-analysis of three trials found that the proportion of women who responded to treatment at 5 to 6 months was much higher in the group who received topical imiquimod than in the group who received placebo (relative risk (RR) = 11.95, 95% confidence interval (CI) 3.21 to 44.51), according to "Medical interventions for high grade vulval intraepithelial neoplasia" by Pepas L, Kaushik S, Bryant A, Nordin A, Dickinson HO.(5)

6. Estrogen Metabolism
In the investigation of determine whether a breast health supplement containing indole-3-carbinol and hydroxymatairesinol lignan would alter estrogen metabolism to favour C-2 hydroxylation and reduce C-16 hydroxylation, found that Supplementation with a mixture of indole-3-carbinol and HMR lignan in women significantly increased estrogen C-2 hydroxylation. This may constitute a mechanism for the reduction of breast cancer risk as well as risk for other estrogen-related cancers. Further studies with higher numbers of subjects are indicated, according to "Effects of A Breast-Health Herbal Formula Supplement on Estrogen Metabolism in Pre- and Post-Menopausal Women not Taking Hormonal Contraceptives or Supplements: A Randomized Controlled Trial" by Laidlaw M, Cockerline CA, Sepkovic DW.(6)

7. Oral cancer
In the investigation ofthe antitumor effects of OSU-A9, a structurally optimized I3C derivative, in a panel of oral squamous cell carcinoma cell lines, SCC4, SCC15, and SCC2095, showed that The antiproliferative effect of OSU-A9 was approximately two-orders-of-magnitude higher than that of I3C. Importantly, normal human oral keratinocytes were less sensitive to OSU-A9 than oral cancer cells. This antiproliferative effect of OSU-A9 was attributable to the induction of mitochondrial-dependent apoptosis as evidenced by sub-G1 accumulation of cells, poly ADP-ribose polymerase cleavage, and cytochrome c release from the mitochondria. OSU-A9 down regulates Akt and NF-κB signaling pathways, leading to changes in many downstream effectors involved in regulating cell cycle and apoptosis, according to "A novel indole-3-carbinol derivative inhibits the growth of human oral squamous cell carcinoma in vitro" by Weng JR, Bai LY, Omar HA, Sargeant AM, Yeh CT, Chen YY, Tsai MH, Chiu CF.(7)

8. Cancer prevention
In the review of botanical and nutritional compounds have been used for the treatment of cancer throughout history, indicated that several lead compounds, such as genistein (from soybeans), lycopene (from tomatoes), brassinin (from cruciferous vegetables), sulforaphane (from asparagus), indole-3-carbinol (from broccoli), and resveratrol (from grapes and peanuts) are in preclinical or clinical trials for cancer chemoprevention. Phytochemicals have great potential in cancer prevention because of their safety, low cost, and oral bioavailability, according to "Cancer prevention with natural compounds" by Gullett NP, Ruhul Amin AR, Bayraktar S, Pezzuto JM, Shin DM, Khuri FR, Aggarwal BB, Surh YJ, Kucuk O.(8)

9. Nasopharyngeal cancer
In the examination of the
apoptotic effects of indole-3-carbinol (I3C) in many human cancer cells, found that Treatment with I3C significantly suppressed XIAP, c-IAP1 and Survivin protein, while elevated the expression of Omi, Smac and Cyto-c. Fas/FasL and MAPK pathway were involved in the induction of apoptosis. Taken together, these results demonstrated that I3C may induce mitochondria-mediated apoptosis via the Fas death receptor in CNE-2 cells. This molecular mechanism for apoptotic effect of I3C on nasopharyngeal cancer cells suggested that I3C might become a preventive and therapeutic agent against nasopharyngeal cancer, according to "Indole-3-carbinol (I3C)-induced apoptosis in nasopharyngeal cancer cells through Fas/FasL and MAPK pathway" by Xu Y, Zhang J, Dong WG.(9)

10. Colon cancer
In an easy two-step synthesis for 4-methoxyindole-3-carbinol (4MeOI3C), the expected breakdown product of 4-methoxyglucobrassicin during ingestion. 4MeOI3C inhibited the proliferation of human colon cancer cells DLD-1 and HCT 116 with IC(50) values of 116 microM and 96 microM, respectively, found that after 48 h in vitro, and is therefore a more potent inhibitor than indole-3-carbinol (I3C). 4MeOI3C and I3C combined in different molar ratios inhibited proliferation in a nearly additive to slightly synergistic manner. Proliferation was inhibited by 100 microM 4MeOI3C after 48 h without affecting cell cycle phase distribution, indicating an overall-slowdown effect on the cell cycle, according to "Effect of 4-methoxyindole-3-carbinol on the proliferation of colon cancer cells in vitro, when treated alone or in combination with indole-3-carbinol" by Kronbak R, Duus F, Vang O.(10)

11. Etc.

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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/20530686
(2) http://www.ncbi.nlm.nih.gov/pubmed/20603442
(3) http://www.ncbi.nlm.nih.gov/pubmed/21965724
(4) http://www.ncbi.nlm.nih.gov/pubmed/21837756
(5) http://www.ncbi.nlm.nih.gov/pubmed/21491403
(6) http://www.ncbi.nlm.nih.gov/pubmed/21234288
(7) http://www.ncbi.nlm.nih.gov/pubmed/20843730
(8) http://www.ncbi.nlm.nih.gov/pubmed/20709209
(9) http://www.ncbi.nlm.nih.gov/pubmed/20628834
(10) http://pubs.acs.org/doi/abs/10.1021/jf101806t

Phytochemicals in Foods - 11 Health Benefits of 3,3'-Diindolylmethane

3,3'-Diindolylmethane or DIM are phytochemicals derived from the digestion of indole-3-carbinol, belonging to the group of Indoles, found abundantly in broccoli, Brussels sprouts, cabbage and kale, etc.

Health Benefits
1.
Antiinflammatory and chemopreventive effects on Skin
In the examination of the effects of 3,3'-Diindolylmethane (DIM) on antiinflammatory and antitumor promotion activity in mouse skin and explored the relevant mechanism, indicated that Several lead compounds, such as genistein (from soybeans), lycopene (from tomatoes), brassinin (from cruciferous vegetables), sulforaphane (from asparagus), indole-3-carbinol (from broccoli), and resveratrol (from grapes and peanuts) are in preclinical or clinical trials for cancer chemoprevention. Phytochemicals have great potential in cancer prevention because of their safety, low cost, and oral bioavailability. In this review, we discuss potential natural cancer preventive compounds and their mechanisms of action, according to "3,3'-diindolylmethane suppresses 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and tumor promotion in mouse skin via the downregulation of inflammatory mediators" by Kim EJ, Park H, Kim J, Park JH.(1)

2. Antileukemic Activity
In the study of 3,3'-diindolylmethane (DIM), one of the active products derived from Brassica plants, for it antitumor effects, showed that DIM significantly induced apoptosis in U937 human leukemia cells in dose- and time-dependent manners. These events were also noted in other human leukemia cells (Jurkat and HL-60) and primary human leukemia cells (AML) but not in normal bone marrow mononuclear cells. DIM-induced lethality is associated with caspases activation, myeloid cell leukemia-1 (Mcl-1) down-regulation, p21(cip1/waf1) up-regulation, and Akt inactivation accompanied by c-jun NH2-terminal kinase (JNK) activation. Enforced activation of Akt by a constitutively active Akt construct prevented DIM-mediated caspase activation, Mcl-1 down-regulation, JNK activation, and apoptosis, according to "3, 3'-Diindolylmethane Exhibits Antileukemic Activity In Vitro and In Vivo through a Akt-Dependent Process" by Gao N, Cheng S, Budhraja A, Liu EH, Chen J, Chen D, Yang Z, Luo J, Shi X, Zhang Z.(2)

3. Cervical Cancer
In the examination of
3,3'-Diindolylmethane (DIM) prevention or inhibition of the progression from cervical dysplasia to Human papilloma viral causes of cervical neoplasia (CIN), found that significant increases in IFN-γ serum concentrations that correlate with the percentage of CIN free mice in each group indicate that 1000 ppm of DIM in food may be the most effective dose for future studies. These results may eventually lead to new and effective vaccination strategies in women already infected with the human papilloma virus, according to '3,3'-Diindolylmethane Increases Serum Interferon-γ Levels in the K14-HPV16 Transgenic Mouse Model for Cervical Cancer" by Sepkovic DW, Raucci L, Stein J, Carlisle AD, Auborn K, Ksieski HB, Nyirenda T, Bradlow HL.(3)

4. Esophageal cancer
In the study of
3,3'-Diindolylmethane (DIM), an active metabolite of indole-3-carbinol, and its antitumor effects in experimental animals and induction of apoptosis in various cancer cells, showed that DIM significantly inhibited the proliferation of ESCC cells in a dose- and time-dependent manner. The percentage of G1 phase cells increased 48 h after being treated with DIM. DIM also reduced cyclin D1, cyclin E2, cyclin-dependent kinase (CDK) 4 and CDK 6 activities, and increased p15 and p27 levels. Additionally, DIM diminished pro-caspase-9 protein expression levels and induced increased cleaved poly (ADP-ribose) polymerase levels, accoridng to "3,3'-Diindolylmethane suppresses growth of human esophageal squamous cancer cells by G1 cell cycle arrest"by Kim SJ, Lee JS, Kim SM.(4)

5. Prostate cancer
In the stuidy of
whether DIM inhibits the development of prostate cancer using the transgenic adenocarcinoma mouse prostate (TRAMP) model, showed that DIM induced a substantial reduction in the numbers of viable cells and induced apoptosis in LNCaP and DU145 cells. DIM increased the cleavage of caspase-9, -7, -3, and poly (ADP-ribose) polymerase (PARP). DIM increased mitochondrial membrane permeability and the translocation of cytochrome c and Smac/Diablo from the mitochondria. Additionally, DIM induced increases in the levels of cleaved caspase-8, truncated Bid, Fas, and Fas ligand, and the caspase-8 inhibitor Z-IETD-FMK was shown to mitigate DIM-induced apoptosis and the cleavage of caspase-3, PARP, and Bid, according to '3,3'-Diindolylmethane inhibits prostate cancer development in the transgenic adenocarcinoma mouse prostate model" by Cho HJ, Park SY, Kim EJ, Kim JK, Park JH.(5)

6. Oral Cancer
In the
investigation of the antitumor activity of 3,3'-diindolylmethane (DIM), an active metabolite of the phytochemical indole-3-carbinol (I3C), in oral squamous cell carcinoma (OSCC), showed that DIM stimulated the activation of p53 via Ser-15 phosphorylation, leading to increased expression of the BH3-only proapoptotic Bcl-2 members Puma and Noxa. Together, these changes decreased the mitochondrial threshold for apoptosis. G2/M arrest might be attributable to the suppressive effect of DIM on the expression of cyclin B1 and cdc25c. As many downstream effectors of the Akt-NF-κB pathway, including glycogen synthase kinase 3β, IκB kinase α, and cyclooxygenase-2, have been shown to promote oral tumorigenesis, the ability of DIM to inhibit this signaling axis underscores its chemopreventive potential in oral cancer, according to "The dietary phytochemical 3,3'-diindolylmethane induces G2/M arrest and apoptosis in oral squamous cell carcinoma by modulating Akt-NF-κB, MAPK, and p53 signaling" by Weng JR, Bai LY, Chiu CF, Wang YC, Tsai MH.(6)

7. Ovarian cancer
In the
delineation of the mechanism by which DIM suppressed the growth of SKOV3, OVCAR-3 and TOV-21G human ovarian cancer cells, found that DIM treatment also inhibited the kinase activity of ERK as observed by the down regulation of p-ELK in all the three ovarian cancer cell lines. DIM significantly suppressed the growth of ovarian tumors in vivo. Tumor growth suppressive effects of DIM in SKOV-3 tumor xenografts were associated with reduced phosphorylation of EGFR, MEK and ERK, according to "Blocking EGFR activation suppresses ovarian tumor growth in vitro and in vivo" by Kandala PK, Wright SE, Srivastava SK.(7)

8. Colon cancer
In the
analyzing the expression pattern of N-myc downstream regulated gene-1 following treatment of human colonic cancer cell lines, suggested that N-myc downstream regulated gene-1 expression is enhanced by 3,3'-diindolylmethane in poorly differentiated cells and followed by induction of apoptosis. 3,3'-diindolylmethane induced apoptosis may represent a new regulator of N-myc downstream regulated gene-1 in poorly differentiated colonic cancer cells, according to "The indolic diet-derivative, 3,3'-diindolylmethane, induced apoptosis in human colon cancer cells through upregulation of NDRG1" by Lerner A, Grafi-Cohen M, Napso T, Azzam N, Fares F.(8)

9. Osteosarcoma

In the investigation of the effect of the natural product 3,3'-diindolylmethane (DIM) on cytosolic Ca(2+) concentrations ([Ca(2+) ](i) ) and viability in MG63 human osteosarcoma cells, found that DIM-evoked Ca(2+) entry was suppressed by nifedipine, econazole, SK&F96365 and protein kinase C modulators. In the absence of extracellular Ca(2+) , incubation with the endoplasmic reticulum Ca(2+) pump inhibitors thapsigargin or 2,5-di-tert-butylhydroquinone (BHQ) inhibited or abolished DIM-induced [Ca(2+) ](i) rise. Incubation with DIM also inhibited thapsigargin or BHQ-induced [Ca(2+) ](i) rise. Inhibition of phospholipase C with U73122 abolished DIM-induced [Ca(2+) ](i) rise. At concentrations of 10-50 μM, DIM killed cells in a concentration-dependent manner, according to "3,3'-Diindolylmethane Alters Ca(2+) Homeostasis and Viability in MG63 Human Osteosarcoma Cells" by Lu YC, Chen IS, Chou CT, Huang JK, Chang HT, Tsai JY, Hsu SS, Liao WC, Wang JL, Lin KL, Liu SI, Kuo CC, Ho CM, Jan CR.(9)

10. Breast cancer
in the assessment of the effects of DIM on cell-cycle regulation in both estrogen-dependent MCF-7 and estrogen receptor negative p53 mutant MDA-MB-468 human breast cancer cells,
showed that DIM inhibited the breast cancer cell growth in vitro and in vivo, and caused cell-cycle arrest by down-regulating protein levels of cell-cycle related kinases CDK1, CDK2, CDK4, and CDK6, as well as Cyclin B1 and Cdc25A. Meanwhile, it was revealed that Ser(124) phosphorylation of Cdc25A is primarily responsible for the DIM-induced Cdc25A degradation. Furthermore, treatment of MCF-7 cells with DIM increased miR-21 expression and down-regulated Cdc25A, resulting in an inhibition of breast cancer cell proliferation, according to " 3,3'-Diindolylmethane inhibits breast cancer cell growth via miR-21-mediated Cdc25A degradation' by Jin Y.(10)

11. Thyroid cancer
In the investigation of
the property of a natural dietary compound found in cruciferous vegetables, 3,3'-diindolylmethane (DIM), to target the metastatic phenotype of thyroid cancer cells through a functional estrogen receptor, found that DIM inhibits estrogen mediated increase in thyroid cell migration, adhesion and invasion, which is also supported by ER-α downregulation (siRNA) studies. Western blot and zymography analyses provided direct evidence for this DIM mediated inhibition of E(2) enhanced metastasis associated events by virtue of targeting essential proteolytic enzymes, namely MMP-2 and MMP-9, according to "Estrogen induced metastatic modulators MMP-2 and MMP-9 are targets of 3,3'-diindolylmethane in thyroid cancer' by Rajoria S, Suriano R, George A, Shanmugam A, Schantz SP, Geliebter J, Tiwari RK.(11)

12. Etc.

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 Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/20564344
(2) http://www.ncbi.nlm.nih.gov/pubmed/22363731
(3) http://www.ncbi.nlm.nih.gov/pubmed/22351660
(4) http://www.ncbi.nlm.nih.gov/pubmed/22293900
(5) http://www.ncbi.nlm.nih.gov/pubmed/21229607
(6) http://www.ncbi.nlm.nih.gov/pubmed/22290291
(7) http://www.ncbi.nlm.nih.gov/pubmed/22205686
(8) http://www.ncbi.nlm.nih.gov/pubmed/22187533
(9) http://www.ncbi.nlm.nih.gov/pubmed/21995587
(10) http://www.ncbi.nlm.nih.gov/pubmed/21761201
(11) http://www.ncbi.nlm.nih.gov/pubmed/21267453

Phytochemicals in Foods - 10 Health Benefits of Sinigrin

Sinigrin is a phytochemical glucosinolate, belongs to the family of glucosides found abundantly in Brussels sprouts, broccoli, the seeds of black mustard, etc.

Health Benefits
1. Bladder cancer
In the design of testing the hypothesis of AITC-containing cruciferous vegetables also inhibit bladder cancer development, indicated that Comparison between hydrated MSP-1 and pure sinigrin with added myrosinase suggested that the anticancer effect of MSP-1 was derived principally, if not entirely, from the AITC generated from sinigrin. In an orthotopic rat bladder cancer model, oral MSP-1 at 71.5 mg/kg (sinigrin dose of 9 μmol/kg) inhibited bladder cancer growth by 34.5% (P < 0.05) and blocked muscle invasion by 100%, according to "Allyl isothiocyanate-rich mustard seed powder inhibits bladder cancer growth and muscle invasion" by Bhattacharya A, Li Y, Wade KL, Paonessa JD, Fahey JW, Zhang Y.(1)

2. Multidirectional time-dependent effect
In a research of nutritional significance of parent glucosinolate sinigrin 50 μmol/kg b. w./day and its degradation product allyl isothiocyanate 25 μmol/kg b. w./day and 50 μmol/kg b. w./day was studied by the evaluation of their influence on some parameters of carbohydrate and lipid metabolism in an animal rat model in vivo after their single (4 h) and 2 weeks oral administration, showed that the effect of SIN and AITC is multidirectional, indicating its impact on many organs like liver as well as pancreas, intestine in vivo action and rat adipocytes in vitro. Whilst consumption of cruciferous vegetables at levels currently considered "normal" seems to be beneficial to human health, this data suggest that any large increase in intake could conceivably lead to undesirable effect, according to "Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats" by Okulicz M.(2)

3. Postprandial hypertriglyceridemia
In the examination of the bioactivity of Yamato-mana (Brassica rapa L. Oleifera Group) constituent glucosinolates with 3-butenyl glucosinolate (gluconapin) decreased the plasma triglyceride gain induced by corn oil administration to mice, indicated that phenethyl glucosinolate (gluconasturtiin) had little effect. 2-Propenyl glucosinolate (sinigrin) also reduced the plasma triglyceride level, which suggests that alkenyl glucosinolates might be promising agents to prevent postprandial hypertriglyceridemia, according to "Suppressive effect of Yamato-mana (Brassica rapa L. Oleifera Group) constituent 3-butenyl glucosinolate (gluconapin) on postprandial hypertriglyceridemia in mice" by Washida K, Miyata M, Koyama T, Yazawa K, Nomoto K.(3)

4. Antimicrobial effects
In the investigation of Allyl isothiocyanate (AIT) derived from the glucosinolate sinigrin found in plants of the family Brassicaceae and its antimicrobial agent against a variety of organisms, including foodborne pathogens such as Escherichia coli O157:H7, found that it can be postulated that: 1) AIT is a more effective antimicrobial at low pH values and its degradation reduces this activity; 2) decomposition products in water might not participate in the antimicrobial action of AIT; and 3) AIT seems to have a multi-targeted mechanism of action, perhaps inhibiting several metabolic pathways and damaging cellular structures, according to "Enzymatic inhibition by allyl isothiocyanate and factors affecting its antimicrobial action against Escherichia coli O157:H7" by Luciano FB, Holley RA.(4)

5. Liver cancer
In the determination of the inhibitory effects of AITC and its NAC conjugate on cell proliferation, the expression of matrix metalloproteinases (MMPs), adhesion, invasion, and migration in SK-Hep 1 human hepatoma cells, found that AITC and NAC-AITC suppress SK-Hep 1 cell proliferation in a dose-dependent manner; by 25% and 30% for 10 microM AITC and 10 microM NAC-AITC, respectively. The influence of AITC and NAC-AITC on the gene expression of MMPs and tissue inhibitors of metalloproteinase (TIMPs). Gelatin zymography also revealed a significant downregulation of MMP-2/-9 expression in SK-Hep1 cells treated with 0.1-5 microM AITC and NAC-AITC compared with controls. Reverse transcriptase polymerase chain reaction revealed dose-dependent decreases in MMP-2/-9 messenger RNA levels in both AITC-treated and NAC-AITC-treated cells, according to "Allyl isothiocyanate and its N-acetylcysteine conjugate suppress metastasis via inhibition of invasion, migration, and matrix metalloproteinase-2/-9 activities in SK-Hep 1 human hepatoma cells" by Hwang ES, Lee HJ.(5)

6. Detoxication enzymes
In the examination of the ability of allyl nitrile, a hydrolysis product of the glucosinolate sinigrin, to increase tissue levels of the phase 2 detoxication enzymes glutathione S-transferase and quinone reductase and GSH in a variety of mouse tissues, found that show that allyl nitrile displays its maximum potency in the stomach and lungs, which is of interest in light of epidemiological studies demonstrating an inverse association between crucifer intake and the incidence of stomach and lung cancers, according to "Induction of detoxication enzymes in mice by naturally occurring allyl nitrile" by Tanii H, Higashi T, Nishimura F, Higuchi Y, Saijoh K.(6)

7. Anti-SARS coronavirus 3C-like protease effects
In the study, Isatis indigotica root extract, five major compounds of I. indigotica root, and seven plant-derived phenolic compounds were tested for anti-SARS-CoV 3CLpro effects using cell-free and cell-based cleavage assays, found that Cleavage assays with the 3CLpro demonstrated that IC50 values were in micromolar ranges for I. indigotica root extract, indigo, sinigrin, aloe emodin and hesperetin. Sinigrin (IC50: 217 microM) was more efficient in blocking the cleavage processing of the 3CLpro than indigo (IC50: 752 microM) and beta-sitosterol (IC50: 1210 microM) in the cell-based assay. Only two phenolic compounds aloe emodin and hesperetin dose-dependently inhibited cleavage activity of the 3CLpro, in which the IC50 was 366 microM for aloe emodin and 8.3 microM for hesperetin in the cell-based assay, according to "Anti-SARS coronavirus 3C-like protease effects of Isatis indigotica root and plant-derived phenolic compounds" by Lin CW, Tsai FJ, Tsai CH, Lai CC, Wan L, Ho TY, Hsieh CC, Chao PD.(7)

8. Colorectal cancer
In the investigation of raw juice extracted from Brussels sprouts rich in the glucosinolate sinigrin to explore the effect of naturally occurring glucosinolate breakdown products on cell cycle progression and apoptosis in human colorectal carcinoma cells (HT29), found that the main glucosinolate breakdown products were as follows: the sinigrin breakdown product, 1-cyano-2,3-epithiopropane (ca. 38 mM); the gluconapin hydrolysis product, 3-butenyl isothiocyanate (ca. 2.2.mM); the glucobrassicin metabolite, ascorbigen (ca. 8 mM); and low concentrations of other indole glucosinolate-derived hydrolysis products such as neoascorbigen and 3,3'-diindolylmethane. A variety of biologically active glucosinolate breakdown products are released by mechanical disruption of raw Brussels sprout tissue, but contrary to previous assumptions, allyl isothiocyanate is not the main compound responsible for the inhibition of cell proliferation, according to "Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro" by Smith TK, Lund EK, Clarke RG, Bennett RN, Johnson IT.(8)

9. Tumor cell proliferation and cyclooxygenase inhibitory
In the investigation of Cyclooxygenase and human tumor cell growth inhibitory from 5 compounds, namely plastoquinone-9 (1), 6-O-acyl-beta-d-glucosyl-beta-sitosterol (2), 1,2-dilinolenoyl-3-galactosylglycerol (3), linolenoyloleoyl-3-beta-galactosylglycerol (4), and 1,2-dipalmitoyl-3-beta-galactosylglycerol (5). 3-Acyl-sitosterols, sinigrin, gluconasturtiin, and phosphatidylcholines isolated from horseradish and alpha-tocopherol and ubiquinone-10 from wasabi rhizomes, showed that Compounds 3, 4, and 5 gave 75, 42, and 47% inhibition of COX-1 enzyme, respectively, at a concentration of 250 microg/mL. In a dose response study, compound 3 inhibited the proliferation of colon cancer cells (HCT-116) by 21.9, 42.9, 51.2, and 68.4% and lung cancer cells (NCI-H460) by 30, 39, 44, and 71% at concentrations of 7.5, 15, 30, and 60 microg/mL, respectively. At a concentration of 60 microg/mL, compound 4 inhibited the growth of colon, lung, and stomach cancer cells by 28, 17, and 44%, according to "Tumor cell proliferation and cyclooxygenase inhibitory constituents in horseradish (Armoracia rusticana) and Wasabi (Wasabia japonica)" by Weil MJ, Zhang Y, Nair MG.(9)

10. Antioxidants
In the examination of the effect of an aqueous extract of cooked Brussels sprouts on formation of 7-hydro-8-oxo-2'-deoxyguanosine (8-oxodG) in calf thymus DNA in vitro, found that Sinigrin, a glucosinolate abundant in Brussels sprouts, co-eluted with the most effective fraction and had DNA protective effects. In comparison with other antioxidants the patterns of effect of the extract in the five damage systems were more similar to that of sodium azide than to those of dimethylsulfoxide and vitamin C, according to "Inhibition of oxidative DNA damage in vitro by extracts of brussels sprouts" by Zhu C, Poulsen HE, Loft S.(10)

11. Etc.
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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/20889681
(2) http://www.ncbi.nlm.nih.gov/pubmed/20809411
(3) http://www.ncbi.nlm.nih.gov/pubmed/20530888
(4) http://www.ncbi.nlm.nih.gov/pubmed/19346022
(5) http://www.ncbi.nlm.nih.gov/pubmed/16565438
(6) http://www.ncbi.nlm.nih.gov/pubmed/16277393
(7) http://www.ncbi.nlm.nih.gov/pubmed/16115693
(8) http://www.ncbi.nlm.nih.gov/pubmed/15884814
(9) http://www.ncbi.nlm.nih.gov/pubmed/15740020
(10) http://www.ncbi.nlm.nih.gov/pubmed/10885626

Phytochemicals in Foods - 10 Health Benefits of Alliin

Alliin (S-allyl-L-cysteine-S-oxide) is a phytochemical compound sulfoxide,. a derivative of the amino acid cysteine, belonging to the class of sulfur compounds, found abundantly in fresh garlic and onion.

Health Benefits
1. Antioxidant properties
In the investigation of the antioxidant properties of garlic compounds representing the four main chemical classes, alliin, allyl cysteine, allyl disulfide, and allicin, prepared by chemical synthesis or purification, showed that Alliin scavenged superoxide, while allyl cysteine and allyl disulfide did not react with superoxide. Allicin suppressed the formation of superoxide by the xanthine/xanthine oxidase system, probably via a thiol exchange mechanism. Alliin, allyl cysteine, and allyl disulfide all scavenged hydroxyl radicals; the rate constants calculated based on deoxyribose competitive assay were 1.4-1.7 x 10(10), 2.1-2.2 x 10(9), and 0.7-1.5 x 10(10) M (1) second(1), respectively, according to "The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide" by Chung LY.(1)

2. Anti diabetes
In comparison of the production and therapeutic efficiency of alliin extracted from garlic leaves of plants grown under ex situ and in situ conditions, found that Alliin production noted ~50% enhancement in leaves from plants grown under in situ conditions. Serum glucose, triglycerides, total lipids, total cholesterol, low-density lipoprotein (LDL)-, and very low-density lipoprotein (VLDL)-cholesterol in diabetic rats treated with alliin produced from in situ grown plants noted significant reduction of ~54%, 15%, 14%, 20%, 24%, and 15%, while 35%, 14%, 10%, 12%, 17% and 11% reduction was noted in diabetic rats treated with alliin produced from ex situ grown plants in comparison with those administered with distilled water. High-density lipoprotein (HDL)-cholesterol did not show any significant change. Leaf extract of plants lowered serum enzyme levels (alkaline phosphatase, aspartate aminotransferase, and alanine aminotransferase) toward the norm better than glibenclamide, according to "Alliin obtained from leaf extract of garlic grown under in situ conditions possess higher therapeutic potency as analyzed in alloxan-induced diabetic rats" by Nasim SA, Dhir B, Kapoor R, Fatima S, Mahmooduzzafar, Mujib A.(2)

3. Antibacterial activity
In the investigation of an antimicrobial sulfur compound newly isolated from heated garlic extract, showed that the compound was CH₂=CH-CH₂-S-S-S-CH₂-CH(NH₂)COOH, 3-(allyltrisulfanyl)-2-aminopropanoic acid, a derivative of cysteine, presumably derived from alliin (S-allyl-L-cysteine sulfoxide). This novel compound has comparatively potent anti-yeast activity and rather weak antibacterial activity, similar to other antimicrobial compounds in garlic, according to "3-(allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic" by Kang SS, Lim DR, Kyung KH.(3)

4. Ovarian cancer
In the investigation of a chemical conjugate between daidzein and the garlic enzyme alliinase and its effect on human ovarian cancer cells, suggest that the targeted alliinase conjugates in the presence of alliin, generated therapeutically effective levels of allicin which were capable of suppressing tumor progression of intraperitoneal ovarian cancer in an animal model, according to "Conjugates of daidzein-alliinase as a targeted pro-drug enzyme system against ovarian carcinoma" by Appel E, Rabinkov A, Neeman M, Kohen F, Mirelman D.(4)

5. Mitochondrial dysfunction
In the evaluation of the preventive role of S-allyl cysteine sulphoxide (SACS) in isoproterenol (ISO)-induced cardiotoxicity in male Wistar rats, showed that oral administration of SACS for a period of 35 days to the normal control rats did not show any significant effect. Histopathological studies of the myocardial tissue showed a protective role of SACS in the myocardial-infarcted rats. The effect at a dose of SACS 80 mg/kg was more effective than the dose 40 mg/kg. The results of the study conclude that SACS protect the mitochondria of the ISO-induced myocardial-infarcted rats, according to 'Preventive effect of S-allyl cysteine sulphoxide (Alliin) on mitochondrial dysfunction in normal and isoproterenol induced cardiotoxicity in male Wistar rats: a histopathological study" by Sangeetha T, Darlin Quine S.(5)

6. Anti-fungal efficacy
In the evaluation of the in vitro anti-fungal efficacy of the active principle of garlic, pure allicin and polybutylcyanoacrylate (PBCA) nanoparticles (NPs) loaded with allicin.
found that that pure allicin has stronger in vitro anti-fungal efficacy to six tested fungi than alliinase and alliin. Moreover, it has improved significantly after pure allicin being wrapped into PBCA NP, which may be due to the NP's good prolonged release effect and nano-scale dimensions, according to "Anti-fungal efficacy of polybutylcyanoacrylate nanoparticles of allicin and comparison with pure allicin" by Luo DQ, Guo JH, Wang FJ, Jin ZX, Cheng XL, Zhu JC, Peng CQ, Zhang C.(6)

7. Antithrombotic and anticancer effects
In the review of modern scientific research has revealed that the wide variety of dietary and medicinal functions of garlic can be attributed to the sulfur compounds present in or generated from garlic, indicated that although garlic produces more than 20 kinds of sulfide compounds from a few sulfur-containing amino acids, their functions are different from one another; e.g., allicin, methyl allyl trisulfide, and diallyl trisulfide have antibacterial, antithrombotic, and anticancer activities, respectively, according to "Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review" by Ariga T, Seki T. (7)

8. Anti-angiogenesis
In the demonstartion of dose-dependent of Alliin, a compound derived from garlic, in inhibition of fibroblast growth factor-2 (FGF2)-induced human endothelial cell (EC) tube formation and angiogenesis in the chick chorioallantoic membrane (CAM) model, showed that these data indicated a synergistic effect of antioxidants on the anti-angiogenesis and anticancer efficacy of alliin. These data also suggest the implication of cellular NO and p53 as mediators of anti-angiogenesis and anticancer effects of alliin, according to "Anti-angiogenesis efficacy of the garlic ingredient alliin and antioxidants: role of nitric oxide and p53" by Mousa AS, Mousa SA.(8)

9. Serum lipids, blood pressure and arterial stiffness
in the testing the effect of dried garlic (Allium sativum) powder on blood lipids, blood pressure and arterial stiffness in a 12-week randomised, double-blind, placebo-controlled trial. Seventy-five healthy, normo-lipidaemic volunteers (men and women aged 40-60 years) were assigned to dried garlic powder tablets (10.8 mg alliin (3-(2-propenylsulfinyl)-L-alanine)/d, corresponding to about three garlic cloves) or placebo, showed that garlic powder was associated with a near-significant decrease (12 %) in triacylglycerol concentration (P=0.07). In conclusion, garlic powder tablets have no clinically relevant lipid-lowering and blood pressure-lowering effects in middle-aged, normo-lipidaemic individuals. The putative anti-atherosclerotic effect of garlic may be linked to risk markers other than blood lipids, according to "Effect of garlic (Allium sativum) powder tablets on serum lipids, blood pressure and arterial stiffness in normo-lipidaemic volunteers: a randomised, double-blind, placebo-controlled trial" by Turner B, Mølgaard C, Marckmann P.(9)

10. Hepatoprotective effect
In the study of the interaction of the non-protein amino acid alliin with the enzyme alliinase (alliin lyase, EC 4.4.1.4). D-Galactosamine highly sensitizes the host response of the experimental animal to endotoxin (lipopolysaccharide) and causes fulminant hepatitis within 8h after administration, indicated that In D-galactosamine/lipopolysaccharide (D-GalN/LPS)-induced hepatitis rats, a significant increase of lipid peroxidation and decreased liver antioxidant enzyme levels are observed. Pretreatment with allicin, the active component of freshly crushed garlic cloves, prevented these alterations, according to "Hepatoprotective effect of allicin on tissue defense system in galactosamine/endotoxin challenged rats" by Vimal V, Devaki T.(10)

11. Etc.

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Sources
(1) http://www.ncbi.nlm.nih.gov/pubmed/16822206
(2) http://www.ncbi.nlm.nih.gov/pubmed/21391887
(3) http://www.ncbi.nlm.nih.gov/pubmed/20828317
(4) http://www.ncbi.nlm.nih.gov/pubmed/20678009
(5) http://www.ncbi.nlm.nih.gov/pubmed/19262997
(6) http://www.ncbi.nlm.nih.gov/pubmed/19105898
(7) http://www.ncbi.nlm.nih.gov/pubmed/16823096
(8) http://www.ncbi.nlm.nih.gov/pubmed/16351512
(9) http://www.ncbi.nlm.nih.gov/pubmed/15522140
(10) http://www.ncbi.nlm.nih.gov/pubmed/14698523