• Title/Summary/Keyword: s-allyl cysteine

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Antimicrobial Activity of Chemical Substances Derived from S-Alk(en)yl-L-Cysteine Sulfoxide (Alliin) in Garlic, Allium sativum L.

  • Choi, Mi-Kyung;Chae, Kyung-Yeon;Lee, Joo-Young;Kyung, Kyu-Hang
    • Food Science and Biotechnology
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    • v.16 no.1
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    • pp.1-7
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    • 2007
  • Garlic (Allium sativum L.) contains a specific sulfur compound, the S-allyl derivative of L-cysteine sulfoxide, and has long been known for its antimicrobial activity against various microorganisms, including bacteria, fungi, and protozoa. The principal antimicrobial compound of garlic is S-allyl-L-propenethiosulfinate (allicin) which is generated by an enzyme, alliinase (L-cysteine sulfoxide lyase), from S-allyl-L-cysteine sulfoxide (alliin). This compound exists exclusively in Allium as a major non-protein sulfur-containing amino acid. S-Allyl-L-propenethiosulfinate belongs to the chemical group of thiosulfinates and is a highly potent antimicrobial. The potency of garlic extract is reduced during storage since thiosulfinates are unstable and are degraded to other compounds some of which do not have antimicrobial activity. Diallyl polysulfides and ajoene are sulfur compounds derived from allicin that do possess antimicrobial activity. It was recently found that garlic becomes antimicrobial on heating at cooking temperatures, and that the compound responsible for this is allyl alcohol, which is generated from alliin by thermal degradation.

Lipid Modulatory Functions of Cysteine Compounds Found in Genus Allium Plants in Diabetic Mice (Allium 속 식물 Cysteine화합물이 당뇨 쥐의 지질대사에 미치는 영향)

  • Choi, Seong-Hee;Park, Jeong-Ro
    • The Korean Journal of Food And Nutrition
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    • v.23 no.3
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    • pp.361-367
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    • 2010
  • In this study, cysteine compounds found in genus Allium plants, including N-acetyl cysteine(NAC), S-allyl cysteine(SAC), S-ethyl cysteine(SEC), and S-methyl cysteine(SMC), were examined for effects on blood glucose, glucose tolerance, and plasma lipid concentrations in streptozotocin(STZ)-induced diabetic mice. In the mice, the ingestion of these cysteine compounds did not affect blood glucose levels significantly. However, their ingestion did improve the diabetic symptoms of polydipsia, polyphagia, polyuria, and weight loss. Glucose tolerance was also found to be improved in the STZ diabetic animals by feeding the cysteine compounds. Treatment of the compounds also caused a slight decrease in plasma concentrations of total cholesterol along with increases in HDL-cholesterol and slight decreases in LDL-cholesterol, resulting in a significant decrease in the atherogenic index of plasma in the diabetic animals. They also showed reductions of liver triglyceride content to relieve diabetic fatty liver syndrome. In summary, the cysteine compounds such as NAC, SAC, SEC, and SMC, found in genus Allium plants, had certain beneficial effects on blood glucose metabolism along with preventing abnormalities in lipid metabolism, a complication of diabetes, by improving the atherogenic index of plasma and fatty liver in STZ-induced diabetic mice.

Physicochemical characteristics of domestic garlic by varieties and their quality changes during aging of black garlic (품종별 마늘의 품질 특성 및 흑마늘 숙성 중 품질 변화)

  • Seung Hee Yoo;Gun Su Cha;Dong Gyu Kim;Min Jung Kang
    • Food Science and Preservation
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    • v.30 no.3
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    • pp.446-458
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    • 2023
  • In this study, the quality characteristics of the representative domestic garlic varieties in Korea (Namdo, Daeseo, Hongsan, and Uiseong garlic) were compared and their changes according to the aging process of black garlic were investigated. Each garlic sample was aged for 15 days according to the manufacturing process of black garlic. The total phenolic compound contents were 85.2-109.7 mg GAE/100 g in raw garlic samples, which increased with the aging period, and Hongsan garlic showed the highest content in both raw and aged black garlic. The content of alliin was 848.3-1,087.5 mg/100 g in raw garlic samples, and it decreased significantly on the 5th day (7.3-20.6 mg/100 g) in aged garlic. The contents of GSAC (γ-glutamyl-S-allyl-cysteine) and GS1PC (γ-glutamyl-S-1-propenyl-l-cysteine) in raw garlic samples were 202.1-541.0 mg/100 g and 311.1-474.3 mg/100 g, respectively, but gradually decreased during the aging process. On the other hand, the SAC (S-allyl-cysteine) and S1PC (S-1-propenyll-cysteine) contents of raw garlic were very low in all four varieties, but they were highest on the 5th day of aging and tended to decrease thereafter. On the 5th day of aging, the SAC content of Namdo garlic (208.0 mg/100 g) was highest (p<0.05), and S1PC content was significantly higher in Uiseong garlic (66.2 mg/100 g) than the others.

Effect of Cooking Methods on S-Allyl-L-Cysteine Content of Garlic (마늘의 조리방법에 따른 S-Allyl-L-Cysteine 함량 변화)

  • Lee, Sang Hoon;Jeong, Yun Sook;Hwang, Kyung-A;Song, Jin;Noh, Geon Min;Hwang, In Guk
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.8
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    • pp.1221-1226
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    • 2016
  • This study investigated changes in the S-allyl-L-cysteine (SAC) content of garlic using different cooking methods. Methods for determining SAC were validated by determining specificity, linearity, limit of detection (LOD), limit of quantification (LOQ), precision, and accuracy using an high-performance liquid chromatography-fluorescence detection system. Results showed high linearity in the calibration curve with a coefficient of correlation ($R^2$) of 0.9999. The LOD and LOQ values for SAC were 0.15 and $0.47{\mu}g/mL$, respectively. The relative standard deviations for intra- and inter-day precision of SAC were less than 5%. The recovery rate of SAC was in the range from 97.35% to 97.47%. The SAC content of raw garlic was 2.77 mg/g, and there was no significant difference in SAC content according to blanching and microwave treatment. However, SAC content upon boiling and autoclaving at $110^{\circ}C$ and $121^{\circ}C$ increased from 3.50~9.16 mg/g, 6.52~16.21 mg/g, and 14.15~50.24 mg/g with increasing cooking temperature and time, respectively.

Effect of S-Allyl Cysteine(SAC) on the Proliferation of Umbilical Cord Blood(UCB)-derived Mesenchymal Stem Cells(MSCs) (S-Allyl Cysteine(SAC)이 제대혈 유래 중간엽 줄기세포 증식에 미치는 영향)

  • Park, Ran-Sook
    • The Korean Journal of Food And Nutrition
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    • v.22 no.2
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    • pp.313-319
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    • 2009
  • To improve the growth of human mesenchymal stem cells(hMSCs) under general cell culture conditions(20% $O_2$ and 5% $CO_2$), we examined the effect of s-allylcysteine(SAC), which is known as an antioxidant and the main component of aged-garlic extract, on hydrogen peroxide-induced cellular stress in hMSCs. We found that SAC blocked hydrogen peroxideinduced cell death and cellular apoptosis, but that SAC did not improve the growth of hMSCs during short-term culture. To evaluate the protective effect of SAC, we examined the endogenous expression of the antioxidant enzymes catalase (CAT), superoxide dismutase(SOD), and glutathione peroxidase(Gpx) in hMSCs. Hydrogen peroxide was found to downregulate the expression of CAT, SOD, and Gpx at the protein level. However, in the pre-treatment group of SAC, SAC inhibited the hydrogen peroxide-induced down-regulation of CAT, SOD, and Gpx. Unfortunately, treatment with SAC alone did not induce the up-regulation of antioxidant enzymes and the cell proliferation of hMSCs. Surprisingly, SAC improved cell growth in a single cell level culture of hMSCs. These results indicate that SAC may be involved in the preservation of the self-renewal capacity of hMSCs. Taken together, SAC improves the proliferation of hMSCs via inhibition of oxidative-stress-induced cell apoptosis through regulation of antioxidant enzymes. In conclusion, SAC may be an indispensable component in an in vitro culture system of human MSCs for maintaining self-renewal and multipotent characterization of human MSCs.

Gene Profile of Mesenchymal Stem Cell Induced by SAC or Hydrogen Peroxide (H2O2) (마늘성분 SAC 및 Hydrogen Peroxide에 의한 줄기세포의 유전자 발현 윤곽)

  • Park, Ran-Sook
    • The Korean Journal of Food And Nutrition
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    • v.25 no.4
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    • pp.863-870
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    • 2012
  • Though hydrogen peroxide ($H_2O_2$) causes a deleterious effect to cells with its reactive oxygen species resulting in cell death, S-allyl cysteine (SAC, a bioactive organosulfur compound of aged garlic extract) has been known to have a cytoprotective effect. Few reported profiles of gene expression of $H_2O_2$ and SAC treated human cord blood derived mesenchymal stem cells (MSC). This study revealed changes in the profile of twenty-one genes grouped by oxidative stress, antioxidant, cell death, anti-apoptosis and anti-aging by quantitative real time PCR. A concentration of $100{\mu}M$ of SAC or $50{\mu}M$ of $H_2O_2$ was applied to MSC which show moderate growth and apoptosis pattern. $H_2O_2$ treatment enhanced expression of eleven genes out of twenty-one genes compared with that of control group, on the contrary SAC suppressed expression of eighteen genes out of twenty-one genes except C ros oncogene. SAC decreased expression of oxidative stress genes such as SOD1, CAT and GPX. These results seemed consistent with reports which elucidated over-expression of NF-${\kappa}$B by $H_2O_2$, and suppression of it by SAC. This study will confer basic information for further experiments regarding the effects of SAC on gene levels.

Analysis of Volatile Organosulfur Compounds in Korean Allium Species (국내산 Allium속(마늘, 양파, 대파)의 휘발성 함유황 유기화합물 분석)

  • Song, Hyun-Pa;Shim, Sung-Lye;Jung, In-Sun;Kim, Jun-Hyeong;No, Gi-Mi;Seo, Hye-Yeong;Kim, Dong-Ho;Kim, Kyong-Su
    • Food Science and Preservation
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    • v.16 no.6
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    • pp.929-937
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    • 2009
  • We identified volatile organic compounds in Korean Allium species. Volatile organic components in three Korean Allium species, dried garlic, dried onion, and dried Welsh onion, were extracted using a simultaneous distillation and extraction (SDE) method and identified by GC/MS analysis. The numbers of volatile compounds were 48, 32, and 33 in the three species, respectively. In dried onion, the major compounds were dipropyl trisulfide, methyl propyl trisulfide, and propanethiol. (Z), (E)-propenyl propyl trisulfide, methyl propyl trisulfide, and dipropyl trisulfide were detected at high levels in Welsh onion. In dried garlic, presence of the allyl group identified characteristic volatile organosulfur compounds including diallyl disulfide and diallyl trisulfide. Qualitative and quantitative analysis of volatile compounds in three Korean Allium species showed that sulfur-containing compounds were dominant, and allyl groups derived from (+)-S-(2-propenyl)-L-cysteine sulfoxide (ALLYL CSO, alliin) were more abundant in dried garlic, than in other materials.

Determination of S-Allyl-L-cystein, Diallyl Disulfide, and Total Amino Acids of Black Garlic after Spontaneous Short-term Fermentation (자가숙성발효 후 흑마늘의 S-Allyl-L-cystein, Diallyl Disulfide 및 Total Amino Acids 분석)

  • Kim, Mun-Su;Kim, Min-Ju;Bang, Woo-Suk;Kim, Keun-Sung;Park, Sung-Soo
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.41 no.5
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    • pp.661-665
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    • 2012
  • Garlic (Allium sativum L.) is one of the oldest cultivated plants and has been used throughout the world as a food supplement and a folk medicine for thousands of years. Raw garlic has been processed into a variety of commercial garlic products for consumer convenience. The latest new processing technology, 'spontaneous short-term fermentation', has been developed to process raw garlic into black garlic. The physiologically active effects of garlic have been attributed to its organosulfur compounds. In this study, the proximate compositions and the total amino acid content of raw Namhae garlic and black garlic were determined. The two major organosulfur compounds of garlic, $S$-allyl-L-cysteine (SAC), and diallyl-disulfide (DADS), were also analyzed using RP-HPLC. The proximate compositions were not different between raw and black garlic. The amount of 13 amino acids was greater in black garlic than in raw garlic among a total of 17 amino acids considered. The black garlic had 2-fold higher levels of SAC and 30-fold higher levels of DADS than the raw garlic. Therefore, it is suggested that consuming black garlic produced by spontaneous short-term fermentation is more effective than consuming raw garlic, in order for consumers to take more physiologically active organosulfur compounds (SAC and DADS), which are the compounds that are good for consumer health.

S-Allyl-L-cysteine, a Garlic Compound, Selectively Protects Cultured Neurons from ER Stress-induced Neuronal Death

  • Ito Yoshihisa
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 2004.11a
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    • pp.124-128
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    • 2004
  • We have assessed amyloid ${\beta}-peptide$ $(A{\beta})-induced$ neurotoxicity in primary neurons and organotypic hippocampal slice cultures (OHC) in rat. Exposing cultured hippocampal and cerebellar granule neurons to $A{\beta}$ resulted in a decrease of MTT reduction, and in destruction of neuronal integrity. Treatment of these neurons with tunicamycin, an inhibitor of N-glycosylation in the endoplasmic reticulum (ER), also decreased MTT reduction in these neurons. S-allyl-L-cysteine (SAC), an active organosulfur compound in aged garlic extract, protected hippocampal but not cerebellar granule neurons against $A{\beta}$- or tunicamycin-induced toxicity. In the hippocampal neurons, protein expressions of casapse-12 and GRP 78 were significantly increased after $A{\beta}_{25-35}$ or tunicamycin treatment. The increase in the expression of caspase-12 was suppressed by simultaneously adding $1{\mu}M$ SAC in these neurons. In contrast, in the cerebellar granule neurons, the expression of caspase-12 was extremely lower than that in the hippocampal neurons, and an increase in the expression by $A{\beta}_{25-35}$ or tunicamycin was not detected. In OHC, ibotenic acid (IBO), a NMDA receptor agonist, induced concentration-dependent neuronal death. When $A{\beta}$ was combined with IBO, there was more intense cell death than with IBO alone. SAC protected neurons in the CA3 area and the dentate gyrus (DG) from the cell death induced by IBO in combination with $A{\beta}$, although there was no change in the CA1 area. Although protein expression of casapse-12 in the CA3 area and the DG was significantly increased after the simultaneous treatment of AI3 and IBO, no increase in the expression was observed in the CA1 area. These results suggest that SAC could protect against the neuronal cell death induced by the activation of caspase-12 in primary cultures and OHC. It is also suggested that multiple mechanisms may be involved in neuronal death induced by AI3 and AI3 in combination with IBO.

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