• Title/Summary/Keyword: S-allyl-L-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.

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.

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.

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.

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.

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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Quality Characteristics of Vinegar Added with Different Levels of Black Garlic (흑마늘의 첨가량을 달리한 식초의 품질특성)

  • Sim, Hye Jin;Seo, Weon Taek;Choi, Myoung Hyo;Kim, Kyoung Hwa;Shin, Jung Hye;Kang, Min Jung
    • Korean journal of food and cookery science
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    • v.32 no.1
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    • pp.16-26
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    • 2016
  • In this study, we aimed to develop functional vinegar with different levels of black garlic through two stages of fermentation. Black garlic vinegars were prepared from black garlic and water (w/w) mixed with 1:2 (BG3), 1:5 (BG6), 1:9 (BG9) and 1:11 (BG12), and adding the sugar by adjusting the soluble solids content to $14^{\circ}Brix$. The alcohol content of black garlic vinegar was 5.2-5.5% after 7 days of alcohol fermentation at $25^{\circ}C$. Acetic acid fermented was at $30^{\circ}C$ for 25 days and samples were taken at 3, 6, 9, 12, 15, 20 and 25 days. The pH of black garlic vinegar was not significantly different among the samples, but acidity was increased during fermentation. Total polyphenol contents showed irregular changes with the fermentation periods and were higher by black garlic content. At 25 days fermentation, total polyphenol contents were 18.96-56.56 mg/100 mL. Acetic acid content of black garlic vinegars was higher than other organic acids. S-allyl cysteine (SAC) contents of BG3 and BG6 were 13.03-14.54 and 1.69-2.20 mg/L, respectively. However SAC was not detected in BG9 and BG12. In 25 days fermented black garlic vinegar, the major mineral was K with a content ratio of 61-68% of total minerals. The DPPH and ABTS radical scavenging activity of 25 days fermented black garlic vinegar were stronger at higher black garlic content.

Quality Characteristics and Biological Activity of Fermented Black Garlic with Probiotics (Probiotics를 이용한 흑마늘 발효물의 품질특성 및 생리활성)

  • Tak, Hyun-Min;Kim, Gyeong-Min;Kim, Jong-Su;Hwang, Cho-Rong;Kang, Min-Jung;Shin, Jung-Hye
    • Journal of Life Science
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    • v.24 no.5
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    • pp.549-557
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    • 2014
  • This study examined the quality characteristics of fermented black garlic (BG) with probiotics. Nine strains of probiotics were tested in media containing 20% BG. Four of the strains grew well in the BG media: Lactobacillus rhamnosus, L. paracasei subsp. paracasei, L. casei, and L. plantarum. These four strains were used to make 10, 20, and 30% BG fermented product, respectively. The number of viable cells, pH, acidity, S-allyl cysteine (SAC) concentration, and nitric oxide (NO) and reactive nitrogen species (ROS) generation in Raw 264.7 macrophage cells were measured. L. plantarum showed the best growth of all the strains in the BG media. The pH of all the samples decreased during fermentation, and the acidity increased acidity. However, they did not differ significantly from the pH and acidity of the control. In all four strains, the SAC content did not differ before and after fermentation. However, the SAC content increased, depending on the BG concentration. NO production was inhibited in the L. rhamnosus inoculation strain compared to the other strains. ROS generation was also significantly inhibited in the L. plantarum inoculation strain compared to the other strains. The results show that the characteristics of BG fermentation products are determined by the fermentation strain. Therefore, fermentation products with particular characteristics can be produced using a single strain or mixed strains.

Quality characteristics of vinegar fermented with different amounts of black garlic and alcohol (흑마늘의 첨가량과 초기 알코올 농도를 달리한 발효 식초의 품질특성)

  • Seo, Weon Tack;Choi, Myoung Hyo;Sim, Hye Jin;Kim, Gyeong Wha;Shin, Yeon Mi;Kang, Min Jung
    • Food Science and Preservation
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    • v.23 no.1
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    • pp.34-41
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    • 2016
  • The quality characteristics of black garlic vinegar produced by acetic acid fermentation were analyzed over a 25 day period. Black garlic vinegar was produced using black garlic 3, 6, 9 and 12 folds with water, and initial alcohol concentrations of 6~12%. The pH values of the vinegar samples were in range of 3.85~4.46 after 25 days fermentation, and the sugar contents were highest after 9 days of fermentation ($12.00{\sim}13.50^{\circ}Brix$). The total polyphenol concents of vinegars were in the range of 20.65~52.04 mg/100 mL 25 days fermentation. Pyrogallol and vanillic acid were detected in the completely fermented vinegars, and their contents increased with black garlic content. Five organic acids (lactic acid, acetic acid, citric acid, succinic acid and propionic acid) were detected after 25 days of fermentation, with the total amount of organic acids being 5,327.34~6,307.64 mg/100 mL, and the total abetic acid contents beging the highest of the organic acids at 4208.90~5,570.29 mg/100 mL. After 25 days of fermentation, the total minerals contents were higher, and depending on the quantity of black garlic added. Of the minerals, the of potassium content was the highest (366.23~1,619.67 mg/L).