• Archives of Pharmacal Research
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• v.28 no.4
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• pp.391-394
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• 2005

The allylthio group of allicin and other organosulfur compounds, isolated from garlic, is considered a pharmacophore, and a key structure component of the molecule, which affords biological activities. In the foregoing studies, various 3-alkoxy-6-allylthiopyridazine derivatives (K­compounds) were synthesized, and their biological activities tested in animals. As expected, the various derivatives showed good hepatoprotective activities on carbon tetrachloride-treated mice and aflatoxin B1-treated rats, and chemopreventive activities on hepatocarcinoma cells in rats. Other new pyridazine derivatives, with the oxygen atom at the 3-position of the 3-alkoxy­6-allylthiopyridazine displaced by sulfur (S), were synthesized, and their activities tested in vitro. Thio-K6, one of the sulfur-substituted compounds, showed better chemopreventive activity toward hepatocarcinoma cells.

• 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.

• Journal of the Korean Society of Food Science and Nutrition
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• v.45 no.12
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• pp.1725-1731
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• 2016

This study was carried out to investigate the effects of steam-drying on antioxidant compounds and antioxidant activity of Alliun hookeri root (AHR). The yield of methanolic extracts, total phenolic content (TPC), browning intensity (280 nm and 420 nm), and organosulfur compound contents (alliin and cycloalliin) in raw and steam-dried AHRs were 10.71~37.40%, $15.53{\sim}36.36{\mu}g/mg$, 0.48~2.09, 0.01~0.25, $1.46{\sim}700.61{\mu}g/mg$, and $1,173.95{\sim}2,182.60{\mu}g/mg$, respectively. Yield, TPC, and browning intensity of AHRs increased by steam-drying, whereas organosulfur compound contents decreased. Of all methanolic extracts from raw and steam-dried AHRs, four-time steam-drying showed the lowest $EC_{50}$ values (0.43, 7.53, 0.34, and 0.48 mg/mL, respectively) for DPPH radical scavenging activity, ABTS radical scavenging activity, SOD-like activity, and reducing power, whereas four-time steam-drying resulted in the highest TPC ($36.36{\mu}g/mg$) and browning intensity (2.09 and 0.25 at 280 and 420 nm, respectively). The antioxidant activities of methanolic extracts from raw and steam-dried AHRs were closely correlated with their TPC, browning intensity, and organosulfur compound content, showing correlation determination coefficient ($R^2$) values higher than 0.82. As a result, four-time steam-drying of AHRs could be useful as potential antioxidant sources.

• Journal of Life Science
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• v.19 no.1
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• pp.138-146
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• 2009

Garlic (Allium sativum) are an agronomically important genus because of their sulfur flavour components. The majority of the volatiles flavour principles are generated through the enzymatic hydrolysis of the non-volatile organosulfur compounds. However, these compounds may be possible sources of new novel bioacuve and therapeutic principles. Garlic has strong antioxidant activity, and epidemiological studies support the fad that diets rich of garlic may prevent some of the chronic diseases. The health cares of garlic likely arise from a wide variety of components, which may work synergistically. The chemical changes of garlic composition makes it plausible that a variation in processing can lead to acquisition of differential chemical compositions of garlic products. Especially highly unstable allicin can easily disappear during processing and are quickly transformed into a various organosulfur compounds. Various supplements of garlic, particularly aged garlic extract (AGE), are known to possess a promising antioxidant potential and are effective in prevention of chronic diseases because of the bioactive constituents. Although all of active ingredients of AGE are not elucidated, water-soluble components of AGE, including S-allylcysteine, S-allylmercaptane, steroid saponins, tetrahydro-${\beta}$-carboline derivatives, and fructosyl-arginine, appears to be associated with the pharmacological effects of AGE. Consequently, the allicin free garlic components such as S-allylcysteine, S-allylmercaptane, steroid saponins, tetrahydro-${\beta}$-carboline derivatives, and fructosyl-arginine can be applicable to standardization of the quality of commercial garlic products. This review provides an insight into garlic's biomarkers and presents evidence that they may either prevent or delay chronic disease associated with aging.

• Preventive Nutrition and Food Science
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• v.21 no.2
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• pp.138-146
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• 2016

In this study, we report the optimal extraction conditions for obtaining organosulfur compounds, such as cycloalliin, from garlic by using principal component analysis (PCA). Extraction variables including temperature ($40{\sim}80^{\circ}C$), time (0.5~12 h), and pH (4~12) were investigated for the highest cycloalliin yields. The cycloalliin yield (5.5 mmol/mL) at pH 10 was enhanced by ~40% relative to those (~3.9 mmol/mL) at pH 4 and pH 6. The cycloalliin level at $80^{\circ}C$ showed the highest yield among the tested temperatures (5.05 mmol/mL). Prolonged extraction times also increased cycloalliin yield; the yield after 12 h was enhanced ~2-fold (4 mmol/mL) compared to the control. Isoalliin and cycloalliin levels were inversely correlated, whereas a direct correlation between polyphenol and cycloalliin levels was observed. In storage for 30 days, garlic stored at $60^{\circ}C$ (11 mmol/mL) showed higher levels of cycloalliin and polyphenols than those at $40^{\circ}C$, with the maximum cycloalliin level (13 mmol/mL) on day 15. Based on the PCA analysis, the isoalliin level depended on the extraction time, while cycloalliin amounts were influenced not only by extraction time, but also by pH and temperature. Taken together, extraction of garlic at $80^{\circ}C$, with an incubation time of 12 h, at pH 10 afforded the maximum yield of cycloalliin.

• 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.

• Archives of Pharmacal Research
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• v.29 no.12
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• pp.1125-1131
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• 2006

This study was undertaken to elucidate the effect of diallyl disulfide (DADS), an oil-soluble organosulfur compound found in garlic, in suppressing human nasopharyngeal carcinoma cells. A potent increase (of at least 9-fold) in apoptotic cells has accompanied 1) a decrease in cell viability, 2) a increase of the fraction of S-phase cells by up to 63.8%, and 3) a transient increase of the phospho-p38 and phospho-p42/44 (phosphorylated p38 MAPK and phosphorylated p42/44 MAPK) in a time-and concentration-dependent manner. These results indicate that DADS can induce apoptosis in human nasopharyngeal carcinoma cells via, at least partly, S-phase block of the cell cycle, related to a rise in MAPK phosphorylation.

• Toxicological Research
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• v.22 no.4
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• pp.349-356
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• 2006

Diallyl disulfide (DADS), an oil-soluble organosulfur compound in garlic has been reported to suppress tumor growth and to induce apoptosis in cancer. In the present study, we investigated the effects of DADS on pulmonary metastasis of B16-F10 murine melanoma cells. DADS (i.p. 40 mg/kg) significantly (p<0.05) reduced the number of pulmonary metastatic nodules (48%) in experimental pulmonary metastasis assay. We also found that DADS inhibited adhesion, invasion and migration of B16-F10 melanoma cells in a dose-dependent manner. To study the antimetastatic potential of DADS, we performed the effects of DADS on matrix metalloproteinase activity. DADS significantly inhibited the expression of matrix metalloproteinase-2 activity in B16-F10 cells by gelatin zymography. These results suggest that DADS prevent metastasis in part through suppression of migration of B16-F10 melanoma cells by Inhibiting matrix metalloproteirase-2 responsible for degradation of extracellar matrix.

• Korean Journal of Food Science and Technology
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• v.51 no.3
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• pp.258-262
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• 2019

Although the chemical compositions and biological characteristics of some species of garlic have been investigated, data on Koara garlic are currently lacking. In order to investigate the major compounds and antimicrobial activity of Koara garlic, which was registered as a cultivar in 2012, it was cultivated in Seogwipo, Damyang, and Namhae. Analysis of the chemical composition of the cultivated garlic showed that the alliin, pyruvate contents, and antimicrobial activity were high in garlic grown in Seogwipo ($9.44{\pm}0.28mg/g$, $127.52{\pm}5.50{\mu}M/g$, and 0.31-1.25%, respectively). The total phenol content and reducing sugar contents were abundant in garlic grown in Namhae ($82.23{\pm}0.00g\;GAE/100g$ and $28.59{\pm}0.54mg\;GE/g$, respectively), and the total flavonoid content was high in garlic grown in Damyang ($22.41{\pm}0.77g\;QE/100g$). Although garlics grown in different cultivation areas had different chemical compositions, major compound contents and biological activities of Koara garlic were similar to those of other garlic varieties reported so far. These data will be useful for local farmers, distributors, and consumers.

• Journal of Life Science
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• v.25 no.11
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• pp.1331-1337
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• 2015

S-allylcysteine (SAC) is an aged garlic derived water soluble organosulfur compound and has been suggested to have anticarcinogenic activity against diverse types of cancer cells. This review summarizes the cellular signaling pathways and molecular mechanisms whereby SAC exerts its effects on cellular proliferation, apoptosis, cell cycle progression and metastasis based on the results from both in vitro and in vivo studies. SAC activates proapoptotic proteins including Bax and caspase-3, but suppresses antiapoptotic Bcl-2 family proteins to bring about cancer cell death through mitochondria-mediated intrinsic pathway. SAC also inhibits cellular proliferation by inducing cell cycle arrest in which SAC reduces expression and activation of NF-κB, cyclins, Cdks, PCNA and c-Jun, but elevates expression of cell cycle inhibitor proteins p16 and p21 through suppression of both PI3K/Akt/mTOR and MAPK/ERK signaling pathways. And, SAC inhibits invasion and metastasis of cancer cells by inducing suppression of both angiogenesis and epithelial-mesenchymal transition (EMT) through decreased cyclooxygenase (COX)-2 expression and increased E-cadherin expression which were then caused by suppression of inhibitory transcription factors Id-1 and SLUG from SAC-mediated inactivation of both MAPK/ERK and PI3K/Akt/mTOR/NF-κB signaling pathways. Furthermore, SAC prevents toxic compound-induced carcinogenesis by inducing antioxidant enzymes such as glutathione-s-transferase (GST). Thus, SAC can be considered as a potential chemotherapeutic agent for the prevention and treatment of cancer.