• Proceedings of the Korean Society of Food Science and Nutrition Conference
• /
• 2004.11a
• /
• pp.150-157
• /
• 2004

Cruciferous vegetables are rich in organosulfur compounds such as isothiocyanates and sulfides. While the isothiocyanates, corresponding to pungent principle, are generated from myrosinase-catalyzed hydrolysis of glucosinolates, the sulfides can be generated non-enzymatically. Recent studies provide evidences that some sulfur compounds in these vegetables show a chemopreventive action against carcinogenesis; while isothiocyanates such as sulforaphane induce phase 2 enzymes (glutathione S-transferase/quinone reductase), disulfides tends to elevate the level of phase 1 and 2 enzymes. Especially, sulforaphane rich in Cruciferae vegetables has been reported to express anticarcinogenic effect in some organs such as liver, kidney or intestine. When the level of sulfur compounds in Cruciferous and Alliaceous vegetables was determined by GC/MS (SIM), the richest in sulforaphane is broccoli followed by turnip, cabbage, radish, kale, cauliflower and Chinese cabbage. Meanwhile, the sulfides are predominant in Alliaceous vegetables such as onion. In related study, the administration of vegetable extract elevated the GST level by 1.5 fold for broccoli, 1.4 fold for radish, and 1.3 for onion. Thus, the vegetables frequently used in Korean dish contain relatively high amount of anticarcinogenic sulfur compounds. Moreover, the combination of broccoli and radish extracts elevated the GST induction up to 1.84 folds of control. In addition, the Kakdugi, fermented radish Kimchi was observed to show a comparable GST induction despite the decomposition of methylthio-3-butenylisothiocyanate (MTBI). Therefore, the combination of vegetables including broccoli, and fermented radish Kimchi would be useful as a functional food for chemoprevention.

• YAKHAK HOEJI
• /
• v.58 no.1
• /
• pp.28-32
• /
• 2014

A new series of 3-allylthio-6-alkylthiopyridazines (3)~(12) was synthesized from dichloropyridazine (1) for development of candidates to retain anticancer activity of human breast cancer. The process involves allythiolation and alkylthiolation from 3,6-dichloropyridazine. 6-Substituted allylthiopyridazines (3)~(12) were prepared from 3-allylthiopyridazinyl chloride (2) via nucleophilic substitution with alkylthiol anion as nucleophile. 3-Allylthiopyridazinyl chloride (2) could be converted to pyridazines (3)~(11) using 1 equivalent of alkyl mercaptan at reflux temperature in methanol. 3,6-Diallylthiopyridazine (12) was synthesized from 3,6-dichloropyridazine (1) using allyl mercaptan (4 equivalent) and sodium hydroxide in methanol. Synthetic compounds were fully identified using NMR, IR, GC-MS data.

• Bulletin of the Korean Chemical Society
• /
• v.35 no.7
• /
• pp.2057-2064
• /
• 2014

Thermochemical sulfate reduction (TSR) was conducted in autoclave on the system of crude oil and $MgSO_4$ at different temperatures. Gas chromatography pulsed flame photometric detector (GC-PFPD) was used to detected the composition of organic sulfur compounds in oil phase products. The results of the analysis indicate that with increased temperature, the contents of organic sulfur compounds with high molecular weight and thermal stability, such as benzothiophenes and dibenzothiophenes, gradually became dominated. In order to gain greater insight into the formation and distribution of organic sulphur compounds from TSR, positive ion electrospray Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) was used in detecting the detailed elemental composition and distribution of them. The mass spectra showed that the mass range of sulfur compounds was 200-550 Da. Four sulfur class species, $S_1$, $N_1S_1$, $O_1S_1$ and $O_2S_1$, were assigned in the positive-ion spectrum. Among the identified sulfur compounds, the $S_1$ class species was dominant. The most abundant $S_1$ class species increase associated with the DBE value and carbon number increasing which also indicates the evolution of organic sulfur compounds in TSR is from the labile series to the stable one. In pure blank pyrolysis experiments with crude oil cracking without TSR, different composition and distribution of organic sulfur compounds in oil phase products were seen from mass spectra in order to evaluate their pyrolysis behaviors without $MgSO_4$. FT-IR and XRD were used in analyzing the products of solid phases. Two distinct crystallographic phases MgO and $MgSO_4$ are found to coexist in the products which demonstrated the transformation of inorganic sulfur compounds into organosulfur compounds exist in TSR.

• Korean journal of food and cookery science
• /
• v.22 no.3 s.93
• /
• pp.402-417
• /
• 2006

Research interest on functional food and phytochemicals has mainly focused on their health effects, mechanism of action and structure-activity relationship for the development of nutraceuticals. Considering the intake of phytochemicals via the normal diet, further information is required on changes in food functionality or individual phytochemicals that occur during the cooking or processing of foods, in order to increase the intake of these bioactive compounds, because many of the unit-operating procedures involved in cooking or food processing may result in physicochemical changes of food constituents. This study reviews the changes of selected phytochemicals, i.e. flavonoids, organosulfur compounds and carotenoids, or food functionality by major cooking or processing procedures such as heating, fermentation, and pH changes. In general, heating has a negative effect on food functionality, although in some cases, mild heating increases bioactive phytochemical contents. Some phytochemicals, including anthocyanins and catechins, are stabilized in lower pH conditions. The structures of phytochemicals, including isoflavones and catechins, are changed by fermentation. The loss of bioactive compounds may be decreased by recently developed cooking or processing methods such as microwave cooking or use of high hydrostatic pressure. However, the effects of cooking and processing procedures on food functionality and phytochemicals are so diverse and dependent on test conditions that further research efforts are needed to form accurate conclusions on the effects of cooking and processing of foods.

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

• Analytical Science and Technology
• /
• v.20 no.5
• /
• pp.442-447
• /
• 2007

The properties of garlic (Allium sativum L.) are attributed to organosulfur compounds. In this paper, an analytical technique with a rapid and simple sample preparation procedures for determination of diallyl disulfide (DADS) in garlic was reported. The DADS was simply extracted with various solvents (methanol, benzene or tetrahydrofuran) from garlic and prepared for HPLC analysis. From the results, the methanol was select as an optimal extraction solvent. The mobile phase was composed from methanol and water, and the gradient elution mode was applied. 0.61 mg of DADS per g garlic powder can be extracted with methanol. This work offers some advantages over the currently accepted techniques and would be useful for chemical and biological studies of garlic and its products.

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.41 no.5
• /
• pp.661-665
• /
• 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.

• Biomolecules & Therapeutics
• /
• v.13 no.2
• /
• pp.113-117
• /
• 2005

Organosulfur compounds have been shown to exert an anti-cancer activity. In an attempt to develop novel chemopreventive and anti-cancer agents for liver cancer, we synthesized allylthiopyridazine derivatives. We have previously shown that allylthiopyridazine derivatives exert inhibitory effects on proliferation, invasion and migration of SK-Hep-1 hepatocarcinoma cells in vitro. The in vivo anti-tumor effect of 3-methvl-6-allylthiopy-ridazine, named as K6, was also reported. In this study, we further investigated the preclinical anti-cancer efficacy of K6 for hepatocarcinoma using nude mice xenografted with Hep-G2 hepatocellular carcinoma cells. K6(20-100 mg/kg, orally administered everyday for 30 days) markedly decreased the tumor volume of Hep-G2 cell-transplanted nude mice as evidenced by ultrasonographic and plethysmogranhic analyses. The inhibitory effect on tumor volume was lower than that exerted by doxorubicin (2 mg/kg), intravenously injected) which was used as a positive control. This study shows that K6 efficiently suppresses xenograft tumor growth, revealing K6 as apotential anti-cancer agent for suppressing in vivo progression of liver cancer. Given that hepatocarcinoma is among the most prevalent and lethal malignancies and there is no effective treatment to date, our study may contribute to the potential drug development for liver cancer.

• Archives of Pharmacal Research
• /
• v.22 no.2
• /
• pp.99-107
• /
• 1999

A series of organosulfur compounds were synthesized with the aim of developing chemopreventive compounds active against hepatotoxicity and chemical carcinogesis. 2-(Allylthio) prazine (2-AP) was effective in inhibiting cytochrome P450 2E1-mediated catalytic activities and protein expression, and in inducing microsomal epoxide hydrolase and major glutathione S-transferases. 2-AP reduced the hepatotoxicity caused by toxicant sand elevated cellular GSH content. Development of skin tumors, pulmonary adenoma and aberrant crypt foci in colon by various chemical carcinogens was inhibited by 2-AP pretreatment. Anticarcinogenic effects of 2-AP at the stage of initiation of tumors were also observed in the aflatoxin B1 ($AFB_1$)-induced three-step medium-term hepatocarcinogenesis model. Reduction of $AFB_1$-DNA adduct by 2-AP appeared to result from the decreased formation of $AFB_1$-8,9-epoxide via suppression of cytochrome P450, while induction of GST 2-AP increases the excretion of glutathione-conjugated $AFB_1$ . 2-AP was a radioprotective agent effective against the lethal dose of total body irradiation and reduced radiation-induced injury in association with the elevation of detoxifying gene expression. 2-AP produces reactive oxygen species in vivo, which is not mediated with the thiol-dependent production of oxidants and that NF-KB activation is not involved in the induction of the detoxifying enzymes. the mechanism of chemoprotection by 2-AP may involve inhibition of the P450-mediated metabolic activation of chemical carcinogens and enhancement of electrophilic detoxification through induction of phase II detoxification enzymes which would facilitate the clearance of activated metabolites through conjugation reaction.

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