• Korean Journal of Food Science and Technology
• /
• v.26 no.6
• /
• pp.679-682
• /
• 1994

The volatile sulfur compounds in raw and dried garlic (Allium sativum L.) under various temperatures (50, 60, 70 and $80^{\circ}C$ ) were separated, identified by GC and GC/MS. In hexane extracts of raw garlic, 8 volatile sulfur compounds were identified and 11 compounds were identified in steam distillation extracts. The volatile sulfur compounds of raw and dried garlic were mostly composed of diallyl disulfide, diallyl trisulfide, allyl methyl trisulfide. According to the increase of drying temperature total amounts of volatile sulfur compounds in the hexane extracts decreased to $40{\sim}75$$, and in the steam distillation extracts decreased to $10{\sim}20%$. The amounts of diallyl disulfide, allyl methyl trisulfide decreased more than other volatile sulfur compounds, but diallyl trisulfide comparatively decreased lower.

• The Korean Journal of Pain
• /
• v.33 no.3
• /
• pp.216-225
• /
• 2020

Background: Garlic oil is a rich source of organosulfur compounds including diallyl disulfide and diallyl trisulfide. There have been studies showing the neuroprotective actions of these organosulfur compounds. However, the potential of these organosulfur compounds in neuropathic pain has not been explored. The present study was aimed at investigating the pain attenuating potential of diallyl disulfide and diallyl trisulfide in chronic constriction injury (CCI)-induced neuropathic pain in rats. The study also explored their pain-attenuating mechanisms through modulation of H₂S, brain-derived neurotrophin factor (BDNF) and nuclear factor erythroid 2-related factor 2 (Nrf2). Methods: The rats were subjected to CCI injury by ligating the sciatic nerve in four places. The development of neuropathic pain was measured by assessing mechanical hyperalgesia (Randall-Selittotest), mechanical allodynia (Von Frey test), and cold allodynia (acetone drop test) on 14th day after surgery. Results: Administration of diallyl disulfide (25 and 50 mg/kg) and diallyl trisulfide (20 and 40 mg/kg) for 14 days led to a significant reduction in pain in CCI-subjected rats. Moreover, treatment with these organosulfur compounds led to the restoration of H₂S, BDNF and Nrf2 levels in the sciatic nerve and dorsal root ganglia. Co-administration of ANA-12 (BDNF blocker) abolished pain attenuating actions as well as BDNF and the Nrf2 restorative actions of diallyl disulfide and diallyl trisulfide, without modulating H₂S levels. Conclusions: Diallyl disulfide and diallyl trisulfide have the potential to attenuate neuropathic pain in CCI-subjected rats possibly through activation of H₂S-BDNF-Nrf2 signaling pathway.

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.36 no.3
• /
• pp.332-341
• /
• 2007

The purpose of this study was to investigate the change of flavor compounds of freeze-dried garlic and garlic roasted with soybean oil and sesame oil. Freeze-dried garlic and ground raw garlic roasted with oils was prepared at $180^{\circ}C$ for 5 minutes. Volatile compounds of garlic samples were obtained by Likens-Nickerson distillation/solvent extraction and identified by GC and GC/MS. Sulfur compounds, methyl allyl sulfide, diallyl sulfide, methyl allyl disulfide, dimethyl trisulfide, diallyl disulfide, methyl allyl trisulfide and diallyl trisulfide were the major volatile in garlic flavor which was more than 98% of the total volatile compounds. The total amount of sulfur compounds in freeze-dried garlic roasted with soybean oil was decreased to 20% compare to that of garlic flavor; however, 10 pyrazines such as 2-methyl pyrazine, 2,6-dimethyl pyrazine, 2-ethyl-5-methyl pyrazin and 3-ethyl-2,5-dimethyl pyrazine which were not originated from both freeze-dried garlic and soybean oil were identified. They might be generated from thermal interactions of sugars and nonvolatile flavor precursors of garlic. In freeze-dried garlic roasted with sesame oil, the amount of diallyl sulfide, methyl allyl disulfide, dimethyl trisulfide increased whereas diallyl disulfide completely disappeared. The amount of two cyclic compounds 3,4-dihydro-3-vinyl-1,2-dithiin and 2-vinyl-4H-1,3-dithiin, which were artifacts from allicin, increased in roasted garlic with sesame oil.

• Korean Journal of Food Science and Technology
• /
• v.22 no.7
• /
• pp.840-845
• /
• 1990

An attempt was made in this study to analyze flavor compounds and investigate storage stability of essential oil from garlic distillation. Optimum ratio of solvent between pentane and dichloromethane to get essential oil from garlic distillation was 2 to 1. The yield of essential oil was 0.35%(w/w) in ground garlic(${\phi}\;0.8mm$) and 0.07%(w/w) in whole garlic. From garlic essential oil six components : dimethyl sulfide, diallyl sulfide, methyl-1-propenyl disulfide, diallyl disulfide, allyl methyl sulfide and diallyl trisulfide were identified with GC and GC/MS, and diallyl trisulfide, diallyl disulfide and allyl mothyl sulfide were found to be major volatile components. Quality deterioration of garlic essential oil hardly occurred during storage for 60 days, at $5^{\circ}C$ and $25^{\circ}C$.

• Journal of the East Asian Society of Dietary Life
• /
• v.16 no.3
• /
• pp.299-307
• /
• 2006

Raw whole garlic was pickled in two different ways, in soy sauce and in brine, to test the change of flavor compounds with aging period. The changes of pH, acidity, hardness and flavors were measured, accompanied with sensory evaluation. The pH of whole garlic in soy sauce and in brine was decreased as the aging period increased. The acidity was increased as pH decreased. Hardness tended to decrease as the aging time increased. For whole garlic in soy sauce and in brine, trans propenyl methyl disulfide, allyl methyl trisulfide, diallyl trisulfide, dimethyl trisulfide, allyl- 2,3-epoxypropyl sulfide, and 2-methyl-l,3-dithiane were increased as the aging proceeded but allyl methyl disulfide and diallyl disulfide tended to decrease. Hardness through the sensory evaluation decreased as the aging time increased. When the overall quality was compared between whole garlic in soy sauce and in brine after 60 days, the latter could be better estimated. Pickled garlic increased the flavor compounds such as trans propenyl methyl disulfide, allyl methyl trisulfide, diallyl trisulfide, dimethyl trisulfide, allyl-2,3-epoxypropyl sulfide, and 2-methyl-l,3-dithiane as the aging proceeded. Therefore, the above flavor compounds are considered as the major ingredients of the characterized flavor of pickled garlic.

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.34 no.6
• /
• pp.885-891
• /
• 2005

The study was carried out to find the effect of freeze drying on the volatile organic components in garlic (Allium sativum L.). The volatile organic compounds from fresh and freeze dried garlic were extracted by simultaneous steam distillation and extraction (SDE) method and identified with GC/MS analysis. A total of 42 and 32 compounds were identified in fresh and freeze-dried garlic, respectively. Sulfur containing compounds in the garlic samples were detected as the major compounds, and alcohols, aldehydes and esters were detected as minor compounds. Diallyl disulfide, diallyl trisulfide, allyl methyl disulfide and ally1 methyl trisulfide were the main sulfur compounds in fresh and freeze dried garlic. The amount of sulfur containing compounds were decreased freeze-drying but methyl propyl trisulide, 3- allylthiopropionic acid, cyclopentyl ethyl sulfide etc. were increased. The others, non- sulfur containing compounds such as ethyl acetate, ethanol, 2-propenol, 2- propenal and hexanal were increased in freeze-dried garlic. Consequently, the total amount of volatile organic compounds in garlic became lower during freeze-drying from 853.42 mg/kg to 802.21 /kg, and the composition of major components were nearly same in fresh and freeze-dried garlic.

• Food Science and Preservation
• /
• v.16 no.6
• /
• pp.929-937
• /
• 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.

• Journal of Life Science
• /
• v.17 no.2 s.82
• /
• pp.286-292
• /
• 2007

Free amino acids and volatile compounds of fresh garlic and its liqueur were investigated to search elution profile of those components as basic data for development of garlic liqueur. The garlic was soaked in 20% alcohol solution and then sampled every week for 5 weeks. The major free amino acids were L-aspartic acid, L-glutamic acid, L-arginine, L-alanine, L-proline, L-asparagine and L-serine. Neutral amino acids such as L-threonine, L-proline, L-valine and L-leucine, and aromatic amino acids such as tyrosine and phenylalanine were eluted over 80% of those content in fresh garlic after 3 weeks of soaking, but acidic, basic and sulfur containing amino acids were below 80% even after 5 weeks. Sulfide compounds such as diallyl trisulfide, diallyl disulfide, methyl allyl disulfide, 2-vinyl-4H-1,3-dithi in, 3-vinyl-3,4-dihydro-1,2-dithiin, 3,5-diethyl-1,24-trithiolane, isobutyl isothiocyanate and diallyl sulfide were identified as major volatile compounds of fresh garlic by using GC/MS. Among volatile compounds of fresh garlic, allyl alcohol, diallyl disulfide, 3,5-diethyl-1,2,4-trithiolane, diallyl trisulfide and 3,4-dimethoxy furan were eluted to liqueur, but those compounds except 3,5-diethyl-1,2,4-trithiolane were lowered in liqueur during soaking. Furfural, 5-methylfurfural, 5-hydroxymethylfurfural, dimethyl pyrazine, furfuryl alcohol, 3-hydroxy-2-bytanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyr-an-4-one were generated newly and their content increased in liqueur during soaking.

• Journal of the Korean Society of Food Science and Nutrition
• /
• v.34 no.4
• /
• pp.513-518
• /
• 2005

Volatile compounds of $\gamma-irradiation$ leeks (Aillum tuberosum R.) were isolated by simultaneous steam distillation and extraction method (SDE) and analyzed by gas chromatography/mass spectrometry (GC/MS) along with the non-irradiated sample. Leeks were irradiated at dose of 20 kGy and non-irradiated samples were considered as control sample. 56 and 54 compounds were identified in non-irradiated and irradiated samples, respectively. These components included the functional groups; alcohols, aldehydes, esters, ketones, N- and S-containing compounds. S-containing compounds such as dimethyl trisulfide, methyl-(Z)-l-proenyl trisulfide, dimethyl disulfide, 3-ethyl-l,2-dithi-5-ene and methyl allyl disulfide were the major compounds. Methyl-(Z)-l-propenyl trisulfide, diallyl trisulfide, (E)-2-hexanal and 3-ethyl-l,2-dithi-5-ene were clearly decreased by the $\gamma-irradiation$, but dimethyl disulfide, diallyl sulfide, allyl methyl sulfide and pyridine were increased by the $\gamma-irradiation$.

• Korean Journal of Environmental Agriculture
• /
• v.33 no.4
• /
• pp.381-387
• /
• 2014

BACKGROUND: Garlic (Allium sativum) extract has been allowed as commercial biopesticide material for pesticidal activity in the Environmentally-friendly Agriculture Promotion Act. Nine commercial biopesticides containing A. sativum extract have been marketed in Korea. However, the analytical method of the active substances in these materials has not been studied. METHODS AND RESULTS: Cartridge clean-up method for the determination of dimethyl disulfide(DMDS), diallyl disulfide(DADS), and diallyl trisulfide(DATS) in biopesticides containing A. sativum extract was developed and validated by gas chromatography(GC). The clean-up method was optimized using hydrophilic lipophilic balance (HLB) solid phase extraction(SPE) cartridges for the bioactive sulfides in biopesticides containing A. sativum extract, and the eluate was analyzed to quantify the DMDS, DADS, and DATS using the GC. The developed method was validated, and the LOQ and recovery rates of DMDS, DADS, and DATS were 0.226, 0.063, and $0.051mg\;L^{-1}$ and 80.6, 84.8, and 73.1%, respectively. From the nine commercial biopesticide samples, contents of DMDS, DADS, and DATS were analyzed using the developed method and results showed $2.3mg\;L^{-1}$, respectively. CONCLUSION: The developed method could be used in determining the quality of biopesticides for the manufacture of commercial biopesticides containing A. sativum extract.