1. 마늘, 양파 등에서 항균활성을 나타내는 물질의 전구물질로 알려진 S-allyl-L-cysteine sulfoxide, S-(2-propenyl)-L-cysteine sulfoxide, S-(2-pentenyl)-L-cysteine sulfoxide를 합성하였으며 그 수율은 모두 30％를 나타내었다. 2. 가열마늘에서 항균작용을 나타내는 polysulfides일 diallyl tetrasulfide, diallyl trisulfide를 합성시 각각 52.8％, 45％와 기타물질이 섞여있는 혼합물로 합성되어 Silical gel column을 이용하여 정제하여 순도가 높은 물질을 얻었다. Allylpropyl trisulfide, diethyl-, dipropyl-, dibutyl trisulfide도 같은 방법으로 합성하였으며 Silical gel colum을 이용하여 정제하여 순도를 높였다. Dimethyl tetrasulfide 를 합성할때는 methanethiol이 기체상태이므로 취급에 어려움이 있어 sodium methoxide로 대체하여 합성하였다. 3. 합성한 sulfides를 이용하여 항균활성을 시험하였을 때 sulfides류에 따라 ...
1. 마늘, 양파 등에서 항균활성을 나타내는 물질의 전구물질로 알려진 S-allyl-L-cysteine sulfoxide, S-(2-propenyl)-L-cysteine sulfoxide, S-(2-pentenyl)-L-cysteine sulfoxide를 합성하였으며 그 수율은 모두 30％를 나타내었다. 2. 가열마늘에서 항균작용을 나타내는 polysulfides일 diallyl tetrasulfide, diallyl trisulfide를 합성시 각각 52.8％, 45％와 기타물질이 섞여있는 혼합물로 합성되어 Silical gel column을 이용하여 정제하여 순도가 높은 물질을 얻었다. Allylpropyl trisulfide, diethyl-, dipropyl-, dibutyl trisulfide도 같은 방법으로 합성하였으며 Silical gel colum을 이용하여 정제하여 순도를 높였다. Dimethyl tetrasulfide 를 합성할때는 methanethiol이 기체상태이므로 취급에 어려움이 있어 sodium methoxide로 대체하여 합성하였다. 3. 합성한 sulfides를 이용하여 항균활성을 시험하였을 때 sulfides류에 따라 효모에 대한 항균활성이 강한 것이 대부분인데 비하여 dipropyl tetrasulfide, diisopropyl tetrasulfide 및 dibutyl tetrasulfide는 효모에 대하여보다는 세균에 대하여 더 높은 활성을 나타내는 것이 특이하였다. 4. Sulfide류의 항균작용은 alkyl기의 탄소수가 적고 황의 수가 많을수록 크게 나타났으며, 이중결합이 있는 alkyl(예, allyl) 기의 경우는 탄소수가 동일한 alkyl기에 비해 항균활성이 월등히 높게 나타나는 것이 확인되었다. 5. 마늘즙을 121℃에서 가열하였을 때 45분까지는 항균활성이 지속적으로 증가하다가 45분 이후에는 가열시간이 경과하더라도 120 분까지는 항균활성의 변화가 없었다. 따라서 45분까지 가열하였을 때 항균활성물질의 생성이 완료되었으며 생성된 항균활성물질은 내열성이 매우 높아서 고온의 영향을 받지 않는 것으로 판단되었다. 6. 국내 마늘의 alliin의 함량은 0.54-1.71％의 범위내에 있는 것으로 나타났다. 이들 마늘을 가열하여 Candida utilis ATCC42416을 지표효모로 이용하여 항균활성을 측정하였을 때 항균활성은 alliin함량과 정(+)의 상관 관계를 나타내었다. 따라서 가열마늘의 항균활성은 마늘에 들어있는 alliin의 열분해물질 때문이라는 가설을 제시하였다. 가열마늘의 항균 활성 패턴과 가열 alliin의 항균활성의 패턴을 비교하면 정확하게 일치하는 것으로 나타나서 이 또한 가열마늘의 항균작용은 마늘에 포함되어 있는 alliin 때문이라는 것을 추가로 증명하였다. 7. 가열마늘과 그 항균활성물질의 일종인 diallyl trisulfide의 항균 활성에 대한 cysteine의 불활성화작용을 검토한 결과, cysteine에 의해 항균활성이 감소됨을 발견하였고, 가열마늘의 항균물질은 균체단백질의 SH기와 반응하므로서 항균작용을 갖는다는 가설을 뒷받침하는 결과로 나타났다. 8. 마늘즙을 100℃이상 190℃의 온도에서 가열시간을 달리하여 가열하였을 때 120℃에서 최대활성을 나타내었으나 가열온도가 그 이상이었을 때는 오히려 최대활성에 도달하지 못하였다. 이는 활성물질이 생성되었다가 너무 높은 온도로 인해 분해되는 것으로 추정되었다. 그러나 100℃보다 높으나 120℃보다 낮은 온도(예, 110℃)에서 가열하면 최대활성에 도달하는 데 걸리는 시간이 매우 길어져서 90분이상 가열하여야 최대활성을 나타내는 것으로 나타났다. 9. Alliin (allyl-L-cysteine sulfoxide)과 구조가 유사한 allyl-L-cysteine은 가열하여도 항균활성이 나타나지 않았다. 이것으로 보아 allyl 기와 cysteine을 연결하는 황(S)이 산화되어있는 상태가 활성을 나타내는 데 필수요건임을 알 수 있었다. 10. 미생물의 종류에 따라 alliin 가열액이나 가열마늘에 의해 저해받는 정도가 다르게 나타났다. 따라서 어느 미생물을 대상으로 MIC를 측정하면 고가장비를 이용하여 alliin을 어렵게 분석하지 않더라도 마늘의 alliin함량을 근접되게 추정할 수 있었다. 11. 인공으로 합성한 sulfide류, 가열마늘즙, 및 마늘정유 (garlic oil), 양파정유(onion oil)의 항균작용은 일반적으로 세균에 대해서는 약하였으나 효모에 대하여는 매우 높게 나타났다. 이들 물질들은 유기산 보존료인 sorbate와는 달리 pH에 안정하여 pH 변화에 따라 항균활성에 큰 차이를 보이지 않았다. 또한, 저장안정성이 매우 낮은 생마늘즙과는 달리 비교적 고온에서 저장안정성이 뛰어나 식품 등의 보존료로서 효과적으로 이용될 수 있는 가능성이 높은 것으로 나타났다. 총괄적으로, 가열마늘의 항균활성은 생마늘의 불안정한 항균물질(allicin)파 같은 thiosulfinate가 아니고 주로 sulfide류인 것으로 추정되었으며 세균보다는 효모에 대해 항균활성이 높은 것으로 확인되었다. 항균활성은 안정된 성질을 지녔고 천연식품의 성분인 관계로 침채류, 간장 둥의 장류와 같은 식품에 효모를 방지할 수 있는 보존료로서의 이용가능성이 높게 나타났다.
1. 마늘, 양파 등에서 항균활성을 나타내는 물질의 전구물질로 알려진 S-allyl-L-cysteine sulfoxide, S-(2-propenyl)-L-cysteine sulfoxide, S-(2-pentenyl)-L-cysteine sulfoxide를 합성하였으며 그 수율은 모두 30％를 나타내었다. 2. 가열마늘에서 항균작용을 나타내는 polysulfides일 diallyl tetrasulfide, diallyl trisulfide를 합성시 각각 52.8％, 45％와 기타물질이 섞여있는 혼합물로 합성되어 Silical gel column을 이용하여 정제하여 순도가 높은 물질을 얻었다. Allylpropyl trisulfide, diethyl-, dipropyl-, dibutyl trisulfide도 같은 방법으로 합성하였으며 Silical gel colum을 이용하여 정제하여 순도를 높였다. Dimethyl tetrasulfide 를 합성할때는 methanethiol이 기체상태이므로 취급에 어려움이 있어 sodium methoxide로 대체하여 합성하였다. 3. 합성한 sulfides를 이용하여 항균활성을 시험하였을 때 sulfides류에 따라 효모에 대한 항균활성이 강한 것이 대부분인데 비하여 dipropyl tetrasulfide, diisopropyl tetrasulfide 및 dibutyl tetrasulfide는 효모에 대하여보다는 세균에 대하여 더 높은 활성을 나타내는 것이 특이하였다. 4. Sulfide류의 항균작용은 alkyl기의 탄소수가 적고 황의 수가 많을수록 크게 나타났으며, 이중결합이 있는 alkyl(예, allyl) 기의 경우는 탄소수가 동일한 alkyl기에 비해 항균활성이 월등히 높게 나타나는 것이 확인되었다. 5. 마늘즙을 121℃에서 가열하였을 때 45분까지는 항균활성이 지속적으로 증가하다가 45분 이후에는 가열시간이 경과하더라도 120 분까지는 항균활성의 변화가 없었다. 따라서 45분까지 가열하였을 때 항균활성물질의 생성이 완료되었으며 생성된 항균활성물질은 내열성이 매우 높아서 고온의 영향을 받지 않는 것으로 판단되었다. 6. 국내 마늘의 alliin의 함량은 0.54-1.71％의 범위내에 있는 것으로 나타났다. 이들 마늘을 가열하여 Candida utilis ATCC42416을 지표효모로 이용하여 항균활성을 측정하였을 때 항균활성은 alliin함량과 정(+)의 상관 관계를 나타내었다. 따라서 가열마늘의 항균활성은 마늘에 들어있는 alliin의 열분해물질 때문이라는 가설을 제시하였다. 가열마늘의 항균 활성 패턴과 가열 alliin의 항균활성의 패턴을 비교하면 정확하게 일치하는 것으로 나타나서 이 또한 가열마늘의 항균작용은 마늘에 포함되어 있는 alliin 때문이라는 것을 추가로 증명하였다. 7. 가열마늘과 그 항균활성물질의 일종인 diallyl trisulfide의 항균 활성에 대한 cysteine의 불활성화작용을 검토한 결과, cysteine에 의해 항균활성이 감소됨을 발견하였고, 가열마늘의 항균물질은 균체단백질의 SH기와 반응하므로서 항균작용을 갖는다는 가설을 뒷받침하는 결과로 나타났다. 8. 마늘즙을 100℃이상 190℃의 온도에서 가열시간을 달리하여 가열하였을 때 120℃에서 최대활성을 나타내었으나 가열온도가 그 이상이었을 때는 오히려 최대활성에 도달하지 못하였다. 이는 활성물질이 생성되었다가 너무 높은 온도로 인해 분해되는 것으로 추정되었다. 그러나 100℃보다 높으나 120℃보다 낮은 온도(예, 110℃)에서 가열하면 최대활성에 도달하는 데 걸리는 시간이 매우 길어져서 90분이상 가열하여야 최대활성을 나타내는 것으로 나타났다. 9. Alliin (allyl-L-cysteine sulfoxide)과 구조가 유사한 allyl-L-cysteine은 가열하여도 항균활성이 나타나지 않았다. 이것으로 보아 allyl 기와 cysteine을 연결하는 황(S)이 산화되어있는 상태가 활성을 나타내는 데 필수요건임을 알 수 있었다. 10. 미생물의 종류에 따라 alliin 가열액이나 가열마늘에 의해 저해받는 정도가 다르게 나타났다. 따라서 어느 미생물을 대상으로 MIC를 측정하면 고가장비를 이용하여 alliin을 어렵게 분석하지 않더라도 마늘의 alliin함량을 근접되게 추정할 수 있었다. 11. 인공으로 합성한 sulfide류, 가열마늘즙, 및 마늘정유 (garlic oil), 양파정유(onion oil)의 항균작용은 일반적으로 세균에 대해서는 약하였으나 효모에 대하여는 매우 높게 나타났다. 이들 물질들은 유기산 보존료인 sorbate와는 달리 pH에 안정하여 pH 변화에 따라 항균활성에 큰 차이를 보이지 않았다. 또한, 저장안정성이 매우 낮은 생마늘즙과는 달리 비교적 고온에서 저장안정성이 뛰어나 식품 등의 보존료로서 효과적으로 이용될 수 있는 가능성이 높은 것으로 나타났다. 총괄적으로, 가열마늘의 항균활성은 생마늘의 불안정한 항균물질(allicin)파 같은 thiosulfinate가 아니고 주로 sulfide류인 것으로 추정되었으며 세균보다는 효모에 대해 항균활성이 높은 것으로 확인되었다. 항균활성은 안정된 성질을 지녔고 천연식품의 성분인 관계로 침채류, 간장 둥의 장류와 같은 식품에 효모를 방지할 수 있는 보존료로서의 이용가능성이 높게 나타났다.
The antimicrobial activity of fresh garlic is due to allicin derived from alliin by the action of alliinase. Therefore allicin is generated only after garlic tissues are injured and alliinase react with alliin, because alliin and alliinase are located in different cells of garlic cloves. Naturally h...
The antimicrobial activity of fresh garlic is due to allicin derived from alliin by the action of alliinase. Therefore allicin is generated only after garlic tissues are injured and alliinase react with alliin, because alliin and alliinase are located in different cells of garlic cloves. Naturally heating at high temperatures of garlic abolishes the antimicrobial activity of garlic even after tissue disruption because alliinase enzyme is inactivated by heating. However, heated garlic has been known to possess very potent antiyeast activity, but weak antibacterial activity. Volatile sulfur compounds were, synthesized if necessary, tested for antimicrobial activity and the activities were compared with those of garlic oil and onion oil. 1. Volatile sulfur compounds which were commercially unavailable but related to the antimicrobial activity of garlic were synthesized, and their comparative antimicrobial activities were measured. 2. Precursor compounds including S-allyl-L-cysteine sulfoxide, S-(2-propenyl)-L-cysteine sulfoxide and S-(2-pentenyl)-L-cysteine sulfoxide of antimicrobial activity of garlic and onion were synthesized. The yields were all shown to be about 30％. 3. Polysulfides including diallyl tetrasulfide and diallyl trisulfide were synthesized as a 52.8％ and 45％ mixture, and further purified by silica gel column chromatography. Other kinds of polysulfides including allyl propyl trisulfide, diethyl trisulfide, dipropyl trisulfide and dibutyl trisulfide were synthesized and purified by the same protocol. In case of dimethyl tetrasulfide, methanthiol, a gaseous compound, was replaced by sodium methoxide for the purpose of convenience. 4. Most of polysulfides possessed potent antiyeast activities. Dipropyl tetrasulfide, diisopropyl tetrasulfide and dibutyl tetrasulfide, however, were more antibacterial than antiyeast. 5. The antiyeast activities of polysulfides were more potent as the number of carbons in the compounds was smaller and as the number of sulfur was greater. Those compounds with unsaturated alkyl groups (e.g. allyl-) showed much stronger antlyeast activity compared with those of saturated counterparts. 6. When aqueous extract of garlic was heated at 121℃, the antiyeast activity increased gradually up until 45 min, and no change in antiyeast activity was observed until 120 min. Therefore antiyeast compounds were believed to be formed within 45 min of heating and the compound(s) were Judged to be extremely stable under the condition of extreme heating. 7. The range of alliin content of garlics produced in Korea was between 0.54％ and 1.71％. The alliin content estimated by measuring minimum inhibitory concentrations by using Candida utilis ATCC42416 as an indicator yeast was positively related to the alliin content of garlic measured by HPLC. This is one of the many proofs that alliin of garlic is the precursor of antimicrobial compounds of heated garlic. Another proof that alliin is the Precursor compound of antimicrobial compound of heated garlic was that the growth inhibitory pattern of heated garlic and heated alliin was essentially the same. 8. Diallyl trisulfide which was believed to be the principal antiyeast compound was found to be inactivated by addition of cysteine into the growth medium of yeasts. This indirectly proves that antimicrobial polysulfides including diallyl trisulfide react with SH group of cellular proteins. 9. When aqueous extract of garlic was heated at temperatures between 100℃ and 190℃, the maximum activity was obtained at 120℃. Garlic extract heated at temperatures higher than that showed less potent activities. It was postulated that the antiyeast compound(s) was formed during heating and destroyed because of extremely high temperatures. When garlic was heated between 100℃ and 120℃, the time needed for the antiyeast activity to reach the maximum was longer. 10. Allyl-L-cysteine which is a relative compound of alliin(allyl-L-cysteine sulfoxide) did not show antiyeast activity after heating. It was clear that oxidation of sulfur as sulfoxide in the compound was necessary for the activity of the compound after heating. 11. The potency of antimicrobial activity was different depending upon different species of microorganisms. The antimicrobial activity was very much dependet on the alliin content of garlic. Therefore we can measure alliin content of garlic by using microorganisms, when expensive HPLC is not available. This microbial method of estimating alliin content of garlic is easy and economical. 12. Artificially synthesized polysulfides, heated garlic extract, garlic oil and onion oil all showed weak antibacterial activities, but potent antiyeast activities. The antimicrobial activities of these materials were not influenced by pH, while potassium sorbate, a representative antifungal preservative, is very much influenced by pH. The antimicrobial activity of all those materials were found to be stable under the condition of storage, compared with that of fresh garlic. Heated garlic and related materials are good candidates for alternative antifungal preservatives for food. As a conclusion, the antimicrobial activity of heated garlic is stable and the causative compounds are believed to be polysulfides, but not thiosulfinate which are unstable. Thiosulfinates are principal antimicrobial compounds of fresh garlic and onion. Heated garlic and related materials are substitutive for artificially synthesized food preservatives for vegetable pickles and soy sauces to prevent yeast spoilage.
The antimicrobial activity of fresh garlic is due to allicin derived from alliin by the action of alliinase. Therefore allicin is generated only after garlic tissues are injured and alliinase react with alliin, because alliin and alliinase are located in different cells of garlic cloves. Naturally heating at high temperatures of garlic abolishes the antimicrobial activity of garlic even after tissue disruption because alliinase enzyme is inactivated by heating. However, heated garlic has been known to possess very potent antiyeast activity, but weak antibacterial activity. Volatile sulfur compounds were, synthesized if necessary, tested for antimicrobial activity and the activities were compared with those of garlic oil and onion oil. 1. Volatile sulfur compounds which were commercially unavailable but related to the antimicrobial activity of garlic were synthesized, and their comparative antimicrobial activities were measured. 2. Precursor compounds including S-allyl-L-cysteine sulfoxide, S-(2-propenyl)-L-cysteine sulfoxide and S-(2-pentenyl)-L-cysteine sulfoxide of antimicrobial activity of garlic and onion were synthesized. The yields were all shown to be about 30％. 3. Polysulfides including diallyl tetrasulfide and diallyl trisulfide were synthesized as a 52.8％ and 45％ mixture, and further purified by silica gel column chromatography. Other kinds of polysulfides including allyl propyl trisulfide, diethyl trisulfide, dipropyl trisulfide and dibutyl trisulfide were synthesized and purified by the same protocol. In case of dimethyl tetrasulfide, methanthiol, a gaseous compound, was replaced by sodium methoxide for the purpose of convenience. 4. Most of polysulfides possessed potent antiyeast activities. Dipropyl tetrasulfide, diisopropyl tetrasulfide and dibutyl tetrasulfide, however, were more antibacterial than antiyeast. 5. The antiyeast activities of polysulfides were more potent as the number of carbons in the compounds was smaller and as the number of sulfur was greater. Those compounds with unsaturated alkyl groups (e.g. allyl-) showed much stronger antlyeast activity compared with those of saturated counterparts. 6. When aqueous extract of garlic was heated at 121℃, the antiyeast activity increased gradually up until 45 min, and no change in antiyeast activity was observed until 120 min. Therefore antiyeast compounds were believed to be formed within 45 min of heating and the compound(s) were Judged to be extremely stable under the condition of extreme heating. 7. The range of alliin content of garlics produced in Korea was between 0.54％ and 1.71％. The alliin content estimated by measuring minimum inhibitory concentrations by using Candida utilis ATCC42416 as an indicator yeast was positively related to the alliin content of garlic measured by HPLC. This is one of the many proofs that alliin of garlic is the precursor of antimicrobial compounds of heated garlic. Another proof that alliin is the Precursor compound of antimicrobial compound of heated garlic was that the growth inhibitory pattern of heated garlic and heated alliin was essentially the same. 8. Diallyl trisulfide which was believed to be the principal antiyeast compound was found to be inactivated by addition of cysteine into the growth medium of yeasts. This indirectly proves that antimicrobial polysulfides including diallyl trisulfide react with SH group of cellular proteins. 9. When aqueous extract of garlic was heated at temperatures between 100℃ and 190℃, the maximum activity was obtained at 120℃. Garlic extract heated at temperatures higher than that showed less potent activities. It was postulated that the antiyeast compound(s) was formed during heating and destroyed because of extremely high temperatures. When garlic was heated between 100℃ and 120℃, the time needed for the antiyeast activity to reach the maximum was longer. 10. Allyl-L-cysteine which is a relative compound of alliin(allyl-L-cysteine sulfoxide) did not show antiyeast activity after heating. It was clear that oxidation of sulfur as sulfoxide in the compound was necessary for the activity of the compound after heating. 11. The potency of antimicrobial activity was different depending upon different species of microorganisms. The antimicrobial activity was very much dependet on the alliin content of garlic. Therefore we can measure alliin content of garlic by using microorganisms, when expensive HPLC is not available. This microbial method of estimating alliin content of garlic is easy and economical. 12. Artificially synthesized polysulfides, heated garlic extract, garlic oil and onion oil all showed weak antibacterial activities, but potent antiyeast activities. The antimicrobial activities of these materials were not influenced by pH, while potassium sorbate, a representative antifungal preservative, is very much influenced by pH. The antimicrobial activity of all those materials were found to be stable under the condition of storage, compared with that of fresh garlic. Heated garlic and related materials are good candidates for alternative antifungal preservatives for food. As a conclusion, the antimicrobial activity of heated garlic is stable and the causative compounds are believed to be polysulfides, but not thiosulfinate which are unstable. Thiosulfinates are principal antimicrobial compounds of fresh garlic and onion. Heated garlic and related materials are substitutive for artificially synthesized food preservatives for vegetable pickles and soy sauces to prevent yeast spoilage.
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