Allyl alcohol은 가열 마늘의 주요 항균활성물질로서 황을 함유하지 않는 것이 특징으로 보고되었다. Allyl alcohol의 생성량은 가열시간 90분까지 점진적으로 증가하여 이후 전 가열 시간(300분)동안 일정했고 함량은 2100~2200ppm이었다. 반면 미 조정 시 약 pH 6인 가열 마늘의 Minimum Inhibitory Concentration(...
Allyl alcohol은 가열 마늘의 주요 항균활성물질로서 황을 함유하지 않는 것이 특징으로 보고되었다. Allyl alcohol의 생성량은 가열시간 90분까지 점진적으로 증가하여 이후 전 가열 시간(300분)동안 일정했고 함량은 2100~2200ppm이었다. 반면 미 조정 시 약 pH 6인 가열 마늘의 Minimum Inhibitory Concentration(MIC)는 가열 시간 45분 이후부터 최저치에 달해 전 가열 시간(300분) 동안 일정하게 유지되었다. 이는 가열 시간 45~90분 사이에 allyl alcohol외의 기타 항균활성물질이 존재함을 의미했고, 90분 이후는 항균활성물질이 allyl alcohol만이라 가정했을 때 활성의 약 70%를 담당하고 있음을 뜻하며 나머지는 마늘 가열 시 생성되는 휘발성 황화합물인 diallyl trisulfide, diallyl tetrasulfide, diallyl pentasulfide등의 diallyl sulfides류나 4-Methyl-1,2,3-trithiolane, 5-Methyl-1,2,3,4-tetrathiane, 6-methyl-1,2,3,4,5-pentathiepane를 포함하는 heterocyclic sulfur compounds의 작용에 의한 것으로 확인되었다. 가열 전 pH를 조정해 시간 별로 가열 후 MIC를 측정해보니 pH 2에서 미조정시의 2배에 달하는 강한 항균 활성을 나타내었다. pH를 조정해도 allyl alcohol의 함량은 큰 변화가 없었지만 휘발성 황화합물량은 미조정시보다 최대 7배의 함량을 가졌으며 따라서 pH 조절로 인한 항균 활성의 강화는 휘발성 황화합물의 증가에 의한 것으로 확인되었다. 황의 개수가 4개 이상인 휘발성 황화합물들은 GC 분석 시 열분해에 의해 정량 분석이 불가능했으며 HPLC를 통해 분석했을 때 높은 정확도를 나타냈다. 가열 마늘의 항균 활성은 주로 allyl alcohol과 휘발성 황화합물에 의한 것이나 가열 시간 45분 ~ 90분 사이에 비휘발성 수용성 항균활성물질이 존재할 것이라는 판단 하에 항균 물질을 탐색하였다. 가열 마늘액을 HPLC를 이용해 구간별로 분획한 결과 allyl alcohol 외에 항균 작용이 있는 두 구간이 확인되었고 이들은 각각 30분, 45분 가열 시에 최대 생성량을 나타냈다. 이 중 한 물질을 Recycling HPLC를 이용해 정제한 뒤 LC/MS와 원소분석을 한 결과 분자량 225에 C6H11N1O2S3의 원소구성을 가진 화합물임을 확인했다. 이후 이 물질을 1H-NMR, 13C-NMR, FT-IR로 구조 분석한 결과 CH2=CH-CH2-S-S-S-CH2-CHNH2COOH 의 구조를 갖는 함황 아미노산인 것으로 분석되었고 IUPAC 명명법에 따라 3-(allyltrisulfanyl)-2-aminopropanoic acid로 명명했다. 신 물질의 효모, 세균, 젖산균에 대한 항미생물 활성을 시험한 결과 효모에 대한 MIC는 50ppm 이하를 나타내어 강한 항효모 작용을 가지고 있었고 세균, 젖산균에 대한 항균활성은 강하지 않아 다른 마늘 유래의 항균 활성 물질들과 같은 경향성을 보였다. 신 물질은 마늘 유래의 비휘발성 수용성 함황 항균물질로서 지금까지 보고된 바 없는 새로운 물질로 추정되었다. 또한 항암 작용을 가진 것으로 기존에 보고된 마늘 유래의 수용성 물질인 S-allylcysteine, S-allylmercaptocysteine과 구조적 유사성을 나타내 항균 작용과 항암 효과를 동시에 지닌 물질로 기대되었다.
Allyl alcohol은 가열 마늘의 주요 항균활성물질로서 황을 함유하지 않는 것이 특징으로 보고되었다. Allyl alcohol의 생성량은 가열시간 90분까지 점진적으로 증가하여 이후 전 가열 시간(300분)동안 일정했고 함량은 2100~2200ppm이었다. 반면 미 조정 시 약 pH 6인 가열 마늘의 Minimum Inhibitory Concentration(MIC)는 가열 시간 45분 이후부터 최저치에 달해 전 가열 시간(300분) 동안 일정하게 유지되었다. 이는 가열 시간 45~90분 사이에 allyl alcohol외의 기타 항균활성물질이 존재함을 의미했고, 90분 이후는 항균활성물질이 allyl alcohol만이라 가정했을 때 활성의 약 70%를 담당하고 있음을 뜻하며 나머지는 마늘 가열 시 생성되는 휘발성 황화합물인 diallyl trisulfide, diallyl tetrasulfide, diallyl pentasulfide등의 diallyl sulfides류나 4-Methyl-1,2,3-trithiolane, 5-Methyl-1,2,3,4-tetrathiane, 6-methyl-1,2,3,4,5-pentathiepane를 포함하는 heterocyclic sulfur compounds의 작용에 의한 것으로 확인되었다. 가열 전 pH를 조정해 시간 별로 가열 후 MIC를 측정해보니 pH 2에서 미조정시의 2배에 달하는 강한 항균 활성을 나타내었다. pH를 조정해도 allyl alcohol의 함량은 큰 변화가 없었지만 휘발성 황화합물량은 미조정시보다 최대 7배의 함량을 가졌으며 따라서 pH 조절로 인한 항균 활성의 강화는 휘발성 황화합물의 증가에 의한 것으로 확인되었다. 황의 개수가 4개 이상인 휘발성 황화합물들은 GC 분석 시 열분해에 의해 정량 분석이 불가능했으며 HPLC를 통해 분석했을 때 높은 정확도를 나타냈다. 가열 마늘의 항균 활성은 주로 allyl alcohol과 휘발성 황화합물에 의한 것이나 가열 시간 45분 ~ 90분 사이에 비휘발성 수용성 항균활성물질이 존재할 것이라는 판단 하에 항균 물질을 탐색하였다. 가열 마늘액을 HPLC를 이용해 구간별로 분획한 결과 allyl alcohol 외에 항균 작용이 있는 두 구간이 확인되었고 이들은 각각 30분, 45분 가열 시에 최대 생성량을 나타냈다. 이 중 한 물질을 Recycling HPLC를 이용해 정제한 뒤 LC/MS와 원소분석을 한 결과 분자량 225에 C6H11N1O2S3의 원소구성을 가진 화합물임을 확인했다. 이후 이 물질을 1H-NMR, 13C-NMR, FT-IR로 구조 분석한 결과 CH2=CH-CH2-S-S-S-CH2-CHNH2COOH 의 구조를 갖는 함황 아미노산인 것으로 분석되었고 IUPAC 명명법에 따라 3-(allyltrisulfanyl)-2-aminopropanoic acid로 명명했다. 신 물질의 효모, 세균, 젖산균에 대한 항미생물 활성을 시험한 결과 효모에 대한 MIC는 50ppm 이하를 나타내어 강한 항효모 작용을 가지고 있었고 세균, 젖산균에 대한 항균활성은 강하지 않아 다른 마늘 유래의 항균 활성 물질들과 같은 경향성을 보였다. 신 물질은 마늘 유래의 비휘발성 수용성 함황 항균물질로서 지금까지 보고된 바 없는 새로운 물질로 추정되었다. 또한 항암 작용을 가진 것으로 기존에 보고된 마늘 유래의 수용성 물질인 S-allylcysteine, S-allylmercaptocysteine과 구조적 유사성을 나타내 항균 작용과 항암 효과를 동시에 지닌 물질로 기대되었다.
Garlic has been known for its potent antimicrobial activity for a long time. Allicin, an extremely potent antimicrobial compound of fresh garlic, is formed from alliin when fresh garlic is injured. Since an enzyme is involved in the generation of antimicrobial compound, it had been assumed that heat...
Garlic has been known for its potent antimicrobial activity for a long time. Allicin, an extremely potent antimicrobial compound of fresh garlic, is formed from alliin when fresh garlic is injured. Since an enzyme is involved in the generation of antimicrobial compound, it had been assumed that heated garlic is not antimicrobial. However, it was found that heated garlic has antimicrobial activity because of allyl alcohol and volatile sulfur compounds by previous reports. We have focused on the formation of antimicrobial compounds in garlic on heating and are reporting the findings of antimicrobial compounds generated in heated garlic. This study examined to the antimicrobial activity and variable compounds of garlic depending on condition of heat (pH, heating time) at 120℃, and investigated the water-soluble compounds. They were separated from heated garlic by Prep-HPLC, and identified by elemental analysis, LC/MS, 1H-NMR, 13C-NMR and FT-IR. 1. Anti-yeast activity of garlic depending on pH and heating time at 120℃ of heated garlic against Candida utilis ATCC42416 tested by minimum inhibitory concentration (MIC) test method. pH 4, 6 Garlic (pH treatment, pH of raw garlic: 6) heated at 120℃ for 45 min showed the highest anti-yeast activity (0.5, 0.6%) and did not change when heated for up to 300 min. But, anti-yeast activity of pH 2 garlic is (MIC: 0.3% heated for up to 45 min) decreased to 0.6% with prolonged heating (up to 300 min). The principal antimicrobial compound in heated garlic is allyl alcohol (2-propen-1-ol), formed by the thermal degradation of alliin. Allyl alcohol accounts for more than 70% of antimicrobial activity of garlic heated at 120°C for 45 min of longer. Allyl alcohol differs from all other known antimicrobial compound found in garlic in that it does not contain sulfur atom and highly volatile. 2. There are numerous secondary antimicrobial compounds in heated garlic. In addition to the well-known diallyl sulfides, heterocyclic sulfur compounds have been found as major degradation products of alliin. Change of volatile sulfur compounds in heated garlic depending on pH and heating time at 120℃ was analyzed by HPLC. Diallyl trisulfide (DATS), diallyl tetrasulfide (DATTS), Diallyl pentasulfide (DAPS), 4-methyl-1,2,3-trithiolane(MTTL), 5-methyl-1,2,3,4-tetrathiane(MTTT) and 6-methyl-1,2,3,4,5-pentathiepane(MPTP) were major volatiles of heated garlic. Heating time on 45 min were maximum producing point of DATS and DATTS, and DAPS was the highest at 60 min. However, MTTL, MTTT and MPTP were the highest produced at 90~120 min of heat. Otherwise, total volatiles of heated garlic were decreased when heated for up to 150 min. Difference of volatiles producing pattern depending on pH was not shown. But, total volatiles of pH 2 were lager than control (pH 6) at 5~7 times. 3. MW 181, 193 and 225 compounds were separated from heated garlic by Recycling Preparative HPLC and examined that MW 181, 193 and 225 compounds were water-soluble compounds which L-Tyrosine, S-allylmercaptocysteine and 3-(allyltrisulfanyl)-2-amino-propanoic acid. 3-(allyltrisulfanyl)-2-amino-propanoic acid , a non-volatile and antimicrobial novel compound was purified from heated garlic for the first time and found that it is inhibitory to both bacteria and yeasts. This compound is not soluble in organic solvents and only sparingly soluble in water. It was identified as an allyl disulfide derivative of cysteine, with a MW of 225 daltons and an elemental composition of C6H11N1O2S3. It was analyzed by 1H-NMR, 13C-NMR, FT-IR as molecule structure of CH2=CH-CH2-S-S-S-CH2-CHNH2-COOH. 4. We compared potency of antiyeast activity of water-soluble compounds with allyl alcohol (AA), garlic oil (GO), diallyl sulfides (DAMS, DADS, DATS, DATTS, DAPS) and heterocyclic sulfur compounds(MTTL, MTTT, MPTP). The ranges of MIC of water-soluble compounds were not detected, but 3-(allyltrisulfanyl)-2-amino-propanoic acid was detected against various yeast; 15-100ppm. Also MIC of 3-(allyltrisulfanyl)-2-amino-propanoic acid against Staphyococcus aureus B33 was 20ppm.
Garlic has been known for its potent antimicrobial activity for a long time. Allicin, an extremely potent antimicrobial compound of fresh garlic, is formed from alliin when fresh garlic is injured. Since an enzyme is involved in the generation of antimicrobial compound, it had been assumed that heated garlic is not antimicrobial. However, it was found that heated garlic has antimicrobial activity because of allyl alcohol and volatile sulfur compounds by previous reports. We have focused on the formation of antimicrobial compounds in garlic on heating and are reporting the findings of antimicrobial compounds generated in heated garlic. This study examined to the antimicrobial activity and variable compounds of garlic depending on condition of heat (pH, heating time) at 120℃, and investigated the water-soluble compounds. They were separated from heated garlic by Prep-HPLC, and identified by elemental analysis, LC/MS, 1H-NMR, 13C-NMR and FT-IR. 1. Anti-yeast activity of garlic depending on pH and heating time at 120℃ of heated garlic against Candida utilis ATCC42416 tested by minimum inhibitory concentration (MIC) test method. pH 4, 6 Garlic (pH treatment, pH of raw garlic: 6) heated at 120℃ for 45 min showed the highest anti-yeast activity (0.5, 0.6%) and did not change when heated for up to 300 min. But, anti-yeast activity of pH 2 garlic is (MIC: 0.3% heated for up to 45 min) decreased to 0.6% with prolonged heating (up to 300 min). The principal antimicrobial compound in heated garlic is allyl alcohol (2-propen-1-ol), formed by the thermal degradation of alliin. Allyl alcohol accounts for more than 70% of antimicrobial activity of garlic heated at 120°C for 45 min of longer. Allyl alcohol differs from all other known antimicrobial compound found in garlic in that it does not contain sulfur atom and highly volatile. 2. There are numerous secondary antimicrobial compounds in heated garlic. In addition to the well-known diallyl sulfides, heterocyclic sulfur compounds have been found as major degradation products of alliin. Change of volatile sulfur compounds in heated garlic depending on pH and heating time at 120℃ was analyzed by HPLC. Diallyl trisulfide (DATS), diallyl tetrasulfide (DATTS), Diallyl pentasulfide (DAPS), 4-methyl-1,2,3-trithiolane(MTTL), 5-methyl-1,2,3,4-tetrathiane(MTTT) and 6-methyl-1,2,3,4,5-pentathiepane(MPTP) were major volatiles of heated garlic. Heating time on 45 min were maximum producing point of DATS and DATTS, and DAPS was the highest at 60 min. However, MTTL, MTTT and MPTP were the highest produced at 90~120 min of heat. Otherwise, total volatiles of heated garlic were decreased when heated for up to 150 min. Difference of volatiles producing pattern depending on pH was not shown. But, total volatiles of pH 2 were lager than control (pH 6) at 5~7 times. 3. MW 181, 193 and 225 compounds were separated from heated garlic by Recycling Preparative HPLC and examined that MW 181, 193 and 225 compounds were water-soluble compounds which L-Tyrosine, S-allylmercaptocysteine and 3-(allyltrisulfanyl)-2-amino-propanoic acid. 3-(allyltrisulfanyl)-2-amino-propanoic acid , a non-volatile and antimicrobial novel compound was purified from heated garlic for the first time and found that it is inhibitory to both bacteria and yeasts. This compound is not soluble in organic solvents and only sparingly soluble in water. It was identified as an allyl disulfide derivative of cysteine, with a MW of 225 daltons and an elemental composition of C6H11N1O2S3. It was analyzed by 1H-NMR, 13C-NMR, FT-IR as molecule structure of CH2=CH-CH2-S-S-S-CH2-CHNH2-COOH. 4. We compared potency of antiyeast activity of water-soluble compounds with allyl alcohol (AA), garlic oil (GO), diallyl sulfides (DAMS, DADS, DATS, DATTS, DAPS) and heterocyclic sulfur compounds(MTTL, MTTT, MPTP). The ranges of MIC of water-soluble compounds were not detected, but 3-(allyltrisulfanyl)-2-amino-propanoic acid was detected against various yeast; 15-100ppm. Also MIC of 3-(allyltrisulfanyl)-2-amino-propanoic acid against Staphyococcus aureus B33 was 20ppm.
AI-Helper
※ AI-Helper는 부적절한 답변을 할 수 있습니다.