[학위논문]홍화씨(Carthamus tinctorius L.)로부터 분리된 항산화 및 멜라닌 생성 억제 물질의 분리, 동정 및 특성 Isolation, identification and charaterization of antioxidants and anti-melanogenesis compounds from safflower (Carthamus tinctorius L.) seeds원문보기
노중섭
(Graduate School, Yonsei University
Dept. of Biotechnology
국내박사)
본 연구에서는 새로운 미백제를 개발하기 위해 항산화 및 멜라닌 생성 억제 활성을 갖는 물질을 홍화씨로부터 탐색하여 분리, 정제하고, 유효 성분의 항산화 활성과 멜라닌 생성 억제 활성을 연구, 검토하였다.홍화씨에서 N-feruloylserotonin, N-(p-coumaroyl)serotonin, matairesinol, 8’-hydroxyarctigenin, acacetin 7-O-β-D-glucoside, acacetin을 분리, 정제 하였고, 각 물질들에 대한 DPPH radical 소거 기능과 쥐 간으로부터 분리한 마이크로좀의 ...
본 연구에서는 새로운 미백제를 개발하기 위해 항산화 및 멜라닌 생성 억제 활성을 갖는 물질을 홍화씨로부터 탐색하여 분리, 정제하고, 유효 성분의 항산화 활성과 멜라닌 생성 억제 활성을 연구, 검토하였다.홍화씨에서 N-feruloylserotonin, N-(p-coumaroyl)serotonin, matairesinol, 8’-hydroxyarctigenin, acacetin 7-O-β-D-glucoside, acacetin을 분리, 정제 하였고, 각 물질들에 대한 DPPH radical 소거 기능과 쥐 간으로부터 분리한 마이크로좀의 lipid peroxidation 억제 효과를 검토하였다. 두 개의 serotonin 물질들은 기존 합성 항산화제인 BHT에 비해 강한 DPPH radical 소거 활성과 lipid peroxidation 억제 효과를 나타내었다. Acacetin과 matairesinol 또한 lipid peroxidation 억제효과를 나타냈으나 이들과 구조가 비슷한 8’-hydroxyarctigenin과 acacetin 7-O-β-D-glucoside는 훨씬 약한 활성을 나타내었다. 이는 matairesinol과 acacetin의 기본 골격에 붙어있는 hydroxyl group과 glucosyl group으로 인해 lipid membrane에 대한 친화력이 떨어짐으로써 항산화 활성이 감소하는 것으로 보여진다.80% MeOH 추출물과 ethyl acetate 분획물에서 mushroom tyrosinase에 대한 저해활성을 나타내어 ethyl acetate 분획물로부터 활성을 나타내는 N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D-glucoside, acacetin을 분리, 정제하였고, 기존 미백화장품의 원료인 arbutin (IC50=0.223 mM)과 IC50 값을 비교한 결과, 각각 0.023, 0.074, 1.890, 0.779 mM로 serotonin 화합물들은 arbutin에 비해 강한 tyrosinase 저해활성을 나타내었다. 또한 serotonin 화합물들은 멜라닌을 생성하는 Streptomyces bikiniensis 와 B16 melanoma cells에서도 kojic acid와 arbutin과 비교하여 강력한 멜라닌 생성 억제효과를 나타내었다. 더욱이 B16 melanoma cells에 대한 cytotoxicity를 검토한 결과 serotonin 화합물들에서는 cytotoxicity가 전혀 나타나지 않았다.이러한 결과로 보아 N-feruloylserotonin과 N-(p-coumaroyl)serotonin의 항산화 활성 및 tyrosinase 저해 활성이 복합적으로 작용하여 강력한 멜라닌 생합성 저해 효과를 나타낸다고 판단되어지고, 본 연구에서 처음으로 밝혀진 멜라닌 생성 저해효과를 갖는 serotonin 화합물들은 새로운 미백제로서의 개발 가능성이 기대되어진다.
본 연구에서는 새로운 미백제를 개발하기 위해 항산화 및 멜라닌 생성 억제 활성을 갖는 물질을 홍화씨로부터 탐색하여 분리, 정제하고, 유효 성분의 항산화 활성과 멜라닌 생성 억제 활성을 연구, 검토하였다.홍화씨에서 N-feruloylserotonin, N-(p-coumaroyl)serotonin, matairesinol, 8’-hydroxyarctigenin, acacetin 7-O-β-D-glucoside, acacetin을 분리, 정제 하였고, 각 물질들에 대한 DPPH radical 소거 기능과 쥐 간으로부터 분리한 마이크로좀의 lipid peroxidation 억제 효과를 검토하였다. 두 개의 serotonin 물질들은 기존 합성 항산화제인 BHT에 비해 강한 DPPH radical 소거 활성과 lipid peroxidation 억제 효과를 나타내었다. Acacetin과 matairesinol 또한 lipid peroxidation 억제효과를 나타냈으나 이들과 구조가 비슷한 8’-hydroxyarctigenin과 acacetin 7-O-β-D-glucoside는 훨씬 약한 활성을 나타내었다. 이는 matairesinol과 acacetin의 기본 골격에 붙어있는 hydroxyl group과 glucosyl group으로 인해 lipid membrane에 대한 친화력이 떨어짐으로써 항산화 활성이 감소하는 것으로 보여진다.80% MeOH 추출물과 ethyl acetate 분획물에서 mushroom tyrosinase에 대한 저해활성을 나타내어 ethyl acetate 분획물로부터 활성을 나타내는 N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D-glucoside, acacetin을 분리, 정제하였고, 기존 미백화장품의 원료인 arbutin (IC50=0.223 mM)과 IC50 값을 비교한 결과, 각각 0.023, 0.074, 1.890, 0.779 mM로 serotonin 화합물들은 arbutin에 비해 강한 tyrosinase 저해활성을 나타내었다. 또한 serotonin 화합물들은 멜라닌을 생성하는 Streptomyces bikiniensis 와 B16 melanoma cells에서도 kojic acid와 arbutin과 비교하여 강력한 멜라닌 생성 억제효과를 나타내었다. 더욱이 B16 melanoma cells에 대한 cytotoxicity를 검토한 결과 serotonin 화합물들에서는 cytotoxicity가 전혀 나타나지 않았다.이러한 결과로 보아 N-feruloylserotonin과 N-(p-coumaroyl)serotonin의 항산화 활성 및 tyrosinase 저해 활성이 복합적으로 작용하여 강력한 멜라닌 생합성 저해 효과를 나타낸다고 판단되어지고, 본 연구에서 처음으로 밝혀진 멜라닌 생성 저해효과를 갖는 serotonin 화합물들은 새로운 미백제로서의 개발 가능성이 기대되어진다.
In order to develop a new skin whitening agent, safflower (Carthamus tinctorius L.) seeds were evaluated for antioxidant and anti-melanogenesis activities and its active principles were identified following activity-guided isolation.Six compounds, N-feruloylserotonin, N-(p-coumaroyl) serotonin, mata...
In order to develop a new skin whitening agent, safflower (Carthamus tinctorius L.) seeds were evaluated for antioxidant and anti-melanogenesis activities and its active principles were identified following activity-guided isolation.Six compounds, N-feruloylserotonin, N-(p-coumaroyl) serotonin, matairesinol, 8’-hydroxyarctigenin, acacetin 7-O-β-D-glucoside and acacetin were isolated and identified from the extract of seeds. The inhibitory effects of six compounds on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and lipid peroxidation in rat liver microsomes were determined. N-feruloylserotonin and N-(p-coumaroyl)serotonin showed more potent DPPH radical scavenging activity, and a stronger inhibitory effect on lipid peroxidation than that of BHT. In addition, acacetin and matairesinol also considerably inhibited lipid peroxidation, while 8’-hydroxyarctigenin and acacetin 7-O-β-D- glucoside showed weaker activity than their corresponding matairesinol and acacetin, indicating that addition of hydroxyl and glucosyl groups to matairesinol and acacetin decreased antioxidative activity due to low affinity of them for the lipid membranes.The 80% aqueous methanol extract and ethyl acetate fraction from safflower seeds showed a significant inhibition for mushroom tyrosinase. Four active compounds, N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D- glucoside, and acacetin, were isolated from the ethyl acetate fraction as the active principles. Compared with arbutin (IC50=0.223 mM), the IC50 values of these compounds were 0.023, 0.074, 1.890 and 0.779 mM for N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D- glucoside, and acacetin, respectively. It was also found that N-feruloylserotonin and N-(p-coumaroyl)serotonin strongly inhibited the melanin production of Streptomyces bikiniensis and B16 melanoma cells in comparison with a known melanogenesis inhibitor, arbutin. N-feruloylserotonin and N-(p-coumaroyl)serotonin inhibited the melanin production of S. bikiniensis strongly in comparison with known melanogenesis inhibitors, kojic acid and Arbutin. Two flavonoids also showed significant activity comparable to that of arbutin. However, two lignans showed weaker activity. The IC50 values of inhibition of cultured B16 melanoma cell pigmentation due to melanin synthesis were compared to the cytotoxicity effects of the compounds. N-feruloylserotonin and N-(p-coumaroyl)serotonin were very effective agents, with IC50 of 0.191 and 0.245 mM, respectively. In addition, these compounds did not show any cytotoxicity, while acacetin exhibited some cytotoxicity with IC50 of 0.423 mM. However, two lignans and two flavonoids showed less considerable activity.These results indicate that N-feruloylserotonin and N-(p-coumaroyl)serotonin showed potent antioxidant effect as well as melanin synthesis inhibition. Therefore, the strong effects of N-feruloylserotonin and N-(p-coumaroyl)serotonin on melanin synthesis inhibition may be attributed to combined activities of antioxidant and tyrosinase inhibition.It is meaningful to note that the present investigation revealed N-feruloylserotonin and N-(p-coumaroyl)serotonin to be potent melanin synthesis inhibitors for the first time, thus they could be considered as promising candidates for novel whitening agents.
In order to develop a new skin whitening agent, safflower (Carthamus tinctorius L.) seeds were evaluated for antioxidant and anti-melanogenesis activities and its active principles were identified following activity-guided isolation.Six compounds, N-feruloylserotonin, N-(p-coumaroyl) serotonin, matairesinol, 8’-hydroxyarctigenin, acacetin 7-O-β-D-glucoside and acacetin were isolated and identified from the extract of seeds. The inhibitory effects of six compounds on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and lipid peroxidation in rat liver microsomes were determined. N-feruloylserotonin and N-(p-coumaroyl)serotonin showed more potent DPPH radical scavenging activity, and a stronger inhibitory effect on lipid peroxidation than that of BHT. In addition, acacetin and matairesinol also considerably inhibited lipid peroxidation, while 8’-hydroxyarctigenin and acacetin 7-O-β-D- glucoside showed weaker activity than their corresponding matairesinol and acacetin, indicating that addition of hydroxyl and glucosyl groups to matairesinol and acacetin decreased antioxidative activity due to low affinity of them for the lipid membranes.The 80% aqueous methanol extract and ethyl acetate fraction from safflower seeds showed a significant inhibition for mushroom tyrosinase. Four active compounds, N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D- glucoside, and acacetin, were isolated from the ethyl acetate fraction as the active principles. Compared with arbutin (IC50=0.223 mM), the IC50 values of these compounds were 0.023, 0.074, 1.890 and 0.779 mM for N-feruloylserotonin, N-(p-coumaroyl)serotonin, acacetin 7-O-β-D- glucoside, and acacetin, respectively. It was also found that N-feruloylserotonin and N-(p-coumaroyl)serotonin strongly inhibited the melanin production of Streptomyces bikiniensis and B16 melanoma cells in comparison with a known melanogenesis inhibitor, arbutin. N-feruloylserotonin and N-(p-coumaroyl)serotonin inhibited the melanin production of S. bikiniensis strongly in comparison with known melanogenesis inhibitors, kojic acid and Arbutin. Two flavonoids also showed significant activity comparable to that of arbutin. However, two lignans showed weaker activity. The IC50 values of inhibition of cultured B16 melanoma cell pigmentation due to melanin synthesis were compared to the cytotoxicity effects of the compounds. N-feruloylserotonin and N-(p-coumaroyl)serotonin were very effective agents, with IC50 of 0.191 and 0.245 mM, respectively. In addition, these compounds did not show any cytotoxicity, while acacetin exhibited some cytotoxicity with IC50 of 0.423 mM. However, two lignans and two flavonoids showed less considerable activity.These results indicate that N-feruloylserotonin and N-(p-coumaroyl)serotonin showed potent antioxidant effect as well as melanin synthesis inhibition. Therefore, the strong effects of N-feruloylserotonin and N-(p-coumaroyl)serotonin on melanin synthesis inhibition may be attributed to combined activities of antioxidant and tyrosinase inhibition.It is meaningful to note that the present investigation revealed N-feruloylserotonin and N-(p-coumaroyl)serotonin to be potent melanin synthesis inhibitors for the first time, thus they could be considered as promising candidates for novel whitening agents.
Keyword
#홍화씨(Carthamus tinctorius L.)
#항산화
#멜라닌
#safflower (Carthamus tinctorius L.) seed
#antioxidant
#skin whitening
#anti-melanogenesis
#tyrosinase inhibitor
#tyrosinase
#N-feruloylserotonin
#N-(p-coumaroyl)serotonin
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