찔레(Rosa multiflora)는 장미과 관목 식물로써 야산이나 강변에 넓게 분포하며 많은 나라에서 ‘brier rose‘라는 이름으로 불려지고 있다. 찔레뿌리는 민간에서 당뇨병과 관절염에 사용되어져 왔다. 찔레뿌리를 아세톤, 수용성 MeOH과 EtOH로 추출한 후, EtOAc, n-BuOH, H2O를 사용하여 순차적으로 용매 분획을 실시하였다. 아세톤 추출물과 EtOAc분획에 대하여 silica gel과 ODS column chromatographies를 실시하여 한 개의 ...
찔레(Rosa multiflora)는 장미과 관목 식물로써 야산이나 강변에 넓게 분포하며 많은 나라에서 ‘brier rose‘라는 이름으로 불려지고 있다. 찔레뿌리는 민간에서 당뇨병과 관절염에 사용되어져 왔다. 찔레뿌리를 아세톤, 수용성 MeOH과 EtOH로 추출한 후, EtOAc, n-BuOH, H2O를 사용하여 순차적으로 용매 분획을 실시하였다. 아세톤 추출물과 EtOAc분획에 대하여 silica gel과 ODS column chromatographies를 실시하여 한 개의 lignan, 네 개의 tannins, 두 개의 steroids, 열한 개의 triterpenoid 화합물을 분리하였다. 분리된 화합물에 대해서 NMR, MS, IR spectroscopy data를 해석하여 procyanidin B3 (1), (+)-catechin (2), ent-fisetinidol-(4β→6)-catechin (3), ent-guibouritinidol-(4β→6)-catechin (4) 등 네 개의 tannin 화합물, β-sitosterol (5), doucosterol (16) 등 두 개의 steroid 화합물, 4,4',8',9-tetrahydroxy-3,3'-dimethoxy-7,9'-cyclolignan ((-)-olivil) (14) 한 개의 lignan 화합물, 3β-hydroxylup-20(29)-en-28-oic acid (betulinic acid) (6), 3β-hydroxyurs-12-en-28-oic acid (ursolic acid) (7), 2,19α-dihydroxy-3-oxours-1,12-dien-28-oic acid (fupenzic acid) (8), 3β,19α-dihydroxy-2- oxours-12-en-28-oic acid (2-oxo-pomolic acid) (9), 2α,3α,19α-trihydroxy-12-en-28-oic acid (euscaphic acid) (10), 2α,3β,19α-trihydroxy-12-en-28-oic acid (tormentic acid) (11), 2-hydroxymethyl A(1)nor-19α,24-dihydroxyurs-2,12-dien-28-oic acid (rosamultic acid) (12), 3β-O-(β-D-xylopyranosyl)-pomolic acid (ilexoside B) (13), 2α,19α-dihydroxy-3-oxo-12ursen-28-oic acid 28-O-β-D-glucopyranoside (15), 2α,3α,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (kagi-ichigoside F1) (17) and 2α,3β,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (rosamultin) (18) 등 열한 개의 triterpenoid 화합물의 구도를 동정하였다. 화합물 8, 9, 15는 찔레에서 처음 분리된 화합물이다. 찔레뿌리 추출물, 용매 분획물, 분리된 화합물에 대해서 항산화, 피부 미백(anti- melanogenesis and anti-tyrosinase), 피부 세포 보호 활성을 측정하였다. 아세톤 추출물, RMR-6, RMR-6-2, procyanidin B3 (1), ent-fisetinidol-(4β→6)-catechin (2)의 DPPH radical 소거활성은 79.1%, 74.3%, 70.8%, 88.2%, 72.5%로 나타났다(final concentration : 25 μg/mL). 화합물 1, 2, (+)-catechin (3), ent-guibouritinidol-(4β→6)-catechin (4)의 ABTs radical 소거 활성은 259.2 mgVCE/100mg, 270.3 mgVCE/100mg, 250.9 mgVCE/100mg, 208.5 mgVCE/100mg으로 나타났다. 또한, 이들 화합물의 DPPH radical 소거 활성은 195.9 mgVCE/100mg, 173.2 mgVCE/100mg, 208.0 mgVCE/100mg, 155.0 mgVCE/100mg으로 나타났다. 그리고, ORAC capacity는 491.1 mgVCE/100mg, 485.5 mgVCE/100mg, 547.3 mgVCE/100mg, 594.8 mgVCE/100mg으로 매우 높은 활성을 나타냈다. 화합물 4의 tyrosinase 활성 억제와 melanin 생합성 억제 효과는 IC50 값이 148.6 μg/mL와 49.3 μg/mL으로 나타났다. 화합물 2, 3, 4의 과산화소수에 의해 유도된 세포 손상에 대한 세포 보호 효과는 LD50 값이 88.3 μg/mL, 67.3 μg/mL, 162.4 μg/mL로 나타났고, UV에 의한 세포 손상에 대해서는 LD50 값이 74.6 μg/mL, 152.2 μg/mL, 105.3 μg/mL로 나타났다. 화합물 3과 4의 UV에 의해 유도된 collagen 저하 억제 효과는 IC50 값이 188.2 μg/mL, 92.4 μg/mL로 나타났고, elastin 저하 억제 효과는 IC50 값이 142.6 μg/mL, 122.3 μg/mL로 나타났다. 결론적으로, 찔레뿌리 추출물, 용매 분획물, 분리된 화합물은 높은 항산화 활성을 나타냈으며, 피부 미백과 피부 세포 보호 효과에서도 비교적 우수한 활성을 보였다.
찔레(Rosa multiflora)는 장미과 관목 식물로써 야산이나 강변에 넓게 분포하며 많은 나라에서 ‘brier rose‘라는 이름으로 불려지고 있다. 찔레뿌리는 민간에서 당뇨병과 관절염에 사용되어져 왔다. 찔레뿌리를 아세톤, 수용성 MeOH과 EtOH로 추출한 후, EtOAc, n-BuOH, H2O를 사용하여 순차적으로 용매 분획을 실시하였다. 아세톤 추출물과 EtOAc분획에 대하여 silica gel과 ODS column chromatographies를 실시하여 한 개의 lignan, 네 개의 tannins, 두 개의 steroids, 열한 개의 triterpenoid 화합물을 분리하였다. 분리된 화합물에 대해서 NMR, MS, IR spectroscopy data를 해석하여 procyanidin B3 (1), (+)-catechin (2), ent-fisetinidol-(4β→6)-catechin (3), ent-guibouritinidol-(4β→6)-catechin (4) 등 네 개의 tannin 화합물, β-sitosterol (5), doucosterol (16) 등 두 개의 steroid 화합물, 4,4',8',9-tetrahydroxy-3,3'-dimethoxy-7,9'-cyclolignan ((-)-olivil) (14) 한 개의 lignan 화합물, 3β-hydroxylup-20(29)-en-28-oic acid (betulinic acid) (6), 3β-hydroxyurs-12-en-28-oic acid (ursolic acid) (7), 2,19α-dihydroxy-3-oxours-1,12-dien-28-oic acid (fupenzic acid) (8), 3β,19α-dihydroxy-2- oxours-12-en-28-oic acid (2-oxo-pomolic acid) (9), 2α,3α,19α-trihydroxy-12-en-28-oic acid (euscaphic acid) (10), 2α,3β,19α-trihydroxy-12-en-28-oic acid (tormentic acid) (11), 2-hydroxymethyl A(1)nor-19α,24-dihydroxyurs-2,12-dien-28-oic acid (rosamultic acid) (12), 3β-O-(β-D-xylopyranosyl)-pomolic acid (ilexoside B) (13), 2α,19α-dihydroxy-3-oxo-12ursen-28-oic acid 28-O-β-D-glucopyranoside (15), 2α,3α,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (kagi-ichigoside F1) (17) and 2α,3β,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (rosamultin) (18) 등 열한 개의 triterpenoid 화합물의 구도를 동정하였다. 화합물 8, 9, 15는 찔레에서 처음 분리된 화합물이다. 찔레뿌리 추출물, 용매 분획물, 분리된 화합물에 대해서 항산화, 피부 미백(anti- melanogenesis and anti-tyrosinase), 피부 세포 보호 활성을 측정하였다. 아세톤 추출물, RMR-6, RMR-6-2, procyanidin B3 (1), ent-fisetinidol-(4β→6)-catechin (2)의 DPPH radical 소거활성은 79.1%, 74.3%, 70.8%, 88.2%, 72.5%로 나타났다(final concentration : 25 μg/mL). 화합물 1, 2, (+)-catechin (3), ent-guibouritinidol-(4β→6)-catechin (4)의 ABTs radical 소거 활성은 259.2 mgVCE/100mg, 270.3 mgVCE/100mg, 250.9 mgVCE/100mg, 208.5 mgVCE/100mg으로 나타났다. 또한, 이들 화합물의 DPPH radical 소거 활성은 195.9 mgVCE/100mg, 173.2 mgVCE/100mg, 208.0 mgVCE/100mg, 155.0 mgVCE/100mg으로 나타났다. 그리고, ORAC capacity는 491.1 mgVCE/100mg, 485.5 mgVCE/100mg, 547.3 mgVCE/100mg, 594.8 mgVCE/100mg으로 매우 높은 활성을 나타냈다. 화합물 4의 tyrosinase 활성 억제와 melanin 생합성 억제 효과는 IC50 값이 148.6 μg/mL와 49.3 μg/mL으로 나타났다. 화합물 2, 3, 4의 과산화소수에 의해 유도된 세포 손상에 대한 세포 보호 효과는 LD50 값이 88.3 μg/mL, 67.3 μg/mL, 162.4 μg/mL로 나타났고, UV에 의한 세포 손상에 대해서는 LD50 값이 74.6 μg/mL, 152.2 μg/mL, 105.3 μg/mL로 나타났다. 화합물 3과 4의 UV에 의해 유도된 collagen 저하 억제 효과는 IC50 값이 188.2 μg/mL, 92.4 μg/mL로 나타났고, elastin 저하 억제 효과는 IC50 값이 142.6 μg/mL, 122.3 μg/mL로 나타났다. 결론적으로, 찔레뿌리 추출물, 용매 분획물, 분리된 화합물은 높은 항산화 활성을 나타냈으며, 피부 미백과 피부 세포 보호 효과에서도 비교적 우수한 활성을 보였다.
Rosa multiflora, a deciduous shrub (Rosaceae), is widely distributed at the base of mountain or riverside worldwide and is also known as brier rose in many countries. The roots of Rosa multiflora have been used for the treatment of diabetes mellitus and rheumatoid arthritis in folk medicine. The dri...
Rosa multiflora, a deciduous shrub (Rosaceae), is widely distributed at the base of mountain or riverside worldwide and is also known as brier rose in many countries. The roots of Rosa multiflora have been used for the treatment of diabetes mellitus and rheumatoid arthritis in folk medicine. The dried and powdered Rosa multiflora roots were extracted with acetone, 80% aqueous EtOH and 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH, and H2O, successively. The repeated silica gel and ODS column chromatographies of the EtOAc fraction led to the isolation of a lignan, four tannins, two steroids and eleven triterpenoids. From the results of spectroscopic data including NMR, MS, and IR, they were identified to be procyanidin B3 (1), (+)-catechin (2), ent-fisetinidol-(4β→6)-catechin (3) and ent-guibouritinidol-(4β→6)-catechin (4) for four tannins, β-sitosterol (5) and doucosterol (16) for two steroids, 4,4',8',9-tetrahydroxy-3,3'-dimethoxy-7,9'- cyclolignan (-)-olivil (14) for a lignan and 3β-hydroxylup-20(29)-en-28-oic acid (betulinic acid) (6), 3β-hydroxyurs-12-en-28-oic acid (ursolic acid) (7), 2,19α-dihydroxy-3-oxours-1,12-dien-28-oic acid (fupenzic acid) (8), 3β,19α-dihydroxy-2- oxours-12-en-28-oic acid (2-oxo-pomolic acid) (9), 2α,3α,19α-trihydroxy-12-en-28-oic acid (euscaphic acid) (10), 2α,3β,19α-trihydroxy-12-en-28- oic acid (tormentic acid) (11), 2-hydroxymethyl A(1)nor-19α,24-dihydroxyurs-2,12-dien-28-oic acid (rosamultic acid) (12), 3β-O-(β-D-xylopyranosyl)-pomolic acid (ilexoside B) (13), 2α,19α-dihydroxy-3-oxo-12ursen-28-oic acid 28-O-β-D-gluco pyranoside (15), 2α,3α,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (kagi-ichigoside F1) (17) and 2α,3β,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (rosamultin) (18) for eleven triterpenoids. Compounds 8, 9 and 15 were isolated for the first time from the Rosa multiflora. The extract from the Rosa multiflora roots, the solvent fractions from the extract and the isolated compounds were evaluated for the antioxidant, skin whitening (anti-melanogenesis and anti-tyrosinase) and skin cell protective activities. DPPH radical scavenge activity of extracts RMR-6, RMR-6-2, procyanidin B3 (1) and ent-fisetinidol-(4β→6)-catechin (2) isolated from RMR were 79.1%, 74.3%, 70.8%, 88.2% and 72.5% at the final concentration of 25 μg/mL, respectively. ABTs radical scavenge activity of compounds 1, 2, 3 and 4 were showed 259.2 mgVCE/100mg, 270.3 mgVCE/100mg, 250.9 mgVCE/100mg and 208.5 mgVCE/100mg. DPPH radical scavenge activity of compounds 1, 2, 3 and 4 appeared as 195.9 mgVCE/100mg, 173.2 mgVCE/100mg, 208.0 mgVCE/100mg and 155.0 mgVCE/100mg, respectively. ORAC capacity of compounds 1, 2, 3 and 4 were 491.1 mgVCE/100mg, 485.5 mgVCE/100mg, 547.3 mgVCE/100mg and 594.8 mgVCE/100mg respctively. Ent-guibouritinidol-(4β→6)-catechin (4) exhibited inhibition effects on tyrosinase activity and melanin synthesis with IC50 of 148.6 μg/mL and 49.3 μg/mL, respectively. Compounds 2, 4 and (+)-catechin (3) exhibited cell protective effects on cytotoxicity induced by hydrogen peroxide with LD50 of 88.3 μg/mL, 162.4 μg/mL and 67.3 μg/mL, respectively and the effects on cytotoxicity induced by UV with LD50 of 74.6 μg/mL, 105.3 μg/mL and 152.2 μg/mL, respectively. Compounds 3 and 4 exhibited inhibition effects on reducing collagen induced by UV with IC50 of 188.2 μg/mL and 92.4 μg/mL, respectively and on reducing elastin with IC50 of 142.6 μg/mL and 122.3 μg/mL, respectively. Therefore, the extracts, fractions and compounds from the Rosa multiflora roots showed high antioxidant potentials, and also relatively excellent skin whitening and cell protective effect.
Rosa multiflora, a deciduous shrub (Rosaceae), is widely distributed at the base of mountain or riverside worldwide and is also known as brier rose in many countries. The roots of Rosa multiflora have been used for the treatment of diabetes mellitus and rheumatoid arthritis in folk medicine. The dried and powdered Rosa multiflora roots were extracted with acetone, 80% aqueous EtOH and 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH, and H2O, successively. The repeated silica gel and ODS column chromatographies of the EtOAc fraction led to the isolation of a lignan, four tannins, two steroids and eleven triterpenoids. From the results of spectroscopic data including NMR, MS, and IR, they were identified to be procyanidin B3 (1), (+)-catechin (2), ent-fisetinidol-(4β→6)-catechin (3) and ent-guibouritinidol-(4β→6)-catechin (4) for four tannins, β-sitosterol (5) and doucosterol (16) for two steroids, 4,4',8',9-tetrahydroxy-3,3'-dimethoxy-7,9'- cyclolignan (-)-olivil (14) for a lignan and 3β-hydroxylup-20(29)-en-28-oic acid (betulinic acid) (6), 3β-hydroxyurs-12-en-28-oic acid (ursolic acid) (7), 2,19α-dihydroxy-3-oxours-1,12-dien-28-oic acid (fupenzic acid) (8), 3β,19α-dihydroxy-2- oxours-12-en-28-oic acid (2-oxo-pomolic acid) (9), 2α,3α,19α-trihydroxy-12-en-28-oic acid (euscaphic acid) (10), 2α,3β,19α-trihydroxy-12-en-28- oic acid (tormentic acid) (11), 2-hydroxymethyl A(1)nor-19α,24-dihydroxyurs-2,12-dien-28-oic acid (rosamultic acid) (12), 3β-O-(β-D-xylopyranosyl)-pomolic acid (ilexoside B) (13), 2α,19α-dihydroxy-3-oxo-12ursen-28-oic acid 28-O-β-D-gluco pyranoside (15), 2α,3α,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (kagi-ichigoside F1) (17) and 2α,3β,19α-trihydroxy-12-en-28-oic acid 28-O-β-D-glucopyranoside (rosamultin) (18) for eleven triterpenoids. Compounds 8, 9 and 15 were isolated for the first time from the Rosa multiflora. The extract from the Rosa multiflora roots, the solvent fractions from the extract and the isolated compounds were evaluated for the antioxidant, skin whitening (anti-melanogenesis and anti-tyrosinase) and skin cell protective activities. DPPH radical scavenge activity of extracts RMR-6, RMR-6-2, procyanidin B3 (1) and ent-fisetinidol-(4β→6)-catechin (2) isolated from RMR were 79.1%, 74.3%, 70.8%, 88.2% and 72.5% at the final concentration of 25 μg/mL, respectively. ABTs radical scavenge activity of compounds 1, 2, 3 and 4 were showed 259.2 mgVCE/100mg, 270.3 mgVCE/100mg, 250.9 mgVCE/100mg and 208.5 mgVCE/100mg. DPPH radical scavenge activity of compounds 1, 2, 3 and 4 appeared as 195.9 mgVCE/100mg, 173.2 mgVCE/100mg, 208.0 mgVCE/100mg and 155.0 mgVCE/100mg, respectively. ORAC capacity of compounds 1, 2, 3 and 4 were 491.1 mgVCE/100mg, 485.5 mgVCE/100mg, 547.3 mgVCE/100mg and 594.8 mgVCE/100mg respctively. Ent-guibouritinidol-(4β→6)-catechin (4) exhibited inhibition effects on tyrosinase activity and melanin synthesis with IC50 of 148.6 μg/mL and 49.3 μg/mL, respectively. Compounds 2, 4 and (+)-catechin (3) exhibited cell protective effects on cytotoxicity induced by hydrogen peroxide with LD50 of 88.3 μg/mL, 162.4 μg/mL and 67.3 μg/mL, respectively and the effects on cytotoxicity induced by UV with LD50 of 74.6 μg/mL, 105.3 μg/mL and 152.2 μg/mL, respectively. Compounds 3 and 4 exhibited inhibition effects on reducing collagen induced by UV with IC50 of 188.2 μg/mL and 92.4 μg/mL, respectively and on reducing elastin with IC50 of 142.6 μg/mL and 122.3 μg/mL, respectively. Therefore, the extracts, fractions and compounds from the Rosa multiflora roots showed high antioxidant potentials, and also relatively excellent skin whitening and cell protective effect.
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