Melanin is related to the color of the skin and hair, and protects skin against UV light. However, overexposure to UV radiation can lead to hyperpigmentation, melasma and skin cancer. Tyrosinase is the enzyme that catalyzes the initial steps in the formation of melanin. Therefore, inhibition of tyro...
Melanin is related to the color of the skin and hair, and protects skin against UV light. However, overexposure to UV radiation can lead to hyperpigmentation, melasma and skin cancer. Tyrosinase is the enzyme that catalyzes the initial steps in the formation of melanin. Therefore, inhibition of tyrosinase activity prevents hyperpigmentation and leads to skin whitening. In the course of screening tyrosinase inhibitory activity, CH2Cl2 and EtOAc-soluble fraction of aerial and underground parts of H. jaoinicus showed significant inhibition. The aerial and underground parts of Humulus japonicus (Moraceae) are called hop in South Korea and have been used as diuretic, antimutagen in oriental medicines. Further fractionation of CH2Cl2 and EtOAc-soluble fraction of aerial parts of H. japonicus led to the isolation of two new phenolic glycosides, humulusides A and B (1-2), together with ten phenolic compounds, acetic acid ethyl ester (3), p-salicylic acid (4), benzoic acid (5), benzaldehyde (6), 2-hydroxybenzoic acid (7) vanillic acid (8), isovanillin (9), acetoisovanillone (10), acetoveratrone (11), eugenol glucoside (12), twelve alkaloids, 4-hydroxycinnamamide (13), N-acetylamine (14), trans-N-coumaroyltyramine (15), cis-N-coumaroyltyramine (16), trans-N-feruloyltyramine (17), cis-N-feruloyltyramine (18), trans-cinnamoyl-p-hydroxybenzenethylamine (19), nicotinamide (20), uracil (21), indole-3-carboxylicacid (22), indole-3-carboxaldehyde (23) and 3-carbomethoxyindole (24), six megastigmanes, grasshopper ketone (25), (+)-epiloliolide (26), (-)-loliolide (27), (3R,6R,7E)-3-hydroxymegastigma-4,7-dien-9-one (28), 5,6-epoxy-3-hydroxy-7-megastigmen
-9-one (29), (+)-dehydrovomifoliol (30), six flavonoids, luteolin (35), apigenin (36),
4'-O-methylalpiniumisoflavone (37), cyranoside (38), cosmosiin (39), vitexin (40) and two coumarins, scopoletin (41) and isoscopoletin (42). Likewise, repeated separation of CH2Cl2 and EtOAc-soluble fraction of underground parts of H. japonicus led to the isolation of a phenolic compound, 2-hydroxybenzoate (6), a alkaloid, trans-cinnamoyl-p-hydroxybenzenethy
lamine (17), and four megastigmanes, 3-oxo-retro-a-ionol (31), dihydrovomifoliol (32), corchoionoside C (33), phaseic acid (34). Their structures were elucidated on the basis of spectroscopic methods such as 1D-NMR (1H, 13C), 2D-NMR (HMQC, HMBC) and ESI-MS. Among them, compounds 13 and 14 showed strong inhibitory effects on tyrosinase activity. These results revealed that the aerial and underground parts of H. japonicus might be developed as whitening product.
Melanin is related to the color of the skin and hair, and protects skin against UV light. However, overexposure to UV radiation can lead to hyperpigmentation, melasma and skin cancer. Tyrosinase is the enzyme that catalyzes the initial steps in the formation of melanin. Therefore, inhibition of tyrosinase activity prevents hyperpigmentation and leads to skin whitening. In the course of screening tyrosinase inhibitory activity, CH2Cl2 and EtOAc-soluble fraction of aerial and underground parts of H. jaoinicus showed significant inhibition. The aerial and underground parts of Humulus japonicus (Moraceae) are called hop in South Korea and have been used as diuretic, antimutagen in oriental medicines. Further fractionation of CH2Cl2 and EtOAc-soluble fraction of aerial parts of H. japonicus led to the isolation of two new phenolic glycosides, humulusides A and B (1-2), together with ten phenolic compounds, acetic acid ethyl ester (3), p-salicylic acid (4), benzoic acid (5), benzaldehyde (6), 2-hydroxybenzoic acid (7) vanillic acid (8), isovanillin (9), acetoisovanillone (10), acetoveratrone (11), eugenol glucoside (12), twelve alkaloids, 4-hydroxycinnamamide (13), N-acetylamine (14), trans-N-coumaroyltyramine (15), cis-N-coumaroyltyramine (16), trans-N-feruloyltyramine (17), cis-N-feruloyltyramine (18), trans-cinnamoyl-p-hydroxybenzenethylamine (19), nicotinamide (20), uracil (21), indole-3-carboxylicacid (22), indole-3-carboxaldehyde (23) and 3-carbomethoxyindole (24), six megastigmanes, grasshopper ketone (25), (+)-epiloliolide (26), (-)-loliolide (27), (3R,6R,7E)-3-hydroxymegastigma-4,7-dien-9-one (28), 5,6-epoxy-3-hydroxy-7-megastigmen
-9-one (29), (+)-dehydrovomifoliol (30), six flavonoids, luteolin (35), apigenin (36),
4'-O-methylalpiniumisoflavone (37), cyranoside (38), cosmosiin (39), vitexin (40) and two coumarins, scopoletin (41) and isoscopoletin (42). Likewise, repeated separation of CH2Cl2 and EtOAc-soluble fraction of underground parts of H. japonicus led to the isolation of a phenolic compound, 2-hydroxybenzoate (6), a alkaloid, trans-cinnamoyl-p-hydroxybenzenethy
lamine (17), and four megastigmanes, 3-oxo-retro-a-ionol (31), dihydrovomifoliol (32), corchoionoside C (33), phaseic acid (34). Their structures were elucidated on the basis of spectroscopic methods such as 1D-NMR (1H, 13C), 2D-NMR (HMQC, HMBC) and ESI-MS. Among them, compounds 13 and 14 showed strong inhibitory effects on tyrosinase activity. These results revealed that the aerial and underground parts of H. japonicus might be developed as whitening product.
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#Humulus japonicus tyrosinase inhibitory activity
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