Torilis japonica belongs to Umbelliferae family, and previous bioactivity studied show anti-cancer and anti-melanogenesis activities. T. japonica is known as a rich source of sesquiterpenes. Recently, it has been found that torilin of T. japonica showed a hypopigmenting effect on melanogenesis. Ther...
Torilis japonica belongs to Umbelliferae family, and previous bioactivity studied show anti-cancer and anti-melanogenesis activities. T. japonica is known as a rich source of sesquiterpenes. Recently, it has been found that torilin of T. japonica showed a hypopigmenting effect on melanogenesis. Therefore, the objective of this study was to investigate the anti-melanogesis effects of torilin derivatives. The total methanolic extract was partitioned with n-hexane, CH2Cl2, EtOAc, n-BuOH and H2O. Further fractionation of n-hexane, CH2Cl2, EtOAc and n-BuOH-soluble fractions resulted in the isolation of three new sesquiterpenes, Epoxytorilinol (8), Elematorilone (9) and Cadinatoriloside (13) together with seventeen known compounds, torilin (1), 1β-1-hydroxytorilin (2), 11-acetoxy -8-propionyl-4-guaien-3-one (3), 11-O-acetyl-torilolone8-O-β-D-glucopyranoside (4), torilolone (5), 1β-hydroxytorilolone (6), 2α,7-dihydroxykessane (7), oxytorilolide (10), 1β-hydroxy-4(15),5E,10(14)-germacratriene (11), 4α,5,6,7,8,8α-hexahydro –4,8-dimethyl-6-(1- methylethenyl)-2(1H)-naphthalenone (12), p-hydroxy-benzaldehyde (14), 2-hydroxyhenzoate (15), optivanin (16) 7-hydroxy-4- chromone (17), liquiritigenin (18), uracil (19) and adenosine (20). Their structures were elucidated on the basis of spectroscopic methods such as 1D-NMR (1H, 13C), 2D-NMR (HMQC, HMBC, NOESY), CD spectrum, ESI-MS and HRESI-TOF-MS. Furthermore, all isolates were tested for their inhibitory effects on the melanin producion in ⍺-MSH- activated B16 melanoma cells, with arbutin as a postive control. as a result, most compounds showed remarkable inhibitory activities with IC50 values ranging from 80 uM. Thus, T. japonica might be a valuable candidate for melanin-associated hyperpigmentation disorders.
Torilis japonica belongs to Umbelliferae family, and previous bioactivity studied show anti-cancer and anti-melanogenesis activities. T. japonica is known as a rich source of sesquiterpenes. Recently, it has been found that torilin of T. japonica showed a hypopigmenting effect on melanogenesis. Therefore, the objective of this study was to investigate the anti-melanogesis effects of torilin derivatives. The total methanolic extract was partitioned with n-hexane, CH2Cl2, EtOAc, n-BuOH and H2O. Further fractionation of n-hexane, CH2Cl2, EtOAc and n-BuOH-soluble fractions resulted in the isolation of three new sesquiterpenes, Epoxytorilinol (8), Elematorilone (9) and Cadinatoriloside (13) together with seventeen known compounds, torilin (1), 1β-1-hydroxytorilin (2), 11-acetoxy -8-propionyl-4-guaien-3-one (3), 11-O-acetyl-torilolone8-O-β-D-glucopyranoside (4), torilolone (5), 1β-hydroxytorilolone (6), 2α,7-dihydroxykessane (7), oxytorilolide (10), 1β-hydroxy-4(15),5E,10(14)-germacratriene (11), 4α,5,6,7,8,8α-hexahydro –4,8-dimethyl-6-(1- methylethenyl)-2(1H)-naphthalenone (12), p-hydroxy-benzaldehyde (14), 2-hydroxyhenzoate (15), optivanin (16) 7-hydroxy-4- chromone (17), liquiritigenin (18), uracil (19) and adenosine (20). Their structures were elucidated on the basis of spectroscopic methods such as 1D-NMR (1H, 13C), 2D-NMR (HMQC, HMBC, NOESY), CD spectrum, ESI-MS and HRESI-TOF-MS. Furthermore, all isolates were tested for their inhibitory effects on the melanin producion in ⍺-MSH- activated B16 melanoma cells, with arbutin as a postive control. as a result, most compounds showed remarkable inhibitory activities with IC50 values ranging from 80 uM. Thus, T. japonica might be a valuable candidate for melanin-associated hyperpigmentation disorders.
Keyword
#sesquiterpene 사상자 torilin 멜라닌
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