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Synthesis of Glabridin Derivatives as Tyrosinase Inhibitors
Warunee Jirawattanapong,Chamnan Patarapanich,Ekarin Saifah 대한약학회 2009 Archives of Pharmacal Research Vol.32 No.5
A novel 3'',4''-dihydroglabridin was successfully prepared for studying on tyrosinase inhibitory activity. The result demonstrated that 3'',4''- dihydroglabridin exhibited higher activity than glabridin (IC50 value = 11.40 μM), which is probably due to the 4-substituted resorcinol skeleton and the lacking of double bond between carbon atom 3'' and 4'' on its structure giving more conformational flexibily to interact with the enzyme more effectively. In addition, various acylated derivatives were synthesized as glabridin prodrugs. The chemical and enzymatic hydrolysis of prodrugs revealed that the diacetate ester was rapidly hydrolyzed by porcine liver esterase with the half-life of 2.36 minute, while those of the dihexanoate was 14.8 hour. Both of them were sufficiently stable in phosphate buffer, both pH 5.5 and 7.4, at 37℃ with more than 15 days half-life.
A New Sesquiterpene and Other Terpenoid Constituents of Chisocheton penduliflorus
Phongmaykin, Jarinporn,Kumamoto, Takuya,Ishikawa, Tsutomu,Suttisri, Rutt,Saifah, Ekarin 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.1
A new aromadendrane sesquiterpene, allo-aromadendrane-10${\alpha}$, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane-10${\beta}$, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.
A New Sesquiterpene and Other Terpenoid Constituents ofChisocheton penduliflorus
Jarinporn Phongmaykin,Takuya Kumamoto,Rutt Suttisri,Tsutomu Ishikawa,Ekarin Saifah 대한약학회 2008 Archives of Pharmacal Research Vol.31 No.1
A new aromadendrane sesquiterpene, allo-aromadendrane-10α, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane- 10 β, 14-diol (2) and allo-aromadendrane-10 β, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.