Chemical transformations of oxyresveratrol (trans-2,4,30,50-tetrahydroxystilbene)into a potent tyrosinase inhibitor and a strong cytotoxic agent (Record no. 48779)

MARC details
000 -LEADER
fixed length control field 02175nam a2200181Ia 4500
003 - CONTROL NUMBER IDENTIFIER
control field MX-MdCICY
005 - DATE AND TIME OF LATEST TRANSACTION
control field 20250625153944.0
040 ## - CATALOGING SOURCE
Transcribing agency CICY
090 ## - LOCALLY ASSIGNED LC-TYPE CALL NUMBER (OCLC); LOCAL CALL NUMBER (RLIN)
Classification number (OCLC) (R) ; Classification number, CALL (RLIN) (NR) B-14593
008 - FIXED-LENGTH DATA ELEMENTS--GENERAL INFORMATION
fixed length control field 250602s9999 xx |||||s2 |||| ||und|d
245 10 - TITLE STATEMENT
Title Chemical transformations of oxyresveratrol (trans-2,4,30,50-tetrahydroxystilbene)into a potent tyrosinase inhibitor and a strong cytotoxic agent
490 0# - SERIES STATEMENT
Volume/sequential designation Bioorganic & Medicinal Chemistry Letters, 16(21), p.5650-5653, 2006
520 3# - SUMMARY, ETC.
Summary, etc. From oxyresveratrol (trans-2,4,30,50-tetrahydroxystilbene 1), seven derivatives were prepared, including trans-2-methoxy- 4,30,50-trihydroxystilbene (2), trans-2,30-dimethoxy-4,50-dihydroxystilbene (3), trans-4,30-dimethoxy-2,50-dihydroxystilbene (4), trans-2,4,30,50-tetramethoxystilbene (5)and cis-2,4,30,50-tetramethoxystilbene (6), 2,4,30,50-tetrahydroxybibenzyl (7), and 2,4,30,50- tetramethoxybibenzyl (8). The tetrahydroxybibenzyl 7, a hydrogenation product of 1, exhibited more potent tyrosinase inhibitory activity than the parent compound, without cytotoxicity. A kinetic study revealed that 7 was a reversible and non-competitive inhibitor of mushroom tyrosinase with L-dopa as the substrate. Analysis of the Ki values indicated that 7 has a slightly higher affinity to the enzyme than 1. Compound 6, a tetra-O-methylated analogue of 1 with cis-configuration, was deprived of inhibitory effect on the enzyme tyrosinase, but showed very strong cytotoxicity against the human cancer cells KB, BC, and NCI-H187, with potency comparable to those of the anticancer agents ellipticine and doxorubicin. Data on the tyrosinase inhibitory activity and cytotoxicity of 1-8 indicated that O methylation on stilbene 1 destroyed anti-tyrosinase activity but generated cytotoxicity. Thus, facile preparations of a potent tyrosinase inhibitor (7)and a strong cytotoxic agent (6)from the natural product 1 were achieved through simple chemical reactions.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Likhitwitayawuid, K.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Sornsute, A.
856 40 - ELECTRONIC LOCATION AND ACCESS
Uniform Resource Identifier <a href="https://drive.google.com/file/d/1rUTRNdZIjPQU0mWwdpbpNyL9zO9ypMxM/view?usp=drivesdk">https://drive.google.com/file/d/1rUTRNdZIjPQU0mWwdpbpNyL9zO9ypMxM/view?usp=drivesdk</a>
Public note Para ver el documento ingresa a Google con tu cuenta: @cicy.edu.mx
942 ## - ADDED ENTRY ELEMENTS (KOHA)
Source of classification or shelving scheme Clasificación local
Koha item type Documentos solicitados
Holdings
Lost status Source of classification or shelving scheme Damaged status Not for loan Collection Home library Current library Shelving location Date acquired Total checkouts Full call number Date last seen Price effective from Koha item type
  Clasificación local     Ref1 CICY CICY Documento préstamo interbibliotecario 25.06.2025   B-14593 25.06.2025 25.06.2025 Documentos solicitados