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Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata
Author(s) -
Muhammad Ilias,
Takamatsu Satoshi,
Walker Larry A.,
Mossa Jaber S.,
Fong Harry H. S.,
ElFeraly Farouk S.
Publication year - 2003
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.1237
Subject(s) - antioxidant , chemistry , benzoquinone , cytotoxic t cell , ether , ic50 , stereochemistry , quinone , pharmacognosy , cytotoxicity , cell culture , in vitro , biochemistry , biological activity , biology , organic chemistry , genetics
The natural and semi‐synthetic analogs of substituted 1,4‐benzoquinones were evaluated for in vitro cytotoxic and antioxidant activities. Maesanin, dihydromaesanin, maesanin dimethyl ether and isomeric mixtures of 3‐[(Z)‐10′‐pentadecenyl]‐benzoquinone derivatives exhibited cytotoxic activity against HL‐60 cell line (IC 50 values 4.5, 2.2, 0.43 and 2.8 µg/mL, respectively), while it was found to be inactive against ROS (Reactive Oxygen Species) generation in HL‐60. In contrast, the isomeric acylated benzoquinones with shorter alkyl substituents, namely, 2‐acetoxy‐5‐hydoxy‐6‐methyl‐3‐tridecyl‐1,4‐benzoquinone and 2‐hydoxy‐5‐acetoxy‐6‐methyl‐3‐tridecyl‐1,4‐benzoquinone showed most prominent antioxidant and antiproliferative effect on HL‐60 (IC 50 values 6.2 and 2.2 µg/mL, respectively), as well as cytotoxicities against SK‐MEL, KB, BT‐549 and SK‐OV‐3 carcinomas (IC 50 values <1.1–4.2 µg/mL). All benzoquinones were found to be inactive against cell aggregation and cell adhesion assays, thus showing no effect on immune responses and inammation. Copyright © 2003 John Wiley & Sons, Ltd.