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Cytotoxic and antioxidant activities of alkylated benzoquinones from Maesa lanceolata.

Abstract
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 (IC50 values 4.5, 2.2, 0.43 and 2.8 microg/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 (IC50 values 6.2 and 2.2 microg/mL, respectively), as well as cytotoxicities against SK-MEL, KB, BT-549 and SK-OV-3 carcinomas (IC50 values <1.1-4.2 microg/mL). All benzoquinones were found to be inactive against cell aggregation and cell adhesion assays, thus showing no effect on immune responses and inflammation.
AuthorsIlias Muhammad, Satoshi Takamatsu, Larry A Walker, Jaber S Mossa, Harry H S Fong, Farouk S El-Feraly
JournalPhytotherapy research : PTR (Phytother Res) Vol. 17 Issue 8 Pg. 887-91 (Sep 2003) ISSN: 0951-418X [Print] England
PMID13680818 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S.)
CopyrightCopyright 2003 John Wiley & Sons, Ltd.
Chemical References
  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Benzoquinones
  • Plant Extracts
Topics
  • Antineoplastic Agents, Phytogenic (administration & dosage, chemistry, pharmacology, therapeutic use)
  • Antioxidants (administration & dosage, chemistry, pharmacology, therapeutic use)
  • Benzoquinones (administration & dosage, chemistry, pharmacology, therapeutic use)
  • Cell Adhesion (drug effects)
  • Cell Aggregation (drug effects)
  • Cell Line, Tumor (drug effects)
  • Dose-Response Relationship, Drug
  • Fruit
  • HL-60 Cells (drug effects)
  • Humans
  • Inhibitory Concentration 50
  • Magnoliopsida
  • Phytotherapy
  • Plant Extracts (administration & dosage, chemistry, pharmacology, therapeutic use)
  • Plant Leaves
  • Structure-Activity Relationship

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