Comparative antioxidant, prooxidant and cytotoxic activity of sigmoidin A and eriodictyol

Planta medica
Solomon Habtemariam, E Dagne

Abstract

Sigmoidin A (SGN) is a prenylated flavanone derivative of eriodictyol (ERD) with reported moderate antioxidant, antimicrobial and anti-inflammatory activity. Since ERD and other structurally similar antioxidant phenolic compounds have been shown to induce prooxidative macromolecular damage and cytotoxicity in cancer cells, the comparative IN VITRO effects of these structural analogues on cancer cell viability and Cu(II)-dependent DNA damage were studied. In the presence of Cu(II) ions, both SGN and ERD (7.4-236 microM) caused comparable concentration-dependent pBR322 plasmid DNA strand scission. The DNA damage induced by SGN and ERD could be abolished by ROS scavengers, glutathione (GSH) and catalase as well as EDTA and a specific Cu(I) chelator neocuproine. Both ERD and SGN readily reduce Cu(II) to Cu(I) suggesting a prooxidative mechanism of DNA damage. In a cell free system, ERD and SGN did also show comparable radical scavenging activity. SGN was, however, by an order of magnitude more cytotoxic to cancer cells than ERD and this effect was significantly attenuated by GSH suggesting a prooxidative mechanism of cell death. A depletion of intracellular GSH level by SGN in cancer cells is also demonstrated.

Citations

Aug 16, 2014·Pharmacognosy Reviews·Katrin Sak
Mar 5, 2016·Evidence-based Complementary and Alternative Medicine : ECAM·Solomon Habtemariam
May 8, 2013·The Journal of Pharmacy and Pharmacology·Seyed Mohammad NabaviAli Mohammad Latifi
Sep 18, 2012·Pharmaceutical Biology·Solomon Habtemariam
Jul 18, 2015·Cancer Letters·Sylwia GorlachUrszula Lewandowska
Apr 13, 2015·Food Chemistry·Fernanda M F RoleiraFernanda Borges
Nov 16, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Roberta GualdaniSolomon Habtemariam
Oct 13, 2017·Nutrients·Tarun BelwalSolomon Habtemariam
Dec 22, 2017·International Journal of Molecular Sciences·Solomon Habtemariam
Jan 11, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Solomon Habtemariam
Sep 15, 2017·Evidence-based Complementary and Alternative Medicine : ECAM·Taiwo Olayemi ElufioyeSolomon Habtemariam
May 16, 2019·Journal of Cellular Physiology·Khashayar AfshariAmir Hossein Abdolghaffari
Aug 8, 2020·European Journal of Pharmacology·Rujuta R DeshpandeManisha Modak
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marcos Antonio Custódio Neto da SilvaJoão Ernesto de Carvalho

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