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Article

Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species

1
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
2
Department of Anatomy, Faculty of Science, Mahidol University, Ratchathewi, Bangkok 10400, Thailand
*
Author to whom correspondence should be addressed.
Academic Editor: Chih-Chien Lin
Received: 22 April 2021 / Revised: 24 May 2021 / Accepted: 31 May 2021 / Published: 3 June 2021
Possessing the quinone moiety, ilimaquinone (1), a sponge–derived sesquiterpene quinone, has been hypothesised to express its cytotoxicity through a redox cycling process, yielding active product(s) that can cause DNA damage. To determine the DNA damaging effects of 1 and examine whether a redox transformation may participate in its functions, the DNA damaging properties of 1, the corresponding hydroquinone (2) and hydroquinone triacetates (3) and their 5-epimeric counterparts (46) were tested and compared. When incubated directly with plasmid DNA, the hydroquinones were the only active species capable of cleaving the DNA. In cell-based assays, however, the quinones and hydroquinone triacetates were active in the same range as that of the corresponding hydroquinones, and all damaged the cellular DNA in a similar manner. The in situ reduction of 1 and 4 were supported by the decreases in the cytotoxicity when cells were pre-exposed to dicoumarol, an NAD(P)H:quinone oxidoreductase 1 (NQO1) inhibitor. The results confirmed the DNA damaging activities of the ilimaquinones 1 and 4, and indicated the necessity to undergo an in-situ transformation into the active hydroquinones, thereby exerting the DNA damaging properties as parts of the cytotoxic mechanisms. View Full-Text
Keywords: sesquiterpene quinones; cytotoxicity; redox cycling; marine natural products sesquiterpene quinones; cytotoxicity; redox cycling; marine natural products
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MDPI and ACS Style

Jiso, A.; Yurasakpong, L.; Janta, S.; Chaithirayanon, K.; Plubrukarn, A. Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species. Sci. Pharm. 2021, 89, 26. https://0-doi-org.brum.beds.ac.uk/10.3390/scipharm89020026

AMA Style

Jiso A, Yurasakpong L, Janta S, Chaithirayanon K, Plubrukarn A. Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species. Scientia Pharmaceutica. 2021; 89(2):26. https://0-doi-org.brum.beds.ac.uk/10.3390/scipharm89020026

Chicago/Turabian Style

Jiso, Apisada, Laphatrada Yurasakpong, Sirorat Janta, Kulathida Chaithirayanon, and Anuchit Plubrukarn. 2021. "Exerting DNA Damaging Effects of the Ilimaquinones through the Active Hydroquinone Species" Scientia Pharmaceutica 89, no. 2: 26. https://0-doi-org.brum.beds.ac.uk/10.3390/scipharm89020026

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