Isolation of Natural Naphthoquinones from Juglans regia and In Vitro Antioxidant and Cytotoxic Studies of Naphthoquinones and the Synthetic Naphthofuran Derivatives
- Authors: Mathiyazhagan K.1, Kumaran A.2, Arjun P.3
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Affiliations:
- Sri Ganesh Labs PVT Ltd.
- Corporate R&D Center, HLL Lifecare Ltd., Akkulam
- Department of Life Sciences, PRIST University
- Issue: Vol 44, No 3 (2018)
- Pages: 346-353
- Section: Article
- URL: https://journals.rcsi.science/1068-1620/article/view/228943
- DOI: https://doi.org/10.1134/S1068162018030111
- ID: 228943
Cite item
Abstract
The naphthoquinones and their derivatives containing hydroxyl group exhibit wide range of pharmacological activities, such as antioxidant, antibacterial, antiviral, anticancer, antimalarial, and antifungal activities. In particular, the antioxidant and anticancer behaviors of these compounds continue to draw attention of researchers. In the present communication, three natural naphthoquinones—juglone, lawsone, and plumbagin—isolated from the chloroform extract of nutshells of Juglans regia Linn. and two 1,4-naphthoquinone derivatives—ethyl-5-hydroxynaphtho[ 1,2-b]furan-3-carboxylate and diethylnaphtho[1,2-b:4,3-b′]difuran-3,4-dicarboxylate—and three 5-hydroxy- 1,4-naphthoquinone derivatives—diethyl-7-hydroxynaphtho[1,2-b:4,3-b']difuran-3,4-dicarboxylate,4-ethoxycarbonyl- 7-hydroxynaphtho[1,2-b:4,3-b']difuran-3-carboxylic acid, and 7-hydroxynaphtho[1,2-b:4,3-b']difuran-3,4- dicarboxylic acid were synthesized and examined for their in vitro antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) bioassays. In addition, the cytotoxicity test using human hepatocellular liver carcinoma cell line (HepG2) was carried out for all the compounds. The 5-hydroxy-1,4-naphthoquinone derivatives displayed almost equivalent scavenging activity in DPPH assay and higher activity in ABTS assay relative to ascorbic acid. On the other hand, naphthoquinones Juglone and Plumbagin showed lesser antioxidant activity, but higher cytotoxic activity than naphthofurans except for diethyl naphtho[1,2-b:4,3-b′]difuran-3,4-dicarboxylate, which showed excellent cytotoxic activity.
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About the authors
Kasinathan Mathiyazhagan
Sri Ganesh Labs PVT Ltd.
Author for correspondence.
Email: mathi10789@yahoo.co.in
India, Visakhapatnam, Andhra Pradesh, 530012
Alaganandam Kumaran
Corporate R&D Center, HLL Lifecare Ltd., Akkulam
Email: mathi10789@yahoo.co.in
India, Kerala, 695017
Pandian Arjun
Department of Life Sciences, PRIST University
Email: mathi10789@yahoo.co.in
India, Vallam, Thanjavur, Tamil Nadu, 613403