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Molecules 2018, 23(4), 833; https://doi.org/10.3390/molecules23040833

Flavonoid 8-O-Glucuronides from the Aerial Parts of Malva verticillata and Their Recovery Effects on Alloxan-Induced Pancreatic Islets in Zebrafish

Graduate School of Biotechnology & Department of Oriental Medicine Biotechnology, Kyung-Hee University, Yongin 17104, Korea
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Author to whom correspondence should be addressed.
Academic Editor: Isabel C. F. R. Ferreira
Received: 20 February 2018 / Revised: 3 April 2018 / Accepted: 4 April 2018 / Published: 4 April 2018
(This article belongs to the Collection Bioactive Compounds)
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Abstract

Malva verticillata (Cluster mallow), a leafy vegetable that has been popular in East Asia for a long time, has also been used in herbal teas and medicines. The aqueous fraction of the aerial parts of Malva verticillata, exhibiting a very high quantity of flavonoids compared to the EtOAc and n-BuOH fractions, exhibited significant recovery effects on pancreatic islets damaged by alloxan in zebrafish larvae. Thus, the bioactive components responsible for this anti-diabetic activity were investigated. A new flavonoid glucuronide (1) and five known flavonoids were isolated from the aqueous fraction. Based on several spectroscopic methods, compound 1 was identified to be nortangeretin-8-O-β-d-glucuronide, and was named malvaflavone A. The A-ring of compound 1 had a 5,6,7,8-tetrahydroxy moiety, which rarely occurs in plant systems. Also 8-O-glucuronide attached to the flavonoid moiety was rarely occurred in plant system. Compounds 1, 3, 4, and 6 significantly improved the pancreatic islet size in zebrafish at 0.1 μM, and compounds 1 and 6 were found to block β-cell K+ channels in experiments with diazoxide. In ABTS, ORAC, and SOD assays, compounds 15 exhibited high anti-oxidant activities compared with quercetin and BHA (positive controls), indicating that the 8-O-glucuronide attached to the flavonoid moiety is a key structure for the expression of anti-oxidant activity. This is the first report of the isolation of compounds 16 from M. verticillata as well evaluated for anti-diabetic and anti-oxidant ativities. View Full-Text
Keywords: Malva verticillata; malvaflavone A; flavonoid 8-O-glucuronide; zebrafish; anti-diabetes; anti-oxidant Malva verticillata; malvaflavone A; flavonoid 8-O-glucuronide; zebrafish; anti-diabetes; anti-oxidant
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ko, J.-H.; Nam, Y.H.; Joo, S.-W.; Kim, H.-G.; Lee, Y.-G.; Kang, T.H.; Baek, N.-I. Flavonoid 8-O-Glucuronides from the Aerial Parts of Malva verticillata and Their Recovery Effects on Alloxan-Induced Pancreatic Islets in Zebrafish. Molecules 2018, 23, 833.

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