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Flavonoid 8-O-Glucuronides from the Aerial Parts of Malva verticillata and Their Recovery Effects on Alloxan-Induced Pancreatic Islets in Zebrafish
- Source :
- Molecules, Vol 23, Iss 4, p 833 (2018), Molecules; Volume 23; Issue 4; Pages: 833, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
- Publication Year :
- 2018
- Publisher :
- MDPI AG, 2018.
-
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 1–5 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 1–6 from M. verticillata as well evaluated for anti-diabetic and anti-oxidant ativities.
- Subjects :
- 0301 basic medicine
Flavonoid
Pharmaceutical Science
Article
Analytical Chemistry
lcsh:QD241-441
Islets of Langerhans
03 medical and health sciences
chemistry.chemical_compound
Glucuronides
malvaflavone A
lcsh:Organic chemistry
Alloxan
Drug Discovery
medicine
Animals
Moiety
Malva verticillata
anti-diabetes
Physical and Theoretical Chemistry
chemistry.chemical_classification
Malva
030109 nutrition & dietetics
ABTS
biology
Plant Extracts
Chemistry
anti-oxidant
Pancreatic islets
fungi
Organic Chemistry
food and beverages
flavonoid 8-O-glucuronide
zebrafish
Plant Components, Aerial
biology.organism_classification
030104 developmental biology
medicine.anatomical_structure
Biochemistry
Chemistry (miscellaneous)
Molecular Medicine
Quercetin
Glucuronide
Subjects
Details
- ISSN :
- 14203049
- Volume :
- 23
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....882fb27e29e0f97636be1eba62e507cb