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

Ko, Jung‐Hwan; Nam, Youn Hee; Joo, Susanna; Kim, Hyoung‐Geun; Lee, Yeong‐Geun; Kang, Tong Ho; Baek, Nam‐In

doi:10.3390/molecules23040833

Cited by 21 publications

(44 citation statements)

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“…As shown in Table 1, LSE is mainly composed of Q3G and isoquercetin, which are considered to contribute to their biological properties in addition to quercetin and kaempferol. Previous studies have indicated that Q3G, a major antioxidative quercetin metabolite in human plasma, may exert antioxidant effects on alloxan-induced pancreatic islet damage in zebrafish [42]. Additionally, Q3G is reported to be as effective as quercetin in ameliorating insulin resistance by regulating the insulin receptor substrate 1 (IRS-1) function of the endothelium [43].…”

Section: Discussionmentioning

confidence: 99%

Flavonoids Identification and Pancreatic Beta-Cell Protective Effect of Lotus Seedpod

et al. 2020

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Oxidative stress is highly associated with the development of diabetes mellitus (DM), especially pancreatic beta-cell injury. Flavonoids derived from plants have caused important attention in the prevention or treatment of DM. Lotus seedpod belongs to a traditional Chinese herbal medicine and has been indicated to possess antioxidant, anti-age, anti-glycative, and hepatoprotective activities. The purpose of this study was to demonstrate the pancreatic beta-cell protective effects of lotus seedpod aqueous extracts (LSE) against oxidative injury. According to HPLC/ESI-MS-MS method, LSE was confirmed to have flavonoids derivatives, especially quercetin-3-glucuronide (Q3G). In vitro, LSE dose-dependently improved the survival and function of rat pancreatic beta-cells (RIN-m5F) from hydrogen peroxide (H2O2)-mediated loss of cell viability, impairment of insulin secretion, and promotion of oxidative stress. LSE showed potential in decreasing the H2O2-induced occurrence of apoptosis. In addition, H2O2-triggered acidic vesicular organelle formation and microtubule-associated protein light chain 3 (LC3)-II upregulation, markers of autophagy, were increased by LSE. Molecular data explored that antiapoptotic and autophagic effects of LSE, comparable to that of Q3G, might receptively be mediated via phospho-Bcl-2-associated death promoter (p-Bad)/B-cell lymphoma 2 (Bcl-2) and class III phosphatidylinositol-3 kinase (PI3K)/LC3-II signal pathway. In vivo, LSE improved the DM symptoms and pancreatic cell injury better than metformin, a drug that is routinely prescribed to treat DM. These data implied that LSE induces the autophagic signaling, leading to protect beta-cells from oxidative stress-related apoptosis and injury.

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Section: Discussionmentioning

confidence: 99%

Flavonoids Identification and Pancreatic Beta-Cell Protective Effect of Lotus Seedpod

et al. 2020

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“…Each of the solvent Frs-EtOAc, n-BuOH, and aqueous-and compounds 1-4 were evaluated for their recovery effects against alloxan-induced PI damage in zebrafish larvae. Alloxan, a well known diabetogenic chemical, is reported to decrease β-cell mass in PIs [3]. Alloxan treatment significantly decreased PI size by 44.3% (p<0.0001) compared to the normal group (Figures 2 A, B, D, and E).…”

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confidence: 91%

“…Diabetes mellitus is one of the leading causes of mortality and disability worldwide and their relationship with pancreatic -cell in both patients and animal models was well known in several literatures [1][2][3]. Allopathic drugs for diabetes mellitus are limited due to a variety of side effects [4].…”

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confidence: 99%

“…Malva verticillata (Cluster mallow), an annual vegetable, has been used to make herbal tea as well as medicine in Far East Asia. Several pharmacological effect of the plant such as anti-cancer, immunomodulation, NK anti-tumor, anti-diabetes and anti-oxidant activities were reported by far [3,7,8]. Its seeds have also been used in traditional Chinese medicine for the treatment of various diseases including diabetes [9].…”

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confidence: 99%

“…The safety of M. verticillata was vertified by the Korea Ministry of Food and Drug Safety (KMFDS) and the Codex Alimentarius Commission (CAC). In our preliminary study, the toxicity of the EtOAc, n-BuOH, and aqueous Frs from M. verticillata was evaluated through zebrafish embryos survival rate test and the LC 50 values of them were determined to be 91.5, 270.9 and 401.1 μg/mL, respectively [3]. Each of the solvent Frs-EtOAc, n-BuOH, and aqueous-and compounds 1-4 were evaluated for their recovery effects against alloxan-induced PI damage in zebrafish larvae.…”

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confidence: 99%

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Phenolic Compounds from the Aerial Parts of Malva verticillata and their Anti-diabetic Effect

Nuankaew

Joo

et al. 2018

Natural Product Communications

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The EtOAc, n-BuOH, and aqueous fractions from the aerial parts of Malva verticillata have been shown to promote significant recovery from alloxan-induced pancreatic islet (PI) damage in zebrafish larvae at 10 μg/mL. Therefore, this study aimed to identify the principal active components of these plant parts and their pharmacological properties. Repeated SiO 2 and octadecyl SiO 2 column chromatography with the aerial parts of M. verticillata led to isolation of four phenolic compounds; these compounds were identified as benzyl--D-galactopyranoside (1), (-)-secoisolariciresinol-9′-O--D-glucopyranoside (2), transferulic acid (3), and trans-ferulic acid methyl ester (4) on the basis of physicochemical and spectroscopic analyses including infrared, nuclear magnetic resonance, and fast atom bombardment-mass spectroscopy. Compounds 1-4 were first isolated from M. verticillata in this study. Furthermore, compounds 1-4 recovered alloxan-induced PI damage in zebrafish. Especially, compound 3 recovered the size of the injured PIs by 83.8% (p=0.0007) compared to the alloxaninduced group, while compound 4 by 33.4% (p=0.0072). It is the first report that trans-ferulic acid (3) exhibited the protective effect on zebrafish larvae PIs damaged by alloxan.

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Metabolite profiling reveals organ‐specific flavone accumulation in Scutellaria and identifies a scutellarin isomer isoscutellarein 8‐O‐β‐glucuronopyranoside

et al. 2021

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Scutellaria is a genus of plants containing multiple species with well‐documented medicinal effects. S. baicalensis and S. barbata are among the best‐studied Scutellaria species, and previous works have established flavones to be the primary source of their bioactivity. Recent genomic and biochemical studies with S. baicalensis and S. barbata have advanced our understanding of flavone biosynthesis in Scutellaria . However, as over several hundreds of Scutellaria species occur throughout the world, flavone biosynthesis in most species remains poorly understood. In this study, we analyzed organ‐specific flavone profiles of seven Scutellaria species, including S. baicalensis , S. barbata , and two species native to the Americas ( S. wrightii to Texas and S. racemosa to Central and South America). We found that the roots of almost all these species produce only 4′‐deoxyflavones, while 4′‐hydroxyflavones are accumulated exclusively in their aerial parts. On the other hand, S. racemosa and S. wrightii also accumulated high levels of 4′‐deoxyflavones in their aerial parts, different with the flavone profiles of S. baicalensis and S. barbata . Furthermore, our metabolomics and NMR study identified the accumulation of isoscutellarein 8‐ O ‐β‐glucuronopyranoside, a rare 4′‐hydroxyflavone, in the stems and leaves of several Scutellaria species including S. baicalensis and S. barbata , but not in S. racemosa and S. wrightii . Distinctive organ‐specific metabolite profiles among Scutellaria species indicate the selectivity and diverse physiological roles of flavones.

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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

Cited by 21 publications

References 42 publications

Flavonoids Identification and Pancreatic Beta-Cell Protective Effect of Lotus Seedpod

Flavonoids Identification and Pancreatic Beta-Cell Protective Effect of Lotus Seedpod

Phenolic Compounds from the Aerial Parts of Malva verticillata and their Anti-diabetic Effect

Metabolite profiling reveals organ‐specific flavone accumulation in Scutellaria and identifies a scutellarin isomer isoscutellarein 8‐O‐β‐glucuronopyranoside

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