Synthesis and Biological Activity of trans-Tiliroside Derivatives as Potent Anti-Diabetic Agents

Zhu, Yujin; Zhang, Yanjun; Liu, Yi; Chu, Hongwan; Duan, Hong‐Quan

doi:10.3390/molecules15129174

Cited by 30 publications

(20 citation statements)

References 24 publications

(26 reference statements)

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“…Due to the very interesting biological activities observed for tiliroside, reported the synthesis and biological activity of trans ‐tiliroside derivatives, particularly as potent antidiabetic agents. These derivatives were all characterized using 1 H NMR and 13 C NMR (1D, and 2D), HR‐MS, and IR (Zhu, Zhang, Liu, Chu, & Duan, ). Unfortunately, no other papers report other synthetic approaches in order to confirm, and to improve, the interesting antidiabetic activity of this flavonoid and/or its derivatives.…”

Section: Quantitative Analysismentioning

confidence: 99%

“…Guided by these outcomes, Zhu et al. () assayed the antidiabetic activity of tiliroside's derivatives with a modified phenolic ring in the cinnamoyl group (Figure ).…”

Section: Activity Of Tiliroside Derivativesmentioning

confidence: 99%

“…The results showed that modification of the benzene ring in the cinnamoyl group with electron‐withdrawing groups (cyano and chloride as in 7c and 7 h) in the para and/or meta position resulted in an activity level higher than that of tiliroside. The EC 50 for compounds 7a, 7c, and 7 h was equal to 0.109, 0.048, and 0.011 μM, respectively, exhibiting a stronger glucose uptake‐inducing potential than tiliroside and metformin (ED 50 values were 0.155 and 0.270 μM, respectively; Zhu et al., ).…”

Section: Activity Of Tiliroside Derivativesmentioning

confidence: 99%

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A Review on the Dietary Flavonoid Tiliroside

Grochowski

Locatelli

Granica

et al. 2018

Comp Rev Food Sci Food Safe

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Among flavonoid derivatives, tiliroside is a flavonoid contained in several edible plants or specific plant parts (fruits, leaves, or roots). These parts are often widely used as both food and medicines, in the treatment of various ailments and, in some cases, as food supplements. Considering the easy access to many publications concerning tiliroside and the lack of a review that summarizes the current progress in studies on its safety, efficacy, and presence in the plant kingdom, we present here a review paper on tiliroside and its principal derivatives. The paper also highlights the basic knowledge regarding this molecule, its derivatives, and the analytical approaches used for extraction and quantification, as well as reports on the biological activities against different key enzymes linked to various human diseases. The reported information is also devoted to highlighting the concept "learn from nature to discover new products," particularly in the development of new drugs, food supplements, and nutraceuticals, starting from a natural lead compound such as tiliroside and improving its biological activities (and selectivities) against a specific target for therapeutic purposes.

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Section: Quantitative Analysismentioning

confidence: 99%

“…Guided by these outcomes, Zhu et al. () assayed the antidiabetic activity of tiliroside's derivatives with a modified phenolic ring in the cinnamoyl group (Figure ).…”

Section: Activity Of Tiliroside Derivativesmentioning

confidence: 99%

Section: Activity Of Tiliroside Derivativesmentioning

confidence: 99%

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A Review on the Dietary Flavonoid Tiliroside

Grochowski

Locatelli

Granica

et al. 2018

Comp Rev Food Sci Food Safe

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“…1), is the major component of AP extracts. Tiliroside has been reported to exhibit the following: Anti-diabetic properties by enhancing glucose consumption by insulin-resistant HepG2 cells (11,12); antihypertensive and vasorelaxant effects in resistance arteries (13); anti-hyperglycemic, anti-hyperlipidemic and antioxidant activities (14); as well as an inhibitory effect on important human liver cytochrome p450 enzymes (15). Tiliroside and two other flavonoids have been analyzed in vitro for their antioxidant properties and in vivo for their anti-inflammatory properties.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tiliroside, the major component of Agrimonia pilosa Ledeb ethanol extract, inhibits MAPK/JNK/p38-mediated inflammation in lipopolysaccharide-activated RAW 264.7 macrophages

Jin

Song

Wang

et al. 2016

Experimental and Therapeutic Medicine

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Abstract. In the present study, the in vivo anti-inflammatory activity of Agrimonia pilosa Ledeb (AP) ethanol extract was confirmed in experimental animal models, including xylene-induced ear edema in mice and carrageenan-induced paw edema in rats. Tiliroside, the major component of AP extract, was isolated and purified by high-performance liquid chromatography. The anti-inflammatory mechanism of tiliroside was then examined using lipopolysaccharide (LPS)-activated RAW 264.7 macrophage cells. An MTT assay was used to determine cytotoxicity and a Griess assay was used to determine nitric oxide (NO) production. Concentration levels of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) were determined by enzyme-linked immunosorbent assay. Protein expression levels of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), phosphorylated (p)-extracellular signal-regulated kinase (ERK) 1/2, p-c-Jun N-terminal kinases (JNK), p-p38 and inhibitor of κB-α were detected by western blot analysis. AP ethanol extract was revealed to inhibit xylene-induced ear edema in mice and carrageenan-induced paw edema in rats. Tiliroside significantly suppressed the overproduction of NO (P<0.01), but revealed no notable inhibition of the release of TNF-α and IL-6. In addition, tiliroside significantly downregulated the elevated expression levels of iNOS and COX-2 induced by LPS (P<0.01). The phosphorylation of JNK and p38 proteins were also significantly inhibited (P<0.01), however, tiliroside exhibited no obvious inhibition on the phosphorylation of ERK 1/2 and the degradation of IκB-α protein.In conclusion, the anti-inflammatory molecular mechanism of tiliroside may involve the downregulation of iNOS and COX-2 protein expression levels, and the inactivation of mitogen-activated protein kinase (MAPK)/JNK, in addition to the MAPK/p38 signaling pathway. IntroductionAgrimonia pilosa Ledeb (Rosaceae; AP) is a perennial herbaceous flowering plant distributed in the temperate regions of the Northern hemisphere, including Asia. As a traditional medicinal plant, it has been used for the treatment of abdominal pain, sore throat, headaches, bloody discharge, parasitic infections and eczema (1). Pharmacological research has revealed that AP extracts possess diverse pharmacological properties, including antinociceptive (1), antiplatelet (2) and antihemostatic effects (3), in addition to antioxidant (4), antiviral (5), antitumor (6), anti-inflammatory, anti-allergic (7,8), anti-microbial (9) and anti-hyperglycemic (10) activity, amongst others. Tiliroside, a glycosidic flavonoid (Fig. 1), is the major component of AP extracts. Tiliroside has been reported to exhibit the following: Anti-diabetic properties by enhancing glucose consumption by insulin-resistant HepG2 cells (11,12); antihypertensive and vasorelaxant effects in resistance arteries (13); anti-hyperglycemic, anti-hyperlipidemic and antioxidant activities (14)

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New Activities for Isolated Compounds fromConvolvulus austro-aegyptiacusas Anti-ulcerogenic, Anti-Helicobacter pyloriand Their Mimic Synthesis Using Bio-guided Fractionation

et al. 2015

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Bio-guided fractionation of the total alcoholic extract of Convolvulus austro-aegyptiacus was screened for its anti-ulcerogenic activity, using an absolute-ethanol-induced ulcer model at 500 and 1000 mg/kg doses. Two compounds were isolated from the butanol extract of C. austro-aegyptiacus and identified by H and C nuclear magnetic resonance as scopoletin and scopolin. The isolated compounds (50 mg/kg) showed a remarkable anti-ulcerogenic activity because they exhibited control-ulcer protection by 16.7% and 90.8%, respectively. The acute toxicity study showed that the extract is highly safe; the median lethal dose (LD was more than 4000 mg/kg. Moreover, the obtained results were confirmed by the sub-chronic toxicity because the rats that have been administered 1000 mg/kg of the extract for 15 consecutive days showed no alteration in the liver and kidney functions. Copyright © 2015 John Wiley & Sons, Ltd.

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Synthesis and Biological Activity of trans-Tiliroside Derivatives as Potent Anti-Diabetic Agents

Cited by 30 publications

References 24 publications

A Review on the Dietary Flavonoid Tiliroside

A Review on the Dietary Flavonoid Tiliroside

Tiliroside, the major component of Agrimonia pilosa Ledeb ethanol extract, inhibits MAPK/JNK/p38-mediated inflammation in lipopolysaccharide-activated RAW 264.7 macrophages

New Activities for Isolated Compounds fromConvolvulus austro-aegyptiacusas Anti-ulcerogenic, Anti-Helicobacter pyloriand Their Mimic Synthesis Using Bio-guided Fractionation

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