Quantitation of phenylpropanoids and iridoids in insulin‐sensitising extracts of <i>Leonurus sibiricus</i> L. (Lamiaceae)

Pitschmann, Anna; Zehl, Martin; Heiss, Elke H.; Purevsuren, Sodnomtseren; Urban, Ernst; Dirsch, Verena M.; Glasl, Sabine

doi:10.1002/pca.2583

Cited by 22 publications

(11 citation statements)

References 12 publications

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“…The presence of 11 was noteworthy since it is not an ubiquitous compound, especially in the Stachys genus where it has been recognized only in a few species such as S. lavandulifolia [36], S. sieboldii [15], and S. tymphaea [8]. This compound resulted to be a constituent of other systematically related genera such as Leonurus [37,38], Lagochilus [39], and Sideritis [40]. …”

Section: Discussionmentioning

confidence: 99%

“…From recent studies on iridoid activities, 8-O-acetylharpagide (2) and ajugoside (1) resulted to be useful compounds in the treatment of diabetes mellitus since they were able to stimulate the cellular glucose intake and lower the glucose blood level [38]. Another target of iridoids for the antidiabetic activity is represented by the inhibitory action, verified by docking studies, on glycogen phosphorylase-a [48].…”

Section: Discussionmentioning

confidence: 99%

“…In fact, several plant species rich in iridoids have been largely used in traditional medicine for the treatment of diabetes, e.g., Scrophularia deserti Del. [49] and Leonurus sibiricus L. [38]. …”

Section: Discussionmentioning

confidence: 99%

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Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

Venditti

Frezza

Lorenzetti

et al. 2017

J Intercult Ethnopharmacol

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Background:The phytochemical analysis of Stachys alopecuros subsp. divulsa, an endemic Italian species, has been recently reported and has showed the presence of 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), and 4¢-O-galactopyranosyl-teuhircoside (5). In this paper, an in deep study of its glycosidic fraction with the aim to widen the knowledge on its secondary metabolites content is reported.Materials and Methods:Chromatographic techniques were used for the isolation of constituents while spectroscopic and spectrometric techniques were applied for the structures elucidation.Results:Besides the known constituents, all of them reconfirmed, ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7) were also identified among the iridoids while the phenolic components resulted to be chlorogenic acid (8), b-arbutin (9), verbascoside (10), and stachysoside A (11), instead.Conclusion:The iridoid pattern of S. alopecuros subsp. divulsa has been expanded with the identification of not previously reported compounds as well as for the phenolic fraction. Except for the reconfirmed verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported, and both the chemotaxonomic and pharmacological relevance of the isolated compounds is largely discussed.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

Venditti

Frezza

Lorenzetti

et al. 2017

J Intercult Ethnopharmacol

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“…In HepG2 hepatocellular carcinoma cells quercetin was found to mediate autophagy by release of Ca 2+ from intracellular stores [42] and to enhance apoptosis by induction of a positive feedback loop consisting of p53, miR-34a miRNA and SIRT1 [43]. The present study was performed to investigate short and long-term effects of quercetin and rutin on beta-cells [1,2]. While most studies which describe insulinotropic influences of flavonoids on beta-cells focus on short term effects, data on chronic exposure are lacking.…”

Section: Introductionmentioning

confidence: 99%

“…The present study was performed to identify LS extract compounds accounting for the observed effects on beta-cell viability, insulin release and electrophysiological behavior. We focused on the flavonoid quercetin and its glycoside rutin, two phytochemicals which could be identified as constituents of LS extracts by HPLC analyses [1,2] and which are known to exert comparable effects in different cell systems.…”

Section: Introductionmentioning

confidence: 99%

Quercetin Stimulates Insulin Secretion and Reduces the Viability of Rat INS-1 Beta-Cells

Kittl

Beyreis

Tumurkhuu

et al. 2016

Cell Physiol Biochem

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Background/Aims: Previously we described insulinotropic effects of Leonurus sibiricus L. plant extracts used for diabetes mellitus treatment in Traditional Mongolian Medicine. The flavonoid quercetin and its glycoside rutin, which exert anti-diabetic properties in vivo by interfering with insulin signaling in peripheral target tissues, are constituents of these extracts. This study was performed to better understand short- and long-term effects of quercetin and rutin on beta-cells. Methods: Cell viability, apoptosis, phospho-protein abundance and insulin release were determined using resazurin, annexin-V binding assays, Western blot and ELISA, respectively. Membrane potentials (V_mem), whole-cell Ca²⁺ (ICa)- and ATP-sensitive K⁺ (IK_ATP) currents were measured by patch clamp. Intracellular Ca²⁺ (Ca_i) levels were measured by time-lapse imaging using the ratiometric Ca²⁺ indicator Fura-2. Results: Rutin, quercetin and the phosphoinositide-3-kinase (PI3K) inhibitor LY294002 caused a dose-dependent reduction in cell viability with IC₅₀ values of ∼75 µM, ∼25 µM and ∼3.5 µM, respectively. Quercetin (50 µM) significantly increased the percentage of Annexin-V+ cells within 48 hrs. The mean cell volume (MCV) of quercetin-treated cells was significantly lower. Within 2 hrs, quercetin significantly decreased basal- and insulin-stimulated Akt(T308) phosphorylation and increased Erk1/2 phosphorylation, without affecting P-Akt(S473) abundance. Basal- and glucose-stimulated insulin release were significantly stimulated by quercetin. Quercetin significantly depolarized V_mem by ∼25 mV which was prevented by the K_ATP-channel opener diazoxide, but not by the L-type ICa inhibitor nifedipine. Quercetin significantly stimulated ICa and caused a 50% inhibition of IK_ATP. The effects on V_mem, ICa and IK_ATP rapidly reached peak values and then gradually diminished to control values within ∼1 minute. With a similar time-response quercetin induced an elevation in Ca_i which was completely abolished in the absence of Ca²⁺ in the bath solution. Rutin (50 µM) did not significantly alter the percentage of Annexin-V+ cells, MCV, Akt or Erk1/2 phosphorylation, insulin secretion, or the electrophysiological behavior of INS-1 cells. Conclusion: We conclude that quercetin acutely stimulates insulin release, presumably by transient K_ATP channel inhibition and ICa stimulation. Long term application of quercetin inhibits cell proliferation and induces apoptosis, most likely by inhibition of PI3K/Akt signaling.

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Isolation of three glucaric acids from Leonurus japonicus Houtt. by using high‐speed countercurrent chromatography combined with semi‐preparative high‐performance liquid chromatography

Jia

Zhang

et al. 2022

J of Separation Science

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The isomerism of glucaric acids and the complexity of the composition of Leonurus japonicus Houtt. increased the difficulty of the separation of glucaric acids from the herb. In the present study, three glucaric acids were isolated from Leonurus japonicus Houtt. by using high-speed countercurrent chromatography combined with semi-preparative high-performance liquid chromatography. Cation exchange resin chromatography was applied to remove the alkaloids and enrich the glucaric acid fractions. Preliminary separation of the glucaric acid extract by high-speed countercurrent chromatography was carried out at 45°C by using an optimized solvent system of ethyl acetate/n-butanol/formic acid/water (1:1:0.01:2, v/v/v/v) with satisfied stationary phase retention and separation factor. The semi-preparative high-performance liquid chromatography was used for further separation and purification of the target fractions, and three monomeric compounds were obtained with purities of 90.0, 91.0, and 95.3%. UV spectroscopy, NMR spectroscopy, and mass spectrometry were employed to identify their structures, which were assigned as 2-syringyl glucaric acid, 2,4-disyringyl glucaric acid, and 3,4-disyringyl glucaric acid, respectively, and 2,4-disyringyl glucaric acid was reported for the first time.

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Quantitation of phenylpropanoids and iridoids in insulin‐sensitising extracts of Leonurus sibiricus L. (Lamiaceae)

Abstract: HPLC-CAD analysis allowed sensitive quantitation of the selected marker compounds in Leonurus sibiricus, thereby providing a reliable tool for its quality control.

Cited by 22 publications

References 12 publications

Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.

Quercetin Stimulates Insulin Secretion and Reduces the Viability of Rat INS-1 Beta-Cells

Isolation of three glucaric acids from Leonurus japonicus Houtt. by using high‐speed countercurrent chromatography combined with semi‐preparative high‐performance liquid chromatography

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