Bioactive constituents of oleanane-type triterpene saponins from the roots of<i>Glycyrrhiza glabra</i>

Wei, Juan-Hua; Zheng, Yun‐Feng; Li, Cunyu; Tang, Yuping; Peng, Guoping

doi:10.1080/10286020.2014.960857

Cited by 23 publications

(11 citation statements)

References 21 publications

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“…The configuration of the sugars of compounds 1 and 3 was determined by acid hydrolysis and GC experiments based of the literature procedure [ 6 , 9 ]. The specific steps were as follows: a solution of compounds 1–3 (1.0 mg each) in 1 N HCl (1 mL) was stirred at 90 °C for 2 h. After cooling, the solution was evaporated under a stream of N 2 .…”

Section: Methodsmentioning

confidence: 99%

“…Phytochemical studies have showed that triterpenoid saponins and flavonoids were the two of major kinds of active substances of Glycyrrhiza , which have a variety of pharmacological activities, including hepatoprotective [ 1 , 2 ], antiviral [ 3 ], anti-inflammatory [ 4 ] and antioxidative [ 5 ] effects. Recently, we reported the chemical constituents of G. uralensis and G. glabra , as well as their cytotoxic or neuraminidase bioactivities [ 6 , 7 ]. As part of our ongoing research on the genus Glycyrrhiza , an extensive phytochemical investigation on the roots of G. inflata has now led to the isolation of two new oleanane-type saponins 1 , 3 and nine known saponins 2 , 4–11 .…”

Section: Introductionmentioning

confidence: 99%

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Hepatoprotective Triterpene Saponins from the Roots of Glycyrrhiza inflata

et al. 2015

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Two novel oleanane-type triterpene saponins, licorice-saponin P2 (1) and licorice-saponin Q2 (3), together with nine known compounds 2, 4–11, have been isolated from the water extract of the roots of Glycyrrhiza inflata. The structures of these compounds were elucidated on the basis of spectroscopic analysis, including 2D-NMR experiments (1H–1H COSY, HSQC, HMBC and ROESY). In in vitro assays, compounds 2–4, 6 and 11 showed significant hepatoprotective activities by lowering the ALT and AST levels in primary rat hepatocytes injured by D-galactosamine (D-GalN). In addition, compounds 2–4, 6, 7 and 11 were found to inhibit the activity of PLA2 with IC50 values of 6.9 μM, 3.6 μM, 16.9 μM, 27.1 μM, 32.2 μM and 9.3 μM, respectively, which might be involved in the regulation of the hepatoprotective activities observed.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hepatoprotective Triterpene Saponins from the Roots of Glycyrrhiza inflata

et al. 2015

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“…In addition, similar triterpene saponins, such as licorice-saponin G2 (9) and araboglycyrrhizin (16), were also observed in G. uralensis, G. glabra, and G. inflate. Eleven triterpene saponins (2, 4, 5, 10-12, 14, 25, 26, 36, and 41) were also found both in G. uralensis and G. glabra, including uralsaponin B (2) [16,21], licorice-saponin B2 (4) [22,23], licorice-saponin C2 (5) [22,23], licorice-saponin H2 (10) [23,24], licorice-saponin J2 (11) [23,24], licorice-saponin K2 (12) [21,24], 18α-glycyrrhizic acid (14) [17], licorice-saponin M3 or uralsaponin T (25) [27,31], licorice-saponin N4 (26) [31,32], uralsaponin V (36) [21,27], and 3-O-β-d-glucuronopyranosylglycyrrhetinic acid (41) [21,27].…”

Section: Hepatoprotective Activitiesmentioning

confidence: 97%

Review of Constituents and Biological Activities of Triterpene Saponins from Glycyrrhizae Radix et Rhizoma and Its Solubilization Characteristics

Liu

et al. 2020

Molecules

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Glycyrrhizae Radix et Rhizoma is regarded as one of the most popular and commonly used herbal medicines and has been used in traditional Chinese medicine (TCM) prescriptions for over 2000 years. Pentacyclic triterpene saponins are common secondary metabolites in these plants, which are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid aglycone containing a hydrophilic sugar chain. This paper systematically summarizes the chemical structures of triterpene saponins in Glycyrrhizae Radix et Rhizoma and reviews and updates their main biological activities studies. Furthermore, the solubilization characteristics, influences, and mechanisms of Glycyrrhizae Radix et Rhizoma are elaborated. Solubilization of the triterpene saponins from Glycyrrhizae Radix et Rhizoma occurs because they contain the nonpolar sapogenin and water-soluble sidechain. The possible factors affecting the solubilization of Glycyrrhizae Radix et Rhizoma are mainly other crude drugs and the pH of the decoction. Triterpene saponins represented by glycyrrhizin from Glycyrrhizae Radix et Rhizoma characteristically form micelles due to amphiphilicity, which makes solubilization possible. This overview provides guidance regarding a better understanding of GlycyrrhizaeRadix et Rhizoma and its TCM compatibility, alongside a theoretical basis for the further development and utilization of Glycyrrhizae Radix et Rhizoma.

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“…Oleanolic acid (3b-hydroxy-olea-12-en-28-oic acid, OA) has been isolated from several plants, including Olea europaea L. , Glycyrrhiza sp. , Forsythia suspensa , Dendrobium sp ., and other plants [ 2 , 3 ]. A pentacyclic triterpenoid compound, OA has been used in hepatitis and cirrhosis patients for over 20 years in China because of its hepatoprotective effect [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Hypoxia Imaging and Biological Evaluation of the Radiosensitizing Effect of Oleanolic Acid

Wang

Xue

et al. 2018

BioMed Research International

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Background and Purpose The aim of this study was to evaluate the radiosensitizing effect of oleanolic acid (OA) on C6 rat glioma and the changes in tumor biology during radiosensitization therapy on 18F-fluoromisonidazole (18F-FMISO) positron emission tomography/computed tomography (PET/CT). Methods The radiosensitizing effect of OA on C6 tumors was assessed in vivo by measuring the tumor inhibitory rate and rat survival time. Meanwhile, rats with C6 tumors were imaged with 18F-FMISO PET/CT during radiosensitization therapy. Tumor-to-muscle ratio (TMR) of 18F-FMISO maximum uptake was calculated by region of interest analysis. Changes in tumor biology after therapy were assessed with immunohistochemical staining. 18F-FMISO uptake was analyzed in relation to expression of tumor biomarkers including hypoxia-inducible factor (HIF)-1α, glucose transporter (Glut-1), the proliferation antigen Ki67, tumor suppressor P53, and microvessel density (MVD). Results The results showed that OA combined with radiation inhibited the growth rates of tumors and prolonged the survival period of tumor-bearing rats effectively (χ2 = 12.5, p < 0.01). 18F-FMISO PET/CT indicated decreases in hypoxia after radiosensitization therapy. Statistical differences were observed in TMR of the irradiation group and OA combined with irradiation group (t = 3.32, p < 0.05). HIF-1α, Glut-1, Ki67, P53, and MVD expressions in tumors were downregulated by OA combined with radiation as well as with radiation alone. Additionally, there was a significant positive linear correlation between TMR and HIF-1α, Glut-1, Ki67, P53, and MVD. Conclusions These results suggest that OA has a radiosensitizing effect on C6 tumors in terms of tumor volume inhibition, survival extension, and multiple poor prognosis biological markers downregulation. 18F-FMISO PET/CT can be of value for tumor biology noninvasive capture and radiosensitization response evaluation.

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Bioactive constituents of oleanane-type triterpene saponins from the roots ofGlycyrrhiza glabra

Cited by 23 publications

References 21 publications

Hepatoprotective Triterpene Saponins from the Roots of Glycyrrhiza inflata

Hepatoprotective Triterpene Saponins from the Roots of Glycyrrhiza inflata

Review of Constituents and Biological Activities of Triterpene Saponins from Glycyrrhizae Radix et Rhizoma and Its Solubilization Characteristics

Hypoxia Imaging and Biological Evaluation of the Radiosensitizing Effect of Oleanolic Acid

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