Triterpenoids from Hippophae rhamnoides L. and Their Nitric Oxide Production-Inhibitory and DPPH Radical-Scavenging Activities

Yang, Zhigang; Li, Heran; Wang, Liyan; Li, Yonghai; Lu, Shunguang; Wen, Xiufeng; Wang, Jue; Daikonya, Akihiro; Kitanaka, Susumu

doi:10.1248/cpb.55.15

Cited by 82 publications

(54 citation statements)

References 16 publications

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“…We have evaluated the OA ability to scavenge three radical species (ABTS+, DPPH and peroxyl), finding that it can capture ABTS+ radicals in a moderate and dose-dependent manner, but it lacks the ability to scavenge DPPH species. These results are in agreement with those previously provided by other authors (Yang et al, 2007;Wang et al, 2010;Allouche et al, 2011).…”

Section: Discussionsupporting

confidence: 94%

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Free radical scavenging and α-glucosidase inhibition, two potential mechanisms involved in the anti-diabetic activity of oleanolic acid

et al. 2016

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SUMMARY:This work investigates the role of oleanolic acid (OA), isolated from the olive (Olea europaea L.) leaf, as a radical scavenger and inhibitor of the hydrolyzing enzymes of dietary carbohydrates. New evidence is provided showing that OA may capture 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) and peroxyl radicals, and also exert a strong and non-competitive inhibition of α-glucosidase (IC 50 10.11 ± 0.30 µM). The kinetic and spectrometric analyses performed indicate that OA interacts with this enzyme inside a hydrophobic pocket, through an endothermic and non spontaneous process of a hydrophobic nature. These are two possible mechanisms by which OA may facilitate a better control of post-prandial hyperglycaemia and oxidative stress, so contributing to preserving insulin signalling. Obesity, insulin resistance and Type 2 Diabetes Mellitus are considered the first pandemics of the 21st century. In this sense, OA might be used in future preventive and therapeutic strategies, as an ingredient in new drugs and functional foods.KEYWORDS: Anti-diabetic activity; Antioxidant; α-glucosidase inhibitor; Olea europaea; Oleanolic acid RESUMEN: La Captación de radicales libres y la inhibición de α-glucosidasa, dos posibles mecanismos involucrados en la actividad antidiabética del ácido oleanólico. Este trabajo estudia el papel del ácido oleanólico (OA), aislado de la hoja de olivo, como secuestrador de radicales libres e inhibidor de enzimas implicados en la hidrolisis de los carbohidratos de la dieta, dos mecanismos por los que el triterpeno podría mitigar la hiperglicemia postprandial y el estrés oxidativo. Se aportan nuevas evidencias que muestran que el OA puede capturar radicales ácido 2,2'-azino-bis-(3-etilbenzotiazolín)-6-sulfónico y peroxilo, y que ejerce una potente inhibición nocompetitiva de α-glucosidasa (IC 50 10.11±0.30 µM). El análisis cinético y espectrométrico llevado a cabo indica que OA interacciona con este enzima en el interior de un bolsillo hidrofóbico, mediante un proceso endotér-mico no espontáneo, de naturaleza hidrofóbica. Estos son dos posibles mecanismos por los cuales el OA puede facilitar un mejor control de la hiperglucemia postprandial y el estrés oxidativo, lo que contribuye a preservar la señalización de la insulina. La obesidad, la resistencia a la insulina y la diabetes mellitus tipo 2 se consideran la primera pandemia del siglo XXI. En este sentido, el OA podría ser utilizado en futuras estrategias preventivas y terapéuticas, como ingrediente de nuevos fármacos y alimentos funcionales. Free radical scavenging and α-glucosidase inhibition, two potential mechanisms involved in the anti-diabetic activity of oleanolic acid. Grasas Aceites 67 (3): e142. doi: http://dx

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Section: Discussionsupporting

confidence: 94%

“…Its ability to react with diverse radical species has been evaluated, having obtained an array of varied results (Yin and Chan, 2007;Yang et al, 2007;Wang et al, 2010;Allouche et al, 2011). The OA effect on α-amylase is not completely clear (Khati et al, 2013;Wang et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Free radical scavenging and α-glucosidase inhibition, two potential mechanisms involved in the anti-diabetic activity of oleanolic acid

et al. 2016

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“…In addition, Yang et al (2007) drew attention to sea buckthorn fruits as a significant inhibitor of nitric oxide. Nitric oxide has many physiological functions, including vasodilatation or synaptic plasticity in the central nervous system.…”

Section: Discussionmentioning

confidence: 99%

Antioxidant and radical scavenging activities in fruits of 6 sea buckthorn (Hippophae rhamnoides L.) cultivars

Rop¹,

Erċışlı²,

Mlček³

et al. 2014

Turk J Agric For

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Sea buckthorn (Hippophae rhamnoides L.) is a minor fruit crop. The most important breeding activities focused on the production of sea buckthorn fruits as a top-quality food product have been performed in Russia, Germany, and the Czech Republic. Over the past several decades, plant breeders have selected a number of cultivars that show excellent physical and nutritional properties. The aim of this study was to monitor and determine the total contents of phenols and flavonoids as well as antioxidant capacity and scavenging activity of methanolic extracts on reactive oxygen species and lipid peroxidation in some cultivars of sea buckthorn suitable for growing in Central Europe. Altogether, 6 cultivars of this fruit species presented total phenolic contents ranging from 8.62 g of gallic acid kg -1 of fresh mass to 14.17 g of gallic acid kg -1 of fresh mass. There were high correlations between the contents of phenols and flavonoids on the one hand and the antioxidant properties of sea buckthorn berries on the other. This study indicates that for Central European conditions, sea buckthorn is a promising fruit species that can be used for consumption due to its antioxidant properties.

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“…1) Investigations of H. rhamnoides have yielded flavonols, [2][3][4] triterpenoids, 5,6) and tannins.…”

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confidence: 99%

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Yang

Wen

et al. 2013

Chem. Pharm. Bull.

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Three new flavonol glycosides, hippophaeosides A-C (1-3), together with 27 known constituents, were isolated from Hippophae rhamnoides L. leaves. Their structures were determined by spectroscopic analyses. Their inhibitory activities on 3T3-L1 preadipocyte differentiation and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW264.7 cells were examined.Key words Hippophae rhamnoides; flavonol glycoside; triterpenoid; adipocyte; macrophage Hippophae rhamnoides L. (Elaeagnaceae), known as "sea buckthorn," is a deciduous shrub distributed throughout Asia and Europe. The fruit has been used as a traditional medicine for the treatment of cough indigestion and blood stasis in China.1) Investigations of H. rhamnoides have yielded flavonols, 2-4) triterpenoids, 5,6) and tannins.3) The leaf has been reported to have anti-inflammatory, 7) antioxidant, 4) anti-obesity, 8,9) and α-glucosidase inhibitory activities. 4)In our previous study, we investigated anti-obesity and antiinflammatory compounds that not only inhibit triglyceride (TG) accumulation by 3T3-L1 adipocytes but also inhibit the secretion of nitric oxide (NO) from RAW264.7 cells. In that study, several crude drugs were examined. [10][11][12] In the present study, the 80% methanol extract of the leaves of H. rhamnoides L. and the chloroform-and ethyl acetatesoluble portions of the extract were observed to inhibit the TG accumulation in 3T3-L1 cells, and inhibit NO production in lipopolysaccharide (LPS) and interferon-γ (IFN-γ) activated macrophages. Furthermore, an attempt to identify the bioactive compounds present in this plant led to the isolation of three new flavonol glycosides, Hippophaeosides A (1), B (2), and C (3), along with 27 known constituents. Results and DiscussionThe leaves of H. rhamnoides L. were extracted with 80% aqueous methanol, followed by evaporation of the solvent under reduced pressure from the combined extract to give the 80% methanol extract. The extract [TG and NO inhibitory activity: 35% and 63%, respectively (30 µg/mL) [42, 15% (30 µg/mL)]. We focused our efforts on investigating the chemical constituents of the chloroform-and ethyl acetate-soluble fractions. The ethyl acetate layer was separated by Sephadex LH-20 column chromatography to yield four fractions from which 22 compounds including three new compounds 1-3 were isolated. Eight compounds were isolated from the chloroform layer. Compounds 4-30 were identified by detailed comparisons of their

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Triterpenoids from Hippophae rhamnoides L. and Their Nitric Oxide Production-Inhibitory and DPPH Radical-Scavenging Activities

Cited by 82 publications

References 16 publications

Free radical scavenging and α-glucosidase inhibition, two potential mechanisms involved in the anti-diabetic activity of oleanolic acid

Free radical scavenging and α-glucosidase inhibition, two potential mechanisms involved in the anti-diabetic activity of oleanolic acid

Antioxidant and radical scavenging activities in fruits of 6 sea buckthorn (Hippophae rhamnoides L.) cultivars

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

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