Two new dammarane-type triterpene saponins from Korean red ginseng and their anti-inflammatory effects

Vinh, Le Ba; Lee, Yun-Jeong; Han, Yoo Kyong; Kang, Jong Seong; Park, Jung Up; Kim, Young Ran; Yang, Seo Young; Kim, Young Ho

doi:10.1016/j.bmcl.2017.10.058

Cited by 24 publications

(17 citation statements)

References 34 publications

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“…Inflammatory cells produce cytokines, including interleukin (IL)-12 p40, IL-6, and tumor necrosis factor (TNF)-α. IL-12 p40, IL-6, and TNF-α play important roles in the inflammatory response, as well as cell apoptosis and transformation [ 1 ]. Many studies have focused on the inhibition of pro-inflammatory cytokines in an effort to decrease inflammation-related diseases [ 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Vinh

Heo

Phong

et al. 2020

Plants

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The roots of Polygala tenuifolia Wild (Polygalaceae), which is among the most important components of traditional Chinese herbal medicine, have been widely used for over 1000 years to treat a variety of diseases. In the current investigation of secondary metabolites with anti-inflammatory properties from Korean medicinal plants, a phytochemical constituent study led to the isolation of 15 compounds (1–15) from the roots of P. tenuifolia via a combination of chromatographic methods. Their structures were determined by means of spectroscopic data such as nuclear magnetic resonance (NMR), 1D- and 2D-NMR, and liquid chromatography-mass spectrometry (LC-MS). As the obtained results, the isolated compounds were divided into two groups—phenolic glycosides (1–9) and triterpenoid saponins (10–15). The anti-inflammatory effects of crude extracts, fractions, and isolated compounds were investigated on the production of the pro-inflammatory cytokines interleukin (IL)-12 p40, IL-6, and tumour necrosis factor-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells. The IC50 values, ranging from 0.08 ± 0.01 to 21.05 ± 0.40 μM, indicated potent inhibitory effects of the isolated compounds on the production of all three pro-inflammatory cytokines. In particular, compounds 3–12, 14, and 15 showed promising anti-inflammatory activity. These results suggest that phenolic and triterpenoid saponins from P. tenuifolia may be excellent anti-inflammatory agents.

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Section: Introductionmentioning

confidence: 99%

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Vinh

Heo

Phong

et al. 2020

Plants

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“…Triterpene glycosides isolated from rare medicinal plants often display a wide range of pharmacological activities, such as anti-inflammatory [21], antifungal [22], antimicrobial [23], anti-cancer [24], anti-diabetic [25] and immunomodulatory [26] effects. Indeed, triterpene saponins are the key active constituents of major medicinal herbs such as Panax ginseng (Araliaceae), Gynostemma pentaphyllum (Cucurbitaceae) and Glycyrrhiza uralensis (Fabaceae) [27,28].…”

Section: Discussionmentioning

confidence: 99%

Enhancement of an In Vivo Anti-Inflammatory Activity of Oleanolic Acid through Glycosylation Occurring Naturally in Stauntonia hexaphylla

et al. 2020

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Stauntonia hexaphylla (Lardizabalaceae) has been used as a traditional herbal medicine in Korea and China for its anti-inflammatory and analgesic properties. As part of a bioprospecting program aimed at the discovery of new bioactive compounds from Korean medicinal plants, a phytochemical study of S. hexaphylla leaves was carried out leading to isolation of two oleanane-type triterpene saponins, 3-O-[β-d-glucopyranosyl (1→2)-α-l-arabinopyranosyl] oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (1) and 3-O-α-l-arabinopyranosyl oleanolic acid-28-O-[β-d-glucopyranosyl (1→6)-β-d-glucopyranosyl] ester (2). Their structures were established unambiguously by spectroscopic methods such as one- and two-dimensional nuclear magnetic resonance and infrared spectroscopies, high-resolution electrospray ionization mass spectrometry and chemical reactions. Their anti-inflammatory activities were examined for the first time with an animal model for the macrophage-mediated inflammatory response as well as a cell-based assay using an established macrophage cell line (RAW 264.7) in vitro. Together, it was concluded that the saponin constituents, when they were orally administered, exerted much more potent activities in vivo than their sapogenin core even though both the saponins and the sapogenin molecule inhibited the RAW 264.7 cell activation comparably well in vitro. These results imply that saponins from S. hexaphylla leaves have a definite advantage in the development of oral medications for the control of inflammatory responses.

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“…The extract of Korean red ginseng was subjected to various separation procedures and 11 compounds were isolated (1-11). Their structures were identified as 6-O-b-D-glucopyranosyl-20R-protopanaxadiol-3-one (1), 20R-ginsenoside Rh1 6 0 -acetate (2), 20S-ginsenoside Rh1 6 0 -acetate (3), ginsenoside Rk3 (4), ginsenoside RT5 (5), 20R-ginsenoside Rh1 (6), 20S-ginsenoside Rh2 (7), 20R-ginsenoside Rg3 (8), oleanolic acid b-D-glucopyranosyl ester (9), ginsenoside Rh4 (10), and 9,12,13-trihydroxy-10E-octadecenoic acid (11) based on spectral and chemical evidence, consistent with previously published paper (Vinh et al, 2017) (Fig. 1).…”

Section: Phytochemical Analysismentioning

confidence: 99%

“…Previously, we isolated eleven compounds, including two new ginsenosides from Korean red ginseng and evaluated their anti-inflammatory activities (Vinh et al, 2017). These results showed that compound 1 (3-oxo-20R-ginsenoside Rh1) significantly reduced the level of proinflammatory cytokines IL-6 and TNF-a secretion and inhibited the expression of COX-2 and iNOS in LPS-activated RAW264.7 cells.…”

Section: Introductionmentioning

confidence: 99%

Ginsenosides from Korean red ginseng modulate T cell function via the regulation of NF-AT-mediated IL-2 production

Vinh

Park

Duy

et al. 2018

Food Sci Biotechnol

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Korean red ginseng is a traditional health food frequently used to prevent or treat various diseases worldwide. In this study, we evaluated the immunomodulatory activities of eleven compounds (1-11) isolated from Korean red ginseng, focusing on T cell function. First, the effects of the eleven compounds were studied on the regulation of IL-2, a potent T cell growth factor. Compounds 5, 7, and 9 significantly increased IL-2 secretion in phorbol 12-myristate 13-acetate (PMA)/ionomycin (Io)-induced EL-4 T cells. Next, we examined the effects of compounds 5, 7, and 9 on the regulation of transcription factors related to IL-2 production in T cells. Compound 9 significantly increased the PMA/Io-induced promoter activity of nuclear factor of activated T cells (NF-AT) in EL-4 T cells, but did not have any significant effects on the promoters of NF-jB. These results suggest that compound 9 activates T cell function via the regulation of NF-AT-mediated IL-2 production.

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Two new dammarane-type triterpene saponins from Korean red ginseng and their anti-inflammatory effects

Cited by 24 publications

References 34 publications

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Bioactive Compounds from Polygala tenuifolia and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Pro-inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

Enhancement of an In Vivo Anti-Inflammatory Activity of Oleanolic Acid through Glycosylation Occurring Naturally in Stauntonia hexaphylla

Ginsenosides from Korean red ginseng modulate T cell function via the regulation of NF-AT-mediated IL-2 production

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