Anti-inflammatory effects of vina-ginsenoside R2 and majonoside R2 isolated from Panax vietnamensis and their metabolites in lipopolysaccharide-stimulated macrophages

Jeong, Jin-Ju; Le, Thi Hong Van; Lee, Sang-Yun; Eun, Su-Hyeon; Nguyen, Mai; Park, Jeong Hill; Kim, Dong-Hyun

doi:10.1016/j.intimp.2015.07.025

Cited by 30 publications

(24 citation statements)

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“…In extensive experiments, TNF-α was significantly inhibited by majonoside-R2 [ 19 ]. Vina-ginsenoside-R2 and majonoside-R2 were also suggested to inhibit the binding of LPS to TLR4 on the macrophages that resulted in anti-inflammatory effects [ 20 ].…”

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confidence: 99%

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In silico studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (Panax vietnamesis)

Kim

Trinh

et al. 2016

BIOPHYSICS

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Tumor necrosis factor-alpha (TNF-α) is a cytokine that plays an important role in inflammatory process and tumor development. Recent studies demonstrate that triterpene saponins from Vietnamese ginseng are efficient inhibitors of TNF-α. But the interactions between TNF-α and the saponins are still unclear. In this study, molecular docking and molecular dynamics simulations of TNF-α with three different triterpene saponins (majonoside R2, vina-ginsenoside R1 and vina-ginsenoside R2) were performed to evaluate their binding ability. Our results showed that the triterpene saponins have a good binding affinity with protein TNF-α. The saponins were docked to the pore at the top of the “bell” or “cone” shaped TNF-α trimer and the complexes were structurally stable during 100 ns molecular dynamics simulation. The predicted binding sites would help to subsequently investigate the inhibitory mechanism of triterpene saponins.

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confidence: 99%

“…The ginseng saponins are potential therapeutic agents, which can suppress TNF-α expression. Among these saponins, the ocotillol-type majonoside-R2 showed the highest inhibitory effect [ 20 , 25 ]…”

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confidence: 99%

In silico studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (Panax vietnamesis)

Kim

Trinh

et al. 2016

BIOPHYSICS

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“…Moreover, pseudoginsenoside F11, a minor ocotillol-type saponin in Panax ginseng, was reported to have a protective effect against cisplatin-induced acute renal failure in an in vivo model [30]. These findings could be explained by a study by Jeong et al, which described the metabolism of these saponins to ocotillol genin by gut microbiota in a human faecal suspension [39]. This suggests that the kidney cell protective effect of ocotillol-type saponins mainly comes from the genin form, which is produced by the digestive procedure in human intestines.…”

Section: Discussionmentioning

confidence: 99%

Increase in Protective Effect of Panax vietnamensis by Heat Processing on Cisplatin-Induced Kidney Cell Toxicity

Vu-Huynh

Nguyen

et al. 2019

Molecules

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Cisplatin is a platinum-based anticancer agent used for treating a wide range of solid cancers. One of the side effects of this drug is its severe nephrotoxicity, limiting the safe dose of cisplatin. Therefore, many natural products have been studied and applied to attenuate the toxicity of this compound. In this study, we found that steamed Vietnamese ginseng (Panax vietnamensis) could significantly reduce the kidney damage of cisplatin in an in vitro model using porcine proximal tubular LLC-PK1 kidney cells. From processed ginseng under optimized conditions (120 °C, 12 h), we isolated seven compounds (20(R,S)-ginsenoside Rh2, 20(R,S)-ginsenoside Rg3, ginsenoside Rk1, ginsenoside-Rg5, and ocotillol genin) that showed kidney-protective potential against cisplatin toxicity. By comparing the 50% recovery concentration (RC50), the R form of ginsenoside, Rh2 and Rg3, had RC50 values of 6.67 ± 0.42 µM and 8.39 ± 0.3 µM, respectively, while the S forms of ginsenoside, Rh2 and Rg3, and Rk1, had weaker protective effects, with RC50 ranging from 46.15 to 88.4 µM. G-Rg5 and ocotillol, the typical saponin of Vietnamese ginseng, had the highest RC50 (180.83 ± 33.27; 226.19 ± 66.16, respectively). Our results suggest that processed Vietnamese gingseng (PVG), as well as those compounds, has the potential to improve kidney damage due to cisplatin toxicity.

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“…It has been found that they have a wide spectrum of biological activities, such as anti-amnesic [7], anti-inflammatory [8], neuroprotective [9] and cardio-protective [10] properties. Natural ocotillol-type saponins share a 20(S)-form, but it has been found that the 20(R)-stereoisomers have different pharmacological effects [11].…”

Section: Commentmentioning

confidence: 99%

The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C₃₄H₅₆O₆

Hong-zhang

Wang

2018

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1581228The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materials(3S,12R,20R,24S)-20,24-epoxy-dammarane-3,12,25-triol was prepared by oxidation of 20(R)-protopanaxadiol with metachloroperoxybenzoic acid (m-CPBA) as described in literature [5]. Subsequently, the title compound was obtained by acetylation reaction as described in literature [6]. Crystals of the title compound were obtained by slow evaporation from acetone at room temperature within 5 days. Experimental detailsHydrogen atoms were placed in idealized positions and treated as riding, with C-H distances of 0.96−0.97 Å, O-H = 0.82 Å. The U iso values of the hydrogen atoms of methyl groups were set to 1.5Ueq and the U iso values of all other hydrogen atoms were set to 1.2Ueq(C). The application of SQUEEZE [3] led to a lower R index and the solvent molecule was presumed to be a acetone molecule on the basis of the 164 Å 3 void and the fact that methanol is commonly used as solvent for growing the crystals. CommentOcotillol-type saponins, sharing a tetrahydrofuran ring and a dammarane skeleton, is one class of rare ginsenosides. It has been found that they have a wide spectrum of biological activities, such as anti-amnesic [7], anti-inflammatory [8], neuroprotective [9] and cardio-protective [10] properties. Natural ocotillol-type saponins share a 20(S)-form, but it has been found that the 20(R)-stereoisomers have different pharmacological effects [11]. In order to discover new chemical entities with pharmacological activity, 20(R)-ocotillol-type saponins were semisynthesized through configuration transformation. The asymmetric unit of the title compound consists of one independent dammarane and one acetone molecule. The tetrahydrofuran ring adopts an envelope conformation with C20 forming the flap. The C23-C22-C20-C21 torsion angle is −78.71(6)°, suggesting the C20 with R form. The C22-C23-C24-H24 and C22-C23-C24-C25 torsion angles are

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Anti-inflammatory effects of vina-ginsenoside R2 and majonoside R2 isolated from Panax vietnamensis and their metabolites in lipopolysaccharide-stimulated macrophages

Cited by 30 publications

References 30 publications

<i>In silico</i> studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (<i>Panax vietnamesis</i>)

<i>In silico</i> studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (<i>Panax vietnamesis</i>)

Increase in Protective Effect of Panax vietnamensis by Heat Processing on Cisplatin-Induced Kidney Cell Toxicity

The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C₃₄H₅₆O₆

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Anti-inflammatory effects of vina-ginsenoside R2 and majonoside R2 isolated from Panax vietnamensis and their metabolites in lipopolysaccharide-stimulated macrophages

Cited by 30 publications

References 30 publications

<i>In silico</i> studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (<i>Panax vietnamesis</i>)

<i>In silico</i> studies for the interaction of tumor necrosis factor-alpha (TNF-α) with different saponins from Vietnamese ginseng (<i>Panax vietnamesis</i>)

Increase in Protective Effect of Panax vietnamensis by Heat Processing on Cisplatin-Induced Kidney Cell Toxicity

The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C34H56O6

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The crystal structure of (3S,12R,20R,24S)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25-triol acetone solvate, C₃₄H₅₆O₆