Four New Sesquiterpenoids from the Roots of Incarvillea arguta and Their Inhibitory Activities against Lipopolysaccharide-Induced Nitric Oxide Production

Fu, Jianjun; Qin, Jiang‐Jiang; Zeng, Qi; Huang, Ying; Jin, Hui; Zhang, Wei‐Dong

doi:10.1248/cpb.58.1263

Cited by 18 publications

(4 citation statements)

References 10 publications

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“…The LPS-activated signal transduction in macrophages, which involves a cascade of the Toll-like receptor 4/JNK/P38/NF-κB pathway, is commonly investigated in cell models for assessing anti-inflammatory activities of a variety of candidate compounds [ 22 – 24 ]. Consistent with the traditional use of Schisandra fruits for the treatment of inflammation in Chinese medicine, both Sch A and Sch B were found to reduce the extent of inflammation in LPS-activated RAW264.7 macrophages, with Sch A being more potent.…”

Section: Discussionmentioning

confidence: 99%

Differential Action between Schisandrin A and Schisandrin B in Eliciting an Anti-Inflammatory Action: The Depletion of Reduced Glutathione and the Induction of an Antioxidant Response

et al. 2016

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Schisandrin A (Sch A) and schisandrin B (Sch B) are active components of Schisandrae Fructus. We compared the biochemical mechanism underlying the anti-inflammatory action of Sch A and Sch B, using cultured lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages and concanavalin (ConA)-stimulated mouse splenocytes. Pre-incubation with Sch A or Sch B produced an anti-inflammatory action in LPS-stimulated RAW264.7 cells, as evidenced by the inhibition of the pro-inflammatory c-Jun N-terminal kinases/p38 kinase/nuclear factor-κB signaling pathway as well as the suppression of various pro-inflammatory cytokines and effectors, with the extent of inhibition by Sch A being more pronounced. The greater activity of Sch A in anti-inflammatory response was associated with a greater decrease in cellular reduced glutathione (GSH) level and a greater increase in glutathione S-transferase activity than corresponding changes produced by Sch B. However, upon incubation, only Sch B resulted in the activation of the nuclear factor (erythroid-derived 2)-like factor 2 and the induction of a significant increase in the expression of thioredoxin (TRX) in RAW264.7 cells. The Sch B-induced increase in TRX expression was associated with the suppression of pro-inflammatory cytokines and effectors in LPS-stimulated macrophages. Studies in a mouse model of inflammation (carrageenan-induced paw edema) indicated that while long-term treatment with either Sch A or Sch B suppressed the extent of paw edema, only acute treatment with Sch A produced a significant degree of inhibition on the inflammatory response. Although only Sch A decreased the cellular GSH level and suppressed the release of pro-inflammatory cytokines and cell proliferation in ConA-simulated splenocytes in vitro, both Sch A and Sch B treatments, while not altering cellular GSH levels, suppressed ConA-stimulated splenocyte proliferation ex vivo. These results suggest that Sch A and Sch B may act differentially on activating GST/ depleting cellular GSH and inducing an antioxidant response involved in their anti-inflammatory actions.

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Section: Discussionmentioning

confidence: 99%

Differential Action between Schisandrin A and Schisandrin B in Eliciting an Anti-Inflammatory Action: The Depletion of Reduced Glutathione and the Induction of an Antioxidant Response

et al. 2016

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“…In spite of the popular use, there is so far no report about chemical composition of the plant. Previous investigations on the genus Incarvillea have led to the isolation of monoterpenoid alkaloids (Chi et al 2005;Fu et al 2007), iridoids (Lu et al 2007), and sesquiterpenes (Fu et al 2010;Yan et al 2012). Several studies on antinociceptive effect were also carried out (Nakamura et al 1999(Nakamura et al , 2001.…”

Section: Introductionmentioning

confidence: 99%

Hepatoprotective effect of phenylethanoid glycosides from Incarvillea compacta against CCl4-induced cytotoxicity in HepG2 cells

Shen

Zhang

et al. 2015

J Korean Soc Appl Biol Chem

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The extraction and solvent partition of roots of Incarvillea compacta, a traditional Tibetan folk medicine, and repeated column chromatography and preparative high-performance liquid chromatography for n-butanol fraction yielded four phenylethanoid glycosides, crenatoside (1), 3 000 -O-methylcrenatoside (2), leucoseceptoside A (3), and martynoside (4). The chemical structures were identified on the basis of spectroscopic data analyses including NMR and MS. All compounds were isolated for the first time from the plant. Compound 1 exerted better 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activity. In addition, compounds 1-4 were evaluated for their hepatoprotective activity on carbon tetrachloride (CCl 4 )-induced liver injury in HepG2 cells. Pretreatment of HepG2 cells with compound 1-4 significantly increased the viability on CCl 4 -induced cell death. Furthermore, compounds 1-4 also alleviated CCl 4 -induced hepatotoxicity by enhancement of the antioxidant enzyme activities of superoxide dismutase and reduction of the malondialdehyde content, intracellular ROS as well as NF-jB transactivation. Our results suggest that phenylethanoid glycosides ameliorate CCl 4 -induced cell injury, and this protection was likely due to antioxidative activity and down-regulation of NF-jB.

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“…However, there are quite a few of eremophilane sesquiterpenoids bearing differently orientated substituents at C-7 and C-10 as well as of CH 3 -14 and CH 3 -15 groups [1] and various stereochemical variants may be occurred in the same plant. For example, having the same planar structure (4α,5α-dimethyl-7αH)-9-oxoeremophila-1(10),11(13)-diene-12-ol, (4β,5β-dimethyl-7αH)-9-oxoeremophila-1(10),11(13)-diene-12-ol and (4α,5β-dimethyl-7αH)-9-oxoeremophila-1(10),11(13)-diene-12-ol were isolated from Incarvillea arguta [17]. Therefore, the supposition about orientation of methyl groups as well as biogenetic considerations regarding eremophilane derivatives need to be used cautiously.…”

Section: Structural Determination and Diversitymentioning

confidence: 99%

Eremophilane-type Glycosides: A Mini-Review

Ponomarenko

Stonik

2018

Natural Product Communications

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Four New Sesquiterpenoids from the Roots of Incarvillea arguta and Their Inhibitory Activities against Lipopolysaccharide-Induced Nitric Oxide Production

Cited by 18 publications

References 10 publications

Differential Action between Schisandrin A and Schisandrin B in Eliciting an Anti-Inflammatory Action: The Depletion of Reduced Glutathione and the Induction of an Antioxidant Response

Differential Action between Schisandrin A and Schisandrin B in Eliciting an Anti-Inflammatory Action: The Depletion of Reduced Glutathione and the Induction of an Antioxidant Response

Hepatoprotective effect of phenylethanoid glycosides from Incarvillea compacta against CCl4-induced cytotoxicity in HepG2 cells

Eremophilane-type Glycosides: A Mini-Review

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