Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities

Dang, Ting; Zheng, Guijuan; Zhang, Qihua; Jin, Pengfei; Zhang, Hanqi; Su, Linjie; Dong-mei, Qin; Yao, Guangmin

doi:10.1016/j.fitote.2019.104170

Cited by 21 publications

(13 citation statements)

References 27 publications

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“…Earlier experiments demonstrated the most significant anti-inflammatory activity of Lactucin in CGEA ( Dang et al, 2019 ). In the present experiments we further determined the content of Lactucin and the HPLC results showed that the content of Lactucin in CGEA was 6%.Lactucin being the major compound in CGEA, we predict that the anti-inflammatory activity exhibited by CGEA is mainly due to the anti-inflammatory effect exerted by Lactucin.…”

Section: Discussionmentioning

confidence: 98%

“…Fraction B was subjected to a MCI CC to remove pigment eluted excessively with 70, 80, 90 and 100% methyl alcohol to give subfractions B1. Fraction B1 was separated by an RP C18 silica gel CC to give compound 10 (38 mg), and the compound 10 was identified by 1 H NMR and 13 C NMR spectroscopy as Lactucin ( Dang et al, 2019 ) ( Supplementary Figure S1 ).…”

Section: Methodsmentioning

confidence: 99%

“…Studies have shown that the main components of CGEA are sesquiterpene lactones, and the main components are Lactucin and Lactucopicrin ( Pyrek, 1985 ). Our group isolated a total of 25 compounds from CGEA, 14 of which were sesquiterpene lactones ( Supplementary Table S3 ), and preliminary experimental results showed that Lactucin has extremely strong anti-inflammatory activity ( Dang et al, 2019 ). Lactucin is the most abundant terpenoid in CGEA with significant antibacterial, adipogenesis-inhibiting effects ( Wang et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

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Cichorium pumilum Jacq Extract Inhibits LPS-Induced Inflammation via MAPK Signaling Pathway and Protects Rats From Hepatic Fibrosis Caused by Abnormalities in the Gut-Liver Axis

et al. 2021

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The development of liver fibrosis is closely related to the gut microbiota, and the “gut-liver axis” is the most important connection between the two. ethyl acetate extract of Cichorium pumilum Jacq (CGEA) is an herbal extract consisting mainly of sesquiterpenoids. The anti-inflammatory and hepatoprotective effects of CGEA have been reported, but the anti-fibrotic effects of CGEA via intestinal microbes and the “gut-liver axis” cycle have rarely been reported. In this study, we observed that CGEA not only directly attenuated inflammatory factor levels in inflamed mice, but also attenuated liver inflammation as well as liver fibrosis degeneration in rats with liver fibrosis caused by colitis. We observed in vitro that CGEA significantly promoted the growth of Bifidobacterium adolescentis. Similarly, fecal 16S rDNA sequencing of liver fibrosis rats showed that CGEA intervention significantly altered the composition of the intestinal microbiota of liver fibrosis rats. CGEA increased the abundance of intestinal microbiota, specifically, CGEA increased the ratio of Firmicutes to Bacteroidetes, CGEA could significantly increase the levels of Ruminococcus. In addition, CGEA intervention significantly protected intestinal mucosal tissues and improved intestinal barrier function in rats. Lactucin is the main sesquiterpenoid in CGEA, and HPLC results showed its content in CGEA was up to 6%. Lactucin has been reported to have significant anti-inflammatory activity, and in this study, we found that Lactucin decreased p38 kinases (p38), phosphorylation of the extracellular signal-regulated kinase (ERK) and protein kinase B (AKT) protein phosphorylation in lipopolysaccharide (LPS)-activated RAW264.7 cells, thereby reducing mRNA expression and protein expression of pro-inflammatory factors inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), and inhibiting the release of inflammatory factors interleukin (IL)-6 and nitric oxide (NO), exerting anti-inflammatory effects. In summary, the prevention of liver fibrosis caused by intestinal inflammation by CGEA may be achieved by regulating the intestinal microbiota and restoring the intestinal barrier thereby improving the “gut-liver axis” circulation, reducing liver inflammation, and ultimately alleviating liver fibrosis. Notably, the direct anti-inflammatory effect of CGEA may be due to its content of Lactucin, which can exert anti-inflammatory effects by inhibiting the phosphorylation of Mitogen-activated protein kinase (MAPK) and Akt signaling pathways.

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Section: Discussionmentioning

confidence: 98%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cichorium pumilum Jacq Extract Inhibits LPS-Induced Inflammation via MAPK Signaling Pathway and Protects Rats From Hepatic Fibrosis Caused by Abnormalities in the Gut-Liver Axis

et al. 2021

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“…108.5, C-15) and six carbons of a glucose. The 1D, 2D-NMR (figure 2) data as well as the good compatibility of its NMR data with those in the literature suggested 7 was scorzoside [18] (table 1).…”

Section: (C-2′-c-6′mentioning

confidence: 60%

Chemical constituents of Launaea sarmentosa roots

Hanh

Dung

Huy

et al. 2020

Vietnam Journal of Chemistry

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By investigating the chemical constituents of the roots of Launaea sarmentosa, collected at Can Gio beach, Can Gio district, Ho Chi Minh city, nine compounds were isolated including α‐amyrin acetate (1), β‐amyrin acetate (2), lupeol acetate (3), ψ‐taraksasterol acetate (4), luteolin (5), 4‐allyl‐2,6‐dimethoxyphenol glucopyranoside (6), scorzoside (7), ixerisoside D (8) and 9α‐hydroxypinoresinol (9). To the best of our knowledge, all compounds were reported in other species, but this is the first time they were known in L. sarmentosa. Four compounds (1‐4) from the n‐hexane extract were identified by 4‐dimethylaminopyridine‐catalyzed benzoylation. Their chemical structures were elucidated by means of 1D and 2D NMR, HR‐ESI‐MS data analysis and compared with those reported in the literature.

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“…Later Bischoff et al [ 20 ] attributed it to Lactucin, making Chicory the most famous source of Lactucin. Besides antimalarial properties, Lactucin also exerts or potentially exerts anti-inflammatory [ 21 ], sedatives [ 17 ], anti-adipogenic [ 22 ], and anthelmintics [ 23 ] effects. Zhang et al [ 24 ] reported Lactucin induces apoptosis and sub-G 1 cell cycle arrest in HL-60 (human leukemia cancer) cells.…”

Section: Introductionmentioning

confidence: 99%

Lactucin, a Bitter Sesquiterpene from Cichorium intybus, Inhibits Cancer Cell Proliferation by Downregulating the MAPK and Central Carbon Metabolism Pathway

et al. 2022

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Lung cancer, especially adenocarcinoma, is the second most occurring and highest fatality-causing cancer worldwide. Many natural anticancer compounds, such as sesquiterpene lactones (SLs), show promising anticancer properties. Herein, we examined Lactucin, an SL from the plant Cichorium intybus, for its cytotoxicity, apoptotic-inducing, cell cycle inhibiting capacity, and associated protein expression. We also constructed a biotinylated Lactucin probe to isolate interacting proteins and identified them. We found that Lactucin stops the proliferation of A549 and H2347 lung adenocarcinoma cell lines while not affecting normal lung cell MRC5. It also significantly inhibits the cell cycle at G0/G1 stage and induces apoptosis. The western blot analysis shows that Lactucin downregulates the MAPK pathway, cyclin, and cyclin-dependent kinases, inhibiting DNA repair while upregulating p53, p21, Bax, PTEN, and downregulation of Bcl-2. An increased p53 in response to DNA damage upregulates p21, Bax, and PTEN. In an activity-based protein profiling (ABPP) analysis of A549 cell’s protein lysate using a biotinylated Lactucin probe, we found that Lactucin binds PGM, PKM, and LDHA PDH, four critical enzymes in central carbon metabolism in cancer cells, limiting cancer cells in its growth; thus, Lactucin inhibits cancer cell proliferation by downregulating the MAPK and the Central Carbon Metabolism pathway.

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Sesquiterpenoids with diverse carbon skeletons from the roots of Cichorium glandulosum and their anti-inflammatory activities

Cited by 21 publications

References 27 publications

Cichorium pumilum Jacq Extract Inhibits LPS-Induced Inflammation via MAPK Signaling Pathway and Protects Rats From Hepatic Fibrosis Caused by Abnormalities in the Gut-Liver Axis

Cichorium pumilum Jacq Extract Inhibits LPS-Induced Inflammation via MAPK Signaling Pathway and Protects Rats From Hepatic Fibrosis Caused by Abnormalities in the Gut-Liver Axis

Chemical constituents of Launaea sarmentosa roots

Lactucin, a Bitter Sesquiterpene from Cichorium intybus, Inhibits Cancer Cell Proliferation by Downregulating the MAPK and Central Carbon Metabolism Pathway

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