A new <i>ent</i>-kaurane diterpene derivative from the stems of <i>Eurya chinensis</i> R.Br

Song, Jia-Ling; Yao, Yuan; Nie, Ling-Hui; Li, Bailin; Qin, Xu-Bing; Li, Yan; Wu, Jiunn‐Tzong; Qiu, Shaofu

doi:10.1080/14786419.2017.1343327

Cited by 6 publications

(4 citation statements)

References 18 publications

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“…The subfractions were subjected to silica gel (200–300 mesh, Qingdao Marine Chemical Inc., Qingdao, China), Sephadex LH-20 gel (CHP20P, 75–150 μm, Mitsubishi Chemical Industries Ltd, Tokyo, Japan), C18 reversed-phase silica gel (150–200 mesh, Merck, Darmstadt, Germany) column chromatography to obtain the pure compounds by following similar procedures as we described previously (J. Song et al, 2018a , 2018b ) with minor modification. 1D and 2D NMR spectra were recorded on a Bruker Advance-500 spectrometer with TMS as internal standard (Bruker BioSpin AG, Fallanden, Switzerland).…”

Section: Methodsmentioning

confidence: 99%

“…Our group previously found that the main chemical constituents of E. chinensis stems include mainly terpenoids, coumarins and flavonoids (J. Song et al, 2018a , 2018b ) possessing anti-inflammatory and antibacterial activity (J. L. Song et al, 2017 ). However, there are no reports on the chemical profile and efficacy of its leaves, which were widely used as “Dagang Tea” for clinical care and the treatment of fever and viral infections.…”

Section: Introductionmentioning

confidence: 99%

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Multi-target mechanisms against coronaviruses of constituents from Chinese Dagang Tea revealed by experimental and docking studies

Qin

Lin

Xie

et al. 2022

Journal of Ethnopharmacology

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multi-target mechanisms against coronaviruses of constituents from Chinese Dagang Tea revealed by experimental and docking studies

Qin

Lin

Xie

et al. 2022

Journal of Ethnopharmacology

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“…Using scales of 100 μmol of diterpenoid instead of 20 mmol, the reaction yielded (4S,8S)-15,16-epoxy-8,17-dihydroxy-13(16),14-ent-labdadien-18-oic acid (1c), a previously undescribed compound, and the known compound 16α,17-dihydroxy-ent-kauran-19-oic acid (2c). Whereas the latter compound was identified by comparison of MS and NMR spectra to literature data (Song et al 2018), structure elucidation of compound 1c is described in "Structure Elucidation and Configuration of Compound 1c".…”

Section: Dihydroxy Derivativesmentioning

confidence: 99%

Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives

Çiçek

Wenzel‐Storjohann

Girreser

et al. 2020

Rev. Bras. Farmacogn.

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The oleoresin of Copaifera reticulata Ducke, Fabaceae, is a traditional Brazilian remedy used for a wide range of applications. Commonly named copaiba, the oleoresin has been found to exhibit strong antimicrobial effects in our previous study, which could be attributed to some of its diterpenoid constituents. In order to find new biological activities and to eventually enhance the before observed effects, (−)-polyalthic acid (1) and kaurenoic acid (2), together with eight prepared semi-synthetic derivatives (1a-1c and 2a-2e) were evaluated for their cytotoxic, antibacterial and antifungal properties. Regarding the gram-positive bacteria Enterococcus faecium and methicillin-resistant Staphylococcus aureus, we found that both the exocylic methylene group and the carboxyl group were crucial for the activity against these two clinically relevant bacterial strains. Investigation of the antifungal activity, in contrast, showed that the carboxyl group is unnecessary for the effect against the dermatophytes Trichophyton rubrum and Cryptococcus neoformans, indicated by low micromolar IC 50 values for both (−)-polyalthic acid diethylamide (1a) as well as (−)-polyalthic acid methyl ester (1b). Apart from studying the biological activity, the structure of one semi-synthetic derivative, compound 1c, is being reported for the first time. During the course of the structure elucidation of the new compound, we discovered inconsistencies regarding the stereochemistry of polyalthic acid and its stereoisomers, which we clarified in the present work.

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“…It was reported that inflammation-related signaling pathways might be affected in the liver tissues of mice treated with E. chinensis extract [13]. Recently, phytochemistry studies on the E. chinensis started to afford a series of novel diterpenes which have been proved to possess promising anti-inflammatory activities [14][15][16]. However, as a great potential phytomedicine, the investigations of its phytochemical and pharmacological properties are still scarce, and the scientific basis for liver protection of this plant has never been reported.…”

Section: Introductionmentioning

confidence: 99%

Euryachincoside, a Novel Phenolic Glycoside with Anti-Hepatic Fibrosis Activity from Eurya chinensis

Liang

et al. 2022

Planta Med

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Eurya chinensis has been recorded as a folk medicine traditionally used for treatment of a variety of symptoms. However, the phytochemical and pharmacological investigations on this plant are still scarce. A novel phenolic glycoside named Euryachincoside (ECS) was isolated by chromatographic separation from E. chinensis and its chemical structure was identified by analysis of HRMS and NMR data. Its anti-hepatic fibrosis effects were evaluated in both HSC-T6 (rat hepatic stellate cells) and carbon tetrachloride (CCl4)-induced mice with Silybin (SLB) as the positive control. In vitro study, ECS showed barely cytotoxicity and inhibited transforming growth factor-beta (TGF-β)-induced Collagen I (Col1) along with alpha-smooth muscle actin (α-SMA) expressions in HSC-T6. In vivo study suggested ECS significantly ameliorated hepatic injury, secretions of inflammatory cytokines and collagen depositions. Moreover, ECS markedly mediated Smad2/3, nuclear factor kappa B (NF-κB) and nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathways both in vitro and vivo. These present findings confirmed that ECS is a novel phenolic glycoside from E. chinensis with promising curative effects on hepatic fibrosis, and its mechanisms may include decreasing extracellular matrix accumulation, reducing inflammation and attenuating free radicals via Smad2/3, NF-κB and Nrf2 signaling pathways, which may shed light on the exploration of more effective phenolic glycoside-based anti-fibrotic agents.

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A new ent-kaurane diterpene derivative from the stems of Eurya chinensis R.Br

Cited by 6 publications

References 18 publications

Multi-target mechanisms against coronaviruses of constituents from Chinese Dagang Tea revealed by experimental and docking studies

Multi-target mechanisms against coronaviruses of constituents from Chinese Dagang Tea revealed by experimental and docking studies

Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives

Euryachincoside, a Novel Phenolic Glycoside with Anti-Hepatic Fibrosis Activity from Eurya chinensis

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