A New Human Cancer Cell Proliferation Inhibition Sesquiterpene, Dryofraterpene A, from Medicinal Plant Dryopteris fragrans (L.) Schott

Zhong, Zheng-Chang; Zhao, Dandan; Liu, Zhendong; Jiang, Shuai; Zhang, Yanlong

doi:10.3390/molecules22010180

Cited by 12 publications

(4 citation statements)

References 25 publications

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“…Aspidin PB, which is another phloroglucinol derivative from D. fragrans , has been recorded as a tumor cell-inhibiting agent for its impact on cyclin p53/p21 and mitochondrial changes in human osteosarcoma cells Saos-2, U2OS, and HOS [ 10 ]. In addition, there have been many other reports on compounds from D. fragrans with cytotoxicity [ 11 , 12 , 13 ]. To further study cytotoxic constituents from D. fragrans , a cytotoxicity-guided isolation of the extract of D. fragrans was designed.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxicity-Guided Isolation of Two New Phenolic Derivatives from Dryopteris fragrans (L.) Schott

et al. 2018

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Dryopteris fragrans is a valuable medicinal plant resource with extensive biological activities including anti-cancer, anti-oxidation, and anti-inflammation activities. This work aims to study further the cytotoxic constituents from Dryopteris fragrans. In this work, two new phenolic derivatives known as dryofragone (1) and dryofracoumarin B (2) with six known compounds (3–8) were isolated from the petroleum ether fraction of the methanol extract of the aerial parts of Dryopteris fragrans (L.) Schott by two round cytotoxicity-guided tracking with the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay and cell counting kit-8 (CCK-8) assay. Their structures were elucidated by the extensive spectroscopic analysis (1H-NMR, 13C-NMR, and two dimensions NMR), chemical derivatization, and comparison with data reported in the literature. All the isolates were evaluated for their cytotoxicity against nine cancer cell lines as well as their in vitro immunomodulatory activity. The results showed that compounds have a modest cytotoxicity toward human HeLa cell line with IC50 value below 30 μM and compounds 4 and 5 may modulate immunity to affect the growth of tumor cells.

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Section: Introductionmentioning

confidence: 99%

Cytotoxicity-Guided Isolation of Two New Phenolic Derivatives from Dryopteris fragrans (L.) Schott

et al. 2018

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“…Su [ 8 ] reported that Dryofragin, a phloroglucinol derivative from D. fragrans , could stop human osteosarcoma U2OS cells from migrating and invading by lowering MMP-2 and MMP-9 expression and up-regulating the expression of TIMP-2 and TIMP-1 through the p38 MAPK and PI3K/AKT signal pathways. Zhong [ 9 ] obtained a novel sesquiterpene—Dryofraterpene A—from D. fragrans , which could significantly inhibit the proliferation of five kinds of cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Anticancer Phenolics from Dryopteris fragrans (L.) Schott

et al. 2018

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Cancer is one of the most major diseases that threatens human health and life. The aim of this work was to obtain novel anticancer molecules from D. fragrans, a kind of medicinal plant. The structure of the new compound was identified using spectroscopic data (1H-NMR, 13C-NMR and two dimensions NMR). Its anticancer properties were evaluated using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay against four human cells including lung cancer cells (A549), breast cancer cells (MCF-7), gastric cancer cells (SGC7901) and noncancerous human umbilical vein endothelial cells (HUVEC). A new phenylpropanoid—(E)-caffeic acid-9-O-β-d-xylpyranosyl-(1→2)-β-d-glucopyranosyl ester (1), with seven known compounds (2–8)—was isolated. The IC50 value of compound 1 against MCF-7 cells was 2.65 ± 0.14 µM, and the IC50 values of compound 8 against three cancer cells were below 20 µM.

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“…Dryopteris fragrans is mainly used as a folk medicine at present. It has been found that the main active compounds from Dryopteris fragrans have a significant effect on a variety of skin diseases caused by fungi [11,12]. Our group isolated a variety of phloroglucinols from the plant and activity experiment showed that the phloroglucinols had strong antifungal activity such as the minimal inhibition concentration (MIC) values activity of aspidin BB against some clinical S. aureus was ranged from 15.63 mg/mL to 62.5 mg/mL [13,14,15,16].…”

Section: Introductionmentioning

confidence: 99%

Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives

Teng

Wang

et al. 2018

Molecules

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Pseudoaspidinol is a phloroglucinol derivative with Antifungal activity and is a major active component of Dryopteris fragrans. In our previous work, we studied the total synthesis of pseudoaspidinol belonging to a phloroglucinol derivative and investigated its antifungal activity as well as its intermediates. However, the results showed these compounds have low antifungal activity. In this study, in order to increase antifungal activities of phloroglucinol derivatives, we introduced antifungal pharmacophore allylamine into the methylphloroglucinol. Meanwhile, we remained C1–C4 acyl group in C-6 position of methylphloroglucinol using pseudoaspidinol as the lead compound to obtain novel phloroglucinol derivatives, synthesized 17 compounds, and evaluated antifungal activities on Trichophyton rubrum and Trichophyton mentagrophytes in vitro. Molecular docking verified their ability to combine the protein binding site. The results indicated that most of the compounds had strong antifungal activity, in which compound 17 were found to be the most active on Trichophyton rubrum with Minimum Inhibitory Concentration (MIC) of 3.05 μg/mL and of Trichophyton mentagrophytes with MIC of 5.13 μg/mL. Docking results showed that compounds had a nice combination with the protein binding site. These researches could lay the foundation for developing antifungal agents of clinical value.

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A New Human Cancer Cell Proliferation Inhibition Sesquiterpene, Dryofraterpene A, from Medicinal Plant Dryopteris fragrans (L.) Schott

Cited by 12 publications

References 25 publications

Cytotoxicity-Guided Isolation of Two New Phenolic Derivatives from Dryopteris fragrans (L.) Schott

Cytotoxicity-Guided Isolation of Two New Phenolic Derivatives from Dryopteris fragrans (L.) Schott

Anticancer Phenolics from Dryopteris fragrans (L.) Schott

Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives

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