New phenolic acids from <i>Salvia yunnanensis</i> C.H.Wright

Yu, Yun; Wang, Yin-Ru; Dong, Zhen-Huan; Li, Wei; Li, Shu-Ming; Huang, Xuefeng

doi:10.1080/14786419.2017.1315577

Cited by 12 publications

(4 citation statements)

References 26 publications

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“…The two trans olefinic protons centered at δ H 7.70 (d, J = 15.4 Hz, H-7, 1H) and 6.50 (d, J = 15.4 Hz, H-8, 1H) were also revealed by 1 H-NMR spectrum. The two aliphatic protons at δ H 5.90 (d, J = 4.8 Hz, H-7′, 1H) and 4.70 (d, J = 4.8 Hz, H-8′, 1H) were trans oriented to each other as suggested by their coupling constant value of 4.8 Hz [34]. The trans orientation of H-7′ and H-8′ was further supported by NOE experiment.…”

Section: Resultsmentioning

confidence: 83%

“…Similarly, two doublets for other aromatic protons were also revealed in 1 H-NMR spectrum at δ H 6.80 (d, J = 1.8 Hz, H-2′, 1H), δ H 6.61 (d, J = 8.2 Hz, H-5′, 1H,) while doublet of doublet was observed for proton at δ H 6.63 (dd, J = 8.2, 1.8 Hz, H-6′, 1H). The coupling observed between two aliphatic protons at δ H 5.92 (d, J = 5.2 Hz, H-7′, 1H) and δ H 4.68 (d, J = 5.2 Hz, H-8′, 1H) suggested the presence of dihydrobenzofuran ring [34]. The protons at position H-7′ and H-8′ were suggested at trans position to each other as indicated by value of coupling constant, i.e.…”

Section: Resultsmentioning

confidence: 99%

“…In addition both olefinic protons (H-7 and H-8) showed strong HMBC correlation with C-9, and C-1. Finally, the structure of compound 2 was deduced as ( E )-3-((2 S ,3 S )-2-(3,4-dimethoxyphenyl)-7-methoxy-3-(methoxycarbonyl)-2,3-dihydrobenzofuran-4-yl)acrylic acid on the basis of all spectral data and literature comparison [34].…”

Section: Resultsmentioning

confidence: 99%

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Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

et al. 2019

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BackgroundEthnomedicinally, the family Polygonaceae is famous for the management of cancer. Various species of this family have been reported with anticancer potentials. This study was designed to isolate anticancer compounds from ethnomedicinally important species Polygonum barbatum.MethodsThe column chromatography was used for the isolation of compounds from the solvent fraction of P. barbatum. The characterization of isolated compounds was performed by various spectroscopic techniques like UV, IR, mass spectrometry and 1D-2D NMR spectroscopy. Keeping in view the ethnomedicinal importance of the family, genus and species of P. barbatum, the isolated compounds (1–3) were screened for anticancer potentials against oral cancer (CAL-27) and lungs cancer (NCI H460) cell lines using MTT assay. Active compound was further investigated for apoptosis by using morphological changes and flow cytometry analysis. In vivo anti-angiogenic study of the isolated compounds was also carried using chorioallantoic membrane assay. Docking studies were carried out to explore the mechanism of anticancer activity.ResultsThree dihydrobenzofuran derivatives (1–3) have been isolated from the ethyl acetate fraction of P. barbatum. The structures of isolated compounds were elucidated as methyl (2S,3S)-2-(3,4-dimethoxyphenyl)-4-((E)-3-ethoxy-3-oxoprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzo-furan-3-carboxylate (1), (E)-3-((2S,3S)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-(methoxy carbonyl)-2,3-dihydrobenzofuran-4-yl)acrylic acid (2) and (2S,3S)-4-((E)-2-carboxyvinyl)-2-(3,4-dimethoxyphenyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carboxylic acid (3). The compound 1 was found to be more potent with IC50 of 48.52 ± 0.95 and 53.24 ± 1.49 against oral cancer cells as compared to standard drug (IC50 = 97.76 ± 3.44 μM). Both compound also inhibited lung cancer cells but at higher concentrations. Morphological and flow cytometry analysis further confirms that compound 1 induces apoptosis after 24 to 48 h treatment. In antiangiogenesis assay, compounds 1, 2 and 3 exhibited IC50 values of 8.2 ± 1.1, 13.4 ± 1.1 and 57.7 ± 0.3 μM respectively. The docking studies revealed that the compounds under study have the potential to target the DNA and thymidylate synthase (TS).ConclusionBased on its overwhelming potency against the tested cell lines and in angiogenesis assay, compound 1 can be further evaluated mechanistically and can be developed as anticancer drug candidate.Electronic supplementary materialThe online version of this article (10.1186/s40659-018-0209-0) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

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Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

et al. 2019

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“…Rosmarinic acid 6) ([M−H] − at m/z 359) exerted a λ max at 331 nm, its identity being further confirmed by comparison with an authentic standard, while baicalein 7) ([M−H] − at m/z 269) was also identified based on main fragment ions resulted after MS 2 fragmentation. Compound 4 showed a molecular ion [M−H] − at m/z 463 and λ max at 341 nm, releasing common fragment ions (m/z 359, m/z 197, m/z 179, and m/z 161) with rosmarinic acid (6), being tentatively identified as sagerinic acid; both compounds were cited as main constituents of Salvia species, with the mention that sagerinic acid exerted a fragmentation pattern specific for cyclobutane-type lignans (bioactive secondary metabolites common for Lamiaceae species) (Yu et al, 2017;Sharma et al, 2020). Compounds 9 and 10 produced, after MS 2 fragmentation, the common abundant ion fragment with m/z 295, which indicated the loss of a deprotonated 3-(3,4-dihydroxyphenyl) lactic acid unit (known as danshensu), describing a characteristic fragmentation for salvianolic acids with trimeric structure (Liu et al, 2007).…”

Section: Lc-dad-esi/mass Spectrometer Quantitative and Qualitative An...mentioning

confidence: 99%

Potential therapeutic applications of infusions and hydroalcoholic extracts of Romanian glutinous sage (Salvia glutinosa L.)

et al. 2022

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Ethnopharmacological relevance:Salvia glutinosa, also known as the glutinous sage, has been used in Romanian folk medicine in the treatment of inflammation, injuries, and mild infections. However, there is no direct scientific evidence to demonstrate these activities.Aim of the Study: The present research was based on evaluating antioxidant, antiproliferative, and α-glucosidase inhibitory activity of S. glutinosa extracts, as well as the in vivo anti-inflammatory activity.Materials and Methods: Infusions and 70% (v:v) ethanol solution extracts of S. glutinosa stems and leaves, collected from two different locations in Romania, were prepared. Ten phenolic compounds were identified and quantified using the LC-DAD-ESI/MSn method, and total phenolic and flavonoid content, as well as in vitro antioxidant (DPPH, ABTS, and FRAP assays), antiproliferative, anti-inflammatory and alpha-glucosidase inhibitory activities were determined. A rat model of induced inflammation with turpentine oil was used for the examination of in vivo effects of the extracts, using diclofenac as an anti-inflammatory control.Results: The highest inhibitory α-glucosidase activity was determined to be IC50 = 0.546 mg/ml for the hydroalcoholic extract made with plant material collected on the road to Sighișoara. The highest cytotoxic activity against HepG2 cell line was determined to be GI50 = 131.68 ± 5.03 μg/ml, for the hydroalcoholic extract made with plant material from Sighișoara. In vivo administration of extract (200 mg lyophilized powder/ml) showed a significant reduction of NO production.Conclusion: Our findings indicate that S. glutinosa extracts exhibit antioxidant, α-glucosidase inhibitory activity, as well as a modest cytotoxic effect on HepG2 cell line. By in vivo administration, the extracts show anti-inflammatory and antioxidant activity, which correlates with the traditional use of the species. The environmental conditions seemed to induce important changes in the chemical composition and the bioactivity of the herbal preparations derived from S. glutinosa.

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A comparative study of complete chloroplast genome for the genus salvia

Liang

Wang

et al. 2020

J. Plant Biochem. Biotechnol.

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New phenolic acids from Salvia yunnanensis C.H.Wright

Cited by 12 publications

References 26 publications

Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

Isolation of dihydrobenzofuran derivatives from ethnomedicinal species Polygonum barbatum as anticancer compounds

Potential therapeutic applications of infusions and hydroalcoholic extracts of Romanian glutinous sage (Salvia glutinosa L.)

A comparative study of complete chloroplast genome for the genus salvia

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