Phenanthrene and phenylpropanoid constituents from the roots of Cymbidium Great Flower ‘Marylaurencin’ and their antimicrobial activity

Yoshikawa, Kazuko; Baba, Chihiro; Iseki, Kanako; Ito, Takuya; Asakawa, Yoshinori; Kawano, Sachiko; Hashimoto, Toshihiro

doi:10.1007/s11418-014-0854-8

Cited by 23 publications

(20 citation statements)

References 6 publications

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“…Among of them, phenanthrenes are a relatively uncommon class of aromatic metabolites in the plant kingdom, and are mainly found in the Orchidaceae and Juncaceae ( Kovács et al, 2008 ; Tóth et al, 2018 ). As typical phytoalexins of these plants, phenanthrenes have been shown to possess antimicrobial activities against various pathogens including drug-resistant strains ( Kovács et al, 2008 ; Tang et al, 2008 ; Yoshikawa et al, 2014 ; Qian et al, 2015 ; Tóth et al, 2018 ). Correspondingly, some phenanthrene-containing plants have been used in traditional medicine for the treatment of infectious diseases ( Sun et al, 2010 ; Namukobe et al, 2011 , 2014 ).…”

Section: Introductionmentioning

confidence: 99%

Phenanthrene Antibiotic Targets Bacterial Membranes and Kills Staphylococcus aureus With a Low Propensity for Resistance Development

et al. 2018

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New classes of antibiotics with different mechanisms of action are urgently required for combating antimicrobial resistance. Blestriacin, a dihydro-biphenanthrene with significant antibacterial activity, was recently isolated from the fibrous roots of Bletilla striata. Here, we report the further characterization of the antimicrobial potential and mode of action of blestriacin. The phenanthrene compound inhibited the growth of all tested clinical isolates of Staphylococcus aureus including methicillin-resistant S. aureus (MRSA). The minimum inhibitory concentrations (MICs) of blestriacin against these pathogens ranged from 2 to 8 μg/mL. Minimum bactericidal concentration (MBC) tests were conducted, and the results demonstrated that blestriacin was bactericidal against S. aureus. This effect was confirmed by the time-kill assays. At bactericidal concentrations, blestriacin caused loss of membrane potential in B. subtilis and S. aureus and disrupted the bacterial membrane integrity of the two strains. The spontaneous mutation frequency of S. aureus to blestriacin was determined to be lower than 10-9. The selection and whole genome sequencing of the blestriacin –resistant mutants of S. aureus indicated that the development of blestriacin resistance in S. aureus involves mutations in multi-genes. All these observations can be rationalized by the suggestion that membrane is a biological target of blestriacin.

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Section: Introductionmentioning

confidence: 99%

Phenanthrene Antibiotic Targets Bacterial Membranes and Kills Staphylococcus aureus With a Low Propensity for Resistance Development

et al. 2018

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“…As for purification compounds, the RP-preparative-HPLC (RP-prep-HPLC) is widely used due to its online detection, high selectivity, excellent reproducibility, as well as wide application range [29][30][31][32][33][34]. This technique has been widely used for the purification of phenolics, flavonoids, alkaloids, phenylpropanoids, and iridoid glucosides from plant extracts [35][36][37][38]. However, the main drawback of RP-prep-HPLC is the limited elution window for the complex components of strongly polar compounds.…”

Section: Introductionmentioning

confidence: 99%

Preparative isolation of antioxidative gallic acid derivatives from Saxifraga tangutica using a class separation method based on medium‐pressure liquid chromatography and reversed‐phase liquid chromatography

Dang

Wang

et al. 2021

J of Separation Science

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Saxifraga tangutica is widely used as a medicinal herb to treat hepatic diseases. Here, we developed a class separation method to separate gallic acid derivatives 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors from the methanol extract of Saxifraga tangutica. Firstly, an MCI GEL CHP20P medium‐pressure liquid chromatography was used to pretreat the crude extract from Saxifraga tangutica (500 g) and the target sample (fraction Fr1, 1.7 g) was obtained. Then, an online reversed‐phase liquid chromatography–1,1‐diphenyl‐2‐picrylhydrazyl assay was employed for recognizing potential 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors and six 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors fractions were recognized from fraction Fr1. Subsequently, the six 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors fractions were isolated via a ReproSil‐Pur C18 AQ preparative column. During the separation process, the hydrophilic liquid chromatography was used to enrich the target compounds (Fr1‐3‐1‐1 and Fr1‐3‐1‐2) from the fraction Fr1‐3, which were hardly isolated only by one step reversed‐phase liquid chromatography. Finally, six gallic acid derivatives were obtained and identified as gallic acid (Fr1‐1‐1), gallic acid 3‐O‐β‐D‐glucoside (Fr1‐1‐2), protocatechuic acid (Fr1‐2), 4‐O‐galloyl‐(‐)‐shikimic acid (Fr1‐3‐1‐1), 5‐O‐galloyl‐(‐)‐shikimic acid (Fr1‐3‐1‐2), and 3‐O‐galloyl‐shikimic acid (Fr1‐4), respectively. Thus, the present study indicated that this method was highly efficient for the preparative separation of gallic acid derivatives 1,1‐diphenyl‐2‐picrylhydrazyl inhibitors from natural products.

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“…During our search for bioactive substances from C . Great Flower ‘Marylaurencin’, which is a cultivar, we have already reported some phenanthrene derivatives with antibacterial effect and cytotoxic activity, and some aromatic glycosides with antioxidant activity from its root, stem and flower [1,2,3,4]. The leaves of C. Great Flower ‘Marylaurencin’ are sold as an herb tea in this area.…”

Section: Introductionmentioning

confidence: 99%

Marylosides A-G, Norcycloartane Glycosides from Leaves of Cymbidium Great Flower ‘Marylaurencin’

et al. 2019

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Seven novel norcycloartane glycosides, maryloside A–G (1–7), were isolated from the leaves of Cymbidium Great Flower ‘Marylaurencin’, along with a known norcycloartane glycoside, cymbidoside (8). These structures were determined on the basis of mainly NMR experiments as well as chemical degradation and X-ray crystallographic analysis. The isolated compounds (1–6 and 8) were evaluated for the inhibitory activity on lipopolysaccharide (LPS) and interferon-γ (IFN-γ)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Consequently, 1 and 3 exhibited moderate activity.

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Phenanthrene and phenylpropanoid constituents from the roots of Cymbidium Great Flower ‘Marylaurencin’ and their antimicrobial activity

Cited by 23 publications

References 6 publications

Phenanthrene Antibiotic Targets Bacterial Membranes and Kills Staphylococcus aureus With a Low Propensity for Resistance Development

Phenanthrene Antibiotic Targets Bacterial Membranes and Kills Staphylococcus aureus With a Low Propensity for Resistance Development

Preparative isolation of antioxidative gallic acid derivatives from Saxifraga tangutica using a class separation method based on medium‐pressure liquid chromatography and reversed‐phase liquid chromatography

Marylosides A-G, Norcycloartane Glycosides from Leaves of Cymbidium Great Flower ‘Marylaurencin’

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