Anti-staphylococcal acylphloroglucinols from Hypericum beanii

Shiu, Winnie Ka Po; Gibbons, Simon

doi:10.1016/j.phytochem.2006.09.037

Cited by 61 publications

(41 citation statements)

References 16 publications

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“…Compound 4 showed identical numbers of methyl, methine, methylene, and quaternary carbon to that of 3, which indicated that 4 should be a hydroperoxyl derivative of 3. Careful comparison of their NMR data displayed that the chemical shifts of C-13 in 4 (d 85.1) were obviously shifted downfield compared to that in 3 (d 73.2) in their 13 C-NMR spectra. So, the hydroperoxyl group was deduced to be attached at C-13 in 4, 30) which can be further proved by the HMBC correlations of H-12, H-14, and Me-15 with C-13.…”

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confidence: 99%

“…12) Two anti-staphylococcal acylphloroglucinols have been isolated from this plant previously. 13) Our phytochemical investigation on the methanol extract of this plant led to the isolation of four new acylphloroglucinols, hyperbeanols A-D (1-4), together with the known hypercalin B (5), 14) (1S,4S,5S,10R)-4,10-guaianediol (6), 15) (ϩ)-alismoxide (7), 16) guaia-6,10(14)-dien-4-ol (8), 17 calycinoxanthone D (9), 18) ugaxanthone (10), 19) 2,5-dihydroxyxanthone (11), 20) 1,3-dihydroxy-6-methoxyxanthone (12), 21) 3,6,7-trihydroxy-1-methoxyxanthone (13), 22) 1,2,5-trihydroxyxanthone (14), 23) 1,5-dimhydroxy-2-methoxyxanthone (15), 24) 1,3,5-trihydroxy-6-methoxyxanthone (16), 25) 1-hydroxyxanthone (17), 26) garcimangosone D (18), 27) quercetin-3-O-b-D-glalactopyranoside (19), 28) and quercetin-3-O-a-L-rhamnopyranoside (20). 28) The cytotoxicity of 1-5 against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 were examined.…”

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confidence: 99%

“…1 H-, 13 C-, and 2D-NMR were recorded on Bruker AM-400 or DRX-500 spectrometers with tetramethylsilane (TMS) as internal standard. FAB-MS and HR-ESI-MS spectra were performed on a VG Autospec-3000 spectrometer and Finnigan MAT instrument, respectively.…”

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Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Chen

et al. 2011

Chem. Pharm. Bull.

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Polyprenylated acylphloroglucinols, featured a highly oxygenated bicyclo[3.3.1]-nonane-2,4,9-trione or bicyclo[3.2.1]-octane-2,4,8-trione core decorated with C 5 H 9 or C 10 H 17 (prenyl, geranyl, etc.) side chains, were only isolated from the Guttiferae plants so far.1) This type of metabolites were reported to possess a wide variety of biological activities such as antimicrobial, antidepressant, antioxidant, cytotoxic, and anti-human immunodeficiency virus (HIV) effects. 2-7)As an important member of the family Guttiferae, the genus Hypericum have been proved to be a prolific source of this special type metabolites. [8][9][10][11] H. beanii N. Robson is a shrub of this genus and widely distributed in Guizhou and Yunnan Provinces, P. R. China. 12) Two anti-staphylococcal acylphloroglucinols have been isolated from this plant previously.13) Our phytochemical investigation on the methanol extract of this plant led to the isolation of four new acylphloroglucinols, hyperbeanols A-D (1-4), together with the known hypercalin B (5), 14) (1S,4S,5S,10R)-4,10-guaianediol (6), 15) (ϩ)-alismoxide (7), 16) guaia-6,10(14)-dien-4-ol (8), 17 calycinoxanthone D (9), 18) ugaxanthone (10), 19) 2,5-dihydroxyxanthone (11), 20) 1,3-dihydroxy-6-methoxyxanthone (12), 21) 3,6,7-trihydroxy-1-methoxyxanthone (13), 22) 1,2,5-trihydroxyxanthone (14),28) The cytotoxicity of 1-5 against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 were examined. Reported herein are the isolation, structure elucidation, and cytotoxic evaluation of compounds 1-5. The MeOH extract (611 g) of the aerial parts of H. beanii (5.3 kg) was successively partitioned with petroleum ether and ethyl acetate. The petroleum ether soluble fraction (252 g) was subjected to silica gel column chromatography, Sephadex LH-20, and preparative HPLC to afford compounds 1-8. The ethyl acetate portion (167 g) was also purified by column chromatography, semipreparative, and preparative HPLC to obtain compounds 9-20.Compound 1 (d 197.3, 113.6, 193.7), one monobenzoyl group (d 197.0, 136.9, 127.8ϫ2, 128.0ϫ2, 132.2) Four new acylphloroglucinols with an unusual 6/6/5 spirocyclic skeleton, hyperbeanols A-D (1-4), were isolated from the methanol extract of Hypericum beanii along with 16 known compounds. Their structures were established on the basis of spectroscopic and X-ray diffraction analysis. Hyperbeanols A-C were three stereoisomers different only at the relative configuration of C-4 and C-13, which were distinguished by the nuclear Overhauser effect spectroscopy (NOESY) spectroscopic data in combination with the single X-ray analysis of hyperbeanol A (1). The cytotoxic activity of hyperbeanols A-D against the cancer cell lines SK-BR-3, HL-60, SMMC-7721, PANC-1, MCF-7, and K562 was also evaluated.

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Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Chen

et al. 2011

Chem. Pharm. Bull.

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“…The minimum inhibitory concentrations (MICs) of the antibiotics and plant extract were determined against resistant bacteria using the method described by Shiu and Gibbons [33].…”

Section: Minimum Inhibitory Concentration (Mic) Assaymentioning

confidence: 99%

In vitro assessment of antibiotic-resistance reversal of a methanol extract from Rosa canina L

Oyedemi

Oyedemi²,

Prieto³

et al. 2016

South African Journal of Botany

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Rosa canina (RC, the Dog Rose) is used in European folk medicine for the treatment of various human ailments. The crude methanol extract of this botanical was tested against multidrug-resistant (MDR) bacterial strains including methicillin-resistant Staphylococcus aureus SA1199B, EMRSA-16 and XU212 harbouring NorA, PBP2a and TetK resistance mechanisms, respectively, as well as S. aureus ATCC25923, a standard antimicrobialsusceptible laboratory strain. Inhibition of the conjugal transfer of plasmids PKM101 and TP114 by the RC extract was also evaluated. The RC extract demonstrated a mild to poor antibacterial activity against the panel of bacteria having MIC values ranging from 256 to >512 mg/L, but strongly potentiated tetracycline activity (64-fold) against XU212, a tetracycline-effluxing and resistant strain. Furthermore, the extract showed moderate capacity to inhibit the conjugal transfer of TP114 and PKM101; transfer frequencies were between 40% and 45%. Cytotoxicity analysis of the RC extract against HepG2 cells line showed the IC50 >500µg/mL and thus was considered non-toxic toward human cells. Phytochemical characterisation of the extracts was performed by the assessment of total phenolic content (RC: 60.86 mg TAE/g) and by HPLC fingerprint determination. The results from this study provide new mechanistic evidence justifying, at least in part, the traditional use of this extract. However, the inhibition of bacterial plasmid conjugation opens the possibility of combination therapies to overcome antibiotic-resistance.

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“…[17] Inocula of the test organisms were diluted in normal saline (9 mg/ mL) and the suspensions were adjusted to 5£10 5 (CFU/ mL). A volume of 100 mL MuellerÀHinton broth (MHB) was dispensed into the sterilized 96-well plates.…”

Section: Minimum Inhibitory Concentration (Mic) Determinationmentioning

confidence: 99%

Antibacterial and ciprofloxacin modulating activity of Ptaeroxylon obliquum (Thunb.) Radlk leaf used by the Xhosa people of South Africa for the treatment of wound infections

Oyedemi

Falowo

et al. 2016

Biotechnology & Biotechnological Equipment

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The present work investigated the antibacterial activity of Ptaeroxylon obliquum leaves (POL) extracts in the presence or absence of ciprofloxacin by the broth microdilution method and timeÀkill assay against bacterial strains associated with wound infections. Free-radicalÀscavenging activity (FRSA) was determined using the stable 2,2-diphenyl-2-picrylhydrazyl hydrate (DPPH) bioassay method. The chemical composition of the most active antioxidant extract was analysed using a gas chromatograph interfaced with a mass spectrometer (GC-MS). All POL extracts showed good antibacterial activity against the bacterial strains, with a minimum inhibitory concentration (MIC) ranging from 4 to 128 mg/mL. The exposure of bacterial strains to POL extracts resulted in 2À64-fold reductions in the MIC of ciprofloxacin. Correspondingly, the timeÀkill curves showed that combined POL extracts and ciprofloxacin treatment inhibited bacterial growth below the lowest detectable limit after 24 h of incubation. Furthermore, the ethanol extract from P. obliquum (POE) had the highest total flavonoids content (TFC: 62.7 mg/quercetin equivalent/g), while the methanol extract of P. obliquum (POM) had the best total phenolic content (TPC: 275 mg/quercetin equivalent/g) and DPPH Ã -scavenging activity having 50% inhibitory concentration (IC 50 ) of 0.125 mg/mL. The chemical composition indicated the presence of aromatic and aliphatic compounds that are known to have a wide biological effect. The findings from this study suggest that POL extracts could be a source of pharmaceutical agents for treatment of skin diseases, wound infections and as putative candidates to modulate the multidrug resistance mechanism. KEYWORDSAntibacterial activity; modulation of resistance; Ptaeroxylon obliquum; timeÀkill kinetics; wound infection Abbreviations CFU colony-forming unit DPPH 2,2-diphenyl-2-picrylhydrazyl hydrate DMSO dimethyl suphuroxide FCR FolinÀCiocalteu reagent FRSA free-radicalÀscavenging activity GAE gallic acid equivalents GC-MS gas chromatographyÀmass spectrometry IC inhibitory concentration MHB MuellerÀHinton broth MIC minimum inhibitory concentration MTT 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide MW molecular weight POA Ptaeroxylum obliquum acetone POC Ptaeroxylum obliquum chloroform POL Ptaeroxylum obliquum leaf POM Ptaeroxylum obliquum methanol ROS reactive oxygen species SIC sub-inhibitory concentration TFC total flavonoids content TPC total phenolic content

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Anti-staphylococcal acylphloroglucinols from Hypericum beanii

Cited by 61 publications

References 16 publications

Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

Spirocyclic Acylphloroglucinol Derivatives from <i>Hypericum beanii</i>

In vitro assessment of antibiotic-resistance reversal of a methanol extract from Rosa canina L

Antibacterial and ciprofloxacin modulating activity of Ptaeroxylon obliquum (Thunb.) Radlk leaf used by the Xhosa people of South Africa for the treatment of wound infections

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