Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae)

Lukaseder, Brigitte; Vajrodaya, Srunya; Hehenberger, Tina; Seger, Christoph; Nagl, Michael; Lutz‐Kutschera, Gerda; Robien, Wolfgang; Greger, Harald; Hofer, Otmar

doi:10.1016/j.phytochem.2009.05.007

Cited by 32 publications

(33 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, 5-O-MG alone has antibacterial activity, and in combination with AM, a synergistic effect against beta-lactamase producing strains. 5-O-MG was initially characterized and isolated from the leaf extracts of the civilian medicinal plant Glycosmis (Lukaseder et al, 2009). Isoprenylavanoids are the main biological and pharmacological compounds in extracts of Glycosmis species, and glovanon and 5-O-methylglovanon are two compounds with antimicrobial abilities (Na et al, 2006;Jang et al, 2008).…”

Section: Discussionmentioning

confidence: 99%

“…Ampicillin (AM) and clavulanic acid (CA) were purchased from Pharmaceutical and Biological Products Inc. Ampicillin stock was prepared in 0.1 mol/L of phosphate buffer (pH 8.0). 5-O-MG was synthesized using isovanillin and 2, 4, 6-trihydroxyacetophenone as starting chemicals at the College of Chemistry and Chemical Engineering at Ningxia University (Lukaseder et al, 2009), and was dissolved in DMSO.…”

Section: Chemicalsmentioning

confidence: 99%

“…1 (Lukaseder et al, 2009). The drug susceptibility of eleven clinical, AM-resistant Staphylococcus isolates to 5-O-MG and AM, determined by a microdilution checkerboard technique is listed in Table I.…”

Section: Susceptibility Of Staphylococcus Isolates To 5-o-mg and Ammentioning

confidence: 99%

See 2 more Smart Citations

In Vitro synergistic interaction of 5-O-methylglovanon and ampicillin against ampicillin resistant Staphylococcus aureus and Staphylococcus epidermidis isolates

et al. 2011

View full text Add to dashboard Cite

5-O-methylglovanon (5-O-MG) is a bioactive compound that was first isolated and characterized from Glycosmis plants. In this study, we found that chemically synthesized 5-O-MG has antimicrobial ability against eleven clinical ampicillin resistant Staphylococcus aureus and S. epidermidis isolates. The MICs of 5-O-MG against the S. aureus and S. epidermidis isolates were 12.5-50 μg/mL and 25-50 μg/mL, respectively. In combination with ampicillin, a synergistic interaction between 5-O-MG and ampicillin against the eleven resistant Staphylococcus isolates was observed, with fractional inhibitory concentration indices of 0.03-0125. Moreover, the anti-staphylococcal activity of 5-O-MG in combination with ampicillin was comparable with that of clavulanic acid in combination with ampicillin. The drug combination had no antagonistic effects when tested against any of the strains. Time-killing assays confirmed the synergy between 5-O-MG and ampicillin (p < 0.01). The combination of these two agents yielded greater than a 2 log(10) cfu/mL decrease in comparison with 5-O-MG or ampicillin alone. These findings suggest that 5-O-MG is a promising compound with the potential for future anti-staphylococcal drug development.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Chemicalsmentioning

confidence: 99%

See 1 more Smart Citation

In Vitro synergistic interaction of 5-O-methylglovanon and ampicillin against ampicillin resistant Staphylococcus aureus and Staphylococcus epidermidis isolates

et al. 2011

View full text Add to dashboard Cite

show abstract

“…2 Prenylations at the two benzene rings often increase the lipophilicity of the backbone compounds, leading to enhancement of their affinity to cell membranes and of their interaction with target proteins. 4−6 Owing to the impressive biological activities and their diverse chemical structures, prenylated flavonoids have been studied by scientists from different research disciplines including natural product chemistry, 7 plant physiology, 8 and chemical syntheses. 9,10 In plants, the prenyl moieties are transferred from prenyl diphosphates onto the flavonoid skeleton by membrane-bound prenyltransferases.…”

mentioning

confidence: 99%

Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

Zhou

Xie

et al. 2015

J. Nat. Prod.

View full text Add to dashboard Cite

Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.

show abstract

“…5-O-Methylglovanon was initially characterized and isolated from the leaf extracts of the civilian medicinal plant Glycosmis species (Lukaseder et al, 2009). The combination of 5-O-MG and ampicillin (AM) significantly increased the susceptibility of Staphylococcus strains to the drugs by decreasing MICs (p < 0.05), with the exception of the S. epidermidis 9 isolate, which showed no reaction to the combination of drugs.…”

mentioning

confidence: 99%

Enriching modern pharmacotherapy through synergy assessment for the combination of natural products and synthetic drugs

Brice

Jang

2011

Arch. Pharm. Res.

View full text Add to dashboard Cite

5-O-methylglovanon (5-O-MG) is a bioactive compound first isolated and characterized from Glycosmis plants. In this issue, Zhou et al. evaluated the anti-staphylococcal effects of 5-O-MG against ampicillin-resistant isolates of Staphylococcus aureus and S. epidermidis. The authors showed that the combination of 5-O-MG and ampicillin significantly increased the susceptibility of Staphylococcus strains to the drugs by decreasing MICs with a comparable anti-staphylococcal effect to that of β-lactamase inhibitors, suggesting that herbal compounds such as 5-O-MG may be potential candidates for the inhibitor of β-lactamases. This study is another example of synergy assessment of natural products in drug development to likely enrich modern pharmacotherapy.

show abstract

Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae)

Cited by 32 publications

References 38 publications

In Vitro synergistic interaction of 5-O-methylglovanon and ampicillin against ampicillin resistant Staphylococcus aureus and Staphylococcus epidermidis isolates

In Vitro synergistic interaction of 5-O-methylglovanon and ampicillin against ampicillin resistant Staphylococcus aureus and Staphylococcus epidermidis isolates

Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases

Enriching modern pharmacotherapy through synergy assessment for the combination of natural products and synthetic drugs

Contact Info

Product

Resources

About