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Isolation and characterization of a bactericidal withanolide from Physalis virginiana.

Gibson KA, Reese RN, Halaweish FT, Ren Y - Pharmacogn Mag (2012)

Bottom Line: Isolation of the active component showed it to be a relatively polar compound. (1)H and (13)C NMR chemical shifts together with HRMS indicated a similar structure to withanolides previously identified from Physalis angulata.HRMS analysis showed a molecular mass of 472.2857 which corresponds to a molecular formula C(28)H(40)O(6).The chemical structure was determined by NMR and MS to be the withanolide physagulin V.

View Article: PubMed Central - PubMed

Affiliation: Department of Biology and Microbiology, South Dakota State University, Brookings, SD, USA.

ABSTRACT

Background: Physalis virginiana (Virginia Groundcherry) is a member of the family Solenaceae. Several species of the Physalis genus have been used traditionally by American Indians as medicinal treatments.

Materials and methods: This study investigated the antibacterial activity of chemicals extracted from P. virginiana through antibacterial disc and cytotoxicity assays. Isolation and purification of an antimicrobial compound was achieved through flash chromatography and preparative HPLC. Finally, identification of chemical structure was determined from (1)H and (13)C NMR and MS.

Results: Disc assays showed that crude ethanol extracts were effective antibacterial agents against one gram-negative and seven gram-positive bacterial strains. Cytotoxicity assays indicated that it is less toxic than gentamicin controls. Isolation of the active component showed it to be a relatively polar compound. (1)H and (13)C NMR chemical shifts together with HRMS indicated a similar structure to withanolides previously identified from Physalis angulata. HRMS analysis showed a molecular mass of 472.2857 which corresponds to a molecular formula C(28)H(40)O(6).

Conclusion: An antibacterial withanolide was isolated from P. virginiana using flash chromatography and HPLC separations. The chemical structure was determined by NMR and MS to be the withanolide physagulin V.

No MeSH data available.


Related in: MedlinePlus

Cytotoxicity of Physalis virginiana screened against Artemia salina in concentrations of 10, 100, and 1000 μg/ml. Error bars indicate upper and lower 95% confidence intervals. Linear regression ANOVA results: (negative control) R2 = 0, Prob > F = 1.000, r = 0.0000. (shoots) R2 = 0.1429, Prob > F = 0.6297, r = 0.1614; (fruits) R2 = 0.5588, Prob > F = 0.0859, r = – 0.1465; (roots) R2 = 0.1, Prob > F = 0.7290, r = –0.3152; (gentamicin) R2 = 0.9887, Prob > F = <.0001, r = – 0.9934
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Figure 3: Cytotoxicity of Physalis virginiana screened against Artemia salina in concentrations of 10, 100, and 1000 μg/ml. Error bars indicate upper and lower 95% confidence intervals. Linear regression ANOVA results: (negative control) R2 = 0, Prob > F = 1.000, r = 0.0000. (shoots) R2 = 0.1429, Prob > F = 0.6297, r = 0.1614; (fruits) R2 = 0.5588, Prob > F = 0.0859, r = – 0.1465; (roots) R2 = 0.1, Prob > F = 0.7290, r = –0.3152; (gentamicin) R2 = 0.9887, Prob > F = <.0001, r = – 0.9934

Mentions: P. virginiana cytotoxicity values are shown in Figure 3. At all concentrations and of the shoot, root and fruit extracts showed no cytotoxicity in the brine shrimp assay. In all cases, survival rates were not significantly different from the controls. However, gentamicin was more toxic in this assay, at 1000 μg/ml the gentamicin was almost 100% lethal to the brine shrimp.


Isolation and characterization of a bactericidal withanolide from Physalis virginiana.

Gibson KA, Reese RN, Halaweish FT, Ren Y - Pharmacogn Mag (2012)

Cytotoxicity of Physalis virginiana screened against Artemia salina in concentrations of 10, 100, and 1000 μg/ml. Error bars indicate upper and lower 95% confidence intervals. Linear regression ANOVA results: (negative control) R2 = 0, Prob > F = 1.000, r = 0.0000. (shoots) R2 = 0.1429, Prob > F = 0.6297, r = 0.1614; (fruits) R2 = 0.5588, Prob > F = 0.0859, r = – 0.1465; (roots) R2 = 0.1, Prob > F = 0.7290, r = –0.3152; (gentamicin) R2 = 0.9887, Prob > F = <.0001, r = – 0.9934
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3307198&req=5

Figure 3: Cytotoxicity of Physalis virginiana screened against Artemia salina in concentrations of 10, 100, and 1000 μg/ml. Error bars indicate upper and lower 95% confidence intervals. Linear regression ANOVA results: (negative control) R2 = 0, Prob > F = 1.000, r = 0.0000. (shoots) R2 = 0.1429, Prob > F = 0.6297, r = 0.1614; (fruits) R2 = 0.5588, Prob > F = 0.0859, r = – 0.1465; (roots) R2 = 0.1, Prob > F = 0.7290, r = –0.3152; (gentamicin) R2 = 0.9887, Prob > F = <.0001, r = – 0.9934
Mentions: P. virginiana cytotoxicity values are shown in Figure 3. At all concentrations and of the shoot, root and fruit extracts showed no cytotoxicity in the brine shrimp assay. In all cases, survival rates were not significantly different from the controls. However, gentamicin was more toxic in this assay, at 1000 μg/ml the gentamicin was almost 100% lethal to the brine shrimp.

Bottom Line: Isolation of the active component showed it to be a relatively polar compound. (1)H and (13)C NMR chemical shifts together with HRMS indicated a similar structure to withanolides previously identified from Physalis angulata.HRMS analysis showed a molecular mass of 472.2857 which corresponds to a molecular formula C(28)H(40)O(6).The chemical structure was determined by NMR and MS to be the withanolide physagulin V.

View Article: PubMed Central - PubMed

Affiliation: Department of Biology and Microbiology, South Dakota State University, Brookings, SD, USA.

ABSTRACT

Background: Physalis virginiana (Virginia Groundcherry) is a member of the family Solenaceae. Several species of the Physalis genus have been used traditionally by American Indians as medicinal treatments.

Materials and methods: This study investigated the antibacterial activity of chemicals extracted from P. virginiana through antibacterial disc and cytotoxicity assays. Isolation and purification of an antimicrobial compound was achieved through flash chromatography and preparative HPLC. Finally, identification of chemical structure was determined from (1)H and (13)C NMR and MS.

Results: Disc assays showed that crude ethanol extracts were effective antibacterial agents against one gram-negative and seven gram-positive bacterial strains. Cytotoxicity assays indicated that it is less toxic than gentamicin controls. Isolation of the active component showed it to be a relatively polar compound. (1)H and (13)C NMR chemical shifts together with HRMS indicated a similar structure to withanolides previously identified from Physalis angulata. HRMS analysis showed a molecular mass of 472.2857 which corresponds to a molecular formula C(28)H(40)O(6).

Conclusion: An antibacterial withanolide was isolated from P. virginiana using flash chromatography and HPLC separations. The chemical structure was determined by NMR and MS to be the withanolide physagulin V.

No MeSH data available.


Related in: MedlinePlus