Asphodosides A-E, anti-MRSA metabolites from Asphodelus microcarpus

Mohammed M Ghoneim; Khaled M Elokely; Atef A El-Hela; Abd-Elsalam I Mohammad; Melissa Jacob; Mohamed M Radwan; Robert J Doerksen; Stephen J Cutler; Samir A Ross

doi:10.1016/j.phytochem.2014.06.011

Asphodosides A-E, anti-MRSA metabolites from Asphodelus microcarpus

Phytochemistry. 2014 Sep:105:79-84. doi: 10.1016/j.phytochem.2014.06.011. Epub 2014 Jul 14.

Authors

Mohammed M Ghoneim¹, Khaled M Elokely², Atef A El-Hela³, Abd-Elsalam I Mohammad³, Melissa Jacob⁴, Mohamed M Radwan⁵, Robert J Doerksen⁶, Stephen J Cutler⁶, Samir A Ross⁷

Affiliations

¹ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA; Department of Pharmacognosy, Faculty of Pharmacy, The University of Al-Azhar, Cairo 11371, Egypt.
² Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
³ Department of Pharmacognosy, Faculty of Pharmacy, The University of Al-Azhar, Cairo 11371, Egypt.
⁴ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA.
⁵ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA; Department of Pharmacognosy, Faculty of Pharmacy, The University of Alexandria, Alexandria 21521, Egypt.
⁶ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA; Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
⁷ National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA; Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA. Electronic address: sross@olemiss.edu.

Abstract

Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm. et Viv. (Xanthorrhoeaceae or Asphodelaceae) resulted in isolation of five compounds identified as asphodosides A-E (1-5). Compounds 2-4 showed activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 1.62, 7.0 and 9.0μg/mL, respectively. They also exhibited activity against Staphylococcus aureus (non-MRSA) with IC50 values of 1.0, 3.4 and 2.2μg/mL, respectively. The structure elucidation of isolated metabolites was carried out using spectroscopic data (1D and 2D NMR), optical rotation and both experimental and calculated electronic circular dichroism (ECD).

Keywords: Asphodelaceae; Asphodelus microcarpus; Electronic circular dichroism; MRSA.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification*
Anti-Bacterial Agents / pharmacology*
Circular Dichroism
Drug Resistance, Bacterial
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / isolation & purification*
Heterocyclic Compounds, 4 or More Rings / pharmacology*
Liliaceae / chemistry
Methicillin-Resistant Staphylococcus aureus / drug effects*
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular

Substances

Anti-Bacterial Agents
Heterocyclic Compounds, 4 or More Rings

Abstract

Publication types

MeSH terms

Substances

Grants and funding