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Iridoid and phenylpropanoid glycosides from the roots of Lantana montevidensis

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Abstract

A new iridoid glycoside; 6-O-β-D-xylopyranoside-shanzhiside methyl ester (1) along with six known compounds; shanzhiside methyl ester (2), lamalbid (3), geniposidic acid (4), theveside (5), verbascoside (6) and arenarioside (7) were isolated from the roots of Lantana montevidensis. The structures of the compounds were determined through 1D and 2D NMR spectroscopic data analysis, HRESIMS, electronic circular dichorism and UPLC-UV/MS method. The total extract, chloroformic (F1) and aqueous (F2) fractions together with the isolated compounds were tested for their antimicrobial, antiprotozoal, antiplasmodial, anti-inflammatory, monoamine oxidase inhibition and cell viability activities in addition to free radical scavenging activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The phenylpropanoid compounds (6 and 7) resulted in a potent antioxidant activity. Total methanolic extract together with the aqueous fraction (F2) showed decrease in reactive oxidative stress with 57 and 66%, respectively, while the chloroformic fraction (F1), together with the total methanolic extract, showed a decrease in iNOS with IC50 values 5 and 30 μg/mL, respectively. Compounds 1, 2, 3, 6, and 7 showed inhibition in the reactive oxidative stress with values 50, 60, 57, 63, and 52%, respectively. Both F1 and F2 fractions demonstrated measurable inhibition of MCF-7 breast cancer cell growth, with IC50 value 0.3 mg/mL. Compounds 2 and 7 showed mild monoamine oxidase inhibition. None of the tested compounds showed antimicrobial, antiplasmodial or antiprotozoal activity.

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Acknowledgements

The authors are grateful to the Egyptian Government and the National Center for Natural Products Research, The University of Mississippi, School of Pharmacy, Mississippi, USA for their financial support. The content is solely the responsibility of the authors and does not necessarily represent the official views of the aforementioned institutions. We are also thankful to Dr. Baharthi Avula for providing the HRESIMS, Dr. Babu L. Tekwani and Dr. Narayan D. Chaurasiya for carrying out the MAOI assay and to Dr. Melissa Jacob for performing the antimicrobial assay.

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Authors and Affiliations

  1. National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Oxford, MS, 38677, USA

    Nesma M. Mohamed, Shabana I. Khan, Yan-Hong Wang & Samir A. Ross

  2. Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut, 71526, Egypt

    Nesma M. Mohamed, Makboul A. Makboul & Salwa F. Farag

  3. Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, Oxford, MS, 38677, USA

    Amer H. Tarawneh, Shabana I. Khan, Tracy A. Brooks & Samir A. Ross

  4. Department of Chemistry, Tafila Technical University, P.O. Box 179, Tafila, Jordan

    Amer H. Tarawneh

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  1. Nesma M. Mohamed
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  2. Makboul A. Makboul
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  3. Salwa F. Farag
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  5. Shabana I. Khan
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  8. Samir A. Ross
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Correspondence to Samir A. Ross.

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Mohamed, N.M., Makboul, M.A., Farag, S.F. et al. Iridoid and phenylpropanoid glycosides from the roots of Lantana montevidensis . Med Chem Res 26, 1117–1126 (2017). https://doi.org/10.1007/s00044-017-1817-x

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  • DOI: https://doi.org/10.1007/s00044-017-1817-x

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