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Coumaronochromone as antibacterial and carbonic anhydrase inhibitors from Aerva persica (Burm.f.) Merr.: experimental and first-principles approaches

  • Muhammad Imran EMAIL logo , Ahmad Irfan EMAIL logo , Mohammed A. Assiri , Sajjad H. Sumrra , Muhammad Saleem , Riaz Hussain and Abdullah G. Al-Sehemi
Published/Copyright: September 9, 2020
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Zeitschrift für Naturforschung C
From the journal Zeitschrift für Naturforschung C Volume 76 Issue 1-2

Abstract

The Aerva plants are exceptionally rich in phytochemicals and possess therapeutics potential. Phytochemical screening shows that Aerva persica (Burm.f.) Merr. contains highest contents i.e., total phenolics, flavonoids, flavonols, tannins, alkaloids, carbohydrates, anthraquinones and glycosides. In-vitro antibacterial and enzymatic (carbonic anhydrase) inhibition studies on methanol extracts of A. persica indicated the presence of biological active constituents within chloroform soluble portions. Investigation in the pure constituents on the chloroform portions of A. persica accomplished by column chromatography, NMR and MS analysis. The bioguided isolation yields four chemical constituents of coumaronochromone family, namely aervin (1-4). These pure chemical entities (1-4) showed significant antibacterial activity in the range of 60.05–79.21 µg/ml against various bacterial strains using ampicillin and ciprofloxacin as standard drugs. The compounds 1-4 showed promising carbonic anhydrase inhibition with IC50 values of 19.01, 18.24, 18.65 and 12.92 µM, respectively, using standard inhibitor acetazolamide. First-principles calculations revealed comprehensive intramolecular charge transfer in the studied compounds 1-4. The spatial distribution of highest occupied and lowest unoccupied molecular orbitals, ionization potential, molecular electrostatic potential and Hirshfeld analysis revealed that these coumaronochromone compounds would be proficient biological active compounds. These pure constituents may be used as a new pharmacophore to treat leaukomia, epilepsy, glaucoma and cystic fibrosis.

Keywords: Aerva persica (Burm.f.) Merr.; antibacterial activity; carbonic anhydrase; coumaronochromone; density functional theory; molecular electrostatic potential
Corresponding author: Muhammad Imran, Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia, E-mail: ; and Ahmad Irfan, Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia; and Research Center for Advanced Materials Science (RCAMS), King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia, E-mail:

Funding source: King Khalid University

Award Identifier / Grant number: GRP-85/41

Acknowledgments

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University Saudi Arabia for funding this work through General Research Project under grant number (GRP-85/41).

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University Saudi Arabia for funding this work through General Research Project under grant number (GRP-85/41).

  3. Conflict of interest statement: The authors declare no conflict of interest.

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Supplementary Material

The online version of this article offers supplementary material https://doi.org/10.1515/ZNC-2020-0138

Received: 2020-06-15
Accepted: 2020-08-22
Published Online: 2020-09-09
Published in Print: 2021-01-27

© 2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

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  2. Review Article
  3. The fate of chlorophyll in phytophagous insects goes beyond nutrition
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  6. Absolute configuration of tetrandrine and isotetrandrine influences their anti-proliferation effects in human T cells via different regulation of NF-κB
  7. Safflower injection inhibits pulmonary arterial remodeling in a monocrotaline-induced pulmonary arterial hypertension rat model
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  9. Isolation of secondary metabolites from the Iranian medicinal plant Eremurus persicus
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  13. Coumaronochromone as antibacterial and carbonic anhydrase inhibitors from Aerva persica (Burm.f.) Merr.: experimental and first-principles approaches
  14. Ethyl acetate extract from Cistus x incanus L. leaves enriched in myricetin and quercetin derivatives, inhibits inflammatory mediators and activates Nrf2/HO-1 pathway in LPS-stimulated RAW 264.7 macrophages
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https://doi.org/10.1515/znc-2020-0138
Keywords for this article
Aerva persica (Burm.f.) Merr.; antibacterial activity; carbonic anhydrase; coumaronochromone; density functional theory; molecular electrostatic potential

Articles in the same Issue

  1. Frontmatter
  2. Review Article
  3. The fate of chlorophyll in phytophagous insects goes beyond nutrition
  4. Research Articles
  5. Eleven isoquinoline alkaloids on inhibiting tissue factor activity: structure-activity relationships and molecular docking
  6. Absolute configuration of tetrandrine and isotetrandrine influences their anti-proliferation effects in human T cells via different regulation of NF-κB
  7. Safflower injection inhibits pulmonary arterial remodeling in a monocrotaline-induced pulmonary arterial hypertension rat model
  8. Gas chromatography coupled to mass spectrometry (GC-MS) characterization and evaluation of antibacterial bioactivities of the essential oils from Piper arboreum Aubl., Piper aduncum L. e Piper gaudichaudianum Kunth
  9. Isolation of secondary metabolites from the Iranian medicinal plant Eremurus persicus
  10. Decumbic anhydride from the stem barks of Swintonia floribunda (Anacardiaceae)
  11. Phytochemical characterization of different yarrow species (Achillea sp.) and investigations into their antimicrobial activity
  12. Monitoring of changes in 5-n-alkylresorcinols during wheat seedling development
  13. Coumaronochromone as antibacterial and carbonic anhydrase inhibitors from Aerva persica (Burm.f.) Merr.: experimental and first-principles approaches
  14. Ethyl acetate extract from Cistus x incanus L. leaves enriched in myricetin and quercetin derivatives, inhibits inflammatory mediators and activates Nrf2/HO-1 pathway in LPS-stimulated RAW 264.7 macrophages
  15. Rapid Communication
  16. A new xanthone dimer and cytotoxicity from the stem bark of Calophyllum canum
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