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Bioactive compounds from Matricaria chamomilla: structure identification, in vitro antiproliferative, antimigratory, antiangiogenic, and antiadenoviral activities

  • Mohamed Shaaban ORCID logo EMAIL logo , Ali M. El-Hagrassi , Abeer F. Osman and Maha M. Soltan ORCID logo
Published/Copyright: June 22, 2021
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Zeitschrift für Naturforschung C
From the journal Zeitschrift für Naturforschung C Volume 77 Issue 3-4

Abstract

During our exploring the anticancer activity of some medicinal plants and their major metabolites, the aerial parts of the Egyptian Matricaria chamomilla (flowers and stems) were studied. GC–MS analysis of the organic soluble extracts of the flowers and stems fractions revealed the presence of 43 and 45 compounds, respectively. Individual chromatographic purification of the flowers and stems’ extracts afforded three major compounds. Structures of these compounds were identified by 1D- and 2D-NMR and HRESI-MS spectroscopic data as bisabolol oxide A (1) and (E)-tonghaosu (2) (as mixture of ratio 2:1) from the flowers extract, meanwhile apigenin-7-β-d-glucoside (3) from the stems fraction. Biologically, the chamomile extracts announced significant antiproliferative activities exceeded in potency by ∼1.5 fold in case of the stem, recording GI50 13.16 and 17.04 μg/mL against Caco-2 and MCF-7, respectively. Both fractions were approximately equipotent against the migration of the same cell type down to 10 μg/mL together, compounds 1, 2 but not 3, showed considerable growth inhibition of the same cells at GI50 13.36 and 11.83 μg/mL, respectively. Interestingly, they were able to suppress Caco-2 colon cancer cells migration at 5.8 μg/mL and potently inactivate the VEGFR2 angiogenic enzyme (1.5-fold relative to sorafenib. The obtained compounds and corresponding chamomile extracts were evaluated against Adeno-7 virus, revealing that both chamomiles’ extracts (flowers and stems) and their corresponding obtained compounds (1–3) were potent in their depletion to the Adeno 7 infectivity titer, however, the flower extract and compounds 1–2 were more effective than those of the stem extract and its end-product (3).

Keywords: Matricaria chamomilla ; bioactive compounds; antiproliferative; antimigratory; Antiangiogenic; antiadeno-7 virus activity
Corresponding author: Mohamed Shaaban, Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, El-Behoos St. 33, Dokki-Cairo 12622, Egypt; and Department of Biotechnology and Biomedicine, Technical University of Denmark, Søltofts Plads, Building 221, 2800 Kgs. Lyngby, Denmark, E-mail:

Funding source: Lundbeck Foundation

Award Identifier / Grant number: R317-2018-2541

Acknowledgments

The authors are thankful to Vacsera Vaccination Center (Al Agouzah, Dokki, Giza Governorate) for carrying out the antiviral activity testing. We thank Associate Prof. Ahmed S. Abdelrazek (Microbial Chemistry Department, National Research Centre) for the antimicrobial activity testing.

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

  2. Research funding: M. Shaaban is thankful to the Lundbeck Foundation (R317-2018-2541) for visiting professorship (June–November 2019) supporting at DTU, Denmark, at where the isolation and structure elucidation of the bioactive compounds under study have been carried out.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary material

The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2021-0083).

Received: 2021-03-21
Accepted: 2021-05-21
Published Online: 2021-06-22
Published in Print: 2022-03-28

© 2021 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Research Articles
  3. Bioactive compounds from Matricaria chamomilla: structure identification, in vitro antiproliferative, antimigratory, antiangiogenic, and antiadenoviral activities
  4. Antimicrobial synergism and antibiofilm activities of Pelargonium graveolens, Rosemary officinalis, and Mentha piperita essential oils against extreme drug-resistant Acinetobacter baumannii clinical isolates
  5. Chemical composition, antioxidant, and antimicrobial activities of two essential oils from Algerian propolis
  6. Stability of proteins involved in initiation of DNA replication in UV damaged human cells
  7. Bioguided isolation of antiplasmodial secondary metabolites from Persea americana Mill. (Lauraceae)
  8. Biological activities of some Salvia species
  9. Secondary metabolites of downy birch buds (Betula pubescens Erch.)
  10. (−)-Brunneusine, a new phenolic compound with antibacterial properties in aqueous medium from the leaves of Agelanthus brunneus (Engl.) Tiegh (LORANTHACEAE)
  11. Novel thiazolyl-hydrazone derivatives including piperazine ring: synthesis, in vitro evaluation, and molecular docking as selective MAO-A inhibitor
https://doi.org/10.1515/znc-2021-0083
Keywords for this article
Matricaria chamomilla; bioactive compounds; antiproliferative; antimigratory; Antiangiogenic; antiadeno-7 virus activity

Articles in the same Issue

  1. Frontmatter
  2. Research Articles
  3. Bioactive compounds from Matricaria chamomilla: structure identification, in vitro antiproliferative, antimigratory, antiangiogenic, and antiadenoviral activities
  4. Antimicrobial synergism and antibiofilm activities of Pelargonium graveolens, Rosemary officinalis, and Mentha piperita essential oils against extreme drug-resistant Acinetobacter baumannii clinical isolates
  5. Chemical composition, antioxidant, and antimicrobial activities of two essential oils from Algerian propolis
  6. Stability of proteins involved in initiation of DNA replication in UV damaged human cells
  7. Bioguided isolation of antiplasmodial secondary metabolites from Persea americana Mill. (Lauraceae)
  8. Biological activities of some Salvia species
  9. Secondary metabolites of downy birch buds (Betula pubescens Erch.)
  10. (−)-Brunneusine, a new phenolic compound with antibacterial properties in aqueous medium from the leaves of Agelanthus brunneus (Engl.) Tiegh (LORANTHACEAE)
  11. Novel thiazolyl-hydrazone derivatives including piperazine ring: synthesis, in vitro evaluation, and molecular docking as selective MAO-A inhibitor
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