A Novel 4H-Chromen-4-One Derivative from Marine Streptomyces ovatisporus S4702T as Potential Antibacterial and Anti-Cancer Agent

Anticancer Agents Med Chem. 2022;22(2):362-370. doi: 10.2174/1871520621666210311085748.

Abstract

Background: Marine actinomycetes are among indispensable sources of natural bioactive compounds with unique antimicrobial and anti-cancer activities.

Objective: Herein, it was aimed to elucidate the bioactive potential of a marine-derived Streptomyces ovatisporus S4702T, isolated previously.

Methods: Streptomyces ovatisporus S4702T was cultured in N-Z Amine broth, and extraction was carried out using different organic solvents. Bioassay-guided purification was followed by chemical characterization using NMR and LC-MS/MS. The compound was then evaluated for its antibacterial, antioxidant and cytotoxic activities.

Results: Etyl acetate extracts gave the highest antibacterial activity, and chemical characterization of this extract indicated the formula as C15H29O5N3 and the corresponding possible molecular structure as 4H-chromen-4-one derivative. It was found highly potent against Bacillus subtilis ATCC 6633 (MIC: 0.25 μg ml-1) and Micrococcus luteus ATCC 9341 (MBC: 0.5 μg ml-1). It has no remarkable antioxidant activity, but a higher EC50 value and less cytotoxicity against normal cells. The EC50 values of this chromen derivative were found as 9.68 μg ml-1 for human colon carcinoma, 9.93 μg ml-1 for human prostate adenocarcinoma and 25.5 μg ml-1 for human embryonic kidney cells.

Conclusion: Overall, the presented 4H-chromen-4-one derivative is a remarkable bioactive compound with potent antibacterial and cytotoxic activity. With its high bioactive potential, it is proposed as a good candidate in medicine.

Keywords: 4H-chromen-4-one; LC-MS/MS; NMR; Streptomyces ovatisporus S4702T; antibacterial activity; cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Apoptosis / drug effects
  • Benzothiazoles / antagonists & inhibitors
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Cells, Cultured
  • Chromones / chemistry
  • Chromones / isolation & purification
  • Chromones / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenethylamines / antagonists & inhibitors
  • Streptomyces / chemistry*
  • Structure-Activity Relationship
  • Sulfonic Acids / antagonists & inhibitors

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Antioxidants
  • Benzothiazoles
  • Chromones
  • Phenethylamines
  • Sulfonic Acids
  • 1-(2,6-dimethylphenoxy)-2-(3,4-dimethoxyphenylethylamino)propane
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid

Supplementary concepts

  • Streptomyces ovatisporus