Three new sesquiterpene aminoquinones from a Vietnamese Spongia sp. and their biological activities

J Nat Med. 2018 Jan;72(1):298-303. doi: 10.1007/s11418-017-1130-5. Epub 2017 Sep 22.

Abstract

Sesquiterpenoid quinones with remarkable properties, such as anti-inflammatory, antibacterial, antiviral, antitumor, antiangiogenic, and differentiation-inducing activities, have reportedly been isolated from the marine sponge genera Dysidea, Spongia, and Dactylospongia. In our continuing search for bioactive compounds from marine sponges, three new sesquiterpenoid quinones, langcoquinones D-F (1-3), were isolated from the ethyl acetate extract of Spongia sp. collected from Vietnam. Their chemical structures were elucidated on the basis of extensive spectroscopic analyses. The newly isolated compounds 1-3 were assessed for their antibacterial activities against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Klebsiella pneumoniae and Escherichia coli, as well as their cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast). All compounds were inactive against the Gram-negative bacteria. Furthermore, langcoquinones E (2) and F (3) lacked antibacterial activities against the Gram-positive bacteria and cytotoxic activities against the tested cell lines. However, langcoquinone D (1) exhibited good antibacterial activities against Bacillus subtilis and Staphylococcus aureus, with MIC values of 12.5 and 25.0 µM, respectively. Furthermore, 1 exhibited significant cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast).

Keywords: Antibacterial activity; Cytotoxic activity; Sesquiterpene quinones; Spongia sp.; Vietnam.

MeSH terms

  • A549 Cells
  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Drug Screening Assays, Antitumor
  • Dysidea / chemistry*
  • Escherichia coli / drug effects
  • Fluorouracil / pharmacology
  • HeLa Cells
  • Humans
  • Klebsiella pneumoniae / drug effects
  • MCF-7 Cells
  • Microbial Sensitivity Tests
  • Quinones / chemistry
  • Quinones / isolation & purification
  • Quinones / pharmacology
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Staphylococcus aureus / drug effects
  • Vietnam

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Quinones
  • Sesquiterpenes
  • Fluorouracil