Libertellenones O-S and Eutypellenones A and B, Pimarane Diterpene Derivatives from the Arctic Fungus Eutypella sp. D-1

J Nat Prod. 2018 Jul 27;81(7):1553-1560. doi: 10.1021/acs.jnatprod.8b00039. Epub 2018 Jun 27.

Abstract

Seven new pimarane-type diterpene derivatives, libertellenones O-S (1-5) and eutypellenones A and B (6 and 7), together with two known compounds (8 and 9), were isolated from the culture of Eutypella sp. D-1 obtained from high-latitude soil of the Arctic. Their structures were elucidated from spectroscopic data, as well as experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 1-5 possess a cyclopropyl-fused pimarane diterpene moiety, whereas compounds 6 and 7 share an unusual cyclobutyl-fused pimarane diterpene skeleton. Compounds 1-9 exhibited cytotoxicities against HeLa, MCF-7, HCT-116, PANC-1, and SW1990 cells, with IC50 values in the range of 0.3 to 29.4 μM. Compounds 6 and 7 could dose-dependently inhibit the activity of NF-κB and exhibited significantly inhibitory effects on nitric oxide production induced by lipopolysaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Arctic Regions
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • HEK293 Cells
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Soil Microbiology
  • Xylariales / chemistry*

Substances

  • Abietanes
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents