Micaryolanes A and B, Two New Caryolane-Type Sesquiterpenoids from Marine Streptomyces sp. AH25

Chem Biodivers. 2020 Dec;17(12):e2000769. doi: 10.1002/cbdv.202000769. Epub 2020 Nov 26.

Abstract

Caryolanes, known as β-caryophyllene alcohols, are widely occurring sesquiterpenes in plants. From the cultures of marine Streptomyces sp. AH25, two new caryolane sesquiterpenes, micaryolanes A and B (1 and 2), together with caryolan-1,9β-diol (3) were isolated. Their structures were elucidated by extensive analyses of HR-MS and NMR spectroscopic data. The absolute configurations were assigned via the CD data of the in situ formed [Rh2 (OCOCF3 )4 ] complex and supported by comparison of experimental and calculated specific rotation values. Compounds 1-3 exhibited no activities against Hep3B or MG-63 cell lines or against Gram-positive and Gram-negative bacteria. The results not only enriched the caryolane family, but also proved bacteria as a productive source of terpene metabolites.

Keywords: Streptomyces; bacterial terpene; caryolane; sesquiterpene; β-caryophyllene alcohol.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Cell Line, Tumor
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Marine Biology*
  • Microbial Sensitivity Tests
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology*
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Sesquiterpenes