Abscisic acid-type sesquiterpenes and ansamycins from Amycolatopsis alba DSM 44262

J Asian Nat Prod Res. 2017 Oct;19(10):946-953. doi: 10.1080/10286020.2017.1285909. Epub 2017 Feb 22.

Abstract

Two new abscisic acid-type sesquiterpenes (1, 2), and one new ansamycin (3), together with four known ansamycins, namely ansacarbamitocins 4-7, were isolated from the fermentation extract of Amycolatopsis alba DSM 44262. The structures of the new compounds were elucidated to be (E)-3-methyl-5-(2,6,6-trimethyl-3-oxocyclohex-1-enyl)pent-2-enoic acid (1) and (E)-3-methyl-5-(2,6,6-trimethyl-4-oxocyclohex-2-enyl)pent-2-enoic acid (2), and 9-O-methylansacarbamitocin A1 (3), on the basis of comprehensive analysis of spectroscopic data, respectively. The antimicrobial activities were also evaluated for all seven compounds.

Keywords: Amycolatopsis alba DSM 44262; ansacarbamitocins; ansamycins; antimicrobial activity; sesquiterpenes.

MeSH terms

  • Abscisic Acid / chemistry
  • Abscisic Acid / isolation & purification*
  • Abscisic Acid / pharmacology
  • Actinomycetales / chemistry*
  • Bacillus subtilis / drug effects
  • Candida albicans / drug effects
  • Fatty Acids, Monounsaturated
  • Lactams, Macrocyclic / chemistry
  • Lactams, Macrocyclic / isolation & purification*
  • Lactams, Macrocyclic / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pseudomonas aeruginosa / drug effects
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Staphylococcus aureus / drug effects
  • Stereoisomerism

Substances

  • Fatty Acids, Monounsaturated
  • Lactams, Macrocyclic
  • Sesquiterpenes
  • pent-2-enoic acid
  • Abscisic Acid