New phenylpropanoids from Bulbophyllum retusiusculum

Arch Pharm Res. 2018 Nov;41(11):1074-1081. doi: 10.1007/s12272-018-1067-6. Epub 2018 Aug 27.

Abstract

Two new phenylpropanoids, retusiusines A (1) and B (2), and a pair of new phenylpropyl enantiomers, (±)-retusiusine C (3a and 3b), together with eight known compounds, dihydroconiferyl dihydro-p-coumarate (4), methyl 3-(4-hydroxyphenyl) propionate (5), 3-(4-hydroxyphenyl)-propanoic acid (6), dihydroferulic acid (7), methyl 3-(4-methoxyphenyl) propionate (8), 3-(3,4-dimethoxyphenyl)-2-propenal (9), trans-p-coumaric acid (10) and dihydroconiferyl alcohol (11), were isolated from the tubers of Bulbophyllum retusiusculum. The absolute configurations of the new compounds were determined by calculating their electronic circular dichroism (ECD), spectra and specific optical rotations and comparing the calculated values with the experimental data. Compound 2 exhibited potent antifungal activity against Candida albicans (16 μg/mL). Compound 3 showed moderate antibacterial activity against Bacillus subtilis (64 μg/mL).

Keywords: Absolute configuration; Antibacterial activity; Antifungal activity; Bulbophyllum retusiusculum; Phenylpropanoid; Retusiusine.

MeSH terms

  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Orchidaceae / chemistry*
  • Phenylpropionates / isolation & purification*
  • Phenylpropionates / pharmacology
  • Plant Tubers / chemistry*
  • Plants, Medicinal
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Phenylpropionates