Rauvolfianine, a new antimycobacterial glyceroglycolipid and other constituents from Rauvolfia caffra. Sond (Apocynaceae)

Nat Prod Res. 2018 Aug;32(16):1971-1976. doi: 10.1080/14786419.2017.1356832. Epub 2017 Aug 16.

Abstract

The chemical investigation of the extract of the dried leaves of Rauvolfia caffra (Sond) (synonym Rauvolfia macrophylla) (Apocynaceae) led to isolation of a new glycoside derivative, rauvolfianine (1) as well as six known compounds: oleanolic acid (2), sitosterol-3-O-β-D-glucopyranoside (3), betulinic acid (4), vellosimine (5), sarpagine (6) and D-fructofuranosyl-β-(2→1)-α-D-glucopyranoside (7). Compounds 1, 2, 3, 4 and 7 were evaluated for antitubercular activity. Compounds 1 and 2 were the most active (MIC = 7.8125 and 31.25 μg/mL) towards the Isoniazid resistant strain of Mycobacterium tuberculosis AC45. Their structures and relative stereochemistry were elucidated by spectroscopic methods.

Keywords: 1D and 2D NMR; Apocynaceae; Rauvolfia caffra; Rauvolfianine; antitubercular activity; glycerol ester.

MeSH terms

  • Antitubercular Agents / chemistry
  • Antitubercular Agents / isolation & purification*
  • Antitubercular Agents / pharmacology
  • Apocynaceae / chemistry*
  • Betulinic Acid
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Oleanolic Acid / analysis
  • Pentacyclic Triterpenes
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Rauwolfia
  • Sitosterols
  • Triterpenes

Substances

  • Antitubercular Agents
  • Glycosides
  • Pentacyclic Triterpenes
  • Plant Extracts
  • Sitosterols
  • Triterpenes
  • gamma-sitosterol
  • Oleanolic Acid
  • Betulinic Acid