Quali-Quantitative Characterization of Volatile and Non-Volatile Compounds in Protium heptaphyllum (Aubl.) Marchand Resin by GC-MS Validated Method, GC-FID and HPLC-HRMS2

Molecules. 2021 Mar 7;26(5):1447. doi: 10.3390/molecules26051447.

Abstract

Protium heptaphyllum (Aubl.) Marchand (PH) trees are endemic to the tropical region of South America, mostly Brazil. Antibacterial, antinociceptive, anti-inflammatory, anxiolytic, antidepressant and anti-hyperlipidemic/anti-hypercholesterolemic effects were reported for its resinous exudate Protiumheptaphyllum resin (PHR). This work aims to provide a qualitative and quantitative consistent chemical profiling of the major constituents of this resin and two extracts enriched in acid (acidic triterpene concentrated extract, ATCE) and neutral triterpenes (α and β-amyrin concentrated extract, AMCE). GC-MS/GC-FID was used for volatile terpene fraction, a validated GC-MS method was developed for quantification of neutral α and β-amyrin and HPLC-APCI HRMS2 was used for acidic triterpenes analysis. The chemical investigation reported 29 molecules, including 14 volatile terpenes, 6 neutral triterpenes and 11 acid triterpenes. The most abundant compounds were α-amyrin (251.28 g kg-1, 123.98 g kg-1 and 556.82 g kg-1 in PHR, ATCE and AMCE, respectively), β-amyrin (172.66 g kg-1, 95.39 g kg-1 and 385.58 g kg-1 in PHR, ATCE and AMCE, respectively), 3-oxo-tirucalla-7,24-dien-21-oic acid (80.64 g kg-1, 157.10 g kg-1 and 15.31 g kg-1 in PHR, ATCE and AMCE, respectively) and 3α-hydroxy-tirucalla-8,24-dien-21-oic acid (77.71 g kg-1, 130.40 g kg-1 and 11.64 g kg-1 in PHR, ATCE and AMCE, respectively). Results showed specific enrichment of acidic and neutral triterpenoids in the two respective extracts.

Keywords: Breu branco; GC–MS; HPLC–APCI–HRMS; Protium heptaphyllum; amyrin; chemical profiling; oleum resin; triterpenes; validated method; volatile compounds.

MeSH terms

  • Burseraceae / chemistry*
  • Chromatography, High Pressure Liquid / methods
  • Gas Chromatography-Mass Spectrometry / methods
  • Pentacyclic Triterpenes / analysis
  • Plant Extracts / analysis
  • Plant Extracts / chemistry
  • Reproducibility of Results
  • Resins, Plant / chemistry*
  • Terpenes / analysis
  • Triterpenes / analysis
  • Triterpenes / chemistry
  • Volatile Organic Compounds / chemistry*

Substances

  • Pentacyclic Triterpenes
  • Plant Extracts
  • Resins, Plant
  • Terpenes
  • Triterpenes
  • Volatile Organic Compounds
  • alpha-amyrin