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

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.

Extraction of High-Value Chemicals from Plants for Technical and Medical Applications

“…GC-MS and HPLC-MS can produce valuable results, even when the yield of the extraction process may be low (potentially too low for other methods that require significant amounts of the sample, e.g., nuclear magnetic resonance spectroscopy) [ 190 ]. Examples of natural products analysed by variants of GC-MS and HPLC-MS are depicted in Figure 11 [ 191 ].…”

“… Examples of natural products analysed by variants of GC-MS and HPLC-MS. Reproduced from [ 191 ] with permission (open access, Attribution 4.0 International (CC BY 4.0)). …”

Recent Advances in Mass Spectrometry-Based Structural Elucidation Techniques

“…Among these so-called hyphenated methods, GC-MS is most commonly used for the separation and analysis of mixtures containing volatile and thermally stable components, such as petroleum samples and volatile organic compounds; therefore, although it is an inexpensive and very sensitive method, its main limitation stems from the fact that it has lower compound coverage compared with the other two techniques [ 12 ]. With the development of GC-MS methods targeted at nonvolatile analytes, the compound coverage issue has been largely resolved [ 13 , 14 , 15 ]. GC-MS is also limited in terms of its ability to analyze molecules that have relatively low MW, typically ≤1000 Da.…”

Thermal Analysis Technologies for Biomass Feedstocks: A State-of-the-Art Review

“…Gas chromatography-mass spectrometry (GC-MS) incorporates the advantages of high-resolution component isolation with highly selective and efficient mass detection. It is common to use GCMS technologies for qualitative identification and the precise quantitative determination of unknown compounds [69]. The combination of the two technologies enables both qualitative and quantitative analyses of a sample containing a variety of organic compounds.…”

“…titative determination of unknown compounds [69]. The combination of the two technologies enables both qualitative and quantitative analyses of a sample containing a variety of organic compounds.…”