Terpenoid Oligomers of Dammar Resin

Dammar is a triterpenoid resin containing a volatile fraction, a monomeric fraction, and a high-molecular weight fraction. Although the low-molecular-weight components comprising sesquiterpenoids and triterpenoids have been extensively studied, the nature of the macromolecular components is still not fully understood, and different and sometimes contradictory theories have been proposed. The aim of this paper is to clarify the nature of the macromolecular components of dammar resin. A multianalytical approach was adopted based on thermoanalytical-thermogravimetric analysis (TGA), and thermogravimetric analysis coupled with Fourier transform infrared spectroscopy (TGA/FTIR)--and mass spectrometric techniques-direct exposure mass spectrometry (DE/MS), pyrolysis coupled to gas chromatography and mass spectrometry (Py/GC/MS), flow injection analysis electrospray ionization mass spectrometry (FIA/ESI/MS), and gas chromatography/mass spectrometry (GC/MS). The data indicate that the oligomeric fraction comprises triterpenoids bound through ester bonds, and that these triterpenoids are the same as those found in the free terpenoid fraction. The oligomeric fraction also includes triterpenoids containing carbonyl moieties, such as formyl groups, thus suggesting that these are involved in the esters in their corresponding enolic form.