Phyllocladane in brown coal from Handlová, Slovakia: Isolation and structural characterization

Aliphatic diterpenes were isolated from brown coal from Handlová, Slovakia, using microwave assisted extraction of mechanically activated coal powder. The parameters of the extraction procedure were optimized to get the target compounds in high yield. The total extract was separated using adsorption chromatography. GC-MS revealed tetracyclic and tricyclic diterpanes in the aliphatic fraction; they were identified as 16α(H)-phyllocladane (83%), isopimarane (11%), 18-norisopimarane (4%), abietane (2%) and fichtelite (<0.1%). It was found that more than 2 g of the most abundant diterpane, 16α(H)-phyllocladane could be extracted from 1 kg of Handlová coal. Because of the scarcity of relevant analytical data, 16α(H)-phyllocladane was thoroughly characterized by spectroscopic and chromatographic methods. A complete set of 1H and 13C NMR data is given including their comparison with published values and ab initio calculations. EI mass and IR spectra of 16α(H)-phyllocladane are shown and discussed. Kováts retention indices measured on two common GC stationary phases are also given.