A study of the properties and13C NMR spectra of pinifolic acid and its derivatives
The properties and13C NMR spectra of pinifolic acid (13S-labd-8,17-ene-15,18-dioic acid), its monomethyl ester, its dimethyl ester, its dicyclohexylammonium salt, dihydropinifolic acid, 18-hydroxy-13S-labd-8(17)-en-15-oic acid, the cyclohexylammonium salt of the monomethyl ester, the bis(diethylammonium) salt, pinifodiol (13S-labd-8(17)-ene-15,18-diol), the acetate of 18-hydroxy-13S-labd-8(17)-en-15-oic acid, and the diacetate of pinifodiol have been studied.
Chemical Fingerprinting of Conifer Needle Essential Oils and Solvent Extracts by Ultrahigh-Resolution Fourier Transform Ion Cyclotron Resonance Mass Spectrometry
Extractives are an important class of compounds in plants because they contribute to many of their physicochemical properties such as color, odor, density, strength, permeability, and hygroscopicity. Moreover, they also possess significant biological activity and are thus an important part of the plants’ defense mechanisms against biotic and abiotic stresses. Tree needles are a rich source of extractives, counting for as much as 40% of their dry weight. In this study, chemical fingerprinting of essential oils and solvent extracts, obtained from the needles of four conifer tree species (i.e., pine, spruce, larch, and juniper), was performed by using ultrahigh-resolution Fourier transform ion cyclotron mass spectrometry. A wide variety of compounds were detected in the oil samples, including mono-, sesqui-, and diterpenes, terpenoids, fatty and resin acids, esters, and different phenolic compounds. Although the main compounds were present in all the four essential oil samples, large variations in their relative abundances were observed. In contrast, pine needle hexane and toluene extracts showed a high content of resin acids, including pinifolic acid, a rare labdane-type diterpene diacid, and its mono- and dimethyl esters. Thus, by selecting a suitable solvent, specific types of compounds may be isolated from tree needles for further biotechnological or medicinal applications.
Identification of Dihydroxy Aromatic Compounds in a Low-Temperature Pyrolysis Coal Tar by Gas Chromatography−Mass Spectrometry (GC−MS) and Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS)
Dihydroxy aromatics in coal tar undergo rapid coupling reactions with each other and with some coal-derived species during coal pyrolysis and liquefaction. However, only limited information on the structure of dihydroxy aromatics is known. In this study, Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) and gas chromatography−mass spectrometry (GC−MS) were used to characterize the dihydroxy aromatics in a low-temperature pyrolyzed coal tar and its distillate and residue fractions. Negative-ion electrospray ionization (ESI) FT-ICR MS spectra of coal-tar-derived samples had low molecular masses and narrow mass ranges. Negative-ion ESI is extremely selective for the dihydroxy aromatics present in coal tar. The O2 class species had the highest ion intensity among the species in the negative-ion FT-ICR mass spectrum for each sample. Dihydroxy compounds with an aromatic core structure of benzene, indan, biphenyl (and/or acenaphthene), and naphthalene were identified in the distillate fract...