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The resins bled from stems and in seed cones and leaves of Cryptomeria japonica, Glyptostrobus pensilis , Taxodium distichum , and T. mucronatum were characterized to provide an overview of their major natural product compositions. The total solvent extract solutions were analyzed as the free and derivatized products by gas chromatography-mass spectrometry to identify the compounds, which comprised minor mono- and sesquiterpenoids, and dominant di- and triterpenoids, plus aliphatic lipids (e.g., n -nonacosan-10-ol). Ferruginol, 7α-p-cymenylferruginol, and chamaecydin were the major characteristic markers for the Taxodioideae conifer subfamily. The mass spectrometric data can aid polar compound elucidation in environmental, geological, archeological, forensic and pharmaceutical studies., Competing Interests: The authors declare no conflicts of interest.

The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species ( Cupressaceae ) based on gas chromatography-mass spectrometry have not been reported. Results show that diterpenoids were the most abundant components and callitrisic acid was present in the resin extracts of all Callitris species analyzed. Significant amounts of 4- epi -pimaric and sandaracopimaric acids, with lesser communic, ozic, and lambertianic acids, were also in the mixtures. Phenolic diterpenoids, for example, ferruginol, hinokiol, were found in trace quantities in some samples. Thus, callitrisic acid and 4- epi -pimaric acid are the characteristic diterpenoids of Callitris species that are amenable to molecular biomarker analyses in geological or environmental applications.

A high abundance of isoprenoid hydrocarbons, the botryococcenes, with carbon numbers from 32 to 34 were detected in the Florida Everglades freshwater wetlands. These compounds were present in varying amounts up to 106microg/gdw in periphyton, 278microg/gdw in floc, and 46microg/gdw in soils. Their structures were determined based on comparison to standards, interpretation of their mass spectra and those of their hydrogenation products, and comparison of Kovats indexes to those reported in the literature. A total of 26 cyclic and acyclic botryococcenes with 8 skeletons were identified, including those with fewer degrees of unsaturation, which are proposed as early diagenetic derivatives from the natural products. This is the first report that botryococcenes occur in the Everglades freshwater wetlands. Their potential biogenetic sources from green algae and cyanobacteria were examined, but neither contained botryococcenes. Thus, the source implication of botryococcenes in this ecosystem needs further study.

Numerous saturated and aromatic hydrocarbons, but not polar compounds, originating from plants and microorganisms (biomarkers) have been reported in sediments, coals, and petroleum. Here we describe natural product terpenoids found in two fossil conifers, Taxodium balticum (Eocene) and Glyptostrobus oregonensis (Miocene). A similar terpenoid pattern is also observed in extant Taxodium distichum. The preservation of characteristic terpenoids (unaltered natural products) in the fossil conifers supports their systematic assignment to the Cypress family (Cupressaceae sensu lato). The results also show that fossil conifers can contain polar terpenoids, which are valuable markers for (paleo)chemosystematics and phylogeny.

The compositions of terpenoids from the seed cones and resins of selected fossil and modern species of pine ( Pinus, Pinaceae) were analysed using gas chromatography-mass spectrometry (GC-MS) to study the preservation of chemosystematic markers (biomarkers) in fossil conifers. Diterpenoids of the abietane, pimarane, isopimarane, and labdane types are the major components in the solvent extracts of all fossil and extant pines. Mono- and sesquiterpenoids of the bornane and cadalane classes and two phytosterols were also identified. The terpenoid patterns of the fossil species largely match the terpenoids observed in modern pines. The characteristic features of the fossil and extant Pinus species are abietane-, pimarane-, and isopimarane-type diterpenoids with a high abundance of abietic acids. Several biomolecules were preserved unaltered in the Eocene and Oligocene pine cones. In addition to the biomolecules, the fossil pines contain a series of degradation products (geomolecules) that were generated from their biological precursors before and after burial. The generation of the geomolecules is governed by various oxidative and reductive processes, such as microbial degradation and clay catalysis. In conclusion, the comparative analysis of solvent-extractable biomarkers in fossil and related extant species is a valuable tool for (palaeo)chemosystematic studies of conifers. © 2007 The Linnean Society of London, Botanical Journal of the Linnean Society, 2007, 154, 129–140. [ABSTRACT FROM AUTHOR]