Previous studies have suggested that α-pinene, a common volatile plant metabolite, may have anti-inflammatory effects in human chondrocytes, thus exhibiting potential antiosteoarthritic activity. The objective of this study was to further characterize the potential antiosteoarthritic activity of selected pinene derivatives by evaluating their ability to modulate inflammation and extracellular matrix remodeling in human chondrocytes and to correlate the biological and chemical properties by determining whether the effects are isomer- and/or enantiomer-selective. To further elucidate chemicopharmacological interactions, the activities of other naturally occurring monoterpenes with the pinane nucleus were also investigated. At noncytotoxic concentrations, (+)-α-pinene (1) elicited the most potent inhibition of the IL-1β-induced inflammatory and catabolic pathways, namely, NF-κB and JNK activation and the expression of the inflammatory (iNOS) and catabolic (MMP-1 and -13) genes. (-)-α-Pinene (2) was less active than the (+)-enantiomer (1), and β-pinene (3) was inactive. E-Pinane (4) and oxygenated pinane-derived compounds, pinocarveol (5), myrtenal (6), (E)-myrtanol (7), myrtenol (8), and (Z)-verbenol (9), were less effective or even completely inactive and more cytotoxic than the pinenes tested (1-3). The data obtained show isomer- and enantiomer-selective anti-inflammatory and anticatabolic effects of α-pinene in human chondrocytes, (+)-α-pinene (1) being the most promising for further studies to determine its potential value as an antiosteoarthritic drug.

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The essential oils of OCIMUM CANUM, O. GRATISSIMUM and O. MINIMUM grown in S. Tomé, where they are used in Traditional Medicine mainly as febrifuge and for the treatment of respiratory diseases, were investigated. The essential oils were obtained from the aerial parts by hydrodistillation and subsequently analysed by GC, GC-MS and (13)C-NMR. (13)C-NMR SPECTROSCOPY proved to be an important tool, which can be very useful in the identification of most of the constituents. Major compounds in the volatile oil of O. GROTISSIMUM were thymol (48.1%) and P-cymene (12.5%). The essential oil of O. CANUM was characterized by its high content of TRANS-METHYL cinnamate (79.7%), whereas the most important oil constituent of O. MINIMUM was linalool (52.7%).

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