Effects of tenuiorin and methyl orsellinate from the lichen Peltigera leucophlebia on 5-/15-lipoxygenases and proliferation of malignant cell lines in vitro.

The orcinol derivatives tenuiorin (1) and methyl orsellinate (2) were identified as active components of an extract from the lichen Peltigera leucophlebia (Nyl.) Gyeln. showing in vitro inhibitory activity against 15-lipoxygenase from soybeans. The compounds were subsequently tested for in vitro activity against 5-lipoxygenase from porcine leucocytes and proved to be moderately active, with IC50 values of 41.6 microM and 59.6 microM respectively. Tenuiorin is a known constituent of several Peltigera species but has not previously been isolated from P. leucophlebia. As correlation between 5-lipoxygenase inhibition and antiproliferative effects has earlier been witnessed for related lichen metabolites, tenuiorin and methyl orsellinate were further tested for antiproliferative activity on cultured human breast (T-47D)-, pancreatic (PANC-1)- and colon (WIDR) cancer cell lines. The monomeric methyl orsellinate exhibited no detectable antiproliferative activity whereas the trimeric tenuiorin caused moderate/weak reduction in [3H]-thymidine uptake of the pancreatic- and colon cancer cells, with ED50 values of 87.9 and 98.3 microM respectively.

Stereostructure and anti-inflammatory activity of three diastereomers of ocobullenone from Ocotea bullata.

A novel diastereomer of ocobullenone. designated as sibyllenone, was isolated from the stem bark of mature Ocotea bullata in the course of a search for anti-inflammatory compounds from this plant. The stereostructure was established by X-ray crystallography and corroborated by NOESY analysis. Ocobullenone, obtained previously, was re-isolated and crystallised successfully for X-ray analysis, thus making possible an accurate spatial comparison of ocobullenone, iso-ocobullenone and the new stereoisomer. Tested pharmacologically for cyclooxygenase-1 and 2, and 5-lipoxygenase inhibition, sibyllenone was the only compound from O. bullata which showed good inhibitory activity towards 5-lipoxygenase.

Analytical and pharmacological investigation of Ocotea bullata (black stinkwood) bark and leaves.

Ocotea bullata (Lauraceae), one of the top-ten traditional medicinal plants used in KwaZulu-Natal, is close to extinction through high demand and destructive harvesting methods. The stem bark is traditionally used to cure headaches, urinary disorders and stomach problems. Substitution of leaves for bark provides a possible resource management solution for this threatened medicinal plant. One aim of this study was to compare the chemical composition of O. bullata leaves and bark using TLC, HPLC and GC-MS analysis. The characteristic analytical fingerprints of leaf and bark extracts showed great similarities. A second aim was to investigate the pharmacological properties of O. bullata as a remedy against headaches. Leaf and bark extracts were tested in terms of cyclooxygenase-1 and 5-lipoxygenase inhibition. Extracts from the bark exhibited moderate inhibitory activity in both test systems. Extracts from fresh leaves were superior to bark extracts in terms of their in vitro inhibitory activity against cyclooxygenase-1 and 5-lipoxygenase. Volatiles obtained from n-hexane extracts of leaves and bark showed better inhibitory activity towards cyclooxygenase-1 and especially towards 5-lipoxygenase than the original n-hexane extracts. Volatiles were therefore recognized as one of the main active principles in O. bullata with regards to the anti-inflammatory properties of this medicinal plant. This lends support to the traditional usage of O. bullata bark as an inhalant or snuff.