Anthelmintic and antimicrobial activities of three new depsides and ten known depsides and phenols from Indonesian lichen: Parmelia cetrata Ach.

An extensive phytochemical study of a foliose lichen from Indonesia, Parmelia cetrata, resulted in the successful isolation of 13 phenol and depside derivatives (1-13) including the previously unreported depsides 3'-hydroxyl-5'-pentylphenyl 2,4-dihydroxyl-6-methylbenzoate (7), 3'-hydroxyl-5'-propylphenyl 2,4-dihydroxyl-6-methylbenzoate (8) and 3'-hydroxyl-5'-methylphenyl 2-hydroxyl-4-methoxyl-6-propylbenzoate (9). The anti-infective activity of isolated compounds was evaluated against the gram-negative bacterium Aliivibrio fischeri and the nematode Caenorhabditis elegans. 2,4-Dihydroxyl-6-pentylbenzoate (5) and lecanoric acid (6) induced growth inhibition of A. fischeri with inhibition values of 49% and 100% at a concentration of 100 µM, respectively. The antibacterial activity might be due to their free carboxyl group. A phenolic group at C4 also contributed to the antimicrobial activity of the depsides as shown for compounds 7 and 8, which caused 89% and 96% growth inhibition at 100 µM, respectively. Lecanoric acid (6) in addition possesses significant anthelmintic effects causing 80% mortality of C. elegans at 100 µg/mL.

Anti-cancer Evaluation of Depsides Isolated from Indonesian Folious Lichens: Physcia millegrana, Parmelia dilatata and Parmelia aurulenta.

Cancer is a serious health burden on global societies. The discovery and development of new anti-cancer therapies remains a challenging objective. Although it has been shown that lichen secondary metabolites may be potent sources for new anti-cancer agents, the Indonesian- grown folious lichens, Physcia millegrana,Parmelia dilatata and Parmeila aurulenta, have not yet been explored. In this study exhaustive preparative high-performance liquid chromatography was employed to isolate the lichen constituents with spectroscopic and spectrometric protocols identifying nine depsides 9-17, including the new methyl 4-formyl-2,3-dihydroxy-6-methylbenzoate 13. The cytotoxicity of the depsides towards cancer cells was assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The results indicated lowest toxicity of the depsides towards human A549 lung cancer cells. Importantly, the di-depsides (11, 12 and 17) showed greatest toxicity, indicating that these structures are biologically more active than the mono-depsides against the HepG2 liver cancer, A549 lung cancer and HL-60 leukemia cell lines.