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Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 23
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Research Articles

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

ORCID Icon, , , ORCID Icon, &
Pages 5001-5010 | Received 04 Mar 2020, Accepted 22 Apr 2020, Published online: 06 May 2020
 

Abstract

An extensive phytochemical study of a foliose lichen from Indonesia, Parmelia cetrata, resulted in the successful isolation of 13 phenol and depside derivatives (113) 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.

Graphical Abstract

Acknowledgements

ASN thanks Mr. Aang Yudianto for assisting the field trip to collect the lichen in the high altitude region of Klocing-Bondowoso Indonesia. ASN also thanks the University of Jember and the Leibniz Institute of Plant Biochemistry, Halle (Germany), for research support. Furthermore, the authors acknowledge technical assistance by Gudrun Hahn (NMR), Anke Dettmer (bioassays) and Anja Ehrlich (HPLC).

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The work was financially supported by BMBF (16GW0123) and DAAD (57243965) within the program ‘Biodiversity and Health’.

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