Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri

Maria D A Oliveira; Teresinha de Jesus A Dos S Andrade; Joaquim S C Junior; Nerilson Marques Lima; Hugo G Machado; Jioji N Tabudravu; Francisco das Chagas L Pinto; Lucas Fukui-Silva; Monique C Amaro; Josué de Moraes; Dulce Helena S Silva; Antônia Maria das Graças L Citó; Chistiane Mendes Feitosa

doi:10.1021/acs.jnatprod.4c00546

Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri

J Nat Prod. 2025 Jan 4. doi: 10.1021/acs.jnatprod.4c00546. Online ahead of print.

Authors

Affiliations

¹ Department of Chemistry, Federal University of Piaui, Campus Ministro Petrônio Portela, Teresina, PI 64049-550, Brazil.
² Nucleus of Applied Research to Sciences-NIAC, Federal Institute of Education, Science and Technology of Maranhao-IFMA, Presidente Dutra (Maranhao), Timon, Maranhao 65635-468, Brazil.
³ Department of Chemistry, Federal Institute of Piaui, Campus Central, Praça da Liberdade, Teresina, PI 64049-550, Brazil.
⁴ Institute of Chemistry, Federal University of Alfenas, Alfenas MG 37130-001, Brazil.
⁵ Institute of Chemistry, Federal University of Gioias, Goiania, GO 74690-900, Brazil.
⁶ School of Natural Sciences, Faculty of Science and Technology, University of Central Lancashire, PR1 2HE Preston, U.K.
⁷ Institute of Exact Sciences and Nature, University of International Integration of Afro-Brazilian Lusophony, Redenção, CE 62790970, Brazil.
⁸ Research Center on Neglected Diseases, University of Guarulhos (NPDN-UNG), Guarulhos, SP 07030-010, Brazil.
⁹ Research Center on Neglected Diseases, University Brazil (NPDN-UB), São Paulo, SP 05508-070, Brazil.
¹⁰ Nucleus of Bioassays, Biosynthesis and Ecophysiology of Natural Products (NuBBE), Department of Organic Chemistry, Institute of Chemistry, São Paulo State University (UNESP), P.O. Box 355, Araraquara, SP 14800-900, Brazil.

PMID: 39754587
DOI: 10.1021/acs.jnatprod.4c00546

Abstract

With praziquantel being the sole available drug for schistosomiasis, identifying novel anthelmintic agents is imperative. A chemical investigation of the fruiting body of the bioluminescent mushroom Neonothopanus gardneri Berk. resulted in the isolation of new conjugated long-chain fatty acids (8E,10E,12S,13S)-12,13-dihydroxy-7-oxo-octadeca-8,10-dienoic acid (1) and (7S,8S,9E,11E)-7,8-dihydroxy-13-oxo-octadeca-9,11-dienoic acid (2) and three previously described compounds, (7R,8R,9Z)-7,8-dihydroxyoctadec-9-enoic acid (3), (2E)-dec-2-ene-1,10-dioic acid (4), and a ketolactone marasmeno-1,15-dione (5). Their planar structures were elucidated based on 1D and 2D NMR and MS/MS spectroscopic analyses. Compound 3 displayed significant antiparasitic activity against Schistosoma mansoni ex vivo (EC₅₀ < 10 μM). No toxicity was observed in mammalian cells or Caenorhabditis elegans.