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Open AccessArticle

Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis

1
REQUIMTE/LAQV, Laboratório de Farmacognosia, Departamento de Química, Faculdade de Farmácia, Universidade do Porto, R. Jorge Viterbo Ferreira, nº 228, 4050-313 Porto, Portugal
2
Departamento de Química, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade da Coruña, E-15071 A Coruña, Spain
3
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, Av. Professor Gama Pinto, 1649-003 Lisbon, Portugal
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(6), 330; https://doi.org/10.3390/md17060330
Received: 16 April 2019 / Revised: 27 May 2019 / Accepted: 29 May 2019 / Published: 3 June 2019
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
Sea hares of Aplysia genus are recognized as a source of a diverse range of metabolites. 5α,8α-Endoperoxides belong to a group of oxidized sterols commonly found in marine organisms and display several bioactivities, including antimicrobial, anti-tumor, and immunomodulatory properties. Herein we report the isolation of 5α,8α-epidioxycholest-6-en-3β-ol (EnP(5,8)) from Aplysia depilans Gmelin, based on bioguided fractionation and nuclear magnetic resonance (NMR) analysis, as well as the first disclosure of its anti-inflammatory properties. EnP(5,8) revealed capacity to decrease cellular nitric oxide (NO) levels in RAW 264.7 macrophages treated with lipopolysaccharide (LPS) by downregulation of the Nos2 (inducible nitric oxide synthase, iNOS) gene. Moreover, EnP(5,8) also inhibited the LPS-induced expression of cyclooxygenase-2 (COX-2), interleukin 6 (IL-6), and tumor necrosis factor alpha (TNF-α) at the mRNA and protein levels. Mild selective inhibition of COX-2 enzyme activity was also evidenced. Our findings provide evidence of EnP(5,8) as a potential lead drug molecule for the development of new anti-inflammatory agents. View Full-Text
Keywords: Aplysia depilans; 5α,8α-epidioxycholest-6-en-3β-ol; iNOS; COX-1; COX-2; IL-6; TNF-α Aplysia depilans; 5α,8α-epidioxycholest-6-en-3β-ol; iNOS; COX-1; COX-2; IL-6; TNF-α
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Pereira, R.B.; Pereira, D.M.; Jiménez, C.; Rodríguez, J.; Nieto, R.M.; Videira, R.A.; Silva, O.; Andrade, P.B.; Valentão, P. Anti-Inflammatory Effects of 5α,8α-Epidioxycholest-6-en-3β-ol, a Steroidal Endoperoxide Isolated from Aplysia depilans, Based on Bioguided Fractionation and NMR Analysis. Mar. Drugs 2019, 17, 330.

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