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Marine Drugs
Volume 19
Issue 12
10.3390/md19120677
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Article

Diterpenoids from the Brown Alga Rugulopteryx okamurae and Their Anti-Inflammatory Activity

by
Belén Cuevas
1,2,
Ana I. Arroba
2,3,
Carolina de los Reyes
1,
Laura Gómez-Jaramillo
2,
M. Carmen González-Montelongo
2 and
Eva Zubía
1,*
1
Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, 11510 Puerto Real (Cádiz), Spain
2
Unidad de Investigación, Instituto de Investigación e Innovación Biomédica de Cádiz (INiBICA), Hospital Universitario Puerta del Mar, Avda. Ana de Viya 21, 11009 Cádiz, Spain
3
Departamento de Endocrinología y Nutrición, Hospital Universitario Puerta del Mar, Avda. Ana de Viya 21, 11009 Cádiz, Spain
*
Author to whom correspondence should be addressed.
Mar. Drugs 2021, 19(12), 677; https://doi.org/10.3390/md19120677
Submission received: 4 November 2021 / Revised: 22 November 2021 / Accepted: 25 November 2021 / Published: 27 November 2021
(This article belongs to the Special Issue Tribute to Dr. Guido Cimino’s 80th Birthday and His Outstanding Achievements on Marine Natural Products)
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Abstract

Brown algae of the Family Dictyotaceae produce an array of structurally diverse terpenoids, whose biomedical potential in the anti-inflammatory area has been scarcely explored. Herein, the chemical study of the alga Rugulopteryx okamurae has led to the isolation of ten new diterpenoids: rugukadiol A (1), rugukamurals A–C (2–4), and ruguloptones A–F (6–10). The structures of the new compounds were established by spectroscopic means. Compound 1 exhibits an unprecedented diterpenoid skeleton featuring a bridged tricyclic undecane system. Compounds 2–10 belong to the secospatane class of diterpenoids and differ by the oxygenated functions that they contain. In anti-inflammatory assays, the new diterpenoid 1 and the secospatanes 5 and 10 significantly inhibited the production of the inflammatory mediator NO in LPS-stimulated microglial cells Bv.2 and macrophage cells RAW 264.7. Moreover, compounds 1 and 5 were found to strongly inhibit the expression of Nos2 and the pro-inflammatory cytokine Il1b in both immune cell lines.
Keywords: diterpenoids; brown algae; Rugulopteryx okamurae; anti-inflammatory; nitric oxide; cytokine; microglia; macrophages; invasive algae diterpenoids; brown algae; Rugulopteryx okamurae; anti-inflammatory; nitric oxide; cytokine; microglia; macrophages; invasive algae
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MDPI and ACS Style

Cuevas, B.; Arroba, A.I.; de los Reyes, C.; Gómez-Jaramillo, L.; González-Montelongo, M.C.; Zubía, E. Diterpenoids from the Brown Alga Rugulopteryx okamurae and Their Anti-Inflammatory Activity. Mar. Drugs 2021, 19, 677. https://doi.org/10.3390/md19120677

AMA Style

Cuevas B, Arroba AI, de los Reyes C, Gómez-Jaramillo L, González-Montelongo MC, Zubía E. Diterpenoids from the Brown Alga Rugulopteryx okamurae and Their Anti-Inflammatory Activity. Marine Drugs. 2021; 19(12):677. https://doi.org/10.3390/md19120677

Chicago/Turabian Style

Cuevas, Belén, Ana I. Arroba, Carolina de los Reyes, Laura Gómez-Jaramillo, M. Carmen González-Montelongo, and Eva Zubía. 2021. "Diterpenoids from the Brown Alga Rugulopteryx okamurae and Their Anti-Inflammatory Activity" Marine Drugs 19, no. 12: 677. https://doi.org/10.3390/md19120677

APA Style

Cuevas, B., Arroba, A. I., de los Reyes, C., Gómez-Jaramillo, L., González-Montelongo, M. C., & Zubía, E. (2021). Diterpenoids from the Brown Alga Rugulopteryx okamurae and Their Anti-Inflammatory Activity. Marine Drugs, 19(12), 677. https://doi.org/10.3390/md19120677

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