Marine Natural Products Laboratory

The incomparable biodiversity of the oceans offers great opportunities for the discovery of new bioactive products with applicability in medicine, nutrition, cosmetics, new industrial processes or biotechnology.

The Marine Natural Products research group of the University of Cádiz focuses its research activity on the search for new bioactive products from marine invertebrates. Within this general objective, the main line of work is the isolation and structural characterization of new natural products that may be of pharmacological interest from the point of view of antitumor therapy. In this line, our group has been carrying out the chemical study of a wide variety of invertebrate species coming mostly from the coasts of southwestern Spain. The organisms under study belong mainly to the taxonomic groups of sponges, sea squirts and octocorals. These studies have led to the characterization by spectroscopic techniques, mainly one- and two-dimensional NMR, of more than one hundred new structures of natural products with a wide range of structural variety and complexity.

• Chemical study of marine invertebrates. Isolation of natural products.
• Characterization and structural elucidation of the isolated products.
• Chemical derivatization and establishment of structure-activity relationships.

Natural products Marine pharmacology Marine ecology Structural Characterization Spectroscopic Techniques

• Principal Investigators:
  • María Jesús Ortega Agüera (PI).
  • Eva Zubía Mendoza (Co-PI).
• Predoctoral Researchers:
  • Isabel Casal Porras (Predoctoral fellow).
  • Belén Cuevas Gómez (Predoctoral fellow).

• Ministerio de Ciencia, Innovación y Universidades: Proyectos de I+D de Retos Investigación 2018. RTI2018-101272-B-I00 PI: Mª Jesús Ortega Agüera y Ana Bartual Magro. Explorando la ficosfera: Interacciones entre fitoplancton productor de aldehídos poliinsaturados y sus procariotas acosiados (FICOEXPLORA).
• Ministerio de Economía y Competitividad (MINECO), Agencia Estatal de Investigación, Programa Estatal de I+D+i Orientada a los Retos de la Sociedad [CTM2017-85365-R] Collaboration. Papel de variables controladoras globales en el metabolismo del carbono y flujos de carbono orgánico disuelto en comunidades bentónicas costeras.
• Ministerio de Economía y Competitividad (MINECO), Agencia Estatal de Investigación, Programa Estatal de I+D+i Orientada a los Retos de la Sociedad Collaboration. Regulación a la baja del metabolismo fitoplanctónico en un mundo de alto CO2: consecuencias para la resistencia a los factores abióticos y bióticos.

1. Authors (by order of signature): I. Casal‐Porras, E. Zubía, F.G. Brun. Title: “Dilkamural, a Novel Chemical Weapon Involved in the Invasive Capacity of the Alga Rugulopteryx okamurae in the Strait of Gibraltar”. Ref. Journal: Estuarine, Coastal and Shelf Sicence. Year: 2021, Volume: 257, Article: 107398 DOI: 10.1016/j.ecss.2021.107398. Impact factor (Quartile/Decile): 2.929/Q1 Group: IN‐AS09 (IN31).
2. Authors (by order of signature): I. Casal‐Porras, R. Jiménez‐Ramos, E. Zubía, F.G. Brun. Title: “Importance of the Chemical Defences and Sugars in the Feeding Preference of Paracentrotus lividus over Two Sympatric Template Seagrass Species”. Ref. Journal: Estuarine, Coastal and Shelf Sicence. Year: 2021, Volume: 257, Article: 107466 DOI: 10.1016/j.ecss.2021.107466. Impact factor (Quartile/Decile): 2.929/Q1 Group: IN‐AS09 (IN31).
3. Authors (by order of signature): B. Cuevas, A.I. Arroba, C. de los Reyes, L. Gómez‐Jaramillo, M.C. González‐Montelongo, E. Zubía. Title: “Diterpenoids from the Brown Alga Rugulopteryx okamurae and their Anti‐inflammatory Activity”. Ref. Journal: Marine Drugs. Date: 2021, Volume: 19, Article: 677 DOI: 10.3390/md19120677. Impact factor (Quartile/Decile): 5.118/Q1 Group: IN‐AS09 (IN31) y CO17. INIBICA appears.
4. Authors : G. Hernán, M.J. Ortega, J. Henderson, J. Alos, K. Boyer, S. Cimon, V. Combes, M. Cusson, C.M. Hereu, M. Hessing‐Lewis, K. Hovel, P. Jorgensen, S. Kiriakopolos, N. Kollars, M.I. O´Connor, J. Olsen, P.L. Reynolds, J. Ruesink, E. Voigt, F. Tomas. Title: "Latitudinal variation in plant defence against herbivory in a marine foundation species does not follow a linear pattern: The importance of resource availability”. Ref. Journal: Global Ecol Biogeogr. Date: 2021, Volume: 30, Pages, first: 220‐234 D.O.I.: 10.1111/geb.13217. Impact factor (Quartile/Decile): 7.148/D1 Group: IN‐AS09 (IN31).
5. Authors : A. Ezzanad, R. Gómez‐Oliva, F. Escobar‐Montaño, M. Díez‐Salguero, N. Geribaldi‐Doldan, S. Domínguez‐García, J.M. Botubol‐Ares, C. de los Reyes, R. Durán‐Patrón, P. Nunez‐Abades, A.J. Macías‐Sánchez, C. Castro, R. Hernández‐Galán. Title: "Phorbol Diesters and 12‐Deoxy‐16‐hydroxyphorbol 13,16‐Diesters Induce TGFα Release and Adult Mouse Neurogenesis”. Ref. Journal: Journal of Medicinal Chemistry. Date: 2021, Volume: 64, Pages, first: 6070‐6084 D.O.I.: 10.1021/acs.jmedchem.1c00156. Impact factor (Quartile/Decile): 7.446/D1 Group: IN‐AS09 (IN31). INIBICA appears.

1. Authors (by order of signature): A. Rodríguez-Luna, E. Talero, M.C. Terencio, M.L. Fonzález-Rodríguez, A.M. Rabasco, C. de los Reyes, V. Motilva, J. Ávila. Title: "Topical application of glycopipids from Isochrysis galbana prevents epidermal hyperplasia in mice”. Journal: Mar. Drugs. Year, Volume, Pages: 2018, 168, 2. D.O.I.: 10.3390/md16010002. Impact factor (JCR) / Quartile / Decile: 3.772/Q1.
2. Authors (by order of signature): J. Ávila-Román, E. Talero, C. de los Reyes, S. García-Mauriño, V. Motilva. Title: "Microalgae-derived oxylipins decrease mediators by regulating the subcellular location of NFkB and PPAR-γ”. Journal: Pharmacol. Res. Year, Volume, Pages: 2018, 128, 220-230. D.O.I.: 10.1021/acs.jafc.6b03931. Impact factor (JCR) / Quartile / Decile: 3.154/Q1.
3. Authors (by order of signature): L. Prieto, A. Enrique-Navarro, R.L. Volsi, M.J. Ortega. Title: "The large jellyfish Rhizostoma luteum as sustainable a resource for antioxidant properties, nutraceutical value and biomedical applications”. Ref. Journal: Mar. Drugs. Year, Volume, Pages: 2018, 16, 396. D.O.I.: 10.3390/md16100396. Impact factor (JCR) / Quartile : 3.772/Q1.
4. Authors (by order of signature): A. Cózar, S. Morillo-García, M.J. Ortega, A.P. Li, A. Bartual. Title: "Macroecological patterns of the phytoplankton production of polyunsaturated aldehydes”. Ref. Journal: Scientific Reports. Year, Volume, Pages: 2018, 204, 1-10. D.O.I.: 10.1038/s41598-018-29787-8. Impact factor (JCR) / Quartile: 4.011/Q1.
5. Authors (by order of signature): A. Bartual, S. Morillo-García, M.J. Ortega, A. Cózar. Title: "First report on vertical distribution of dissolved polyunsaturated aldehydes in marine coastal waters”. Journal: Marine Chemistry. Year, Volume, Pages: 2018, 204, 1-10. D.O.I.: 10.1016/j.marchem.2018.05.004. Impact factor (JCR) / Quartile: 2.713/Q1.
6. Authors (by order of signature): R. Zarzuela, M.J. Luna, M.L.A. Gil, M.J. Ortega, J.M. Palacios-Santander, I. Naranjo-Rodríguez, J.J. Delgado, L.M. Cubillana-Aguilera. Title: "Analytical determination of the reducing and stabilization agents present in different Zostera noltii extracts used for the biosynthesis of gold nanoparticles”. Journal: Journal of Photochemistry&Photobiology, B: Biology. Year, Volume, Pages: 2018, 179, 32-38. D.O.I.: 10.1016/j.jphotobiol.2017.12.025. Impact factor (JCR)/Quartile: 4.067/Q1.

1. Authors (by order of signature): M.J. Ortega, J.J. Pantoja, C. de los Reyes, E. Zubía. Title:"5-Alkylresorcinol derivatives from the bryozoan Schizomavella mamillata”. Journal: Mar. Drugs. Year, Volume, Pages: 2017, 15, 344. D.O.I.: 10.3390/md15110344. Impact factor (JCR) / Quartile: 4.379/Q1/D1.
2. Authors (by order of signature): R. Jiménez-Ramos, L.G. Egea, M.J. Ortega, I. Hernández, J.J. Vergara, F.G. Brun. Title: "Global and local disturbances interact to modify seagrass palatability”. Journal: Plos One. Year, Volume, Pages: 2017, 12, e0183256.D.O.I.: 10.1371/journal.pone.0183256. Impact factor (JCR) / Quartile: 3.234/Q1.
3. Authors (by order of signature): G. Hernán, M.J. Ortega, A.M. Gándara, I. Castejón, J. Terrados, F. Tomas. Title: "Future warmer seas: increased stress and susceptibility to grazing in seedlings of a marine habitat-forming species”. Journal: Global change biology. Year, Volume, Pages: 2017, 4530-4543. D.O.I.: 10.1111/gcb.13768. Impact factor (JCR) / Quartile: 8.502/Q1/D1.
4. Authors (by order of signature): L. Manck, E. Quintana, R. Suárez, F.G. Brun, I. Hernández, M.J. Ortega, E. Zubía. Title: "Profiling of phenolic natural products in the seagrass Zostera noltei by UPLC-MS”. Journal: Nat. Prod. Commun. Year, Volume, Pages: 2017, 12, 687-690. Impact factor (JCR) / Quartile: 0.773/Q4.

1. Authors (by order of signature): C. de los Reyes, M.J. Ortega, A. Rodríguez-Luna, E. Talero, V. Motilva, E. Zubía Title: "Molecular characterization and anti-inflammatory activity of galactosylglycerides and galactosylceramides for the microalga Isochrysis galbana”. Journal: J. Agric. Food Chem. Year, Volume, Pages: 2016, 64, 8783-8794. D.O.I.: 10.1021/acs.jafc.6b03931. Impact factor (JCR) / Quartile / decil: 3.154/Q1/D1.
2. Authors (by order of signature): H. Zbakh, E.Talero, J. Ávila, A. Alcaide, C. de los Reyes, E. Zubía, V. Motilva Title: “The Algal Meroterpene 11-hydroxy-1’-O-methylamentadione Ameliorates Dextran Sulfate Sodium-inducedColitis in Mice”. Journal: Mar. Drugs. Year, Volume, Pages: 2016, 14, DOI: 10.3390/md14080149. Impact factor (JCR) / Quartile: 3.503/Q1.
3. Authors (by order of signature): J. Ávila-Román, E. Talero, C. de los Reyes, E. Zubía, V. Motilva, S. García-Mauriño. Title: “Cytotoxic Activity of Microalgae-derived Oxylipins against Human Cancer Cell Lines and their Impact on ATP Levels”. Journal: Nat. Prod. Commun. Year, Volume, Pages: 2016, 11, 1871-1875. Impact factor (JCR) / Quartile: 0.773/Q4.
4. Authors (by order of signature): C. de los Reyes, M.J. Ortega, H. Zbakh, V. Motilva, E. Zubía. Title: "Cystoseira usneoides: A brown alga rich in antioxidant and anti-inflammatory meroditerpenoids”. Journal: J. Nat. Prod. Year, Volume, Pages: 2016, 77, 395-405. D.O.I.: 10.1021/acs.jnatprod.5b01067. Impact factor (JCR) / Quartile: 3.281/Q1.
5. Authors (by order of signature): S.A. van Bergeijk, L. Hernández, E. Zubía, J.P. Cañavate. Title: “Iodine Balance, Growth and Biochemical Composition of Three Marine Microalgae Cultured under Various Inorganic Iodine Concentrations”. Journal: Mar. Biol. Year, Volume, Pages: 2016, 163, artículo 107, DOI: 10.1007/s00227-016-2884-0. Impact factor (JCR) / Quartile: 2.136/Q2.
6. Authors (by order of signature): A.L. García-Cabeza, F.J. Moreno-Dorado, M.J. Ortega, F.M. Guerra. Title: "Copper-catalyzed oxidation of alkenes and heterocycles”. Journal: Synthesis. Year, Volume, Pages: 2016, 2323-2342. D.O.I.: 10.1055/s-0035-1561649. Impact factor (JCR) / Quartile: 2.652/Q2.

1. Authors (by order of signature): A.L. García-Cabeza, R. Marín-Barrios, F.J. Moreno-Dorado, M.J. Ortega, H. Vidal, J.M. Gatica, G.M. Massanet, F.M. Guerra. Title: "Acyloxylation of 1,4-dioxanes and 1,4-dithianes catalyzed by a copper-iron mixed oxide”. Journal: J. Org. Chem. Year, Volume, Pages: 2015, 80, 6814-6821. D.O.I.: 10.1021/acs.joc.5b01043. Impact factor (JCR) / Quartile: 4.721/Q1.
2. Authors (by order of signature): A.L. García-Cabeza, L.P. Ray, R. Marín-Barrios, M.J. Ortega, F.J. Moreno-Dorado, F.M. Guerra, G.M.Massanet. Title: "Optimization by response surface methodology (RSM) of the Kharasch-Sosnovsky oxidation of valencene”. Journal: Org. Process Res. Dev. Year, Volume, Pages: 2015, 19, 1662-1666. D.O.I.: 10.1021/op5002462. Impact factor (JCR) / Quartile: 2.528/Q1.

1. Authors (by order of signature): J. Ávila-Román, E. Talero, A. Alcaide, C.de los Reyes, E. Zubía, S. García-Mauriño, V. Motilva. Title: “Preventive Effect of the Microalga Chlamydomonas debaryana on the Acute Phase of Experimental Colitis in Rats”. Journal: Brit. J. Nutr. Year, Volume, Pages: 2014, 112, 1055-1064. D.O.I.; 101017/S0007114514001895. Impact factor (JCR) / Quartile: 3.453/Q1.
2. Authors (by order of signature): C. de los Reyes, J. Ávila-Román, M.J. Ortega, A. de la Jara, S. García-Mauriño, V. Motilva, E. Zubía. Title: "Oxylipins from the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana and their activity as TNF-α inhibitors”. Journal: Phytochemistry. Year, Volume, Pages: 2014, 152-161. D.O.I.: 10.1016/j.phytochem.2014.03.011. Impact factor (JCR) / Quartile: 2.547/Q2.
3. Authors (by order of signature): A.L. García-Cabeza, R. Marín-Barrios, F.J. Moreno-Dorado, M.J. Ortega, G.M. Massanet, F.M. Guerra. Title: "Allylic oxidation of alkenes catalyzed by a copper-aluminum mixed oxide”. Journal: Org. Lett. Year, Volume, Pages: 2014, 16, 1598-1601. D.O.I.: 10.1021/ol500198c. Impact factor (JCR) / Quartile / Decile: 6.364/Q1/D1.
4. Authors (by order of signature): S. García-Morillo, N. Valcárcel-Pérez, A. Cózar, M.J. Ortega, D. Macías, E. Ramírez-Romero, C.M. García, F. Echevarría, A. Bartual. Title: "Potential polyunsaturated aldehydes in the Strait of Gibraltar under two tidal regimes”. Journal: Mar. Drugs. Year, Volume, Pages: 2014, 12, 1438-1459. D.O.I.: 10.3390/md12031438. Impact factor (JCR) / Quartile: 2.853/Q2.
5. Authors (by order of signature): A. Bartual, N. Arandia-Gorostidi, A. Cózar, S.García-Morillo, M.J. Ortega, M. Vidal, A.M. Cabello, J.I. González-Gordillo, F. Echevarría Title: "Polyunsaturated aldehydes from large phytoplankton of the Atlantic Ocean surface (42°N to 33°S)”. Journal: Mar. Drugs. Year, Volume, Pages: 2014, 12, 682-699. D.O.I.: 10.3390/md12020682. Impact factor (JCR) / Quartile: 2.853/Q2.