Sterols from the brown alga Cystoseira foeniculacea: Degradation of fucosterol into saringosterol epimers

Arabian Journal of Chemistry

Volumn 12, Issue 7, 2019, Pages 1474-1478

  Bouzidi, Naima ^a   Viano, Yannick ^b   Ortalo Magné, Annick ^b   Seridi, Halima ^c   Alliche, Zahia ^a   Daghbouche, Yasmina ^a   Culioli, Gérald ^b   El Hattab, Mohamed ^a  

^a UNIVERSITY OF BLIDA   (Algeria)

^b UNIVERSITÉ DE TOULON   (France)

^c UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

Author keywords

Cystoseira foeniculacea; Fucosterol; Oxidative degradation; Sargassaceae; Saringosterols

Indexed keywords

ALCOHOLS; COLUMN CHROMATOGRAPHY; LIPIDS; MIXTURES;

CYSTOSEIRA FOENICULACEA; FUCOSTEROL; OXIDATIVE DEGRADATION; SARGASSACEAE; SARINGOSTEROLS;

FATTY ACIDS;

EID: 85074261222     PISSN: 18785352     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.arabjc.2014.11.004     Document Type: Article

References (33)

1. Abidi, S.L., Chromatographic analysis of plant sterols in foods and vegetable oils. J. Chromatogr., A 935 (2001), 173–201.
2. Amico, V., Marine brown algae of family Cystoseiraceae: chemistry and chemotaxonomy. Phytochemistry 39 (1995), 1257–1279.
3. Ayyad, S.E.N., Sowellim, S.Z.A., El-Hosini, M.S., Abo-Atia, A., The structural determination of a new steroidal metabolite from the brown alga Sargassum asperifolium. Z. Naturforsch. 58c (2003), 333–336.
4. Balboa, E.M., Conde, E., Moure, A., Falqué, E., Domínguez, H., In vitro antioxidant properties of crude extracts and compounds from brown algae. Food Chem. 138 (2013), 1764–1785.
5. Bouzidi, N., Daghbouche, Y., El Hattab, M., Aliche, Z., Culioli, G., Piovetti, L., Garrigues, S., de la Guardia, M., Determination of total sterols in brown algae by Fourier transform infrared spectroscopy. Anal. Chim. Acta 61 (2008), 185–189.
6. Catalan, C.A.N., Kokke, W.C.M.C., Duque, C., Djerassi, C., Synthesis of (24R)- and (24S)-5,28-stigmastadien-3β-ol and determination of the stereochemistry of their 24-hydroxy analogs, the saringosterols. J. Org. Chem. 48 (1983), 5207–5214.
7. Chen, Z., Liu, J., Fu, Z., Ye, C., Zhang, R., Song, Y., Zhang, Y., Li, H., Ying, H., Liu, H.J., 24(S)-Saringosterol from edible marine seaweed Sargassum fusiforme is a novel selective LXRβ agonist. Agric. Food Chem. 62 (2014), 6130–6137.
8. Draisma, S.G.A., Ballesteros, E., Rousseau, F., Thibaut, T., DNA sequence data demonstrate the polyphyly of the genus Cystoseira and other Sargassaceae genera (Phaeophyceae). J. Phycol. 46 (2010), 1329–1345.
9. El Hattab, M., Ben Messaoud, M., Daoudi, M., Ortalo-Magné, A., Culioli, G., Valls, R., Piovetti, L., Novel trihydroxylated linear diterpenes from the brown alga Bifurcaria bifurcata (Fucales, Phaeophyta). Biochem. Syst. Ecol. 36 (2008), 484–489.
10. El Hattab, M., Bouzidi, N., Ortalo-Magné, A., Daghbouche, Y., Richou, M., Chitour, S.E., de Reviers, B., Piovetti, L., Eicosapentaenoic acid: possible precursor of the phloroglucinol derivatives isolated from the brown alga Zonaria tournefortii (J.V. Lamouroux) Montagne. Biochem. Syst. Ecol. 37 (2009), 55–58.
11. Guiry, M.D., Guiry, G.M., 2013. AlgaeBase. World-wide electronic publication National University of Ireland, Galway. .
12. Hoet, S., Pieters, L., Muccioli, G.G., Habib-Jiwan, J.-L., Opperdoes, F.R., Quetin-Leclercq, J., Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds. J. Nat. Prod. 70 (2007), 1360–1363.
13. Huang, X., Li, M., Xu, B., Zhu, X., Deng, Z., Lin, W., Proteasome and NF-κB inhibiting phaeophytins from the green alga Cladophora fascicularis. Molecules 12 (2007), 582–592.
14. Huh, G.-W., Lee, D.-Y., In, S.-J., Lee, D.-G., Park, S., Yi, T.-H., Kang, H., Seo, W.-D., Baek, N.-I., Fucosterols from Hizikia fusiformis and their proliferation activities on osteosarcoma-derived cell MG63. J. Korean Soc. Appl. Biol. Chem. 55 (2012), 551–555.
15. Hwang, S.H., Jang, J.M., Lim, S.S., Isolation of fucosterol from Pelvetia siliquosa by high-speed countercurrent chromatography. Fish Aquat. Sci. 15 (2012), 191–195.
16. Ikekawa, N., Tsuda, K., Morisaki, N., Saringosterol: a new sterol from brown algae. Chem. Ind., 1966, 1179–1180.
17. 1H HR-MAS NMR analytical methods as useful taxonomical tools within the genus Cystoseira C. Agardh (Fucales; Phaeophyceae). Talanta 83 (2010), 613–622.
18. Kim, K.-B.-W.-R., Kim, M.-J., Ahn, D.-H., Lipase inhibitory activity of chlorophyll a, isofucosterol and saringosterol isolated from chloroform fraction of Sargassum thunbergii. Nat. Prod. Res. 28 (2014), 1310–1312.
19. Knights, B.A., Sterols in Ascophyllum nodosum. Phytochemistry 9 (1970), 903–905.
20. Liu, X., Wang, C.-Y., Shao, C.-L., Wei, Y.-X., Wang, B.-G., Sun, L.-L., Zheng, C.-J., Guan, H.-S., Chemical constituents from Sargassum pallidum (Turn.) C. Agardh. Biochem. Syst. Ecol. 37 (2009), 127–129.
21. Lopes, G., Sousa, C., Bernardo, J., Andrade, P.B., Valentão, P., Ferreres, F., Mouga, T., Sterol profiles in 18 macroalgae of the Portuguese coast. J. Phycol. 47 (2011), 1210–1218.
22. MarinLit, 2013. MarinLit Database, Version 17.3, Department of Chemistry, University of Canterbury, Christchurch, New Zealand. .
23. Milkova, Talev, Christov, Sterols and volatiles in Cystoseira barbata and Cystoseira crinita from the Black Sea. Phytochemistry 45 (1997), 93–95.
24. Mokrini, R., Mesaoud, M.B., Daoudi, M., Hellio, C., Maréchal, J.-P., El Hattab, M., Ortalo-Magné, A., Piovetti, L., Culioli, G., Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties. J. Nat. Prod. 71 (2008), 1806–1811.
25. Okano, M., Fukamiya, N., Fujita, T., Matsumoto, H., Aratani, T., Constituents of marine algae VIII. Non polar constituents of Hizikia fusiformis (Harvey) Okamura. Bull. Jpn. Soc. Sci. Fish. 51 (1985), 1305–1310.
26. Othmani, A., Bouzidi, N., Viano, Y., Alliche, Z., Seridi, H., Blache, Y., El Hattab, M., Briand, J.-F., Culioli, G., Anti-microfouling properties of compounds isolated from several Mediterranean Dictyota spp. J. Appl. Phycol. 26 (2014), 1573–1584.
27. Piovetti, L., Deffo, P., Valls, R., Peiffer, G., Determination of sterols and diterpenoids from brown algae (Cystoseiraceae). J. Chromatograph. 588 (1991), 99–105.
28. Shi, D., Guo, S., Fan, X., A new ketosteroid from red alga Acanthophora spicifera. Chin. J. Oceanol. Limnol. 29 (2011), 674–678.
29. Terasaki, M., Hirose, A., Narayan, B., Baba, Y., Kawagoe, C., Yasui, H., Saga, N., Hosokawa, M., Miyashita, K., Evaluation of recoverable functional lipid components of several brown seaweeds of Japan with special reference to fucoxanthin and fucosterol contents. J. Phycol. 45 (2009), 974–980.
30. Valls, R., Piovetti, L., The chemistry of the Cystoseiraceae (Fucales: Pheophyceae): chemotaxonomic relationships. Biochem. Syst. Ecol. 23 (1995), 723–745.
31. Valls, R., Piovetti, L., Banaigs, B., Praud, A., Secondary metabolites from Morocco brown algae of the genus Cystoseira. Phytochemistry 32 (1993), 961–966.
32. Viano, Y., Bonhomme, D., Ortalo-Magné, A., Thomas, O.P., El Hattab, M., Piovetti, L., Blache, Y., Culioli, G., Dictyotadimer A, a novel dissymmetric bis-diterpene from a brown alga of the genus Dictyota. Tetrahedron Lett. 52 (2011), 1031–1035.
33. Wachter, G.A., Franzblau, S.G., Montenegro, G., Hoffmann, J.J., Maiese, W.M., Timmermann, B.N., Inhibition of Mycobacterium tuberculosis growth by saringosterol from Lessonia nigrescens. J. Nat. Prod. 64 (2001), 1463–1464.