Chromatographic fractionation of the organic extract obtained from the brown alga Cystoseira trinodis led to the isolation of a known carotene pigment (7), five C-29 steroids (2–6), including two new ones (2 and 5), and an unexpected metabolite, halogenated cyclic ene-yne ether (1). Compound 1 was isolated from the genus Cystoseira for the first time. This finding plays an important role in the chemo-taxonomical differentiation of C. trinodis from other Cystoseira species. All compounds (1–7) were evaluated for their in vitro cytotoxic activities against four human tumor cell lines MCF-7, HepG2, WI 38, and Vero. They showed moderate cytotoxicity with IC50 in the range 7–33 μM, where 7 exhibited the highest antioxidant activity with 72.1% inhibition.
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References
V. A. Stonik and G. B. Elyakov, Bioorg. Med. Chem., 2, 43 (1986).
R. V. Sokolova, S. P. Ermakova, S. M. Awada, T. N. Zvyagintseva, and H. M. Kanaan, Chem. Nat. Compd., 47, 329 (2011).
N. I. Gerasimenko, S. V. Logvinov, N. G. Busarova, and E. A. Martyyas, Chem. Nat. Compd., 49, 927 (2013).
R. A. Lincoln, K. Strupinski, and J. M. Walker, Life Chem. Rep., 8, 97 (1991).
S-E. N. Ayyad, M. S. Makki, N. S. Al-kayal, S. A. Basaif, Kh. O. El-Foty, A. M. Asiri, W. M. Alarif, and F. A. Badria, Eur. J. Med. Chem., 46, 175 (2011).
B. Banaigs, C. Francisco, E. Gonzalez, and W. Fenical, Tetrahedron, 39, 629 (1983).
C. Francisco, G. Combaut, G. Teste, and B. F. Maume, Biochim. Biophys. Acta, 487, 115 (1977).
G. Combaut, C. Francisco, L. Piovetti, E. Gonzales, G. Teste, and L. Codomier, Bull. Soc. Chim. Belg., 89, 1063 (1980).
S-E. N. Ayyad, O. B. Abdel-Halim, W. T. Shier, and T. R. Hoye, Z. Naturforsch., 58c, 33 (2003).
A. Bennamara, A. Abourriche, M. Berrada, M. Charrouf, N. Chaib, M. Boudouma, and F. X. Garneau, Phytochemistry, 52, 37 (1999).
Z. S. Abou-Elnaga, W. M. Alarif, and S. S. Al-lihaibi, CLEAN – Soil, Air, Water, 39 (8), 787 (2011).
L. John Goad and T. Akihisa, Analysis of Sterols, 1st. Edn., Blackie Academic & Professional, 1977, pp. 360–422.
C. A. N. Catalan, W. C. M. C. Kokke, C. Duque, and C. Djerassi, J. Org. Chem., 48, 5207 (1983).
X. Yan, Y. Chuda, M. Suzuki, and T. Nagata, Biosci. Biotechnol. Biochem., 63, 605 (1999).
S-E. N. Ayyad, Kh. O. Al-Footy, W. M. Alarif, T. R. Sobahi, S. A. Basaif, M. S. Makki, A. S. Asiri, A. Y. Al Halwani, A. F. Badria, and F. A. Badria, Chem. Pharm. Bull., 59 (10) 1294 (2011).
J. Shen and X. Shao, Anal. Bioanal. Chem., 383 (6), 1003 (2005).
J. A. Haugan, G. Englert, E. Glinz, and S. Liaaen-Jensen, Acta Chem. Scand., 46, 389 (1992).
V. L. Teixeira and A. Kelecom, Sci. Tot. Environ., 75, 271 (1988).
V. L. Teixeira, S. A. S. Almeida, and A. Kelecom, Biochem. Syst. Ecol., 18, 87 (1990).
J. Kobayashi and M. Ishibibashi, Comprehensive Mar. Nat. Prod. Chem., 8, 415 (1999).
A. M. S. El-Gazzar, M. M. Youssef, A. A. Abu-Hashem, and F. A. Badria, Eur. J. Med. Chem., 44, 609 (2009).
H. El-Subbagh, M. Abu-Zaid, M. Mahran, F. A. Badria, and A. Al-Obaid, J. Med. Chem., 43, 2915 (2000).
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The authors would like to acknowledge SABIC, the Saudi Arabian Company for Basic Industries, for financial support of this work (MS-12-268), through the collaboration with the Deanship of Scientific Research (DSR) at King Abdulaziz University.
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Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2015, pp. 601–605.
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Alarif, W.M., Basaif, S.A., Badria, F.A. et al. Two New Cytotoxic C-29 Steroids from the Red Sea Brown Alga Cystoseira trinodis . Chem Nat Compd 51, 697–702 (2015). https://doi.org/10.1007/s10600-015-1387-4
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DOI: https://doi.org/10.1007/s10600-015-1387-4