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. 2016 Jun 18;14(6):117.
doi: 10.3390/md14060117.

Phallusiasterol C, A New Disulfated Steroid from the Mediterranean Tunicate Phallusia fumigata

Concetta Imperatore  1 , Maria Senese  2 , Anna Aiello  3 , Paolo Luciano  4 , Stefano Fiorucci  5 , Claudio D'Amore  6 , Adriana Carino  7 , Marialuisa Menna  8
Affiliations

Phallusiasterol C, A New Disulfated Steroid from the Mediterranean Tunicate Phallusia fumigata

Concetta Imperatore et al. Mar Drugs. .

Abstract

A new sulfated sterol, phallusiasterol C (1), has been isolated from the Mediterranean ascidian Phallusia fumigata and its structure has been determined on the basis of extensive spectroscopic (mainly 2D NMR) analysis. The possible role in regulating the pregnane X receptor (PXR) activity of phallusiasterol C has been investigated; although the new sterol resulted inactive, this study adds more items to the knowledge of the structure-PXR regulating activity relationships in the case of sulfated steroids.

Keywords: PXR modulator; Phallusia fumigata; nuclear receptors; structure elucidation; sulfated sterol; tunicates.

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Figures

Figure 1
Figure 1
Structures of phallusiasterol C (1); solomonsterols A (2) and B (3); phallusiasterols A (4) and B (5); and chalinulasterol (6).
Figure 2
Figure 2
COSY segments (represented as colored bonds) and key ROESY correlations (arrows) for the phallusiasterol C (1).
Figure 3
Figure 3
(a, b) Luciferase reporter assay. HepG2 cells were transiently transfected with pSG5-PXR, pSG5-RXR, pCMV-βgalactosidase and p(CYP3A4)-TK-Luc vectors and then stimulated with (a) 10 μM rifaximin or phallusiasterol C (1) for 18 h, or (b) 10 μM rifaximin alone or in combination with 50 μM of compound 1. Relative Luciferase Units were normalized with β-galactosidase Units (RLU/βgal). All experiments were performed in triplicate. NT, not treated cells. R, Rifaximin. * p < 0.05 versus NT cells. Data are mean ± SE.
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References

    1. Lakshmi V., Kumar R. Metabolites from Sinularia species. Nat. Prod. Res. 2009;23:801–850. doi: 10.1080/14786410802137135. - DOI - PubMed
    1. Sarma N.S., Krishna M.S., Pasha S.G., Rao T.S.P., Venkateswarlu Y., Parameswaran P.S. Marine Metabolites: The Sterols of Soft Coral. Chem. Rev. 2009;109:2803–2828. doi: 10.1021/cr800503e. - DOI - PubMed
    1. Zhang W., Guo Y.W., Gu Y.C. Secondary metabolites from the South China Sea invertebrates: Chemistry and biological activity. Curr. Med. Chem. 2006;13:2041–2090. doi: 10.2174/092986706777584960. - DOI - PubMed
    1. Sica D., Musumeci D. Secosteroids of marine origin. Steroids. 2004;69:743–756. doi: 10.1016/j.steroids.2004.09.001. - DOI - PubMed
    1. Sun P., Meng L.Y., Tang H., Liu B.S., Li L., Yi Y., Zhang W. Sinularosides A and B, Bioactive 9,11-Secosteroidal Glycosides from the South China Sea Soft Coral Sinularia humilis Ofwegen. J. Nat. Prod. 2012;75:1656–1659. doi: 10.1021/np300475d. - DOI - PubMed

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