Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea

Juan Ortega-Vidal; Maggie M. Reddy; Nadia Pérez-Fuentes; Rebeca Alvariño; Svenja Burth; Amparo Alfonso; Carmen Vale; Jorge R. Virués-Segovia; Augustine Mungkaje; Luis M. Botana; Olivier P. Thomas

doi:10.1021/acs.jnatprod.5c00118

Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea

Juan Ortega-Vidal, Maggie M. Reddy, Nadia Pérez-Fuentes, Rebeca Alvariño, Svenja Burth, Amparo Alfonso, Carmen Vale, Jorge R. Virués-Segovia, Augustine Mungkaje, Luis M. Botana, Olivier P. Thomas

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Abstract

Sponges of the genus Neopetrosia are known for the production of a large diversity of bioactive metabolites. Contignasterines A (1) and B (2) were isolated as major metabolites of the sponge Neopetrosia cf. rava collected in the Bismarck Sea along with the known and highly bioactive steroid contignasterol (3) possessing a similar oxidized aglycone. Contignasterines are characterized by the presence of a 2-aminoimidazole branched on the side-chains of the oxidized steroid, and 1 also contains an unusual phosphate group at C-7. The anti-inflammatory activities of these compounds were investigated and revealed that all three compounds inhibited the production of pro-inflammatory mediators.

Original language	English
Journal	Journal of Natural Products
DOIs	https://doi.org/10.1021/acs.jnatprod.5c00118
Publication status	Accepted/In press - 2025

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Ortega-Vidal, J., Reddy, M. M., Pérez-Fuentes, N., Alvariño, R., Burth, S., Alfonso, A., Vale, C., Virués-Segovia, J. R., Mungkaje, A., Botana, L. M., & Thomas, O. P. (Accepted/In press). Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea. Journal of Natural Products. https://doi.org/10.1021/acs.jnatprod.5c00118

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title = "Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea",

abstract = "Sponges of the genus Neopetrosia are known for the production of a large diversity of bioactive metabolites. Contignasterines A (1) and B (2) were isolated as major metabolites of the sponge Neopetrosia cf. rava collected in the Bismarck Sea along with the known and highly bioactive steroid contignasterol (3) possessing a similar oxidized aglycone. Contignasterines are characterized by the presence of a 2-aminoimidazole branched on the side-chains of the oxidized steroid, and 1 also contains an unusual phosphate group at C-7. The anti-inflammatory activities of these compounds were investigated and revealed that all three compounds inhibited the production of pro-inflammatory mediators.",

author = "Juan Ortega-Vidal and Reddy, \{Maggie M.\} and Nadia P{\'e}rez-Fuentes and Rebeca Alvari{\~n}o and Svenja Burth and Amparo Alfonso and Carmen Vale and Viru{\'e}s-Segovia, \{Jorge R.\} and Augustine Mungkaje and Botana, \{Luis M.\} and Thomas, \{Olivier P.\}",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society and American Society of Pharmacognosy.",

year = "2025",

doi = "10.1021/acs.jnatprod.5c00118",

language = "English",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea

AU - Ortega-Vidal, Juan

AU - Reddy, Maggie M.

AU - Pérez-Fuentes, Nadia

AU - Alvariño, Rebeca

AU - Burth, Svenja

AU - Alfonso, Amparo

AU - Vale, Carmen

AU - Virués-Segovia, Jorge R.

AU - Mungkaje, Augustine

AU - Botana, Luis M.

AU - Thomas, Olivier P.

PY - 2025

Y1 - 2025

N2 - Sponges of the genus Neopetrosia are known for the production of a large diversity of bioactive metabolites. Contignasterines A (1) and B (2) were isolated as major metabolites of the sponge Neopetrosia cf. rava collected in the Bismarck Sea along with the known and highly bioactive steroid contignasterol (3) possessing a similar oxidized aglycone. Contignasterines are characterized by the presence of a 2-aminoimidazole branched on the side-chains of the oxidized steroid, and 1 also contains an unusual phosphate group at C-7. The anti-inflammatory activities of these compounds were investigated and revealed that all three compounds inhibited the production of pro-inflammatory mediators.

AB - Sponges of the genus Neopetrosia are known for the production of a large diversity of bioactive metabolites. Contignasterines A (1) and B (2) were isolated as major metabolites of the sponge Neopetrosia cf. rava collected in the Bismarck Sea along with the known and highly bioactive steroid contignasterol (3) possessing a similar oxidized aglycone. Contignasterines are characterized by the presence of a 2-aminoimidazole branched on the side-chains of the oxidized steroid, and 1 also contains an unusual phosphate group at C-7. The anti-inflammatory activities of these compounds were investigated and revealed that all three compounds inhibited the production of pro-inflammatory mediators.

UR - https://www.scopus.com/pages/publications/86000335374

U2 - 10.1021/acs.jnatprod.5c00118

DO - 10.1021/acs.jnatprod.5c00118

M3 - Article

AN - SCOPUS:86000335374

SN - 0163-3864

JO - Journal of Natural Products

JF - Journal of Natural Products

ER -

Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea

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