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Mar. Drugs 2010, 8(3), 429-437; doi:10.3390/md8030429
Article

Inhibition of Nitric Oxide (NO) Production in Lipopolysaccharide (LPS)-Activated Murine Macrophage RAW 264.7 Cells by the Norsesterterpene Peroxide, Epimuqubilin A

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Received: 14 January 2010; in revised form: 20 January 2010 / Accepted: 22 February 2010 / Published: 1 March 2010
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Abstract: Seven norsesterterpene peroxides: epimuqubilin A (1), muqubilone B (2), unnamed cyclic peroxide ester (3), epimuqubilin B (4), sigmosceptrellin A methyl ester (5), sigmosceptrellin A (6), and sigmosceptrellin B methyl ester (7), isolated from the marine sponge Latrunculia sp., were examined with regard to their effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells. The results indicated epimuqubilin A (1) possessed potent NO inhibitory activity against lipopolysaccharide (LPS)-induced nitric oxide release with an IC50 value of 7.4 µM, a level three times greater than the positive control, L-NG-monomethyl arginine citrate, followed by 6 (sigmosceptrellin A, IC50 = 9.9 µM), whereas other compounds exhibited only modest activity (Table 1). These compounds did not show appreciable cytotoxicity at their IC50 values for NO–inhibitory activity. The structure–activity upon NO inhibition could be summarized as follows: (1) a monocyclic carbon skeleton framework was essential for activity,(2) free acids gave higher activity, (3) the orientation of H3-22 with an equatorial position increased activity, and (4) a bicyclic structure reduced activity. This is the first report of a norsesterterpene peroxide with NO–inhibitory activity. In addition, compounds 17 were also evaluated for their inhibitory activities in the yeast glycogen synthase kinase-3βassay. In summary, several norsesterterpene peroxides showed novel biological activities of inhibition in NO production, suggesting that these might provide leads for anti-inflammatory or cancer chemopreventive agents.
Keywords: nitric oxide production; norsesterterpene peroxide; Latrunculia sp.; RAW 264.7 Cells nitric oxide production; norsesterterpene peroxide; Latrunculia sp.; RAW 264.7 Cells
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Cheenpracha, S.; Park, E.-J.; Rostama, B.; Pezzuto, J.M.; Chang, L.C. Inhibition of Nitric Oxide (NO) Production in Lipopolysaccharide (LPS)-Activated Murine Macrophage RAW 264.7 Cells by the Norsesterterpene Peroxide, Epimuqubilin A. Mar. Drugs 2010, 8, 429-437.

AMA Style

Cheenpracha S, Park E-J, Rostama B, Pezzuto JM, Chang LC. Inhibition of Nitric Oxide (NO) Production in Lipopolysaccharide (LPS)-Activated Murine Macrophage RAW 264.7 Cells by the Norsesterterpene Peroxide, Epimuqubilin A. Marine Drugs. 2010; 8(3):429-437.

Chicago/Turabian Style

Cheenpracha, Sarot; Park, Eun-Jung; Rostama, Bahman; Pezzuto, John M.; Chang, Leng Chee. 2010. "Inhibition of Nitric Oxide (NO) Production in Lipopolysaccharide (LPS)-Activated Murine Macrophage RAW 264.7 Cells by the Norsesterterpene Peroxide, Epimuqubilin A." Mar. Drugs 8, no. 3: 429-437.



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