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Mar. Drugs 2013, 11(11), 4510-4526; doi:10.3390/md11114510
Article

Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292

1,2,†
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1,3,†
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1,4
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1,3
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5
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6
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6
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1,2,3,*  and 1,2,3,*
1 Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea 2 Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Korea 3 Standardized Material Bank for New Botanical Drugs, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea 4 Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi 10000, Vietnam 5 College of Medical and Life Sciences, Silla University, Busan 617-736, Korea 6 Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), 30 Yeongudanji-ro, Ochang, Cheongwon 363-883, Korea These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 9 October 2013 / Revised: 30 October 2013 / Accepted: 31 October 2013 / Published: 12 November 2013
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Abstract

In the course of studies on bioactive metabolites from marine fungi, a new 10-membered lactone, named penicillinolide A (1) was isolated from the organic extract of Penicillium sp. SF-5292 as a potential anti-inflammatory compound. The structure of penicillinolide A (1) was mainly determined by analysis of NMR and MS data and Mosher’s method. Penicillinolide A (1) inhibited the production of NO and PGE2 due to inhibition of the expression of iNOS and COX-2. Penicillinolide A (1) also reduced TNF-α, IL-1β and IL-6 production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), a competitive inhibitor of HO activity, it was verified that the inhibitory effects of compound 1 on the production of pro-inflammatory mediators and NF-κB DNA binding activity were partially associated with HO-1 expression through Nrf2 nuclear translocation.
Keywords: Penicillium sp.; marine-derived fungi; 10-membered lactone; anti-inflammatory effect; heme oxygenase-1 Penicillium sp.; marine-derived fungi; 10-membered lactone; anti-inflammatory effect; heme oxygenase-1
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Lee, D.-S.; Ko, W.; Quang, T.H.; Kim, K.-S.; Sohn, J.H.; Jang, J.-H.; Ahn, J.S.; Kim, Y.-C.; Oh, H. Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292. Mar. Drugs 2013, 11, 4510-4526.

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