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Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292
Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea
Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Korea
Standardized Material Bank for New Botanical Drugs, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Caugiay, Hanoi 10000, Vietnam
College of Medical and Life Sciences, Silla University, Busan 617-736, Korea
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; in revised form: 30 October 2013 / Accepted: 31 October 2013 / Published: 12 November 2013
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
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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.
Lee D-S, Ko W, Quang TH, Kim K-S, Sohn JH, Jang J-H, Ahn JS, Kim Y-C, Oh H. Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292. Marine Drugs. 2013; 11(11):4510-4526.
Lee, Dong-Sung; Ko, Wonmin; Quang, Tran H.; Kim, Kyoung-Su; Sohn, Jae H.; Jang, Jae-Hyuk; Ahn, Jong S.; Kim, Youn-Chul; Oh, Hyuncheol. 2013. "Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292." Mar. Drugs 11, no. 11: 4510-4526.