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A new sulfonic acid derivative, (Z)-4-methylundeca-1,9-diene-6-sulfonic acid, isolated from the cold water sea urchin inhibits inflammatory responses through JNK/p38 MAPK and NF-κB inactivation in RAW 264.7

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Abstract

In this study, we isolated a new sulfonic acid derivative, (Z)-4-methylundeca-1,9-diene-6-sulfonic acid (1), from the sea urchin collected from the Sea of Okhotsk. We established the structure of this new compound by analysis of NMR and HRMS data, along with comparison of the data with those of the related compounds reported in the literature. In addition, we investigated its anti-inflammatory effects in LPS-stimulated RAW264.7 macrophages. Compound 1 inhibited the production of NO, iNOS, PGE2, and COX-2, and it also suppressed the production of pro-inflammatory cytokines, such as TNF-α and IL-1β. It inhibited the translocation of the NF-κB subunit p65 into the nucleus by interrupting the phosphorylation and degradation of IκB-α. In addition, compound 1 significantly decreased the phosphorylation of JNK and p38 in LPS-stimulated RAW264.7 macrophages, suggesting that suppression of the inflammation process by compound 1 was mediated through the MAPK pathway. Taken together, this study showed that the anti-inflammatory effects of a new sulfonic acid derivative, (Z)-4-methylundeca-1,9-diene-6-sulfonic acid were mediated through the inhibition of NF-κB and JNK/p38 MAPK signaling pathways.

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Acknowledgments

This research was supported by a grant from the Ministry of Oceans and Fisheries under a project PN12030 (K-POD).

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Authors and Affiliations

  1. Hanbang Body-Fluid Research Center, Wonkwang University, Iksan, 570-749, Republic of Korea

    Dong-Sung Lee, Youn-Chul Kim & Hyuncheol Oh

  2. Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University College of Pharmacy, 977 Gongyuan Road, Yanji, 133002, Jilin, People’s Republic of China

    Xiang Cui & Ren-Bo An

  3. Institute of Pharmaceutical Research and Development, College of Pharmacy, Wonkwang University, Iksan, 570-749, Republic of Korea

    Xiang Cui, Wonmin Ko, Kyoung-Su Kim, Youn-Chul Kim & Hyuncheol Oh

  4. Standardized Material Bank for New Botanical Drugs, College of Pharmacy, Wonkwang University, Iksan, Republic of Korea

    Wonmin Ko, Kyoung-Su Kim, Youn-Chul Kim & Hyuncheol Oh

  5. Korea Polar Research Institute, KORDI, 7-50 Songdo-dong, Yeonsu-gu, Inchon, 406-840, Republic of Korea

    Il Chan Kim & Joung Han Yim

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  1. Dong-Sung Lee
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  2. Xiang Cui
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  3. Wonmin Ko
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  4. Kyoung-Su Kim
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  7. Ren-Bo An
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  8. Youn-Chul Kim
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  9. Hyuncheol Oh
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Correspondence to Youn-Chul Kim or Hyuncheol Oh.

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Dong-Sung Lee and Xiang Cui contributed equally to this work.

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Lee, DS., Cui, X., Ko, W. et al. A new sulfonic acid derivative, (Z)-4-methylundeca-1,9-diene-6-sulfonic acid, isolated from the cold water sea urchin inhibits inflammatory responses through JNK/p38 MAPK and NF-κB inactivation in RAW 264.7. Arch. Pharm. Res. 37, 983–991 (2014). https://doi.org/10.1007/s12272-013-0269-1

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  • DOI: https://doi.org/10.1007/s12272-013-0269-1

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