title: 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.
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.
authors.affiliation: Hanbang Body-Fluid Research Center, Wonkwang University, Iksan, 570-749, Republic of Korea.
authors.forename: Dong-Sung
authors.initials: DS
authors.lastname: Lee
authors.forename: Xiang
authors.initials: X
authors.lastname: Cui
authors.forename: Wonmin
authors.initials: W
authors.lastname: Ko
authors.forename: Kyoung-Su
authors.initials: KS
authors.lastname: Kim
authors.forename: Il Chan
authors.initials: IC
authors.lastname: Kim
authors.forename: Joung Han
authors.initials: JH
authors.lastname: Yim
authors.forename: Ren-Bo
authors.initials: RB
authors.lastname: An
authors.forename: Youn-Chul
authors.initials: YC
authors.lastname: Kim
authors.forename: Hyuncheol
authors.initials: H
authors.lastname: Oh
mesh_terms: D017738:Alkanesulfonic Acids / Q000009:adverse effects / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000009:adverse effects / Q000302:isolation & purification / Q000494:pharmacology*; D015153:Blotting, Western; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003080:Cold Temperature; D048670:MAP Kinase Kinase 4 / Q000037:antagonists & inhibitors; D020935:MAP Kinase Signaling System / Q000187:drug effects*; D008264:Macrophages / Q000187:drug effects* / Q000201:enzymology / Q000276:immunology; D051379:Mice; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D009569:Nitric Oxide / Q000378:metabolism; D009792:Oceans and Seas; D012617:Sea Urchins / Q000737:chemistry* / Q000254:growth & development; D013451:Sulfonic Acids / Q000009:adverse effects / Q000302:isolation & purification / Q000494:pharmacology*; D048051:p38 Mitogen-Activated Protein Kinases / Q000037:antagonists & inhibitors
chemical_list: C000596331:4-methylundeca-1,9-diene-6-sulfonic acid; D017738:Alkanesulfonic Acids; D000893:Anti-Inflammatory Agents; D016328:NF-kappa B; D013451:Sulfonic Acids; D009569:Nitric Oxide; D048051:p38 Mitogen-Activated Protein Kinases; D048670:MAP Kinase Kinase 4