Sulfoquinovosylmonoacylglycerols regulating intestinal inflammation in co-culture system from the brown alga <italic>Turbinaria ornata</italic>

Abstract

The inflammatory bowel diseases (IBD) including ulcerative colitis and Crohn disease are characterized by chronic inflammation throughout the gastrointestinal tract. The prevalence of IBD has been increasing worldwide, and has sometimes led to irreversible impairment of gastrointestinal structure and functions. In the present study, we identified a new sulfoquinovosylmonoacylglycerols (SQMG) (1) together with two known SQMGs (2 and 3) regulating intestinal inflammation from the brown alga Turbinaria ornata. The anti-inflammatory properties of two bioactive SQMGs, 1 and 2 were evaluated using an in vitro co-culture system consisting of human epithelial Caco-2 cells and PMA (phorbol 12-myristate 12-acetate)-differentiated THP-1 macrophages. Treatment with 1 or 2 inhibited the production nitric oxide and prostaglandin E 2 induced by lipopolysaccharide and interferon γ challenge. The expressions of inducible nitric oxide synthase and cyclooxygenase 2 were markedly down-regulated in response to inhibition of nuclear factor κB translocation to nucleus. These findings suggest the potential use of the brown alga T. ornata and its biologically active metabolites SQMGs as pharmaceutical adjuvants in the treatment of inflammation-related diseases, including IBD.

Standardized Fraction of Turbinaria ornata Alleviates Dextran Sulfate Sodium-Induced Chronic Colitis in C57BL/6 Mice via Upregulation of FOXP3+ Regulatory T Cells

“…Using the combination of NMR and high resolution electrospray ionisation mass spectrometry (HRESIMS), and comparing with reported data, 1 was identified as 22 E -3β-cholesta-5,22-dien-24-one [ 32 ]. The structure of 5 was determined to be 1- O -[(7 E )-9-hydroxyoctadeca-7-enoyl]-3- O -(6-sulfo-α- d -quinovopyranosyl)-sn-glycerol, 6 as 1-palmitoyl-3- O -(6-sulfo-α- d -quinovopyranosyl)-sn-glycerol, and 7 as 1-stearoyl-3- O -(6-sulfo-α- d -quinovopyranosyl)-sn-glycerol [ 28 , 33 , 34 ].…”

“…The inhibitory effect on cotton pellet induced by granuloma was the first report to investigate the anti-inflammatory effect of T. ornate [ 27 ]. Recently, our research team reported the anti-inflammatory effect of T. ornata in an in vitro model of IBD comprising human epithelial Caco-2 and THP-1 macrophages [ 28 ]. Sulfoquinovosyl monoacylglycerols and steroids were identified in the extract of T. ornata .…”

“…Sulfoquinovosyl monoacylglycerols and steroids were identified in the extract of T. ornata . Among the isolated compounds, sulfoquinovosyl monoacylglycerols that possess carbon chains of C18 (compounds 5 and 7 in this study) were found to be biologically active metabolites that inhibit the expression of inflammatory proteins and nucleic translocation of NF-κB [ 28 ]. In the present study, the chemical profile of TOE was deduced through LC-QTOF-MS analysis.…”

“…To date, secondary metabolites, including cytotoxic secosqualene carboxylic acid and turbinaric acid, and phenolics with antioxidant and antibacterial activity have been reported from T. ornata [ 23 , 24 , 25 , 26 ] Recently, the anti-inflammatory activity of T. ornata containing fucoidan as the active constituent has been reported [ 27 ]. As a part of further studies to determine the anti-inflammatory potential of T. ornata , our research group newly identified bioactive metabolites, sulfoquinovosyl monoacylglycerols, which regulate intestinal inflammation in vitro [ 28 ]. It was found that the butanolic fraction of T. ornata extract and sulfoquinovosyl monoacylglycerols markedly downregulated inflammatory mediators in response to inhibition of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) translocation to the nucleus in the Caco-2 and THP-1 co-culture system.…”

Isoquinolinequinone Derivatives from a Marine Sponge (Haliclona sp.) Regulate Inflammation in In Vitro System of Intestine

“…Then, the polarized Caco-2 monolayer insert was added. The upper and lower chambers would represent the apical and basolateral sides of the intestinal epithelium, respectively [36][37][38] (Figure S23). To evaluate anti-inflammatory activity, LPS (10 µg/mL) and interferon-gamma (IFNγ, 10 ng/mL) were added to the basolateral compartment of the plate.…”