Anti-inflammatory activity and structure-activity relationships of brominated indoles from a marine mollusc

Article

Ahmad, Tarek B., Rudd, David, Smith, Joshua, Kotiw, Michael, Mouatt, Peter, Seymour, Lisa M., Liu, Lei and Benkendorff, Kirsten. 2017. "Anti-inflammatory activity and structure-activity relationships of brominated indoles from a marine mollusc." Marine Drugs. 15 (5), pp. 1-19. https://doi.org/10.3390/md15050133
Article Title

Anti-inflammatory activity and structure-activity relationships of brominated indoles from a marine mollusc

ERA Journal ID14994
Article CategoryArticle
AuthorsAhmad, Tarek B. (Author), Rudd, David (Author), Smith, Joshua (Author), Kotiw, Michael (Author), Mouatt, Peter (Author), Seymour, Lisa M. (Author), Liu, Lei (Author) and Benkendorff, Kirsten (Author)
Journal TitleMarine Drugs
Journal Citation15 (5), pp. 1-19
Article Number133
Number of Pages19
Year2017
Place of PublicationBasel, Switzerland
ISSN1660-3397
Digital Object Identifier (DOI)https://doi.org/10.3390/md15050133
Web Address (URL)http://www.mdpi.com/1660-3397/15/5/133
Abstract

Marine molluscs are rich in biologically active natural products that provide new potential sources of anti-inflammatory agents. Here we used bioassay guided fractionation of extracts from the muricid Dicathais orbita to identify brominated indoles with anti-inflammatory activity, based on the inhibition of nitric oxide (NO) and tumour necrosis factor (TNF) in lipopolysaccharide (LPS)
stimulated RAW264.7 macrophages and prostaglandin E2 (PGE2) in calcium ionophore-stimulated 3T3 ccl-92 fibroblasts. Muricid brominated indoles were then compared to a range of synthetic indoles to determine structure-activity relationships. Both hypobranchial gland and egg extracts inhibited the production of NO significantly with IC50 of 30.8 and 40 ug/mL, respectively. The hypobranchial gland extract also inhibited the production of TNFa and PGE2 with IC50 of 43.03 ug/mL and 34.24 ug/mL, respectively. The purified mono-brominated indole and isatin compounds showed
significant inhibitory activity against NO, TNFa, and PGE2, and were more active than dimer indoles and non-brominated isatin. The position of the bromine atom on the isatin benzene ring significantly affected the activity, with 5Br > 6Br > 7Br. The mode of action for the active hypobranchial gland extract, 6-bromoindole, and 6-bromoisatin was further tested by the assessment of the translocation of nuclear factor kappa B (NFkB) in LPS-stimulated RAW264.7 mouse macrophage. The extract
(40 ug/mL) significantly inhibited the translocation of NFkB in the LPS-stimulated RAW264.7 macrophages by 48.2%, whereas 40 ug/mL of 6-bromoindole and 6-bromoistain caused a 60.7% and 63.7% reduction in NFkB, respectively. These results identify simple brominated indoles as useful
anti-inflammatory drug leads and support the development of extracts from the Australian muricid D. orbita, as a new potential natural remedy for the treatment of inflammation.

Keywordsmarine natural products; inflammation; NO inhibition; Muricidae; isatin; Tyrian purple
ANZSRC Field of Research 2020420899. Traditional, complementary and integrative medicine not elsewhere classified
Byline AffiliationsSouthern Cross University
Centre for Health Sciences Research
Institution of OriginUniversity of Southern Queensland
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