Geobarrettin D, a Rare Herbipoline-Containing 6-Bromoindole Alkaloid from Geodia barretti

Author:

Di Xiaxia12ORCID,Hardardottir Ingibjorg23ORCID,Freysdottir Jona23ORCID,Wang Dongdong4ORCID,Gustafson Kirk R.4ORCID,Omarsdottir Sesselja1,Molinski Tadeusz F.5

Affiliation:

1. Faculty of Pharmaceutical Sciences, University of Iceland, Hagi, Hofsvallagata 53, IS-107 Reykjavik, Iceland

2. Department of Immunology, Landspitali—The National University Hospital of Iceland, IS-101 Reykjavik, Iceland

3. Faculty of Medicine, Biomedical Center, University of Iceland, Vatnsmyrarvegur 16, IS-101 Reykjavik, Iceland

4. Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702, USA

5. Department of Chemistry and Biochemistry, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, CA 92093, USA

Abstract

Geobarrettin D (1), a new bromoindole alkaloid, was isolated from the marine sponge Geodia barretti collected from Icelandic waters. Its structure was elucidated by 1D, and 2D NMR (including 1H-15N HSQC, 1H-15N HMBC spectra), as well as HRESIMS data. Geobarrettin D (1) is a new 6-bromoindole featuring an unusual purinium herbipoline moiety. Geobarrettin D (1) decreased secretion of the pro-inflammatory cytokine IL-12p40 by human monocyte derived dendritic cells, without affecting secretion of the anti-inflammatory cytokine IL-10. Thus, compound 1 shows anti-inflammatory activity.

Funder

University of Iceland Research Fund

AVS R&D Fund of Ministry of Fisheries and Agriculture

Landspitali University Hospital Research Fund

National Institutes of Health

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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