title: Novel brominated metabolites from Bryozoa: a functional analysis.
abstract: Marine invertebrates are a promising source of novel natural products with biological activities. The phylum Bryozoa is relatively under-investigated in this context, although a number of compounds with medical potential has been discovered in recent years. Here, we report on the novel group of brominated metabolites from the bryozoan Terminoflustra membranaceatruncata, including analysis of biological activities of the tribrominated terminoflustrindole A (Cm-1) and the structures of the related dibrominated variants terminoflustrindoles B and C. Terminoflustrindole A was previously shown to have fungicidal properties. Although they vary by just one bromine group in each case from terminoflustrindole A, in this study, we report that terminoflustrindoles B and C exhibit no antimicrobial activity in the same assays. In addition to displaying antifungal activity, Terminoflustrindole A was also found to exhibit potent cytotoxic activity when tested against tumour cell lines. The gradient distribution of this compound within the bryozoan colony was demonstrated using LC-MS-analysis.
authors.affiliation: a Faculty of Biology, Department of Invertebrate Zoology , Saint Petersburg State University , Saint Petersburg , Russia.
authors.forename: Arina L
authors.identifier: http://orcid.org/0000-0003-1973-4728
authors.initials: AL
authors.lastname: Maltseva
authors.affiliation: a Faculty of Biology, Department of Invertebrate Zoology , Saint Petersburg State University , Saint Petersburg , Russia.
authors.forename: Olga N
authors.identifier: http://orcid.org/0000-0003-1527-6109
authors.initials: ON
authors.lastname: Kotenko
authors.affiliation: a Faculty of Biology, Department of Invertebrate Zoology , Saint Petersburg State University , Saint Petersburg , Russia.
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Kutyumov
authors.affiliation: a Faculty of Biology, Department of Invertebrate Zoology , Saint Petersburg State University , Saint Petersburg , Russia.
authors.forename: Darya A
authors.initials: DA
authors.lastname: Matvienko
authors.affiliation: b Analytical Phytochemistry Laboratory , Komarov Botanical Institute , Saint Petersburg , Russia.
authors.forename: Alexey L
authors.identifier: http://orcid.org/0000-0003-1778-2814
authors.initials: AL
authors.lastname: Shavarda
authors.affiliation: c School of Life Sciences , Heriot-Watt University , Edinburgh , UK.
authors.forename: Michael K
authors.initials: MK
authors.lastname: Winson
authors.affiliation: a Faculty of Biology, Department of Invertebrate Zoology , Saint Petersburg State University , Saint Petersburg , Russia.|d Faculty of Earth Sciences, Geography and Astronomy, Department of Palaeontology, Geozentrum , University of Vienna , Vienna , Austria.
authors.forename: Andrew N
authors.identifier: http://orcid.org/0000-0002-3646-9439
authors.initials: AN
authors.lastname: Ostrovsky
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D002013:Bryozoa / Q000737:chemistry* / Q000378:metabolism*; D045744:Cell Line, Tumor; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D051381:Rats
chemical_list: D000470:Alkaloids; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D007211:Indoles; C000625955:terminoflustrindole A; C000625956:terminoflustrindole C
keywords: Alkaloid; antitumour activity; fungicidal activity; metabolites; natural products; terminoflustrindole