Natural Product Reports REVIEW View Article Online View Journal | View Issue Marine natural products‡ ab c b d Cite this: Nat. Prod. Rep.,2019,36,122 Anthony R. Carroll, * Brent R. Copp, Rohan A. Davis, Robert A. Keyzers e and Mich`ele R. Prinsep Covering: January to December 2017 This review covers the literature published in 2017 for marine natural products (MNPs), with 740 citations (723 for the period January to December 2017) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1490 in 477 papers for 2017), together with the relevant biological Received 12th November 2018 activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and DOI: 10.1039/c8np00092a syntheses that led to the revision of structures or stereochemistries, have been included. Geographic Creative Commons Attribution-NonCommercial 3.0 Unported Licence. rsc.li/npr distributions of MNPs at a phylogenetic level are reported. 1 Introduction 17 Acknowledgements 2 Reviews 18 References 3 Marine microorganisms and phytoplankton 3.1 Marine-sourced bacteria 3.2 Cyanobacteria 1 Introduction 3.3 Marine-sourced fungi (excluding from mangroves) This article is licensed under a This review is of the literature for 2017 and describes 1490 new 3.4 Fungi from mangroves compounds from 477 papers, a 17% increase from the 1277 new 3.5 Dinoagellates compounds in 432 papers reported for 2016.1 As in previous 4 Green algae reviews, the structures are shown only for new MNPs, or for Open Access Article. Published on 21 January 2019. Downloaded 9/29/2021 2:39:06 AM. 5 Brown algae previously reported compounds where there has been a struc- 6 Red algae tural revision or a newly established stereochemistry. Previously 7 Sponges reported compounds for which rst syntheses or new bioactiv- 8 Cnidarians ities are described are referenced, but separate structures are 9 Bryozoans generally not shown. Where the absolute conguration has 10 Molluscs been determined for all stereocentres in a compound, the 11 Tunicates (ascidians) identifying diagram number is distinguished by addition of 12 Echinoderms the † symbol. The review retains the format introduced in 2016, 13 Mangroves with only a selection of highlighted structures (172) now shown 14 Miscellaneous in the review.2 Compound numbers for structures not high- 15 Conclusion lighted in the review are italicised, and all structures are avail- 16 Conicts of interest able for viewing, along with their names, taxonomic origins, locations for collections, and biological activities, in an ESI‡ document associated with this review. The Reviews section (2) aSchool of Environment and Science, Griffith University, Gold Coast, Australia. E-mail: contains selected highlighted reviews, with all other reviews A.Carroll@griffith.edu.au referenced in a section of the ESI.‡ bGriffith Institute for Drug Discovery, Griffith University, Brisbane, Australia cSchool of Chemical Sciences, University of Auckland, Auckland, New Zealand dCentre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University 2 Reviews of Wellington, Wellington, New Zealand eSchool of Science, University of Waikato, Hamilton, New Zealand The number of MNP-related reviews continued to increase ‡ Electronic supplementary information (ESI) available. See DOI: signi cantly in 2017 compared to previous years. Of the 158 10.1039/c8np00092a reviews and general articles relating to MNPs published in this 122 | Nat. Prod. Rep.,2019,36,122–173 This journal is © The Royal Society of Chemistry 2019 View Article Online Review Natural Product Reports period, 24% focussed on specic compounds or compound a high likelihood for novel chemical discoveries.7 Emerging classes, 30% related to the bioactivities of MNPs, 24% had an cheminformatics tools that can be used to identify potential organism or geographic focus, while the remainder were more protein targets for natural products (NPs) has been reviewed.8 general. Some of the reviews with a broad relevance to the eld of MNPs possessing inhibitory activity towards drug resistant viral, MNPs are highlighted here (15) while the remainder (143) can be fungal and parasitic infections, Leishmania,proteintyrosine found in the ESI section.‡ MNPs reported in 2016 have been phosphatase 1B (PTP1B) and quorum sensing have been comprehensively reviewed.3 The open access inventory, the reviewed.9–12 Tricyclic sesquiterpenes and compounds containing World Register of Marine Species (WoRMS), is now ten years old guanidine moieties are highly represented in MNPs and both of and provides a valuable resource for all marine biodiversity these structure classes have been reviewed.13,14 Halogenated researchers. A timely review discusses the importance of expert MNPs are incredibly abundant and the mechanism for their taxonomic knowledge, consistent data entry, and nomenclature biosynthesis has been reviewed.15 A paper has provided detailed as they relate to the WoRMS.4 Two reviews discuss the chemistry insights in to various metabolic aspects of the life cycle of and chemical ecology of nudibranchs5 and the structures and uncultivatable bacteria associated with the sponge Theonella structure determination challenges associated with the chemistry swinhoei.16 A free platform (DEREP-NP) incorporating almost of crinoids.6 Analysis of trends in chemical diversity of microbial 230 000 NPs derived from the non-proprietary Universal Natural and MNPs reported between 1941 and 2015 illustrates that the Product Database (UNPD) has been developed. This platform discovery of new scaffolds has plateaued but also that there is still allows users to rapidly identify compounds through matching of Anthony (Tony) Carroll initially Rohan Davis received a BSc studied the alkaloid and lignan (Hons) degree in chemistry and chemistry of rainforest plants biochemistry from the University Creative Commons Attribution-NonCommercial 3.0 Unported Licence. (BSc (Hons) and PhD, Prof Wal of Melbourne (1992). He worked Taylor, Sydney University) but as a research assistant on the marine natural products became AstraZeneca/Griffith University a major focus aer postdoctoral natural product drug discovery fellowships at the University of program (1994–1996) before Hawaii with Paul Scheuer and undertaking PhD studies (1997– at James Cook University, Aus- 2000) under the supervision of tralia with John Coll and Bruce Professors Ronald Quinn and This article is licensed under a Bowden. Fi een years as head of Anthony Carroll. A er 2 years of natural products chemistry for postdoctoral research at the AstraZeneca/Griffith University drug discovery project University of Utah with Chris Ireland, he returned to Griffith expanded his interests to include high throughput purication and University in 2003 where he is currently an Associate Professor. His Open Access Article. Published on 21 January 2019. Downloaded 9/29/2021 2:39:06 AM. structure determination techniques and cheminformatics. Since current research involves the discovery and development of new 2008 he has held a faculty position at Griffith University, Gold bioactive natural products from plants and marine invertebrates Coast where he is currently a Professor. and is currently the Academic Lead for NatureBank, an Australian- based drug discovery platform. Brent Copp received his BSc Rob Keyzers carried out his BSc (Hons) and PhD degrees from (Hons) and PhD studies at the University of Canterbury, Victoria University of where he studied the isolation, Wellington. His thesis research, structure elucidation and struc- carried out under the guidance ture–activity relationships of of Assoc. Prof. Peter Northcote, biologically active marine a former contributor to this natural products under the review, focused on spectroscopy- guidance of Professors John guided isolation of sponge Blunt and Murray Munro. Two metabolites. He then carried out postdoctoral positions with Jon post-doctoral research with Mike Clardy at Cornell and Chris Davies-Coleman (Rhodes Ireland at the University of Utah University, South Africa) and were then followed with a period spent working in industry as an Raymond Andersen (University of British Columbia, Canada) isolation chemist with Xenova Plc. In 1993 Brent returned to New before a short role as a avour and aroma chemist at CSIRO in Zealand to take a lectureship at the University of Auckland, where Adelaide, Australia. He was appointed to the faculty at his alma he is currently a Professor. mater in 2009 where he is currently a Senior Lecturer. This journal is © The Royal Society of Chemistry 2019 Nat. Prod. Rep.,2019,36,122–173 | 123 View Article Online Natural Product Reports Review fragments derived from 1H, HSQC, HMBC NMR and MS data of puried compounds and semi-puried mixtures with compounds in the database.17 An essential requirement for the preparation of this review is the continuous updating of the structures and literature in the MarinLit database.18 The data derived from MarinLit forms the basis of this review. 3 Marine microorganisms and phytoplankton Fig. 1 Sources of new compounds over the period 2012–2017. The upward trend in the discovery of new MNPs sourced from marine microorganisms continues unabated and now repre- sents 57% of the total new MNPs reported in 2017. Fig. 1 shows the change in discovery efforts across the broad groups of microorganisms,