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Marine Natural Products†† Natural Product Reports REVIEW View Article Online View Journal | View Issue Marine natural products†† *a b c a Nat. Prod. Rep. John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro Cite this: ,2017,34,235 d and Mich`ele R. Prinsep Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382–431 This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) 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 (1340 in 429 papers for 2015), together with Received 14th December 2016 the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic DOI: 10.1039/c6np00124f studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, Creative Commons Attribution-NonCommercial 3.0 Unported Licence. rsc.li/npr have been included. 1 Introduction 1 Introduction 2 Reviews 3 Marine microorganisms and phytoplankton This review is of the literature for 2015 and describes 1340 3.1 Marine-sourced bacteria new compounds from 429 papers, a small reduction from the 3.2 Marine-sourced fungi (excluding from mangroves) 1378 new compounds in 456 papers reported for 2014.1 As in 3.3 Fungi from mangroves previous reviews, the structures are shown only for new This article is licensed under a 3.4 Cyanobacteria compounds, or for previously reported compounds where 3.5 Dinoagellates there has been a structural revision or a newly established 4 Green algae stereochemistry. Previously reported compounds for which Open Access Article. Published on 14 March 2017. Downloaded 9/26/2021 4:51:02 PM. 5 Brown algae rst syntheses or new bioactivities are described are refer- 6 Red algae enced, but separate structures are generally not shown. Where 7 Sponges the absolute conguration has been determined for all 8 Cnidarians stereocentres in a compound, the identifying diagram 9 Bryozoans number is distinguished by addition of the † symbol. The new 10 Molluscs format for this review introduced for the previous review1 has 11 Tunicates (ascidians) been retained, with only a selection of highlighted structures 12 Echinoderms (197) now shown in the review. Compound numbers for 13 Mangroves structures not highlighted in the review are italicised,andall 14 Miscellaneous structures are available for viewing, along with their names, 15 Conclusion taxonomic origins, locations for collections, and biological 16 Acknowledgements activities, in a ESI†† document associated with this review. 17 References The Reviews section (2) contains selected highlighted reviews, with all other reviews referenced in a section of the ESI.†† It is withgreatregretthatwenotethepassingofProfessorTatsuo Higa, University of the Ryukyus and the Open University of a Department of Chemistry, University of Canterbury, Christchurch, New Zealand. Japan, on May 24 2016. Since 1965 Professor Higa has made E-mail: [email protected] many publications of his work, principally on MNPs. Most bSchool of Chemical Sciences, University of Auckland, Auckland, New Zealand cCentre for Biodiscovery, School of Chemical and Physical Sciences, Victoria University notable was his discovery of the manzamines. He was of Wellington, Wellington, New Zealand a regular participant at MNP conferences, and his quiet and dChemistry, School of Science, University of Waikato, Hamilton, New Zealand friendly manner will be remembered and missed. †† Electronic supplementary information (ESI) available. See DOI: 10.1039/c6np00124f This journal is © The Royal Society of Chemistry 2017 Nat. Prod. Rep.,2017,34, 235–294 | 235 View Article Online Natural Product Reports Review 2 Reviews metagenomics in biodiscovery continues to develop as described in two new reviews.20,21 Other emerging concepts for enhancing For 2015 there has been an increase (23% from 2014) in the the biodiscovery effort,22 and recent advances in other experi- number of reviews of various aspects of MNP studies. Some of the mental technologies,23 have been described. The online database comprehensive reviews (23) are given here while a listing of the MarinLit24 continues to be updated and has been the principal remainder (84) is given in the ESI†† section. A full review of MNPs source of information for this review. reported in 2013 has appeared.2 A statistical analysis of bioactive MNPs discovered from 1985 to 2012 has been made.3 The potential for MNPs as antiviral agents has been extensively 3 Marine microorganisms and reviewed.4 Marine fungi as the source of anticancer agents,5 phytoplankton antimicrobial compounds6 and antiviral agents7 have been described. There have been surveys of anticancer compounds 3.1 Marine-sourced bacteria from marine sponges8 and microalgae,9 while the bioactivities of Although the rst paper in this section adds no new compounds specic classes of MNPs such as peptides,10,11 polyacetylenes,12 to the list of MNPs it touches on a vital thread running right indole alkaloids,13 and halogenated compounds14 have been through the chemistry of MNPs. That is the discovery, charac- reviewed. More specic types of bioactivity have been examined in terisation, synthesis, development and commercial production reviews of MNPs for management of diabetes from seaweeds,15 of chemotherapeutic compounds. Endosymbiotic origins of ET- and compounds with neuroprotective activity16 and antifouling 743 (Yondelis®, trabectedin), isolated from the mangrove tuni- properties.17 MNPs from marine cyanobacteria18 and actinomy- cate Ecteinascidia turbinata, have long been postulated. From cetes of the genus Salinispora19 have been discussed. The role of analysis of the metagenomic DNA isolated from the tunicate the John Blunt obtained his BSc Rob Keyzers carried out his BSc Creative Commons Attribution-NonCommercial 3.0 Unported Licence. (Hons) and PhD degrees from the (Hons) and PhD studies at University of Canterbury, fol- Victoria University of Wellington. lowed by postdoctoral appoint- His thesis research, carried out ments in Biochemistry at the under the guidance of Assoc. Prof. University of Wisconsin–Madison, Peter Northcote, a former andwithSirEwartJonesat contributor to this review, focused Oxford University. He took up on spectroscopy-guided isolation a lectureship at the University of of sponge metabolites. He then This article is licensed under a Canterbury in 1970, from where carried out post-doctoral research he retired as an Emeritus with Mike Davies-Coleman (Rho- Professor in 2008. His research des University, South Africa) and interests are with natural prod- RaymondAndersen(Universityof Open Access Article. Published on 14 March 2017. Downloaded 9/26/2021 4:51:02 PM. ucts, the application of NMR techniques to structural problems, and British Columbia, Canada) before a short role as a avour and aroma the construction of databases to facilitate natural product investiga- chemist at CSIRO in Adelaide, Australia. He was appointed to the tions. faculty at his alma mater in 2009 where he is currently a Senior Lecturer. Brent Copp received his BSc Murray Munro, Emeritus (Hons) and PhD degrees from the Professor in Chemistry at the University of Canterbury, where University of Canterbury, has he studied the isolation, structure worked on natural products right elucidation and structure–activity through his career. This started relationships of biologically active with diterpenoids (PhD; Peter marine natural products under Grant, University of Otago), fol- the guidance of Professors Blunt lowed by alkaloids during a post- and Munro. He undertook post- doctoral spell with Alan Battersby doctoral research with Jon Clardy at Liverpool. A sabbatical with at Cornell and Chris Ireland at KenRinehartattheUniversityof the University of Utah. 1992–93 Illinois in 1973 led to an interest was spent working in industry as in marine natural products with an isolation chemist with Xenova Plc, before returning to New Zea- a particular focus on bioactive compounds which has continued to land to take a lectureship at the University of Auckland, where he is this day. In recent years his research interests have widened to include currently an Associate Professor. terrestrial/marine fungi and actinomycetes. 236 | Nat. Prod. Rep.,2017,34, 235–294 This journal is © The Royal Society of Chemistry 2017 View Article Online Review Natural Product Reports complete genome of Candidatus Endoecteinascidia frumentensis, This is the rst occurrence of azepin-3-one alkaloids in the ET-743 producer, has now been assembled. Analysis of the nature and also the rst occurrence of aziridine- and phylogenetic markers and protein coding genes suggest that Ca. pyrazinone-based alkaloids in Gram-negative bacteria. Two new E. frumentensis belongs to a novel family of the g-proteobacteria. peptaibols 10 and 11 were isolated from Microbacterium sed- This better understanding of the biosynthesis of ET-743 will iminis and is the rst reported isolation of peptaibols from an promote efforts to produce the drug directly by in vitro methods actinomycete, not a fungal source.27 Following the discovery of or heterologous expression rather than the current semi- an antitrypanosomal series of macrolactams the genome of the synthetic process starting from cyanosafracin.25 By utilising producing Micromonospora sp. was sequenced
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