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Marine Natural Products NPR 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: ,2015,32,116 d and Mich`ele R. Prinsep Covering: 2013. Previous review: Nat. Prod. Rep., 2014, 31, 160–258 This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) 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 (1163 for 2013), together with the relevant Received 4th November 2014 biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first DOI: 10.1039/c4np00144c syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been Creative Commons Attribution 3.0 Unported Licence. www.rsc.org/npr included. 1 Introduction 16 Acknowledgements 2 Reviews 17 References 3 Marine microorganisms and phytoplankton 3.1 Marine-sourced bacteria (excluding from mangroves) 3.2 Bacteria from mangroves 1 Introduction 3.3 Marine-sourced fungi (excluding from mangroves) This article is licensed under a This review is of the literature for 2013 and describes 1163 3.4 Fungi from mangroves new compounds from 379 articles, a 6% decrease in the 3.5 Cyanobacteria number of compounds reported in 2012.1 As in previous 3.6 Dinoagellates reviews, the structures are shown only for new compounds, or 3.7 Microalgae Open Access Article. Published on 26 January 2015. Downloaded 9/28/2021 10:12:14 AM. for previously reported compounds where there has been a 3.8 Synthetic aspects structural revision or a newly established stereochemistry. 3.9 Assorted bioactivities Previously reported compounds for which rst syntheses or 3.10 Biosynthesis new bioactivities are described are referenced, but separate 4 Green algae structures are generally not shown. Where the absolute 5 Brown algae conguration has been determined for all stereocentres in a 6 Red algae compound, the identifying diagram number is distinguished 7 Sponges by addition of the † symbol. 8 Cnidarians 9 Bryozoans 10 Molluscs 2 Reviews 11 Tunicates (ascidians) 12 Echinoderms A selection of the many reviews on various aspects of MNP 13 Mangroves studies is listed here. A comprehensive review of MNPs reported 14 Miscellaneous in 2011 has appeared,2 as well as the highlights of compounds 15 Conclusion reported in 2012.3 Marine pharmacology papers for 2009–2011 have been collated,4 two reviews summarise natural products (NPs), including from marine sources, as drug leads,5,6 while aDepartment of Chemistry, University of Canterbury, Christchurch, New Zealand. another paper describes recent advances in marine drug E-mail: [email protected] research.7 A synopsis of the project BAMMBO for the sustain- bSchool of Chemical Sciences, University of Auckland, Auckland, New Zealand cCentre for Biodiscovery, and School of Chemical and Physical Sciences, Victoria able production of biologically active molecules of marine 8 University of Wellington, Wellington, New Zealand based origin has appeared. General classes of compounds have dChemistry, School of Science, University of Waikato, Hamilton, New Zealand been reviewed in papers on marine triterpenoids as anticancer 116 | Nat. Prod. Rep.,2015,32, 116–211 This journal is © The Royal Society of Chemistry 2015 View Article Online Review NPR agents,9 alkaloids from corals,10 meroterpenes from marine terpenes from Sarcophyton sp.,15,16 antimicrobial peptides from invertebrates,11 ‘head-to-sidechain’ cyclodepsipeptides,12 proteobacteria,17 diarrhetic shellsh toxins in Washington marine alkaloids containing an 1-(indol-3-yl)ethane-1,2- State.,18 di- and sesquiterpenes from Cystosiera sp.,19 and halo- diamine fragment,13 tetrahydrofuran-containing macrolides,14 genated compounds from Rhodomelaceae.20 Some general reviews on various classes of compounds include data on marine compounds – anticancer steroids,21 sesterterpenoids,22 John Blunt obtained his BSc NPs containing a nitrogen–nitrogen bond,23 and muscarine, (Hons) and PhD degrees from the imidazole, oxazole and thiazole alkaloids.24 Reviews on various University of Canterbury, fol- aspects of specic compounds include lamellarins N and L,25 lowed by postdoctoral appoint- STX,26 lyngbouilloside and related macrolides,27 thiomarinol ments in Biochemistry at the and related dithiolopyrrolone compounds,28 okadaic acid,29 and University of Wisconsin–Madi- the marinopyrroles.30 There have been many reviews covering a son, and with Sir Ewart Jones at variety of groups of marine organisms, including bioprospect- Oxford University. He took up a ing of plankton,31 actinomycetes,32,33 S. China Sea opistho- lectureship at the University of branch molluscs,34 actinobacteria,35,36 lamentous marine Canterbury in 1970, from where – cyanobacteria,37 and microbes in general.38 40 Reviews on he retired as an Emeritus specic organisms include Australian Dicathais orbita,41 Professor in 2008. His research metabolites from Osmundaria spp.,42 Aspergillus spp.,43 and interests are with natural prod- Bacillus spp.44 A focus on bioactivities is made in reviews on ucts, the application of NMR techniques to structural problems, and anti-inammatory compounds,45,46 trypanocidal products,47 the construction of databases to facilitate natural product investi- neuroprotective compounds,48 antitumour/anticancer gations. Creative Commons Attribution 3.0 Unported Licence. 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– through his career. This started activity relationships of biologi- with diterpenoids (PhD; Peter cally active marine natural Grant, University of Otago), fol- products under the guidance of lowed by alkaloids during a This article is licensed under a Professors Blunt and Munro. He postdoctoral spell with Alan Bat- undertook postdoctoral research tersby at Liverpool. A sabbatical with Jon Clardy at Cornell and with Ken Rinehart at the Univer- Chris Ireland at the University of sity of Illinois in 1973 led to an Open Access Article. Published on 26 January 2015. Downloaded 9/28/2021 10:12:14 AM. Utah. 1992–93 was spent interest in marine natural prod- working in industry as an isolation chemist with Xenova Plc, before ucts with a particular focus on bioactive compounds which has returning to New Zealand to take a lectureship at the University of continued to this day. In recent years his research interests have Auckland, where he is currently an Associate Professor. widened to include terrestrial/marine fungi and actinomycetes. Rob Keyzers carried out his Mich`ele Prinsep received her BSc BSc(Hons) and PhD studies at (Hons) and PhD degrees from the Victoria University of Wellington. University of Canterbury, where His thesis research, carried out she studied the isolation and under the guidance of Assoc. Prof. structural elucidation of biologi- Peter Northcote, a former cally active secondary metabo- contributor to this review, lites from sponges and bryozoans focused on spectroscopy-guided under the supervision of Profes- isolation of sponge metabolites. sors Blunt and Munro. She He then carried out post-doctoral undertook postdoctoral research research with Mike Davies-Cole- on cyanobacteria with Richard man (Rhodes University, South Moore at the University of Africa) and Raymond Andersen Hawaii before returning to New (University of British Columbia, Canada) before a short role as a Zealand to take up a lectureship at the University of Waikato, where avour and aroma chemist at CSIRO in Adelaide, Australia. He was she is currently a Senior Lecturer. appointed to the faculty at his alma mater in 2009 where he is currently a Senior Lecturer. This journal is © The Royal Society of Chemistry 2015 Nat. Prod. Rep.,2015,32,116–211 | 117 View Article Online NPR Review agents,49–52 kinase inhibitors,53 anti-Herpes simplex agents,54 anti-HIV actives,55 angiogenesis inhibitors,56 cardioprotective peptides,57 antithrombotic peptides,58 antimicrobial peptides,59 therapeutics for Gram-negative sepsis,60 and bioactives from Antarctic and Arctic organisms.61 The chemical ecology of plankton62 and the possible ecological roles of cyanotoxins63 have been reviewed. The eighth in a companion series providing an overview of synthetic aspects of MNPs has appeared with coverage of publications from 2010.64 Further reviews of syntheses of specic compounds include marine alkyl purines,65 tetrodotoxin,66 (+)-spirastrellolide A methyl ester,67 and 'upenamide, the structure of which still remains elusive.68 A number of papers which, while not necessarily being reviews, are useful to reference here as they describe advances in tech- niques or approaches to discovery that are relevant to MNP studies. These include papers on novel extraction technologies for bioactives from marine algae,69 dereplication of marine actinomycetes by LCHRMS proling,70 X-ray analysis on the nanogram to microgram scale using porous complexes,71,72 rapid screening of bioactive compounds by integrating 5- channel parallel chromatography coupled with on-line mass 73 spectrometry and microplate based assays,
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