Kornprobst, J.-M.
Encyclopedia of Marine Natural Products
2 Edition
2014
Print ISBN: 978-3-527-33429-2, also available as digital format
Berger, S., Sicker, D.
Classics in Spectroscopy
Isolation and Structure Elucidation of Natural Products
2009
Print ISBN: 978-3-527-32516-0
Bertini, I., McGreevy, K.S., Parigi, G. (eds.)
NMR of Biomolecules
Towards Mechanistic Systems Biology
2012
Print ISBN: 978-3-527-32850-5
ISBN: 978-3-527-64450-6, also available as digital format
Kornprobst, J.-M.
Encyclopedia of Marine Natural Products
3 Volume Set
2010
Print ISBN: 978-3-527-32703-4
Edited by
Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty can be created or extended by sales representatives or written sales materials. The Advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.
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Print ISBN: 978-3-527-33465-0
ePDF ISBN: 978-3-527-68152-5
ePub ISBN: 978-3-527-68153-2
mobi ISBN: 978-3-527-68151-8
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Ali Al-Mourabit
Natural Product Chemistry Institute (ICSN)
Department of Natural Products & Medicinal Chemistry (SNCM)
Research Center of the CNRS at Gif sur Yvette
Avenue de la terrasse
91190 Gif sur Yvette
France
Ali.Almourabit@icsn.cnrs-gif.fr
Philippe Amade
Université de Nice Sophia Antipolis
Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences
Parc Valrose
06108 Nice cedex 2
France
amade@unice.fr
Zouher Amzil
IFREMER (Institut Français de Recherche pour l'Exploitation de la Mer)
Laboratoire Phycotoxines
Rue de l'Ile d'Yeu, BP21105
F-44311 Nantes cedex 3
France
Zouher.Amzil@ifremer.fr
Romulo Aráoz
Institut Fédératif de Neurobiologie Alfred Fessard FR2118,
Center de recherche CNRS de Gif-sur-Yvette, Laboratoire de Neurobiologie et Développement UPR 3294
1 avenue de la Terrasse
91198 Gif sur Yvette Cedex
France
araoz@inaf.cnrs-gif.fr
Stéphane S. Bach
Sorbonne Universités
UPMC Univ Paris 06
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
bach@sb-roscoff.fr
and
CNRS
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Christian Bailly
Institut de Recherche Pierre Fabre
Centre de Recherche et Développement
3 Avenue Hubert Curien - BP 13562
31035 Toulouse Cedex 1
France
christian.bailly@pierre-fabre.com
Bernard Banaigs
Université de Perpignan via Domitia
Laboratoire de chimie des biomolécules et de l'environnement, EA4215
52 avenue Paul Alduy
66860 Perpignan cedex
France
banaigs@univ-perp.fr
Georges Barbier
Université Européenne de Bretagne, Université de Brest, ESMISAB
Laboratoire Universitaire de Biodiversité et Ecologie Microbienne (EA3882)
IFR 148, Technopole Brest-Iroise
29280 Plouzané
France
georges.barbier@univ-brest.fr
Gilles Barnathan
Université de Nantes
Groupe Mer-Molécules-Santé MMS/EA 2160, Équipe CHIM – Lipides marins à activité biologique, Faculté des Sciences pharmaceutiques et biologiques, Institut Universitaire Mer et Littoral FR3473 CNRS
9 rue Bias
BP 53508
44035 Nantes
France
gilles.barnathan@univ-nantes.fr
Stephen S. Bates
Fisheries and Oceans Canada
Gulf Fisheries Centre
P.O. Box 5030
Moncton
New Brunswick
E1C 9B6 Canada
Stephen.Bates@dfo-mpo.gc.ca
Elodie Blanchet
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
Franceand
Atlanthera, Atlantic Bone Screen
F-44800 Saint Herblain
Nantes
France
elodie.blanchet@univ-nantes.fr
Isabelle Bonnard
Université de Perpignan via Domitia
Laboratoire de chimie des biomolécules et de l'environnement, EA4215
52 avenue Paul Alduy
66860 Perpignan cedex
France
isabelle.bonnard@univ-perp.fr
Marie-Lise Bourguet-Kondracki
Muséum National d'Histoire Naturelle
Molécules de Communication et Adaptation des Micro-Organismes (MCAM) UMR 7245 CNRS/MNHN
57 rue Cuvier (CP 54)
75005 Paris
France
bourguet@mnhn.fr
Joël Boustie
Université de Rennes 1
Equipe PNSCM (Produits Naturels, Synthèses et Chimie Médicinale), UMR CNRS
6226, Faculté des Sciences Pharmaceutiques et Biologiques
2 Av. du Pr. Léon Bernard
35043 Rennes Cedex
France
Joel.Boustie@univ-rennes1.fr
Catherine Boyen
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
boyen@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Jean-Michel Brunel
Aix-Marseille Université
Centre de Recherche en Cancérologie de Marseille (CRCM), CNRS, UMR7258; Institut Paoli Calmettes
UM 105; Inserm, U1068
F-13009 Marseille
France
bruneljm@yahoo.fr
Gaëtan Burgaud
Université Européenne de Bretagne, Université de Brest, ESMISAB
Laboratoire Universitaire de Biodiversité et Ecologie Microbienne (EA3882)
IFR 148, Technopole Brest-Iroise
29280 Plouzané
France
gaetan.burgaud@univ-brest.fr
Alyssa Carré-Mlouka
National Museum of Natural History
75005 Paris
France
alyssa.carre@mnhn.fr
Stéphane Cérantola
Université de Bretagne Occidentale
Technological Platform of Nuclear Magnetic Resonance, Electron Paramagnetic Resonance and Mass Spectrometry
6, av. Victor Le Gorgeu, CS93837
29238 Brest Cedex 3
France
stephane.cerantola@univ-brest.fr
Bénédicte Charrier
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francecharrier@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Mireille Chinain
Institut Louis Malardé
Laboratoire de recherche sur les Microalgues Toxiques
BP30, 98713 Papeete
Tahiti
French Polynesia
mchinain@ilm.pf
Jonas Collén
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francecollen@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Aurélie Couzinet-Mossion
Université de Nantes
Groupe Mer-Molécules-Santé MMS/EA 2160, Équipe CHIM – Lipides marins à activité biologique, Faculté des Sciences pharmaceutiques et biologiques, Institut Universitaire Mer et Littoral FR3473 CNRS
9 rue Bias
BP 53508
44035 Nantes
France
aurelie.couzinet-mossion@univ-nantes.fr
David J. Craik
The University of Queensland
Institute for Molecular Bioscience
Brisbane
QLD 4072
Australia
d.craik@imb.uq.edu.au
Cécile Debitus
Institut de Recherche pour le Développement
UMR 241
BP 529, 98713 Papeete
Polynésie Française
cecile.debitus@ird.fr
Simon M. Dittami
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francedittami@sb-roscoff.fr
Sergey Dobretsov
Sultan Qaboos University
P. O. Box 50
Muscat 123
Oman
sergey@squ.edu.om
Virginia. P. Edgcomb
Woods Hole Oceanographic Institution
Geology and Geophysics Department
Woods Hole
MA 02543
USA
vedgcomb@whoi.edu
Jean-Baptiste Fournier
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francejbfournier@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Fanny Gaillard
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francegaillard@sb-roscoff.fr
Stjepko Golubic
Boston University
Biological Science Center
5 Cummington Street
Boston
MA 02215
USA
golubic@bu.edu
Olivier Grovel
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
olivier.grovel@univ-nantes.fr
Muriel Gugger
Institut Pasteur, Collection des Cyanobacteéries
Dé??partement de Microbiologie
28 rue du Dr Roux
75015 Paris
France
muriel.gugger@pasteur.fr
Yann Guitton
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
Yann.Guitton@univ-nantes.fr
Tilmann Harder
University of New South Wales
Centre for Marine Bio-Innovation, School of Biological, Earth and Environmental Science
Sydney
Australia 2052
t.harder@unsw.edu.au
Arnaud Hochard
USR3151-CNRS
Protein phosphorylation and human diseases, Kinase Inhibitor Specialized Screening facility (KISSf)
Station Biologique CNRS-UPMC
Place Georges Teissier, CS 90074
29688 Roscoff
Bretagne
France
hochard.arnaud@orange.fr
Nicolas Inguimbert
Université de Perpignan via Domitia
Laboratoire de chimie des biomolécules et de l'environnement, EA4215
52 avenue Paul Alduy
66860 Perpignan cedex
France
nicolas.inguimbert@univ-perp.fr
Quentin Kaas
The University of Queensland
Institute for Molecular Bioscience
Brisbane
QLD 4072
Australia
q.kaas@imb.uq.edu.au
Nelly Kervarec
Université de Bretagne Occidentale
Technological Platform of Nuclear Magnetic Resonance, Electron Paramagnetic Resonance and Mass Spectrometry
6, av. Victor Le Gorgeu, CS93837
29238 Brest Cedex 3
France
nelly.kervarec@univ-brest.fr
Staffan Kjellberg
University of New South Wales
Centre for Marine Bio-Innovation, School of Biotechnology and Biomolecular Science
Sydney
Australia 2052
and
Nanyang Technological University
Singapore Centre on Environmental Life Sciences Engineering
Singapore 639798
s.kjellberg@unsw.edu.au
Jean-Michel Kornprobst (Editor)
Institut Mer et Littoral
Bâtiment Isomer2, rue de la Houssiniére
44322 Nantes BP 92208 Cedex 3France
jean-michel.kornprobst@univ-nantes.fr
Stéphane La Barre (Editor)
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francelabarre@sb-roscoff.fr
Dominique Laurent
Institut de Recherche pour le Développement (IRD)
Pharma-Dev UMR 152
BP529, 98713 Papeete
Tahiti
French Polynesia
domnique.laurent@ird.fr
Catherine Leblanc
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Franceleblanc@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Richard J. Lewis
University of Queensland
Institute for Molecular Bioscience
306, Carmody Road
St Lucia
QLD 4072
Australia
r.lewis@imb.uq.edu.au
Diane McDougald
University of New South Wales
Centre for Marine Bio-Innovation, School of Biotechnology and Biomolecular Science
Sydney
Australia 2052
and
Nanyang Technological University
Advanced Environmental Biotechnology Centre, Nanyang Environment and Water Institute
Singapore 639798
d.mcdougald@unsw.edu.au
Mohamed Mehiri
Université de Nice Sophia Antipolis
Institut de Chimie de Nice, UMR 7272 CNRS, Faculté des Sciences
Parc Valrose
06108 Nice cedex 2
France
mohamed.mehiri@unice.fr
Annick Méjean
Chimie ParisTech, ENSCP
Laboratoire Charles Friedel
11 rue Pierre et Marie Curie
75231 Paris Cedex 05
France
and
CNRS, UMR 7223
11 rue Pierre et Marie Curie
75231 Paris Cedex 05
France
and
Université Paris Diderot
35 rue Hélène Brion
75205 Paris Cedex 13
France
annick-mejean@chimie-paristech.fr
Laurence Meslet-Cladière
Université Européenne de Bretagne, Université de Brest, ESMISAB
Laboratoire Universitaire de Biodiversité et Ecologie Microbienne (EA3882)
IFR 148, Technopole Brest-Iroise
29280 Plouzané
France
laurence.meslet-cladiere@sb-roscoff.fr
Zofia Nehr
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Franceznehr@sb-roscoff.fr
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Olivier Ploux
Chimie ParisTech, ENSCP
Laboratoire Charles Friedel
11 rue Pierre et Marie Curie
75231 Paris Cedex 05
France
and
CNRS, UMR 7223
11 rue Pierre et Marie Curie
75231 Paris Cedex 05
France
olivier-ploux@chimie-paristech.fr
Philippe Potin
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francepotin@sb-roscoff.fr
Yves-François Pouchus
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
yves-francois.pouchus@univ-nantes.fr
Michael Quilliam
National Research Council Canada
Measurement Science and Standards
1411 Oxford Street
Halifax
Nova Scotia
B3 H 3Z1 Canada
michael.quilliam@nrc-cnrc.gc.ca
Luc Reininger
Sorbonne Universités
UPMC Univ Paris 06
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Franceluc.reininger@sb-roscoff.fr
and
CNRS
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Scott A. Rice
University of New South Wales
Centre for Marine Bio-Innovation, School of Biotechnology and Biomolecular Science
Sydney
Australia 2052
and
Nanyang Technological University
Singapore Centre on Environmental Life Sciences Engineering
Singapore 639798
Scott.Rice@unsw.edu.au
Mélanie Roué
Research ScientistIRD-UMR 241 (EIO)Centre Polynésien de Recherche et de valorisation de la Biodiversité Insulaire
B.P. 529, 98713 Papeete, Polynésie Française
melanie.roue@ird.fr
Catherine Roullier
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
catherine.roullier@univ-nantes.fr
Morgane Rousselot
HEMARINA SA
Biotechnopôle
Aéropole Centre
29600 Morlaix
France
morgane.rousselot@hemarina.com
Sandrine Ruchaud
Sorbonne Universités
UPMC Univ Paris 06
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francesandrine.ruchaud@sb-roscoff.fr
and
CNRS
USR 3151
Protein Phosphorylation and Human Diseases
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
Nicolas Ruiz
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
nicolas.ruiz@univ-nantes.fr
Gaëlle Simon
Université de Bretagne Occidentale
Technological Platform of Nuclear Magnetic Resonance, Electron Paramagnetic Resonance and Mass Spectrometry
6, av. Victor Le Gorgeu, CS93837
29238 Brest Cedex 3
France
gaelle.simon@univ-brest.fr
Peter D. Steinberg
University of New South Wales
Centre for Marine Bio-Innovation, School of Biological, Earth and Environmental Science
Sydney
Australia 2052
and
Sydney Institute of Marine Science
Mosman
NSW
Australia 2088
p.steinberg@unsw.edu.au
Torsten Thomas
University of New South Wales
Centre for Marine Bio-Innovation, School of Biotechnology and Biomolecular Science
Sydney
Australia 2052
t.thomas@unsw.edu.au
Thierry Tonon
Sorbonne Universités
UPMC Univ Paris 06
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
France
and
CNRS
UMR 8227
Integrative Biology of Marine Models
Station Biologique de Roscoff
CS 90074
F-29688 Roscoff cedex
Francetonon@sb-roscoff.fr
Jean Turquet
ARVAM
CYROI, La Technopole
2, rue maxime Rivière
97490 Sainte Clotilde
La Réunion
France
jean.turquet@arvam.com
Marieke Vanstellandt
University of Nantes
Faculty of Pharmacy
MMS, 9 rue Bias
F-44000 Nantes Cedex 1
France
mvansteelandt@yahoo.fr
Gaëtane Wielgosz-Collin
Université de Nantes
Groupe Mer-Molécules-Santé MMS/EA 2160, Équipe CHIM – Lipides marins à activité biologique, Faculté des Sciences pharmaceutiques et biologiques, Institut Universitaire Mer et Littoral FR3473 CNRS
9 rue Bias
BP 53508
44035 Nantes
France
wielgosz-collin@univ-nantes.fr
Anne Witzak
Université de Perpignan via Domitia
Laboratoire de chimie des biomolécules et de l'environnement, EA4215
52 avenue Paul Alduy
66860 Perpignan cedex
France
anne.witzak@univ-perp.fr
Franck Zal
HEMARINA SA
Biotechnopôle
Aéropole Centre
29600 Morlaix
France
franck.zal@hemarina.com
Natural products (secondary metabolites) which once were focused on alkaloids and terpenes now cover an infinite molecular diversity, and are merging with primary metabolites through “omics” connections. Today, it is assumed that druggable molecules can also be a matter of bioinspired thinking through close and synergistic partnerships between chemists, biologists and chemical ecologists. Unfortunately, the discovery of new scientific concepts, novel analytical approaches or simply of state-of-the-art techniques tends to be overemphasized, overestimated or overpublicized, relegating essential questioning and basic concerns to the background. In the case of natural products, the isolation of new molecules is currently greatly hampered by this shift in focus, and we feel that the quest for new natural structures (i.e., sourcing) should be actively maintained in the face of pending climate- or humankind-driven habitat degradations and biodiversity destruction. The structural determination of natural new molecules is vital, given its considerable importance for any biological investigation, and includes an understanding of the ecosystems that function at the molecular level and the development of rational products for the treatment of diseases. While structural determination can be achieved more quickly by spectroscopic and crystallographic means, the acquisition of adequate funding for natural products projects is becoming increasingly difficult for both industrial and academic communities alike. The paradox is that the demand for new active molecules is now heralded as a major priority!
Recent advances in organic chemistry and in metabolomics analyses, together with the advent of the postgenomic era, now make it possible to envisage a critical role for natural products chemistry in chemical biology and in chemical ecology, with a timely integration into the multidisciplinary systems biology approach. But, can all of this be envisaged without knowing the structure of the molecule? The answer is definitely: no!
In this book is presented a selection of marine molecules which have attracted the attention of a wide panel of reputed scientists worldwide, and especially within the national research network that I am proud to have managed for several years. To the series of comprehensive chapters on marine molecules, deemed outstanding for their interesting structures, their amazing bioactivities, or their environmental significance, critical and highly documented reviews of modern laboratory experimentation have been added. It is hoped that this contribution will provide inspiration to the generation of new scientists and motivate them to embrace a meaningful human health-oriented career, or to invent environmentally dedicated tools and approaches for the benefit of all.
Ali Al-Mourabit
Director of BioChiMar Network
Natural Product Chemistry Institute (ICSN)
Department of Natural Products & Medicinal Chemistry (SNCM)
Research Center of the CNRS at Gif sur Yvette
France
December 2013
Our original idea was to provide a series of comprehensive chapters, devoted to molecules that are either naturally produced or transformed by marine organisms, each having a recognized influence on human welfare, or having a significant impact on our chemosphere, and thus on depending life forms. The individual chapters would introduce the molecule(s) of interest in its/their historical or its environmental perspective, develop the analytical aspects (chemistry, structure–activity, synthesis), and finally mention the ecological significance and the pertaining biotechnological developments in the light of the existing literature. Graduate students would have access to essential information on a given molecule, all bundled up in a single chapter pointing out useful references for consultation on specific details. Likewise, teachers would be able to structure a complete lecture on a single topic, with references from which they can follow up a specific aspect.
The immediate challenge we had to face was to select 20–25 molecules within the hundreds of eligible candidates. Our second challenge was to contact experts who were willing to spend some of their time and enthusiasm to join our project with at least one contribution. Not an easy task – as excellent textbooks, reviews, handbooks and communications have been published on marine natural products within the past few years. The choice of molecules by our authors naturally fell into three sections: (i) molecules deemed outstanding for their structural originality, their spectral characteristics, or their reactivity and its consequences on synthesis; (ii) molecules that are known to play an important role in isolated organisms or in whole ecosystems; and (iii) molecules that have attracted special interest in the quest for new drugs or new treatments. As the editorial project was being constructed, it was decided that a review of modern analytical approaches, using state-of-the art instrumentation would add a useful complement to the metabolite chapters. Thus, ultimately four Parts were proposed for the book, in which each chapter would be a stand-alone source of information and a useful starting point for someone willing to investigate.
Part One includes six chapters, selected as an assortment based on biodiversity as representative criteria, given the editorial constraints. Cyanobacterial toxins represent a well-known problem in the treatment of freshwater for household and recreational uses, but the occurrence of cyanotoxins in maritime zones is not well documented, and a growing concern for isolated populations which live off their natural resources on a daily basis. The first chapter is devoted to an overview of this subject, by a team of field specialists in association which pharmacologists and neurobiologists (Chapter 1). Highly efficient chemical defenses are produced by microbes or phytoplankton, and concentrated through the food chain, or result from functional interactions between sessile marine organisms and their dedicated microbiomes. In the second chapter are reviewed three major examples of seafood contaminants, which have puzzled generations of investigators and for which prevention remains essential. Some structures are extraordinarily complex, yet highly stable, with surprising bioactivities, as explained by the authors, chemists and pharmacologists who have longstanding experience in working with marine toxins (Chapter 2). The next two chapters deal with marine fungal metabolites, a recently explored source of novel molecules of pharmacological potential. After a review of the importance the genus Penicillium, both as marine fungi and as historical sources of drugs, the first “fungus” chapter expands on three examples of novel structures that have potential as anticancer agents, by leading researchers (Chapter 3). The following chapter explores the hitherto unsuspected source of bioactive drugs from fungi of deep-sea hydrothermal vents, and the biotechnological promises we can anticipate from this newly explored environment – a story told in association between benchtop scientists and field investigators (Chapter 4). The next chapter is devoted to glycoconjugates from marine invertebrates, an often underestimated source of original molecules endowed with bioactivities usually sought in other classes of so-called “secondary metabolites“ (Chapter 5). Part One ends with a very original chapter on molecules found in crinoids which were thought to be extinct since the Triassic–Jurassic extinction event. . .until the unexpected discovery of living representatives in the twentieth century (Chapter 6).
Part Two of the book is devoted to metabolites that have no particular originality in terms of structure, but offer some benefits to the source organism, or act as “positive” communication signals between congeners, or between a host and its microbial associates. On the other hand, some of them have a clearly toxic effect on other taxa, and may be the cause of environmental concern. Leading scientists explore the bases of bacterial communication systems in the first chapter (Chapter 7). In the second chapter, the extraordinary story of the discovery of domoic acid is documented by two pioneers, Steve Bates and Mike Quilliam, and its ecological and pharmacological importance is further examined in the light of the most recent research (Chapter 8). The third chapter introduces us to algal morphoinducers, and to the resemblances and differences of cell differentiation and growth patterns between algae and terrestrial plants (Chapter 9). The fourth and last chapter of this “ecology” Part reviews halogenation processes in marine molecules, from molecular mechanisms involving haloperoxidases, to the biogeoclimatic consequences halogenated molecules have locally (Chapter 10).
In Part Three, more emphasis is placed on the structure–activity and pharmacological applications in which some molecules have recently been involved, during screenings on targets of interest for major and diverse pathologies. The first chapter reviews recent “highlights,” some of which have interesting potential, mostly as inhibitors (Chapter 11). The second chapter provides a prime example of this multifunctionality, as the authors focus on squalamine, an aminosterol produced by dogfish, and which has revealed a wide array of potential therapeutic applications (Chapter 12). The third chapter reviews marine peptides which have been modified to acquire so-called secondary metabolite characteristics, and are actively studied for their potential as anticancer agents. A whole range of microbial and of metazoan examples are reviewed by authors from a group that has gained longstanding expertise in this class of molecules (Chapter 13). Conotoxin venoms and other conopeptides illustrate further the offensive–defensive specialization made by some carnivorous mollusks of these modified peptides, in a well-documented text written by authorities on the subject (Chapter 14). Mycosporine-like amino acids (MAAs) are natural antioxidants and sunscreens used by diverse terrestrial and marine organisms or whole photosystems, enabling them to live totally exposed to solar radiations. The authors focus on MAAs produced by lichens and by reef corals, two models with very different lifestyles (Chapter 15). Next, in the pharmacology applications, is a chapter which relates a successful biotechnological adventure. The authors show how they adapted the hemoglobin produced by a lugworm, to an array of therapeutic applications, from first-aid to the optimal storage of organs prior to transplantation (Chapter 16). The closing chapter for this Part introduces lamellarins, a family of complex alkaloids that were originally produced by didemnid ascidians and which represent a fine example of structure–activity relationship, particularly in relation to sulfation patterns (Chapter 17).
Lastly, Part Four provides a state-of-the art technical complement to whoever extracts, purifies, analyzes, mimics and valorizes marine natural products. The chapter on NMR is written by a team of spectroscopists who have developed a range of tools and approaches to cater for a wide variety of marine samples and address specific challenges posed by fellow chemists and biologists. Through multiple examples, the authors provide a rationale for the treatment of individual situations (Chapter 18). The next three chapters provide a comprehensive overview of “omics”– that is, molecular approaches that can be applied to single cells, organisms (systems biology approach), and to whole ecosystems, in order to study interaction dynamics. The range of analytical techniques (genomes, transcriptomes, proteomes, metabolomes) is explored by a panel of scientists who are leaders in their field, and whose research will undoubtedly revolutionize our examination of the ways in which organisms interact in the oceans (Chapter 19–21). Next, Chapter 22 is devoted to the biosynthesis of natural products, using gene-mining approaches, and is written by world experts in the subject. Finally, a team of young and enthusiastic investigators has devoted the closing chapter to the latest high-throughput screening methods which allow rapid responses to be obtained from a large number of minute samples of molecules exposed to specific molecular targets, especially those that directly control cell division cycles (Chapter 23).
Finally, we wish to thank our fellow members of the French research cluster BioChiMar who responded very rapidly, spared some of their time, and shared their enthusiasm by writing chapters on some of their research or on favorite subjects, for the benefit of others.
Marine natural products is indeed a treasure chest for ecologists to explore, for pharmacologists to investigate, and for humankind to preserve in anticipation of the unprecedented climatic changes that are forecast to occur during the next decades as a consequence of global warming. Undoubtedly, the latter topic will result in massive collapses in species diversity in fragile and complex ecosystems, and especially in areas subjected to direct human interference.
Roscoff and Nantes
January 2014
Stéphane La Barre
Jean-Michel Kornprobst