Encyclopedia of marine natural products

1864 Pages·2014·87.141 MB·English

by  J M Kornprobst

1
Systems of Classification of Living Organisms: Great Steps in Chemical
and Biological Evolution
Westartbydescribingthegeneralprinciplesoftheclassificationoflivingorganisms.Thetaxonomicsystemisarranged
as a hierarchy going from the kingdom (the most general) down to the species level (the most particular), which
comprises the following main groupings, illustrated by the example below (the succession should be read from left
to right):1
Kingdom Phylum Class Order Family Genus Species
Animal Chordata Mammals Primates Hominoidea Homo sapiens
Consideringthebiodiversityoflifeformsonthisplanet,it 1.1
is sometimes necessary to consider intermediate group- Whittaker’s Five Kingdoms System (1959)
ingsaswell.Thus,onemaysometimesrefertoa“super-
class” (or subphylum), “superorder” (or subclass), and
The traditional dichotomy between the animal kingdom
subspecies (sometimes called a race).
and the plant kingdom has been completely abandoned
This latter concept is especially useful in chemo-
sincethe1960s.Systemsofclassificationhavenotstopped
taxonomy,whichisthestudyoftherelationshipbetween
evolving in the face of advances in microbiology and
the membership of a species in a given biological group
molecular biology, and it is probable that an “absolute
and the chemical composition of this same species in
classificationsystem,”basedonthegenome,willbeavail-
relation to other members of the taxonomic group; one
maythenspeakofa“chemicalrace.”2Thisconceptmakes able before the end of the twenty-first century.
The merit of Whittaker was to construct a coherent
it possible to distinguish between species that are
classification system based on two fundamental criteria:
indistinguishable in terms of traditional systematics but
the degree of cellular evolution; and the mode of repro-
which nevertheless exhibit different biochemical, and
duction.Astudyofthefirstcriterionmakesitpossibleto
oftenbiological,characteristics.Ontheotherhand,some-
divide the living world into two great “groups”: Monera
times a thorough chemical analysis of an organism per-
mits it to be “repositioned” in the traditional taxonomic and Eukaryotes. Monera consist only of primitive cells
without a true nucleus, and for this reason they are also
system.Thisprocesswouldseemtohavegreatpotentialin
thesearchforvariousspecificchemicalstructureswhichit called Prokaryotes. Monera are thus almost exclusively
representedbyunicellularorganismsorbycertaincolonial
wouldbefruitlesstoseekingroupsoforganismsinwhich
forms of these primitive cells; the most well-known of
they are lacking; however, one should nevertheless be
cautious in the use of these relationships – it should theseaggregatedformsaretheCyanobacteria(Cyanophy-
cea or blue-green algae). In contrast, Eukaryotes always
always be remembered that in the majority of cases
“one only finds what one is looking for.” consist of “advanced” cells containing a nucleus and,
unlike Monera, they can be either unicellular or multi-
cellular organisms (see Table 1.1).
After the distinction between prokaryotes and eukar-
yoteshasbeenmade,thesecondcriterioncanbeapplied.
1TheLatin“genus–species”unitisalwayswritteninitalics;thenameof According to their mode of reproduction, the eukaryotes
thegenusalwaystakesacapitalinitialletter,whereasthenameofthe can be divided into three separate “groups”: Fungi, Plan-
speciesneverdoes(e.g.,Homosapiens). tae,andAnimalia.Fungihaveonlynon-flagellatecellsand
2However,severaldifferenttermsareused,suchascohort,suborder,
reproduce by spores, either sexually or asexually. Plantae
superfamily,tribe,orsubgenus.
EncyclopediaofMarineNaturalProducts,SecondEdition.Jean-MichelKornprobst.
#2014Wiley-VCHVerlagGmbH&Co.KGaA.Published2014byWiley-VCHVerlagGmbH&Co.KGaA.
4
1 SystemsofClassificationofLivingOrganisms:GreatStepsinChemicalandBiologicalEvolution
Table1.1 Summaryofthemaincharacteristicsofprokaryoteand The third edition of Five Kingdoms by Margulis and
eukaryotecells.a Schwartz (1998) gives an excellent presentation of the
evolution of the concepts underlying various systems
Characteristic Prokaryotes Eukaryotes
for the classification of living organisms.
Dimensions 1–10mm;almostallare 10–100mm;unicellular
unicellularorganisms andmulticellular
organisms 1.2
DNA Includedinanucleoid, Thepresenceofanucleus Discovery of Archaea: Ternary Model of
withoutamembrane equippedwitha
Living Organisms (Woese and Fox, 1977)
ornucleus;no membrane.Thenucleus
chromosomes containschromosomes
madeofDNA,RNAand Intheearly1970s,biologistsdiscoveredanunusualgroup
proteins(histones). ofprokaryoticorganismslivingin“extreme”habitats,such
Cellular Absent Present
as underwater and terrestrial hydrothermal vents or in
organelles
hypersaline water. It soon became apparent that certain
Cytoskeleton No Yes,withmicrotubules
biochemical characteristics of these new bacteria – in
andactin
Enzymesfor Associatedin Gatheredinstructures particular, the structure of their membrane lipids –
photosynthesis chromatophores equippedwitha wereverydifferentfromthoseof“traditional”prokaryotes,
boundtothecell membrane:the andin1977thebiochemistCarlWoesedescribedthemas
membrane. chloroplasts Archaebacteria.4Aternaryclassificationofthelivingworld
Photosynthesismaybe
therefore became possible by considering only one crite-
anaerobicoraerobic
rion: the fundamental characteristics of the cell. There
Anaerobic/ Themajorityare Almostallareaerobic
Aerobicb anaerobic thus remain two kingdoms of prokaryotes and a single
Nitrogen-fixing Yes No kingdom of eukaryotes. Thanks to the techniques of
organisms molecularbiology–andhencethestudyofthenucleotide
sequences of ribosomal RNA 16S5 – very reliable results
aAdaptedfromMargulisandSchwartz(1998)andNelsonandCox(2000).
arebeingobtainedontheevolutionaryrelationshipsofthe
bObligateorfacultative.
organisms of the three kingdoms. It is generally agreed
that there was an “ancestor” common to all of the orga-
developfromanembryowithalternationofgenerations:a nisms now living – LUCA (Last Universal Common
haploidgametophyteandadiploidsporophyte.Asforthe Ancestor) – which led to the first separation between
Animalia,theyhavesexualreproduction,withtwohaploid theEubacteriaandasecond“ancestor,”whichlaterdiver-
gametesgivingrisetoadiploidzygote,anddevelopfroma sifiedintoArchaebacteriaontheonehand,andEukaryotes
blastula (aclusterofcells equippedwithacentral cavity). on the other hand (see Figure 1.1).
The fifth kingdom of Protoctista, is defined only by Withinthesethreekingdoms,biologistscurrentlyagree
exclusion (Whittaker, 1959). Protoctista are unicellular thatthefollowingprincipaldivisionscanbedistinguished,
or multicellular eukaryotes which are not fungi, plants, which all have marine representatives:
or animals; it is in this kingdom that the marine algae (cid:1)
Archaebacteria: Methanogens, Extreme Halophiles,
reside.Thisfifthkingdom,whichisdefinedbyexclusion
Hyperthermophiles.
ratherthanhavingacleardefinition,istheweakpointof (cid:1)
Eubacteria: Proteobacteria, Cyanobacteria, Prochloro-
Whittaker’ssystem,whichwastoevolveintoanewsystem
phyta.
–basedontheternaryconcept–whichiscurrentlyused. (cid:1)
Eukaryotes: Protista, Fungi, Plantae, Animalia.
Whittaker’sfivekingdomssystemwasslightlymodifiedby
the American biologist Stephen Jay Gould in the mid-
1970s (Gould, 1977). In this case, the first criterion
remains unchanged, but the second criterion – based
on the mode of reproduction – is replaced by a “degree
of cell complexity” criterion, which consists simply of
separating unicellular from multicellular eukaryotes.
The first group are then called Protista,3 and the second 4ThetermArchaeaiscurrentlypreferredtoArchaebacteria,
group remains divided into fungi, plants, and animals. Archaeobacteria,ArchebacteriaorArcheobacteria,butallfivetermscan
befoundintheliterature.
5SstandsfortheSvedbergunitofsedimentationvelocityby
ultracentrifugation(1S¼10(cid:3)13second).TheodorSvedberg(1884–1971)
wontheNobelPrizeinChemistryin1926forhisinventionofthe
3Inordertoavoidanyconfusionwiththe“Protoctista”ofWhittaker. ultracentrifuge.
5
1.3CharacteristicsofCellMembranes
Eubacteria
Eubacteria
Prokaryotes
LUCA ?
Archaea
LUCA
?
Archaea Eukaryotes
Eukaryotes
Figure1.1 “Evolutionarydiagramsofthethree“kingdomsoflife.”Theright-handdiagramillustratescertainuncertaintiesabouttheparaphilyof
Archaea(seeChapter2;seealsoLangworthy,1982;Grantetal.,1985;Mancusoetal.,1985;Woese,1987;Forterre,1990,1991,1999;Madiganand
Marrs,1997;Woese,1987;Purvesetal.,1998a,1998b;Schleper,1999;Martin,2005).
1.3 is in this case bound to the hydrophobic part by ester
Characteristics of Cell Membranes bonds. The stabilizing element of Eubacteria is either a
carotenoid – the central part is thus always terpenic, but
Atthephysicalinterfacebetweenthelivingandnonliving, formedbytwicetimesfourunitsbound“tail-to-tail”–ora
cell membranes are essentially composed of phospholi- hopanoid. These polycyclic triterpenes are considered to
pids,whichgloballyexhibitastructurewithapolarhydro- be ancestors of the sterols, which we find as stabilizing
philicendandanonpolarhydrophobicend.Theassembly elementsinalleukaryotecellmembranes.Morethan100
constitutes a kind of “bi-dimensional liquid,” sometimes sterolsareknown,whichallderivefromhopane,apenta-
calleda“fluidmosaicmodel.”Thehydrophilic“heads”are cyclichydrocarbonfoundinallsediments,coalsandfossil
immersedintheaqueousmedium(water)oneachsideof hydrocarbons, everywhere on Earth (Ourisson, Albrecht,
the double layer, and the hydrophobic “tails” congregate andRohmer,1984;Ourisson,1986;Ourissonetal.,1994).
inside the membrane. The thermodynamic stability of Therefore, the three fundamental types of cell – Archae-
such a “liquid” is maximal for a thickness of 40A(cid:4) bacteria,Eubacteria,andEukaryotes–whosemembranes
(4nm),andthemechanicalpropertiesofthemembranes are entirely formed by a bilayer of phospholipids, differ
resultfromthecombinationofthelipidswithstabilizing chemically by the nature of the stabilizing elements of
elements, which maintain the cohesion of the assembly. these double layers. There is, however, a “chemical con-
Thechemicalstudyofthesestabilizingelementsallowsa stancy”inallthis:isoprenicunitswhichwefindassociated
cleardistinctionbetweenthecellmembranesofthethree in different arrangements, but which are present from
fundamental types of organism. archaebacterial lipids tosterols, byway of hopanoidsand
For archean membranes, the stabilizing elements are carotenoids. Figure 1.2 summarizes the role of these
glycerol ethers, mostly tetraethers, with the hydrophobic membrane-stabilizing elements.
central partbeing terpenic,andthus branched out(twice ThemembranephospholipidsofArchaeaareverycom-
times four units bound “head-to-head”). For the mem- plexandcontainstructuralelementsthatareunknownin
branesofotherprokaryotecells(Eubacteria)andalleukar- the other membranes, such as gulose, aminopentanete-
yotecells,thehydrophilicpartofthestabilizingelements trol,sulfuricestersandsulfonicacids,amongothers(Koga
Archaebacteria Prokaryotes Eukaryotes
glycerol tetraethers bacterial carotenoids hopanoids sterols
(cables) (rivets) (nails) (nails)
Figure1.2 Stabilizingelementsofthethreefundamentalmodelsofcellmembranes(accordingtoOurisson,1986).
6
1 SystemsofClassificationofLivingOrganisms:GreatStepsinChemicalandBiologicalEvolution
and Morii, 2005). Some more detailed information on particularly the case for benthic organisms, which live
theseaspectsispresentedinChapter6,whichdealswith anchored to the seabed or submerged structures, and
the Archaea (see also Kates, 1986; de Duve, 1987; whose nutrients come from the circulation of seawater
Bretscher, 1988; Sargent, 1989; Moldoveanu et al., 1990; throughtheirbodies;theseincludeallthespongesanda
Prasad,1996;Purvesetal.,1998c;VandeVossenbergetal., largenumberofcnidarians(e.g.,corals).Glycerolethers
1999;Barenholz,2002;Ohvo-Rekil€aetal.,2002;andVigh and hopanoids have thus been pinpointed in sponges,
et al., 2005). themostprimitivepluricellulareukaryotes;itistherefore
Chemists know how to extract membrane phospholi- possible to deduce from their presence that these
pids in order to study their diverse constituents: these sponges are accommodating Archaebacteria and/or
include classes of phospholipids, fatty acids and unsa- Eubacteria. It is, on the other hand, more complicated
ponifiable elements. The chemical study of membrane todeterminetheoriginofthesesubstances,whichcould
phospholipids thus allows confirmation, in a multi- beasymbioticrelationshiporcouldresultfromthefood
cellularorganism,ofthepresenceofcellscharacterizing Web.Figure1.3presentssomeexamplesofthesevarious
prokaryotic or archaebacterial symbionts. This is membrane stabilizers.
OH
O O
O O
OH
hydrophilic head central hydrophobic chain hydrophilic head
(glycerol) (glycerol)
two regular (head to tail) diterpenic chains linked head to head
Glycerol tetraethers
Archaebacterial membranes
HO
OH
hydrophilic head central hydrophobic chain hydrophilic head
two regular (head to tail) diterpenic chains linked tail to tail
OH
OH OH
HO OH
HO HO
HO
bacteriohopanetetrol bacteriohopanetetrol
Bacterial carotenoids and hopanoids
Prokaryote membranes
HO
OH
cholesterol cholesterol
sterols
Eukaryote membranes
Figure1.3 Examplesofvariousstabilizersofcellmembranes.
7
1.5MainStagesofEvolution
1.4 Rohmer,1999,2003,2008;Bocharetal.,1999;Eisenreich,
Some Recent Data on Terpenes Rohdich, and Bacher, 2001; Fellermeier et al., 2001;
Rohdich et al., 2001; Dubey, Bhalla, and Luthra, 2003;
Terpenes (i.e., all the components formed starting from Kuzuyama and Seto, 2003; Meyer et al., 2003; Kashman
isoprene units) are very numerous in Nature, and their and Rudi, 2004; Dudareva et al., 2005; Oldfield, 2010).
numberisestimatedatapproximately23000.Terpenesare Lastly,athirdpathwayleadingtothebiologicalisoprene
stilldefinedasproductsofthemetabolismofisopentenyl units startingfrom leucine ishighlightedinthe parasitic
diphosphate (ex-pyrophosphate), which comes from ace- ProtozoanLeishmaniamexicanaandinbothMyxobacteria,
tylcoenzymeAbymeansofametabolicpathwaythathas MyxococcusxanthusandStigmatellaaurantiaca.ForEugle-
been studied in great detail: the mevalonic acid (MVA) nobiont, leucine is a constituent of sterols (Ginger et al.,
pathway. This definition has become ambiguous since 2001) and, for the two bacteria, leucine labeled with
1988, when Rohmer and his team showed that another deuterium was found to be a component in a sesqui-
pathway of biosynthesis of biological isoprene units – terpene and one of its degraded derivatives, geosmin
isopentenyl diphosphate (IPP) and dimethylallyl (Dickschat et al., 2005; see also Chapter 8). Myxobacteria
diphosphate (DMAPP)6 – was carried out by certain alsoincorporateleucine,isoleucine,andvalineiniso-and
Eubacteria by way of pyruvic acid and 3-phosphate D- anteiso- long-chain fatty acids, which occur frequently in
glyceraldehyde.Thecondensationofthesetwoprecursors, sponges (Bode et al., 2005; see also Chapter 19).
followedbythelossofacarbondioxidemolecule,leadsto These three biosynthetic pathways leading to terpenes
an intermediate with five carbon atoms, 1-deoxy-D- andsterolsaresummarizedinFigures1.4and1.5,which
xylulose-5-phosphate (DXP or DOXP). This is later show, as a concrete example, the biosynthesis of phytol
transformed into another five-carbon derivative, 2-C- followingtheMEPpathwaybytheCyanobacteriaSynecho-
methyl-D-erythritol-4-phosphate(MEP),whichfinallygives cystis sp.
isopentenyl diphosphate. This new pathway for the bio- Let us remember that the isopreneunit is traditionally
synthesisofterpenesissummarizedbytheinitialsDXP/ represented according to the diagram below, with two
MEP or DOXP/MEP, and is now simplified as MEP. “heads”(h)andone“tail”(t),althoughsomeauthorsadopt
Duringthelastdecadeofthetwentiethcentury,thisnew the reverse convention (one “head” and two “tails”):
biosyntheticpathwayhasbeenintensivelystudied,anditis
h t
now established that it is not limited to Eubacteria (Pro- t h
h t
karyotes), but that it also occurs in many eukaryote orga-
nisms such as Plasmodium falciparum, the agent of
Commonlyusedconvention Less-usedconvention
malaria. The MEP pathway is present in the majority of
bacteria, and some of them – such as Streptomyces sp. –
have both the MEP and the MVA pathways, which are
1.5
expressed differently from each other. The MEP pathway
Main Stages of Evolution
leads to the production of menaquinone prenylated
chains, and the MVA pathway leads to the prenylated
chainsofthesecondarymetabolites,whichhaveantibiotic In a synthetic way, one can distinguish three principal
activity(Rohmer,2003).Inthealgaeandhigherplants,the phases of evolution:
MVA pathway is localized in the cytoplasm and leads to (cid:1) From the formation of the ocean to the first eukaryote
ubiquinones, to triterpenes, and to sterols, whereas the
cell: chemical evolution.
MEP pathway is localized in the chloroplasts. Among (cid:1)
From monocellular eukaryotes to humans: biological
nonphotosynthetic organisms, the MEP pathway has
evolution.
been shown to occur in some Apicomplexa such as Plas- (cid:1) The human “adventure:” cultural evolution.
modiumfalciparum,whichmakesitreasonabletosuppose
thatthe searchfor enzyme inhibitorsof thestages ofthe The common thread joining these three stages is the
MEPpathwaycouldleadtonewantimalarialcompounds progressive control of the environment: from organisms
(Casseraetal.,2004).Manyarticlesanddevelopmentson thatdonothaveanymeansofperceivingtheenvironment
these two biosynthetic pathways of terpenes have been inwhichtheylive,tohumanbeingswhohavetheabilityto
published (in particular, those of Ourisson et al., 1987; modify and, to some extent, control their environment,
OurissonandAlbrecht,1992a,1992b;Rohmeretal.,1993; ranging from some local improvements to the total
destruction of the planet. We illustrate the great stages
of chemical and biological evolution by using the visual
time scale of the vulcanologist Haroun Tazieff (1914–
6TheacronymsIPPandDMAPParewellknownandarestillused,
althoughtheyrefertothetermpyrophosphateinsteadofdiphosphate. 1998), whereby time is represented by imagining a stack
8
1 SystemsofClassificationofLivingOrganisms:GreatStepsinChemicalandBiologicalEvolution
DXP / MEP pathway MVA pathway leucine pathway
O O O NH2
2 C3 CO2 H O P 3 C2 Co-A C6 CO2H
OH
(a) (b) (c)
O
C6 CO2H (d)
C5 COSCoA (e)
C5 COSCoA (f)
OH
OH
C5 O O P C6 C6 HO2C COSCoA (g)
OH CoA
DXP (h) HO2C O S
1-deoxy-
D-xylulose-5-P
OH OH OH
C5 O P MVA
mevalonic ac./
MEP OH OH HO2C OH O O mevalonolactone
2C-methyl- C6
D-erythritol-4-P
O O
C5 O P OOPOO C6 HO2C OH O-PP
(i) OH OH
O-PP O-PP
IPP C5 DMAPP
(a): acetylcoenzyme A ; (b): glyceraldehyde-3-phosphate ; (c): leucine ; (d) α-ketoisocaproic acid
(e): isovalerylcoenzyme A ; (f): 3-methylcrotonylcoenzyme A ; (g): 3-methylglutaconylcoenzyme-A
(h): 3-methyl-3-hydroxy-glutarylcoenzyme A ; (i) 2-C-methyl-D-erythritol-2,4-diphosphate
Figure1.4 Biosyntheticpathwaysforterpenes.
of sheets of paper each 0.1 mm thick, where each sheet oxygen that the anaerobic primitive cells evolved into
represents 10 000 years – that is, the entirety of human aerobic Prokaryotes, and the Cyanobacteria (which for a
historysincetheNeolithicRevolution.Usingthisimagery, longtimeweretermedblue-greenalgae)canberegarded
the principal stages of evolution are visualized in as our true ancestors.
Figure 1.6. The aerobic Prokaryotes then evolved into Eukaryotes
Although theories explaining the appearance of water thanks to another spectacular “invention,” the cell
onEartharestillthesubjectofmuchdebate,thewholeof nucleus, which nevertheless required one billion
the oceans appeared soon after the formation of our years. At that stage one can consider that the chemical
planet, and it took even less time – approximately 200 evolution stage is complete and the biological evolution
millionyears–untilthe first prokaryoticcellsappeared. stage is about to begin. However, nearly two-and-a-half
These were obviously strict anaerobes, since oxygen did billionyearswillhavebeennecessarytotakeusfromthe
not yet exist in the atmosphere. Approximately 400 first anaerobic Prokaryotes to the first pluricellular
million years later, certain Prokaryote cells “invented” organisms that are entirely composed of eukaryote cells
theprocessofphotosynthesisthat,veryslowly,produced and are all aerobes. This stage was the longest of all the
oxygen,whichnowseemstohavestabilizedatabout21% stagesinthehistoryoflife,andoneofthereasonswhyit
of the atmospheric gases. It is undoubtedly thanks to took so long is perhaps related to the fundamental
9
1.6ExceptionalResourcesofMarineBiodiversity
CHO paper heights Ages
OH (meters) (millions years)
13C 2D
HO
human story (0.1 mm) 0,01
OH 45.5
first human traces (8 cm) 8
OH
OH
D-glucose
HO O
O2C OH HO 35.5 first pluricellular organisms 1 000
OH
mevalonate DXP
O-P
first eukaryotes 1 500
30.5
OPP OPP
IPP IPP
20,5 aerobic photosynthetic bacteria 2 500
14.5 photosynthesis 3 000
phytol OH
first unicellular organisms 3 400
Figure1.5 Biosynthesisofphytolbythenon-mevalonicpathwayin 11,5
theCyanobacteriumSynechocystissp.UTEX24707(accordingto
Proteau,1998).
7.5 formation of the ocean 3 800
5.5 first rocks 4 000
problem of the recognition of self-awareness, or at least formation of the Earth 4 550
the recognition of the distinction between self and non- All "human story" is represented by the last page (0.1 mm)
on the top of the stack (45.5 meters)
self.
The biological evolution started in the ocean with the (0.1 mm = 10,000 years, 1 million years = 1cm, 1 billion years = 10 meters of paper)
diversification of all eukaryotes, after which these orga- Figure1.6 Mainstagesofevolution:scaleoftimeaccordingtoH.
Tazieff.Formoredetaileddataonthedates,see:LeGal(1991);De
nismsgraduallybecameadaptedtofreshwatersbymeans
Reviers(2002,Vol.1,p.105);PintiandMarty(2002);Selosse(2005);
oftheestuaries,thenrivers.Finally,someorganisms“left
andLecointreandLeGuyader(2006).
thewater,”adaptedtoanair-breathingwayoflife,andwent
ontoconquertheterrestrialrealm.Despitetheimmense
diversityofmulticellularorganismsonEarth,thekingdom
oftheEukaryotesis,infact,veryrecentbecausetheyhave Cairns-Smith, 1985; Brack, 1990; Brack and Raulin,
all appeared in the last billion years, although many of 1991; Gould, 1994; Orgel, 1994; Blandin, 1996; Forterre,
them – like the dinosaurs – have now completely disap- 1997;Levinton,1997;deDuve,1998;Purvesetal.,1998b;
peared.Ontheotherhand,aconsiderablediversityofvery Doolittle, 2000; Knoll, 2000; Hazen, 2001; Rossello-Mora
primitive organisms – the two Kingdoms of Archaebac- and Amann, 2001; Maurette, 2002; De Ricql(cid:2)es, 2005.
teria and Eubacteria – appeared nearly three-and-a-half
billion years ago, are still very much present, and are
widely distributed throughout the globe. Many articles
1.6
anddevelopmentshavebeenpublished,andthefollowing
Exceptional Resources of Marine
coveronlyaminorpartoftheavailableliteratureconcern-
Biodiversity
ing Evolution: Dickerson, 1978; Schopf, 1978; Valentine,
1978; Schwartz, 1981; Dejours, 1982; Halstead, 1984;
All formsof life first appeared inthe oceans and arestill
there, from Archaea to mammals – which explains why
marine biodiversity is much richer than terrestrial and
7TheabbreviationUTEXmeansthatthestockcomesfromtheUniversity
freshwaterbiodiversity.Thismarinebiodiversityisexam-
ofTexas;Figure1.5summarizeslabelingexperimentscarriedoutwith
13C-labeled1-13C-D-glucose,6,6-2H2-D-glucose,and2-13C-D-glucose. ined in more detail in the following chapters although,
10
1 SystemsofClassificationofLivingOrganisms:GreatStepsinChemicalandBiologicalEvolution
generally speaking, it can be observed that there is a Dickschat, J.S., Bode, H.B., Mahmud, T., Mu€ller, R., and Schulz, S.
greater biodiversity in phyla and genera in the marine (2005)Anoveltypeofgeosminbiosynthesisinmyxobacteria.J.Org.
environment than in the terrestrial environment. At the Chem.,70,5174–5182.
Doolittle,F.(2000)L’arbreduvivant:unbuissonfoisonnant.Pourla
species level it is a different story, however, and bio-
Science,270,84–89.
diversity within species is greater on the ground than in
Dubey,S.,Bhalla,R.,andLuthra,R.(2003)Anoverviewofthenon-
theoceans.Thereasonusuallyputforwardforthisisthat mevalonatepathway forterpenoidbiosynthesis in plants. J. Biosci.,
the marine environment is, overall, more constant, and 28,637–646.
therefore species have evolved very littlewithin the same Dudareva, N., Andersson, S., Orlova, I., Gatto, N., Reichelt, M.,
Rhodes, D., Boland, W., and Gershenzon, J. (2005) The
phylum. On the other hand, the very large variety of
nonmevalonate pathway supports both monoterpene and
biotopes on the ground has resulted in a vast amount of sesquiterpeneformationinsnapdragonflowers.Proc.NatlAcad.Sci.
adaptation in species belonging to the same order or the USA,102,933–938.
same family, or even the same genus. Eisenreich, W., Rohdich, F., and Bacher, A. (2001) Deoxyxylulose
phosphatepathwaytoterpenoids.TrendsPlantSci.,6,78–84.
Fellermeier,M.,Raschke,M.,Sagner,S.,Wungsintaweekul,J.,Schuhr,
C.A., Hecht, S., Kis, K., Radykewicz, T., Adam, P., Rohdich, F.,
Selection of Documentary Resources Eisenreich, W., Bacher, A., Arigoni, D., and Zenk, M.H. (2001)
Studiesonthenon-mevalonatepathwayofterpenebiosynthesis:the
roleof2C-methyl-D-erythritol2,4-cyclodiphosphateinplants.Eur.J.
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