Biosynthesis and Function of Carotenoid Pigments in Microorganisms

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BIOSYNTHESIS AND FUNCTION OF CAROTENOID

1’2
PIGMENTS IN MICROORGANISMS
BY SYNN~VELIAAEN JENSEN
Institute of OrganicChemistry,. The Technical U~i~erslty of Norway,
Trondheim, Norway
CONTENTS
INTRODUCTION.................................................... 163
BIOSYNTHESIS..................................................... 165
THEBIOSYNTHESIS OF THE PRIMARY C,0UNIT
Annu. Rev. Microbiol. 1965.19:163-182. Downloaded from arjournals.annualreviews.org
FROM Low-MoLECULAR WEIGHT

PRECURSORS ....................................................... 166
THE SEQUENTIAL DEI~YDROGENATION O1~ THE PRIMARY C,o PRECURSOR TO
COLOUREDCAROTENOIDS .............................................
by Univ. Nacional de Colombia on 06/10/08. For personal use only.
ULTIMATE ~TEPS OF CAROTENOID ]~IOSYNTHE~IS IN ]~ACTERIA ............. 171

_Photosynthetic
bacteria ..............................................
171
Nonphotosynthet~c
bacteria ...........................................
172
ULTIMATE STEPS OF CAROTENOID BIOSYNTHESIS IN FUNGI ................ 173
FINALSTEPSOF CAROTENOID BIOSYNTFIESISIN ALGAE................... 174
EVOLUTION AND CAROTENOID BIOSYNTHESIS ............................ 175
FUNCTION......................................................... 175
PROTECTORS AGAINST PHOTODYNAMIC DESTRUCTION ................... ...
PHOTOSYNTHESIS .................................................... 177
PHOTOTAXIS ........................................................ 178
OTHERFUNCTIONS
...................................................
179
CONCLUDINGREMARKS..........................................
179
INTRODUCTION
At the presenttimc,carotcnoids arc consideredto bc compoundswhich
arechemically or biochemically
closely related
to thetomatopigment, lyco-
pene(1), withoutregardto the numberof carbonatomsin the molecule
its pigmented nature~-aIthoughmostcarotenolds are yellow-rcdcompounds
containingfortycarbonatoms.
The entireseriesof knowncarotenoids can be formallyderivedfrom
lycopeneby simplechemical reactions. Suchchangesincludepartial hydro-
gcnatlonor dehydrogenation,
cyclizatlon,aromatization,andintroductionof
variousoxygenfunctionsin themolecule.
The carotenoids exhibita plenaryisoprenoid skeletonin commonwith
someothermajortypesof natural products,suchas steroids andterpenolds.
It contrastto theselattertypesof compouDds,
onlya verylimitedcyclization
~ Thesurvey oftheliterature pcrta[nlngtoth~srevlcw wasconcludedinNovember
1964.
* The following abbreviations will be used: ADP(adenosine dlphosphate); ATP
(adenosine triphosphate); FAD(flavln adenine dlnucleotlde); P and PP (phosphate
and pyrophosphate); NAD,NADH,(Nicotlnam~de-aden~ne d~nucleotlde and reduced
form)~ NADP,NADPH,(nlcotinamlde-adenlae dlnucleotlde phosphate and reduced.
form).
163
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164 JENSEN
4’
~ _7._ l_ _ l _ 14’...,12’..,10’_,8" _,’~~,
Structure I
giving rise to substituted cyclohexylidene, phenyl, cyclopentane, and fura-

noid end groups is encountered in carotenoids. The most characteristic fea-
ture of the carotenoids is the isoprenoid polyene chain responsible for the
yellow-red colours of most carotenoids.

Carotenoid pigments are widely distributed in the microbial world. They
are invariably present in all photosynthetic organisms, and are also produced
by some fungi and aerobic, nonphotosynthetlc bacteria.
Table I shows, in generalized form, the characteristic structural features
exhibited by the major carotenoids produced by the main groups of micro-
organisms. The structural features referred to in this table are as follows:
II
HO ’OH
IV
Structures II, III, IV
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CAROTENOID PIGMENTS IN MICROORGANISMS 165

TABLE I
Ct~ARACTERISTIC STRUCTURAL FEATURES OF THE MAIN CAROTENOIDS IN
VARIOUS MAJOR GROUPS O1;" MICROORGANISMS
MICROORGANISM TYFE OF CAROTENOID
tydroxy
Maior Subgroup lated
group
rec.Tert.
Bacteria Photosynthetic + ÷ - -t-~

Nonphotosynthetic + + ÷ + (+)
Fungi + + - + ? + +
Algae Cyanophyceae + + - + + + -
Euglenophyceae + _ + +b - + + -
Crysophyceae + - + - (+) + -
BacilIarlophyceae + _ + +b - + + -
Xanthophyceae + _ + +b - +
Dinophyceae + - + ? - (+)
Chlorophyceae + - + - +
Cryptophyceae +
a Hydroxygroups in 1-position.
b Hydroxygroups in 5- or 6-positions (presumably derived from epoxidic carot-
enoids).
( ) Limited distribution or uncertain.
Data based on (37, 41, 48, 59, 51, 69, 93, 94) and someunpublishedobservations
by the author.
OH-Spheroidenone (II) is an example of an aliphafic, methoxylated keto

carotenoid with a tertiary hydroxyl group in the U-posltion. Chlorobactene
(III) is a typical representative of a monocycllc, aromatic carotene, and
antheraxanthin (IV) is a bicyclic epoxy carotenoid with secondary hydroxyl
groups in 3,3~-positions.
The present review is restricted to a brief, general discussion of the status
of our knowledge of the biosynthesis and function of carotenoids in micro-
orgarfisms. The literature discussed is selective rather than comprehensive.
BIOSYNTHESIS
The available evidence indicates a general biosynthetic pathway for the
formation of the primary C40 unit from low-molecular precursors in all carot-
enogenlc systems. The succeeding sequential desaturatlon is apparently also
of general nature, whereas the ultimate steps, including the insertion of oxy-
gen functions, are characteristic for the different groups of microorganisms.
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166 JENSEN
It is therefore considered convenient to treat the two first-mentioned initial
pathways in a general manner, followed by separate discussions of the final
steps of carotenoid biosynthesis in bacteria and in tho~e of the fungi and al-
gae which can be considered as microorganisms.
THE BIOSYNTHESISOF THEPRIMARYC40 UNIT FROMLow-MOLECULAR

WEIGHT PRECURSORS
The isoprenoid nature and symmetry of the carotenoid skeleton suggest
its formation from 8 branched Ca units added together in the following man-
ner:
8x5
20x2
Scheme A
This simple hypothesis has obtained experimental support. A clue to the

establishment of the. pathway leading from low-molecular weight precursors
to the primary C40 unit was obtained by analogy with terpeneand steroid
biosynthesis, and the remarkable achievements in the latter field have served
as a profitable working hypothesis for the carotenoid biochemists.
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Using Cl*-labelled acetate, Grob and co-workers (1, 2) were able
demonstrate that both carbon atoms of acetic acid were incorporated into B-
carotene in the mould, Mucor hiemalis. The labelling pattern thus observed
for B-carotene by Grob & Biitler (2) corresponded to that of squalene
steroid biosynthesis.
In vivo incorporation of labelled mevalonic acid into/3-carotene was later
reported by many workers, e.g., for the above mould by Grob (3), for
Blakeslea trispora by Anderson, Norgard & Porter (4), for Neurospora crassa
by Krzemenski & Quackenbush (5), for Euglena gracilis by Steele & Gurin
(6), and for Phycomyces blakesleeanus by Braithwaite & Goodwin (7). The
latter authors found that I)L (2-C 1~) mevalonate was more efficiently in-
corporated into fl-carotene than was acetate.
The preparation from microorganisms of-cell-free enzyme systems capa-
ble of carrying out in vitro carotenoid synthesis was first achieved some five
1.)
years ago. Suzue (8) demonstrated the synthesis of phytoene from (2-C
mevalonic acid by a cell-free extract of a particular mutant of Staphylococcus
aureus. ATP, NADPH~,FAD, and manganese were found to be essential co-
factors, and anaerobic conditions stimulated the formation of phytoene.
¥okoyama, Nakayama & Chichester (9) have described a partially puri-
fied cell-free system from P. blakesleeanus capable of synthesizing/~-carotene
from labelled acetate, /~-hydroxy-/~-methyl-glutarate, or from mevalonic
acid, the last named being the most efficient substrate. Cofactor require-
ments for the conversion of mevalonic acid included ATP, NADH,NADP,
NADPH~,and manganese. Coenzyme A was required only when acetate or
fl-hydroxy-fl-methyl-glutarate were used as substrate. The lack of require-
ment of NADwas stressed by the authors, as this compound was needed in
squalene synthesis.
Ohnoki, Suzue & Tanaka (10) have clearly demonstrated the formation
of 5-phospho-mevalonic acid from labelled mevalonic acid in the presence of
ATPand manganese in the same type of cell-free extract of S. aureus as that
mentioned above. 5-Phospho-mevalonic acid was converted enzymically to
phytoene twice as efficiently as DL-mevalonicacid. More recently, Suzue (11)
has presented convincing evidence that 5-pyrophospho-mevalonate is an
intermediate in the enzymic synthesis of bacterial phytoene from mevalon-
ate. Subsequent careful studies by Suzue et al. (12) have unequivocally
demonstrated the enzymic formation of isopentenyl-pyrophosphate from
mevalonate in the presence of iodoacetamide, and the further conversion of
isopentenylpyrophosphate to phytoene in extracts of S. aureus. Adenosine
trlphosphate was not required as a cofactor in the latter reaction, which pro-
ceeded equally well under anaerobic and aerobic conditions,
Yamamotoet al. (13) have reported that purified C14-farnesol pyrophos-
phate, synthesized by a rat-liver extract, was incorporated into/3-carotene in
a cell-free extract of P. blakesleeanus more efficiently than mevalonic acid
under similar conditions. When farnesol pyrophosphate and mevalonic acid
together were used as substrate, higher efficiency in incorporation was ob-
served, thus indicating a condensing unit higher than C15.
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168 JENSEN
In a noteworthy report from Bloch’s school (14), the purification
geranylgeranyl pyrophosphate synthetase from Micrococcus lysodeikticus is
recently described. The highly purified preparation catalyzed the synthesis
of geranylgeranyl pyrophosphate from isopentenyl pyrophosphate and either
dimethylallyl, geranyl, or farnesyl pyrophosphate. Magnesium ions were an
absolute cofactor requirement. Of these reactions the most rapid was the con-
version of farnesyl pyrophosphate to the C~0 pyrophosphate. The interesting
possibility that a single protein catalyzes all reactions was considered.
A labelled C~0 terpenol pyrophosphate has been claimed by Anderson &
Porter (15) to act as substrate for phytoene formation in cell-free tomato
preparations. Information regarding this particular step is lacking for micro-

organisms.
The nature of the primary C,0 unit has caused some discussion, lycoper-
sene and phytoene being the postulated candidates. Gr0b, Kirschner & Lynch
(16) reported that a cell-free system from N. crassa could synthesize radio-
active lycopersene from mevalonate, and Grob & Boschetti (17) claimed
squalene and lycopersene to be the major components of a phytoene-free
fraction of the lipids of N. crassa cultivated in the presence of diphenylamine.
Generally, growth of many microorganisms in the presence of diphenylamine
results in the inhibition of coloured carotenoid synthesis, and the accumula-
tion of saturated precursors such as phytoene, etc. Lycopersene, if a precur-
sor of phytoene, would be expected to accumulate under such conditions.
Davies, Jones & Goodwin (18) were, however, unable to detect lycopersene
under similar conditions, again in N. crassa. Rilling claimed that phytoene in
a gycobacterium sp. was formed by a nonoxidative reaction, thereby exclud-
ing lycopersene as its precursor (19). So far, there is no conclusive evidence
for the role of lycopersene as an intermediate in carotenoid biosynthesis.
On the basis of the results discussed above and the evidence available
from steroid biosynthesis, it appears likely that the carotenoid skeleton is
formed from C5 units (isopentenyl-pyrophosphate) by condensation
geranyl pyrophosphate (C10), then to farnesyl pyrophosphate (C15), geranyl-
geranyl pyrophosphate (C~0), and further by tail-to-tail condensation
lycopersene or phytoene. It is interesting to compare the latter condensation
with the coupling of two molecules of farnesyl pyrophosphate to give squa-
lene. At one time, Cornforth & Popj/~k (20) favoured dehydrosqualene as
intermediate in steroid biosynthesis. This hypothesis was subsequently
abandoned, when it could be demonstrated that three of the C1 hydrogen
atoms in farnesyl-pyrophosphate was incorporated into the squalene mole-
cule; the fourth orginating from NADPH~ in a stereospecific process (21).
Goodwin (38) has adapted the former hypothesis to carotenoid biosynthesis,
which implies coupling of the two C,0 units directly to phytoene.
In summary, the available evidence for carotenoid biosynthesis up to the
C40 level, is in accordance with the pathway depicted in Figure 1, essentially
as outlined by Lynch et al. (22) for squalene synthesis. However, rigorous
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CO2 ~L~/~-Methyl- Crotonyl- CoA ~ Isovaleryl-CoA ~- ~-- Leucine
ATP~
~
ADP÷P
Methyl- glutaconyl- CoA
~ + H20
/~-Hydroxy-~- methyl 2NADPH

~- Mevalonic acid ~ Mev~lonic acid-5-P
Acetyl-CoA
~ ATP
Mevalonic
acid-5-PP
ADP+P+CO~2/- ATP
Isopentenyl-PP
Geranyl-
geranyl-PP
C40
FIG. I. The current picture of the biosynthetic pathway leading from low-
molecular precursors to the carotenoid skeleton (C,0).
confirmation of the individual steps should be sought from studies with puri-
fied enzyme systems and by establishment of cofactor requirements.
The stimulatory effect of leucine on carotenoid biosynthesis has been
studied for many years, mainly by Macklnney’s group. A summarizing dis-
cussion of this phenomenon has been given by Chichester et al. (23). The
results of the incorporation of the individual carbon atoms of leucine into
~3-carotene in P. blakesleeanus appear to be compatible with the scheme out-
lined in Figure 1. Whereas the carboxyl carbon atom (Ct) of leucine is not
incorporated into E-carotene, the carbon atoms of the gemini methyl groups
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170 JENSEN
are incorporated
withconsiderably
moreefficiencythanthe restof the car-
bonatomsof leucine.
The authors
explained
thisresultin termsof recycling
of fl-hydroxy-~-methyl-glutarate
withan activeacetoacetate
pool.
THE SEQUENTIAL DEHYDROGENATION OF THE PRIMARYC40 PRECURSOR

TO COLOUREDCAROTENOIDS
The hypothesis of a stepwise dehydrogenation of a comparatively satu-
rated precursor to coloured carotenoids was, in principle, suggested by Zech-
meister and later.expanded by Porter & Lincoln (24) on the basis of studies
of carotene formation in tomatoes. This ’general principle was highly dis-
puted for many years [see, for instance (25, 26)], but has more recently de-
rived firm support from studies on carotenoid biosynthesis in microorgan-
isms.
The accumulation of relatively saturated carotenoids like phytoene,

phytofluene, ~’-carotene, and neurosporene during growth in the presence of
diphenylamine is a general observation for many carotenoid-producing
mleroorganlsms. Stanier and his associates (27) demonstrated that Rhodo-
spirillurn rubrum, depleted of its normal coloured carotenoids by growth in
the presence of diphenylamine, was, after removal of the inhibitor, capable
of carrying out an endogenous synthesis of its normal carotenoids at the ex-
pense of the more saturated C40 carotenoid precursors that had accumulated
in the inhibited cells. The detailed analysis of these transformations revealed
stoichiometry in favour of the following reaction sequence:
?
Phytoene-~ Phytofluene-~ ~’-Carotene--~ Neurosporene-~ Lycopene,etc.
ColourlessC~0Precursors Normal Carotenoids
The role of phytoene in these transformations could not be definitely demon-

strated. These experiments provided experimental evidence for carotenoid
biosynthesis on the C40 level, according in principle to the Porter-Lincoln
hypothesis for lycopene formation.
Ultraviolet mutants of several carotenoid-producing microorganisms ex-
hibit a block in the synthesis of their normal carotenoids and an accumula-
tion of less coloured carotenoids (28). Such observations provide more indi-
rect evidence for the stepwise dehydrogenation pathway to coloured carot-
enoids, although it may be and frequently has been argued that the accumu-
lated, more saturated carotenolds need not be true intermediates in normal
carotenoid synthesis (29).
Dark-grown cultures of the mould N. crassa produce large amounts of
more saturated carotenoids, mainly phytoene and phytofluene. Whena dark-
grown culture is illuminated in the presence of air, coloured carotenoids are
rapidly formed. Haxo (30), and, particularly, Grob (31), interpreted
results as a stepwise formation of coloured carotenoids from more saturated
C40 precursors, whereas Zalokar (29) claimed that the existing phytoene
could, at most, be only a partial source of the coloured carotenoids.
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A mutant strain of Chlorella vulgaris, described by Claes (32), also ac-
cumulated phytoene, phytofluene, ~’-carotene and neurosporene in the dark.
In the light, coloured carotenoids were formed, accompanied by a decrease
of the polyenes of the Porter-Lincoln series.
Although there are manyconflicting reports [e.g. (5, 33)], the main body
of evidence from various types of microorganisms is in agreement with the
formation of coloured carotenoids by dehydrogenation of more saturated
precursors. These dehydrogenations appear in general to be independent of
oxygen in photosynthetic microorganisms, but oxygen-requiring in non-
photosynthetic microorganisms. Intermediates in the dehydrogenation reac-
tions have not been isolated. A theory of a-hydroxylation followed by dehy-

dration has been considered [e.g. (19, 27, 34)], although a straight NADP-
NAD-requiring dehydrogenation might be equally plausible.
Studies on these particular dehydrogenation steps have been carried out
mainly in vivo. However, Suzue (35) has reported the enzymic conversion
phytoene into the monocyclic/~-carotene by a crude enzyme preparation of
wild-type S. aureus. In a recent report, Kakutani, Suzue & Tanaka (36) have
described the enzymic conversion of phytoene to/~-carotene in cell-free ex-
tracts of Sporobolornyces shibatanus. These results support the role of phyto-
erie as a commonprecursor of all coloured carotenoids, aliphatic as well as
cyclic.
Weshall now turn to a discussion of the final steps of carotenoid biosyn-
thesis in various groups of microorganisms. Emphasis will be placed on bio-
synthetic pathways and some of the major factors governing carotenoid syn-
thesis. Other factors influencing carotenogenesis, such as mediumcomposi-
tion, temperature effects, inhibitors other than diphenylamine, etc., have
been discussed by Goodwin(25, 37, 38) and will not be treated here.
ULTIMATE STEPS OF CAROTENOID BIOSYNTHESIS IN BACTERIA
Photosynthetic bacteria.--The distribution, chemical structure, and bio-

synthesis of carotenoids in photosynthetic bacteria have been rather exten-
sively studied. Recent discussions of this topic have been given by Stanier
(39), Liaaen Jensen, Cohen-Bazire & Stanier (40), and Liaaen Jensen
41).
The Athlorhodaceae are characterized by their content of aliphatic carot-
enolds carrying tertiary hydroxyl and methoxyt groups, sometimes contain-
ing conjugated carbonyl functions (see Table I). The biosynthetic pathway
leading to the formation of these pigments has been established by StaBler
and co-workers (27, 40, 42) and by Eimhjellen & Liaaen Jensen (43).
work involved studies of endogenous carotenoid synthesis in washed cell
suspensions, studies of the diphenylamine effect in R. rubrum and the oxygen
effect on carotenoid biosynthesis in Rhodopseudomonasspp. The pathway is
depicted in Figure 2.
Five main reaction types participate in these transformations: (a) dehy-
drogenation involving the introduction of a double bond between two previ-
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172 JENSEN
FI6. 2. Ultimate steps of carotenoid biosynthesis in Athlorhodaceae. Numbers

refer to the reaction types whichare explained in the text.
ously existing double bonds; (b) dehydrogenation involving the introduction

of a double bond at the hydroxylated side of the polyene chain; (c) hydration
of an isopropylidene end group with the formation of a tertiary alcohol; (d)
methylafion of the tertiary hydroxyl group to give a tertiary methyl ether;
and (e) introduction of a conjugated keto group in a-position to the tertiary
methoxyl group.
The oxygen dependence of the latter reaction was demonstrated by van
Niel (44), and Shnoeur (45) has shown that the oxygen atom in the
group of spheroidenone is indeed derived from molecular oxygen. Braith-
waite & Goodwin (46) have provided evidence for the origin of the super-
numerary carbon atoms of the methoxyl groups in spirilloxanthin fl:om a
one-carbon source (formate). The effect of light and oxygen on carotenoid
biosynthesis in Rhodopseudomonas spheroides has been demonstrated by
Cohen-Bazire, Sistrom & Stanier (42), who included an interpretation .of the
regulation of the photosynthetic pigment synthesis.
The Chlorobacteriaceae hitherto investigated synthesize as their major
carotenoid a monocyclic, aromatic carotene, chlorobactene (III), chemically
related to -r-carotene (47). The biosynthetic pathway leading to chlorobac-
tene is not yet established, although it may tentatively be assumed that it is
formed from ,),-carotene by further dehydrogenations accompanied by
methyl migration.
Of the various organisms of the Thiorhodaceae, some synthesize the carot-
enoids of the "normal" spirilloxanthin series; others synthesize the charac-
teristic carotenoids of the warmingoneand okenone type (41).
Nonphotosynthetic bacteria.--Less information is available concerning the
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carotenoid biosynthesis in other bacteria. Goodwln (37) has compiled the
data available up to 1952 on the distribution of carotenoids in bacteria.
Many of the identifications, however, ought to be rechecked by modern
methods.
Leprotene, synthesized by some Mycobacterium spp., was recently shown
to be identical with isorenieratene, a bicyclic carotene with two aromatic end
groups (48).
The effect of oxygen on carotenoid biosynthesis in an aerobic Mycobac-
terium sp. has recently been reported by Rilllng (19), who concluded that
carotene synthesis could proceed under anaerobic conditions in the presence
of a suitable electron acceptor, whereas the synthesis of hydroxylated carot-

enoids required the presence of molecular oxygen. The same author (49)
has recently discussed the mechanism of aerobic photoinduction of carotene
synthesis in nonphotosynthetic organisms. The’pathway suggested for carot-

enoid biosynthesis in Mycobacterium sp. is in accordance with the current
concept of carotenogenesis.
The diphenylamine effect on various strains of Mycobacterium phlei has
been studied [e.g. (50, 51)], but this work has not led to the establishment
the ultimate steps in the biosynthetic pathway of the cyclic carotenoids
normally produced by these strains.
The enzymic conversion of phytoene to the monocycllc S-carotene under
aerobic conditions in extracts of S. aureus (34) has already been mentioned.
Intermediates were not described.
Some new information is available on the carotenoids of halophillc bac-
teria (34, 52). Strong aeration appears to promote the formation of the
most unsaturated carotenolds, but, again, little is known about the biosyn-
thetic pathway,
ULTIMATE STEPS OF CAROTENOID BIOSYNTHESIS IN FUNGI
The biochemistry of fungal carotenoids has been treated in detail by

Haxo (53) who included a table summarizing the reported distribution
carotenoids in fungi; again, the identification of some of the xanthophylls
seems uncertain. While the dominating pigments of fungi are carotenes, the
carotenoid acid, torularhodin, is also a typical fungal carotenoid and the
keto-carotenoid canthaxanthln and some other xanthophylls have also been
found in various fungi (cf. Table I).
The carotenoid composition in various mutants of Rhodotorula rubra has
been examined by Bonner et al. (54), and that of mutants of N. crassa by
Haxo(55). As already discussed, conclusions as to the path of carotenoid bio-
synthesis cannot be based on such results alone, but the most likely interpre-
tation is that phytoene and phytofluene are precursors of the cyclic carote-
noids synthesized by the wild type, and that the acidic xanthophyll of N.
crassa is formed via its neutral xanthophylls. Recently, Simpson, Nakayama
& Chichester (56) isolated the carotenoid acid, torularhodin, from R. rubra
grown in an atmosphere enriched in ~802. Isotopic analysis indicated that
one 1~O atom was incorporated into the carboxyl group.
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174 JENSEN
From experiments with labelledmevalonate, Davies(57) claimedthat
the formation of -~-carotene was independent of [ycopene synthesis in the
phycomycete, Rhi~ophylctis rosea.Davieset a[.(58)identified ~-zea-caro-
tene (monocyclic neurosporene) in P, blakesleeanus and Rhodotorula glut~nis.
They claimed that ~-carotene was rapidly formed from fl-zea-carotene when
P. blakesleeanus, previously grown in the presence of diphenylamine, was
washed free of inhibitor and resuspended in phosphate buffer containing
glucose as energy source. Since glucose carbon could also be used for carot-
enoid synthesis, there is no unequivocal proof for the role of/~-zea-carotene
as a/~-carotene precursor. Nor is the immediate precursor of the cyclic carot-
enoids known, although one or more of the members of the Porter-Lincoln

series (phytoene, phytofluene, ~’-carotene, neurosporene, and lycopene) are
likely suspects. There is also complete ignorance of the cyclization mecha-
nism, which represent a major unsolved problem in carotenoid biosynthesis.
It has often been suggested that a-carotene (synthesized by green algae and
higher plants) is formed in vivo by isomerization of ~-carotene. There is, how-
ever, no experimental support for this suggestion, and ~- and ~-carotene may
very well result by proton elimination from the same intermediary C~ cyclic
cation.
FINAL STEPS OF CAROTENOID BIOSYNTHESIS IN ALGAE
Microscopic representatives are found within most of the algal classes

(59) (cf. Table I). Algae carry out photosynthesis with the evolution of
gen, a~ do higher plants and, broadly speaking, the carotenoids of algae re-
semble those of higher plants; B-carotene, lutein, and epoxidic carotenoids are
often encountered. The various classes, however, do synthesize certain spe-
cific carotenoids.
The carotenoids of green algae resemble mostly those of the higher plants.
In the euglenids, astaxanthln and related compoundsare reported. The dlno-
flagellates and the diatoms produce some highly oxygenated carotenoids, and
in blue-green algae echinenone and the highly oxygenated myxoxanthophyll
appear to be characteristic carotenoids. A convenient compilation of the
carotenoid distribution in algae has been presented by Goodwin (60) and
Jeffrey (61).
The chemical structures of the poly-oxy-carotenoids have not yet been
established, and little is definitely known about their biologlcal formation.
Biosynthetic studies have been performed mainly with green algae and
Euglena grac~lis.
The studies of Claes (32, 62) have revealed that carotene synthesis i-h
mutant of Chlorella vulgaris is light-dependent, and that xanthophyll synthe-
sis requires molecular oxygen. Claes (63) demonstrated that a- and/~.-caro-
tene synthesized in the light were the immediate precursors of xanthophylls.
subsequently synthesized in the presence of oxygen in darkness. The follow--
ing pathway was suggested.:
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Phytoene
Phytofluene hr a-Carotene darkness Xanthophylls
~’-Carotene ~ ~-Carotene -~
Neurosporene Carotene X O~ Oxidized Carotene X
Prolycopene
Carotene X is an unidentified carotene (62) ; the spectral resemblance to/~-
zea-carotene (64) is striking.
In agreement with the above results, Yamamoto, Nakayama & Chiches-
ter (65) found, by growing C. vulgaris in the dark and using molecular oxygen
or water enriched in 1so, that oxygen from the atmosphere was incorporated
into the xanthophylls lutein, violaxanthin, and neoxanthin. They further
claimed, contrary to predictions, that the epoxidic oxygens were derived from
water and not from molecular oxygen.
Blass, Anderson & Calvin (66) studied the incorporation of I*CO~into the
carotenoids of Chlorella pyrenoidosa and Scenedesmus obliquus during photo-

synthesis. The specific radioactivities of lutein and violaxanthin were found
to be similar, suggesting a rapid interconversion between the two com-
pounds. They suggested that violaxanthin and lutein were interconvertible
in a light-dark reaction. A similar reaction has been studied in E. gracilis by
I(rinsky (67), who demonstrated the light-catalyzed transformation of
mono-epoxide antheraxanthin to zeaxanthin. The same reaction has lately
been studied enzymically (68).
EVOLUTION AND CAROTENOID BIOSYNTHESIS
Goodwin (69) has made an interesting evaluation of the possible evolu-

tion of phototrophs based on the distribution of carotenoid pigments. With-
out accepting the various aspects of Goodwin’s scheme, some simplified bio-
chemical considerations can be made.
Weshall adopt the plausible hypothesis that the photosynthetic bacteria
preceded the higher protists in the evolutionary scale, and that the blue-
green algae belong to an .earlier algal period than do the other algal classes.
From our present discussion on carotenoid biosynthesis, the evolutionary
trends in the structural features of carotenoids in photosynthetic microor-
ganisms can tentatively be depicted as in Figure 3.
FUNCTION
PROTECTORS
AGAINSTPHOTODYNAIVilCDESTRUCTION
Since carotenoids are invariably present in the photosynthetic apparatus
of all phototrophs, the participation of carotenoids in photosynthesis is to be
expected. Whereas light absorbed by carotenoids can be used in photosynthe-
sis (see below), a more universal function of carotenoids appears to be the
protection of cells against deleterious photo-oxidation, discovered some years
ago by Stanler and his associates (70). A blue-green mutant of R. spheroides
which synthesized only slightly less chlorophyll than the parent, but in
Annual Reviews
176 JENSEN
SKELETON OXYGEN FUNCTIONS Evolutionary
scale
OCHa
hliphatic Hydration,tert. OHin 1-position
(anaerobicprocesses)
Monocycfic Sec. OH,epoxy groupings

(aerobic processes)
Ar°matic~/\
BicycHc Highly Oxygenatedcarotenoids
with complexstructure
FIG. 3. Evolutionarytrends in the structural features of carotenolds in

photosynthetic microorganisms.
which coloured carotenoids were replaced by the colourless phytoene, grew

normally under anaerobic, photosynthetic conditions. However, the cells
were rapidly killed by simultaneous exposure to light and oxygen, and death
was accompanied by destruction of the bacteriochlorophyll. Exposure to oxy-
gen in the dark had no lethal effect on the mutant. Since the normally pig-
mented wild type was not affected in this manner, it was concluded that
death resulted from photodynamic action, bacteriochlorophyll being the
sensitizer. Further detailed studies on the photodynamlc killing of the same
mutant have been performed by Dworkin (71), who demonstrated that
death occurred just as rapidly at low temperatures, when the destruction of
chlorophyll could be prevented. The latter process is therefore a secondary,
chemical event.
Specific carotenoid depletion of this blue-green mutant was caused by
gene mutation. Cohen-Bazire & Stanier (72) investigated further the findings
of Goodwin & Osman (73) that a similar derangement of carotenoid synthe-
sis could be obtained in R. rubrum by growth in the presence of diphenyla-
mine, without a change in genotype. Again, such cells, depleted of their
coloured carotenoids, displayed the same symptomsof photosensitivity (kill-
ing and chlorophyll destruction) when exposed to light and oxygen. In cells
grown in the presence of diphenylamlne, coloured carotenoids could be re-
stored after removal of the inhibitor, whereupon photosensitization ce.ased.
Fuller & Anderson (74) subsequently demonstrated the capacity of iso-
lated, carotenoid-depleted chromatophores from diphenylamine-grown
Chromatium strain D to photophosphorylate under anaerobic conditions.
However, activity was completely lost by brief exposure to light and air si-
multaneously. Such photosensitivity was not manifested by normally pig-
mented chromatophores.
The correlation between carotenoid deficiency and aerobic photosensi-
tivity is supported by the observation of Kandler & Sch5tz (75) on carot--
enoid-less mutants of C. vulgaris, which are killed in light under aerobic con-
ditions. The protective effect of the coloured carotenoids is not ascribed to.
shielding effects due to their colour. The protection mechanismhas been dis-
Annual Reviews
cussed by Calvin (76) and by Stanier (39) in terms of reversible oxidation

the carotenoids during photosynthesis, and on structural grounds the carot-
enoids could play a part by orientating the chlorophyll molecules in the
photosynthetic unit such that excitation does not result in photo-oxidation
(39). In a recent study on the effect of carotenoid pigments on photo-oxidation
in purple bacteria, Feldman & LindstrCm (77) claimed that earotenoids fune-
tlon as a buffer for the photo-oxidation.
Stanler subsequently extended his hypothesis on the function of carot-
enoids as protectors against photo-oxidation also to certain chemotrophs
which are exposed to intense solar radiation under aerobic conditions in na-
ture. Porphyrin derivatives, flavins, etc., were anticipated as playing the role
of chlorophyll as photosensitizers. Nonpigmented cells of Corynebacterlum
poinsetliae obtained by mutation in ultraviolet light or cultivation in the
presence of diphenylamine, were employed by Kunisawa & Stanier (78).

Toluidine blue was added as a photosensitizer, and comparative studies on
the effect of dye-sensitized, carotenoid-containing, and carotenoidless cells
showedthat in the presence of air the latter were killed by exposure to visible
light, which had no effect on cells containing the normal complement of ca-
rotenoids.
Mathews& Sistrom (79) investigated the effect of very strong light on the
commonair contaminant, Sarcina lutea, and found that, in contrast to the
yellow wild type. a colourless mutant was killed when thus exposed in the
presence of air, even in the absence of an added photosensitizer.
Dundas & Larsen (80) studied the effect of sunlight on an orange-red
halophilic bacterium and its colourless mutant under aerobic conditions, and
found no measurable killing of either organism under the experi~nental condi-
tions. However, they demonstrated that exposure to tungsten light of an
intensity comparable to that of bright sunlight, inhibited strongly the
growth of the colourless mutant, whereas the growth of the coloured wild type
was unaffected. It was inferred that in the natural habitat of halophilic bac-
teria (salt lakes, tropical lagoons), carotenoid-containing forms are better
able to compete than are colourless forms, because of the inhibitory effect of
light on growth.
P~OTOSYNTHESIS
We have already discussed the role of carotenoid pigments as protectors
against photodynamic killing in photosynthetic organisms. There is also
evidence for the active participation of carotenoids as auxiliary absorbers
of radiant energy which, in turn, can be transferred to chlorophyll and
utilized in photosynthesis. The efficiency of this energy trapping evidently
varies with different carotenoids and organisms.
The Classical demonstration of this phenomenon was that of Engelmann
(81) who showed the capability of algal filaments to photosynthesize in the
spectral region of carotenoids, the ~oncomitant oxygen evolution being
indicated by the accumulation of motile, aerobic bacteria.
According to Dutton & Manning (82), the fucoxanthin in diatoms
Annual Reviews
i78 JENSE.N
particularly effective as an auxiliary light absorber; the carotenoids of
photosynthetic purple bacteria also function in this manner (83).
Since photosynthesis cannot take place in the absence of chlorophyll,
the role of chlorophyll must be an essential one. The contribution of carot-
enoids is of a more supplementary nature since photosynthesis can proceed in
their absence, as demonstrated for carotenoid-deficient bacteria (70, 74, 84).
Energy absorbed by carotenoids can be transferred to chlorophyll, as
revealed by the ability of light absorbed by carotenoids to excite chlorophyll
fluorescence. It was demonstrated by Duysens (85, 86) that the efficiency
of the transfer is close to 100 per cent for some green algae and diatoms,
and less than 50 per cent for photosynthetic purple bacteria, except for
R. spheroldes (90 per cent) (87). The energy transfer probably occurs
inductive resonance, the mechanism of which has been discussed by Good-
win (88).
Carotenoids may also play important roles in photosynthesis other than
those so far discussed. Oxygen-evolving phototrophs usually contain
epoxidic carotenoids (see Table I), and Blass, Anderson & Calvin (66)
advanced the hypothesis that the reversible removal of the epoxydic oxygen
may be part of the oxygen evolution ’sequence in photosynthesis. Epoxidic
carotenoids have so far not been found in photosynthetic bacteria, where
oxygen liberation does not occur during the photosynthetic act. Krlnsky,
Gordon & Stern (89) have pointed out that the epoxidic carotenoid, ne-
oxanthin, is virtually absent in dark-grown E. gracilis, and that the for-
mation of neoxanthin upon illumination of the same organism, previously
grown in the dark, paralleled the development of photosynthetic competence.
PttOTOTAXIS
Phototaxis is defined as light-orientated locomotion of motile organisms.
The phenomenon of phototaxis of photosynthetic microorganisms has been
thoroughly reviewed by Clayton (90).
The pioneering work in this field was again performed by Engelmann
(81), who illuminated cultures of photosynthetic purple bacteria with
microspectrum, and observed the regions in which the bacteria accumulated.
According to Duysens (SS, 86) and Thomas & Goedheer (91), action
spectra of phototaxls in photosynthetic purple bacteria resemble thoseof
photosynthesis with two active regions; one attributable to chlorophyll and
the other to carotenoids. A hypothetical scheme of the carotenoid action in
phototaxis and photosynthesis has been presented by Thomas & Goedheer
(91) (see Fig. 4). The green bacteria so far obtained in pure culture are
motile in the ordinary sense of the word, and their phototactic response, if
any, has not been studied.
Whereas the phototaxis of photosynthetic bacteria apparently can be
mediated also by chlorophyll, only blue and blue-green light cause photo-
tactic response in various algae (92), suggesting that here carotenoids func-
tion as mediators. Whether any particular carotenoids are active is not
yet established.
Annual Reviews

Heat
Heat ~-- CA_~OTENOIDS

--~ BACTERIOCIILOROPHYLL
890 --~ Fluorescence
Energy-yielding ~- PtIOTOSYNTttETICCOMPOUNDS
--~ Other pr~es~es
processes
Phototaxis
I~’IG.
4.Hypothetical
scheme
oFthecarotenoid
action
inphototaxls
and
photosynthcsls
inpurple
bacteria
(91).
OTHERFUNCTIONS
Other functions of the carotenoids in microorganisms have been sug-
gested from time to time. Their possible role in reproduction or in photo-

tropic bending of the sporangia of various moulds has been discussed by
Goodwin (88) rather recently. Such functions are not yet well established
and will not be dealt with here.
CONCLUDING REMARKS
The broad outline of the pathway of carotenoid biosynthesis in micro-
organisms has been defined during recent years. Whereas demonstration of
someof the initial steps of carotenogenesis has been carried out in cell-free
extracts, further characterization of the individual enzymic steps is required,
partieuarly for the final reactions leading to the biosynthetic end products.
Information about the cycllzation mechanismis still lacking.
The specific functions of the carotenoid pigments have been discussed
in the light of the available evidence.
Annual Reviews
180 JENSEN
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Biosynthesis and Function of Carotenoid Pigments in Microorganisms

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Annual Reviews

BIOSYNTHESIS AND FUNCTION OF CAROTENOID

FROM Low-MoLECULAR WEIGHT

ULTIMATE ~TEPS OF CAROTENOID ]~IOSYNTHE~IS IN ]~ACTERIA ............. 171

~ _7._ l_ _ l _ 14’...,12’..,10’_,8" _,’~~,

giving rise to substituted cyclohexylidene, phenyl, cyclopentane, and fura-

yellow-red colours of most carotenoids.

CAROTENOID PIGMENTS IN MICROORGANISMS 165

MICROORGANISM TYFE OF CAROTENOID

Bacteria Photosynthetic + ÷ - -t-~

OH-Spheroidenone (II) is an example of an aliphafic, methoxylated keto

THE BIOSYNTHESISOF THEPRIMARYC40 UNIT FROMLow-MOLECULAR

This simple hypothesis has obtained experimental support. A clue to the

CAROTENOID PIGMENTS IN MICROORGANISMS 167

preparations. Information regarding this particular step is lacking for micro-

CAROTENOID PIGMENTS IN MICROORGANISMS 169

CO2 ~L~/~-Methyl- Crotonyl- CoA ~ Isovaleryl-CoA ~- ~-- Leucine

Methyl- glutaconyl- CoA

/~-Hydroxy-~- methyl 2NADPH

THE SEQUENTIAL DEHYDROGENATION OF THE PRIMARYC40 PRECURSOR

The accumulation of relatively saturated carotenoids like phytoene,

The role of phytoene in these transformations could not be definitely demon-

CAROTENOID PIGMENTS IN MICROORGANISMS 171

tions have not been isolated. A theory of a-hydroxylation followed by dehy-

Photosynthetic bacteria.--The distribution, chemical structure, and bio-

FI6. 2. Ultimate steps of carotenoid biosynthesis in Athlorhodaceae. Numbers

ously existing double bonds; (b) dehydrogenation involving the introduction

CAROTENOID PIGMENTS IN MICROORGANISMS 173

of a suitable electron acceptor, whereas the synthesis of hydroxylated carot-

synthesis in nonphotosynthetic organisms. The’pathway suggested for carot-

ULTIMATE STEPS OF CAROTENOID BIOSYNTHESIS IN FUNGI

The biochemistry of fungal carotenoids has been treated in detail by

enoids known, although one or more of the members of the Porter-Lincoln

Microscopic representatives are found within most of the algal classes

CAROTENOID PIGMENTS IN MICROORGANISMS 175

carotenoids of Chlorella pyrenoidosa and Scenedesmus obliquus during photo-

EVOLUTION AND CAROTENOID BIOSYNTHESIS

Goodwin (69) has made an interesting evaluation of the possible evolu-

Monocycfic Sec. OH,epoxy groupings

FIG. 3. Evolutionarytrends in the structural features of carotenolds in

which coloured carotenoids were replaced by the colourless phytoene, grew

CAROTENOID PIGMENTS IN MICROORGANISMS 177

cussed by Calvin (76) and by Stanier (39) in terms of reversible oxidation

presence of diphenylamine, were employed by Kunisawa & Stanier (78).

CAROTENOID PIGMENTS IN MICROORGANISMS 179

Heat ~-- CA_~OTENOIDS

gested from time to time. Their possible role in reproduction or in photo-

6. Steele, W. J., and Gurin, S., J. Biol. 24, 492-522 (1955)

8. Suzue, G., J. Biochem. (Japan), 51, 477-98 (1958)

CAROTENOID PIGMENTS IN MICROORGANISMS 181

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