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Carotenoids Biosynthesis – a Review Reacções Envolvidas Na Biossíntese Dos Carotenóides a Partir Da Carotenoids Pigments Are Synthesized in the Plastids of Plants

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Carotenoids Biosynthesis – a Review Reacções Envolvidas Na Biossíntese Dos Carotenóides a Partir Da Carotenoids Pigments Are Synthesized in the Plastids of Plants REVISTA LUSÓFONA Estudos e Ensaios DE HUMANIDADES E TECNOLOGIAS Abstract Plants synthesized an enormous variety of metabolites that can be classified into two groups based on their functions: primary metabolites, which participate in nutrition and essen- tial metabolic processes within the plant, and secondary metabolites (also referred to as natural products), which influ- ence ecological interactions between plants and their environ- ment. The carotenoids pigments are secondary metabolites of isoprenoid origin. Despite their diversity of functions and structures, all isoprenoids derive from the common five-car- bon (C 5) building units isopentenyl diphosphate (IPP) and its isomer dimethylallyl diphosphate (DMAPP). More complex isoprenoids are usually formed by «head-to-tail» or «head-to- head» addition of isoprene units. The most prevalent tetrater- penes (C 40 ) are carotenoids, which are pigments in many flowers and fruits. In this paper we discuss some aspects of Carotenoids carotenoid biosynthesis. The pathway involves a series of desaturations, cyclizations, hydroxylations, and epoxidations, Biosynthesis commencing with the formation of phytoene. The pathway 22 begins with the synthesis of IPP from the mevalonic acid (MVA) pathway and/or methylerythritol 4-phosphate (MEP) – a review pathway. Helena Morais Universidade Lusófona de Humanidades e Tecnologias [email protected] Resumo Ana Abram As plantas sintetizam uma enorme variedade de Pontificia Universidade Católica del Perú metabolitos, que podem ser classificados em dois grupos, de acordo com as suas funções: metabolitos primários, que Fernando Ferreira participam na nutrição e processos metabólicos essenciais no Universidad de la República del Uruguay interior da própria planta, e metabolitos secundários (também referidos como produtos naturais), os quais influenciam as interacções ecológicas entre as plantas e o ambiente. Os carotenóides são metabolitos secundários derivados do isopreno. O isopentenil-pirofosfato (IPP) é a unidade básica para a biossíntese dos carotenóides. O esqueleto carbonado dos carotenóides é sintetizado por adição sucessiva das unidades em C 5 que vão formar geranil- geranilpirofosfato, intermediário em C 20 que por condensação origina a estrutura em C 40 . Recentemente assumia-se que todos os isoprenóides se sintetizavam a partir do acetil-CoA via ácido mevalónico. Estudos recentes mostraram que o percurso metabólico começa com a síntese do IPP via ácido mevalónico (MVA) e/ou via metileritritol 4-fosfato (MEP). Neste trabalho discutem-se os avanços no conhecimento destas diferentes vias metabólicas assim como as enzimas e Carotenoids Biosynthesis – a review reacções envolvidas na biossíntese dos carotenóides a partir da carotenoids pigments are synthesized in the plastids of plants. unidade fundamental (IPP). In chloroplasts they accumulate primarily in the photosynthet- ic membranes in association with the light-harvesting and reaction center complexes. In the chromoplasts of ripening 1 fruits and flower petals and in the chloroplasts or senescing Introduction leaves the carotenoids may be bound in membranes or in oil bodies or other structures within the stroma (Cunningham & Plants synthesize an enormous variety of metabolites that Gantt, 1998). can be classified into two groups based on their function: pri- The lipid-soluble carotenoid pigments are but an exam- mary metabolites, which participate in nutrition and essential ple of the plethora of chemical compounds that are produced metabolic processes within the plant, and secondary metabo- by what are collectively known as the pathways of isoprenoids lites (natural products), which influence ecological interac- biosynthesis. The isoprenoids comprise the largest family of tions between plants and their environment (Croteau et al ., natural products: over 23 000 individual compounds were 2000). Isoprenoids (also called terpenoids) play diverse func- identified to data (Tarshis et al ., 1996). tional roles in plants as hormones (gibberellins, abscisic acid), photosynthetic pigments (phytol, carotenoids), electron carri- ers (ubiquinone, plastoquinone), mediators of polysaccharide 2 assembly (polyprenyl phosphates), and structural compo- Formation of Isopentenyl Diphosphate nents of membranes (phytosterols). In addition to these uni- versal physiological, metabolic, and structural, the highest Despite their structural of functions and diversity, all iso- variety of isoprenoids (commonly in the C 10 , C 15 and C 20 fami- prenoids derive from the common five-carbon (C 5) building lies) is secondary metabolites that function in protecting unit isopentenyl diphosphate (IPP) and its isomer dimethylal- 23 plants against herbivores and pathogens, in attracting pollina- lyl diphosphate (DMAPP), also called isoprene units. The IPP tors and seed-dispersing animals, and allelochemicals that formation, first investigated in yeast and in mammalian liver influence competition among plant species (Croteau et al ., tissue, had been described as the acetate/mevalonate pathway 2000). Many compounds with important commercial value as which was later accepted as ubiquitous in all living organisms flavors, pigments, polymers, fibers glues, waxes, drugs, or (Spurgeon & Porter, 1981). Until recently, it was generally agrochemicals are secondary metabolites of isoprenoid origin assumed that all isoprenoids were synthesized from acetil-CoA (Rodríguez-Concepción and Boronat, 2002) via the classical mevalonate pathway to the central precursor Carotenoids are naturally occurring pigments synthe- isopentenyl diphosphate. A few years ago, a totally different sized as hydrocarbons (carotenes) and their oxygenated deriv- route, in which mevalonate, is not a precursor and where IPP atives (xanthophylls) by plants and microorganisms. They is formed from glyceraldehydes 3-phosphate (GAP) and pyru- consist of eight isoprenoid units joined in such a manner that vate was found in bacteria and green algae (Rohmer et al ., the arrangement of isoprenoid units is reversed at the center 1993; Broers, 1994; Rohmer et al ., 1996; Schwender et al ., of the molecule so that the two central methyl groups are in a 1996), and in plants (Schwarz, 1994). This pathway was orig- 1,6-positional relationship and the remaining nonterminal inally named non-mevalonate pathway or Rohmer pathway. methyl groups are in a 1,5 – positional relationship. All After the identification of the first steps of the pathway, its carotenoids may be formally derived from the acyclic C 40 H56 name was changed to indicate the substrates (pyruvate/ glyc- structure, having a long central chain of conjugated double eraldehyde 3-phosphate [G3P] pathway) or the first interme- bonds, by ( I) hydrogenation, ( II ) dehydrogenation, ( III ) cycliza- diate, deoxyxylulose (DX) 5-phosphate (DXP pathway). tion, or ( IV ) oxidation or any combination of these processes. According Rodríguez-Concepción and Boronat (2002), it is Their major function is in protection against oxidative damage becoming more accepted to name the pathway after what is by quenching photosensitizers, interacting with singlet oxygen currently considered its first committed precursor, methylery- (1) and scavenging peroxy radicals (2), thus preventing the thritol 4-phosphate (MEP), following the same rule used to accumulation of harmful oxygen species. name the MVA pathway. Carotenoids, the most diverse and widespread group of Pyruvate and glyceraldehyde are mainly obtained by gly- pigments found in nature, are synthesized de novo by all pho- colysis. In the Embden-Meyerhof-Parnas pathway, glucose is tosynthetic and many non-photosynthetic organisms. The converted into fructose 1,6-diphosphate that is cleaved into REVISTA LUSÓFONA Estudos e Ensaios DE HUMANIDADES E TECNOLOGIAS dihydroxyacetone phosphate and glyceraldehyde 3-phosphate Scenesdemus obliquus (Schwender et al ., 1996). (Figure 1). Labeling experiments, with [ 14 C]acetate and According to this pathway, also found for the formation of 14 [ C]mevalonate, had shown that in several non-green tissues chloroplast isoprenoids, the addition of a C 2 precursor of higher plants (Braithwaite & Goodwin, 1960) and in the alga (derived from pyruvate, most likely by formation of hydro- Euglena gracilis (Steele & Gurin, 1960), the carotenoids were xyethyl thiamine (TPP=thiamine diphosphate) to a C 3 labeled in a pattern that seemed similar to the general iso- precursor (glyceraldehydes 3-phosphate GAP) yields a first prenoid labeling pattern found, for example, in squalene C5 intermediate, most likely D-1-deoxyxylulose 5-phos- derivatives in other organisms. This was interpreted on the phate [(Broers, 1994, in Lichtenthaler et al . (1997)]. The basis of the classical acetate/mevalonate pathway. Thus there carbon skeleton of this intermediate or another related C 5- was no reason to believe that the biosynthesis of isoprenoids in derivative undergoes a rearrangement reaction that pro- higher plants or algae occurred other than via the vides the branched carbon skeleton of IPP. acetate/mevalonate pathway. However, Schwender et al . (1996) found that the antibi- According to 13 C-labeling experiments Lichtenthaler et otic mevinolin, a highly specific inhibitor of mevalonate and al . (1997) have concluded that the cytoplasmic sterols are sterol biosynthesis, efficiently blocked sterol biosynthesis in formed in all three higher plants via the acetate/mevalonate higher plants but did not affect the formation of chlorophylls pathway, whereas the plastidic isoprenoids
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