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Polyamines and Plant Alkaloids

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Polyamines and Plant Alkaloids Indian Journal of Experimental Biology Vol. 38, November 2000, pp. 1086-1091 Review Article Polyamines and plant alkaloids Bharati Ghosh Department of Botany, Bose Institute, Calcutta 700 009, India Naturally occurring alkaloids are nitrogenous compounds th at constitute th e pharmacogenically acti ve basic principles of flowering plants. Alkaloids are classified into several biogenically related groups . Tobacco alkaloids are metabolised from polyamines and diamines putrescine and cadaverine . N-methyl transferase is the tirst enzyme in alk aloid biosynthetic pathway which drives the flow of nitrogen away from polyamine biosynthesis to alkaloid biosynthesis. Arginine decarboxylase has been suggested to be primarily responsible for providing putrescine for nicotine synthesis. Tryptophan is the precursor of indole alkaloids . However, th e biosynthetic pathway of tropane and isoquinoline alkaloids are not clear. Genes for several key biosynthetic enzymes like arginine decarboxylase, ornithine decarboxylase, putrescine N-methyl transferase and spermidine synth ase, hyoscyamine 6 p hydroxylase,tryptophan decarboxylase etc have been cloned from different plant species. These genes arc regulated by plant hormones, li ght, different kinds of stress an e li cito rs like jasmonates and their strong expression is primarily in the cultured roots. In view of thi s, th e axenic hairy root cultures induced by Agrobacterium rhizoge11 es have been utilised to synthesise secondary metabolites. The current development in the knowledge of alk aloid biosynthesis, particularly molecular analysis, has been discussed in this review that may help to open up new avenues of investigation for th e researchers. Plants produce a wide range of natural products instrumentation, precursors labeled with stab le derived from secondary metabolic pathways which isotopes, analysis of products by nuclear magnetic are useful for pharmaceutical,agrochemical, fragrance resonance spectroscopy and the use of plant cell and food industries .These naturally occurring culture as experimental system has helped in secondary metabolites are alkaloids which contain understanding the alkaloid biosynthetic pathway in 2 secondary, tertiary or quaternary nitroge n atoms in different plants . Alkaloids are classified into several their molecules. These nitrogenous compounds biogen ically related groups but the enzymes and constitute the pharmacogenically active 'basic genes have been characterised on ly in following principles' of flowering plants, and have traditionall y groups 26 been of interest due to their various physiological activities in animals and human . Alkaloids are • Nicotine and Tropane alkaloids important for defense of the plant against pathogenic • Indole alkaloids organisms and herbivores, or protoxins for in sects • Isoquinoline alkaloids which further modify the alkaloids and incorporate 1 them into their own defense/secretions • Alkaloids This review describes the bi osynthesis and have been isolated from diverse organi sms . However, molecular aspects of tobacco alkal oids in detail and little information is available regarding the synthesis the rest of the groups in brief. of complex structure of alkaloids which contain multiple asymmetric centers. Nevertheless the Polyamines as precursors of tobacco alkaloids pharmacological effects of these compounds are well The ubiquitous polycationic polyamines, a class of known. Nowadays the sophi sti cated analytical aliphatic amines, are found in almost every cell compartment including the cell wall. They are deeply Abbreviations used: ODC, Ornithine decarboxylase; ADC, Arginine decarboxylase; SPDS, Spermidine synthase; SPMS, involved in a series of cellular events such as Spermine synthase; SAMDC, S-adenosylmcthi onine replicat ion , cell division ,protein synthesis' ;md plant 4 5 decarboxylase; PMT, Putrescine N-methyl transferase; DAO, growth and developmental processes · but the exact di amine oxidase: H6H, Hyoscyamine 6P hydroxylase; PAs, 5 function of polyamines is not known . In plants, Polyamines; PUT, Putrescine; Spd, Spermidine; Spm, Spermine; SAM, S-adenosyl methionine; dSAM , decarboxylated SAM; diamine putresci ne (Put) can be sy nthesized by two MeJA, Methyl esters ofjasmonates independent pathways which involve ornithine GHOSH: POLYAMINES & PLANT ALKALOIDS 1087 decarboxylase (ODC) and argmme decarboxylase SAM to Put. Substrate specifi city studies and (ADC) and these two pathways regulate th e growth, inhibition kineti cs by amines have predicted th at development and stress responses of plants.4 .5 SPDS 11 and partially purified PMT 12 may have Spermidine sy nthase (SPDS) transfers the similar active sites for enzyme catalysis. Previously aminopropyl moiety of decarboxylated S- conflicting hypotheses have been proposed for the adenosylmethionine (dSAM) to Put producing source of Put in nicotine synthes is in tobacco. It was Spermidine(S pd). Spermine (Spm) is similarly beli eved th at the ODC pathway is a major source of synth esized by another enzyme Spermine synthase Put as accumulated ni cotine showed a good (SPMS). dSAM is formed from SAM by SAM correlati on with the increase in ODC activity in roots 13 decarbo xy lase (SAMDC). of decapitated tobacco seedlings . In later A wide va ri ety of secondary metabolites of experiments ADC pathway has been suggested to be biological interest can be metabolized from Put primarily responsi ble for providing Put for ni cotine through largely unelucidated pathways. The synthes is, as nicotine production in tobacco callus is pyrrolidine rings of tobacco alkaloids (ni cotine, effectively inhibited by DFMA, a specific inhibitor of nornicot ine), tropane alkaloids (hyoscyamine, ADC, and incorporat ion of 14C into ni cotine was more hyosc ine, metelod ine), pyrrolizidine (retronecine) are efficient from the uniformly labeled Arg than th at 6 14 Put derivatives . Cadaverine and Spd are precursors from the uniformly labeled Orn • of quinolizidine whil e lunarine alkaloids are derived The bi osynthetic path way of tropane alkaloids is from Pue. not yet clear. Recently activities of two enzymes of Nicotine, the biologically active component of tropane alkaloid biosynthesis, PMT and hyoscyamine tobacco leaves, is found in the genu s Nicotiana and 6~ hydroxy lase (H6H), 2-0xoglutarate-dependent other genu s of Solanaceae th ough it occurs in many enzyme, (EC 1.14. I I .I I), have been shown to be hi gh 7 other pl ants including lycopods and horsetail s . It is in cultured roots but very low in cultured cell s and the predominant alkaloid in mo st commercial cultured shoots. H6H catal yse the first oxidati ve culti vars of tobacco, hi ghl y toxic and se rves as a very reacti on in the bi osyntheti c pathway leading from effective in secticide and fumigant. The tropane hyoscyamin e to scopol amine and requires alkaloid 15 alkaloids th at include the medica ll y important substrate 2-oxoglutarate, ferrous ion, ascorbate etc . • anti cholinergic compounds, hyoscyamine and H6H not onl y hyd roxylates various hyoscyamine scopolamine, have been used traditionall y for their derivatives but also epoxidi zes 6,7- medicinal, hallucinogeni c and poisonous properties. dehydrohyoscyami ne, a sy nth etic alk aloid to 16 In addition to the Solanaceae family , tropane scopolamine • H6H has been purified to alkaloid s are also found in the Convo lvulaceae, homogenei ty from cu ltured roots of Hyoscyamus 8 17 Cruciferae and Rhizophoraceae . Both these niger L . Four monoclonal antibodies were rai sed alkaloid s are sy nthesized in tobacco roots from Arg against purified H6H and Western blot analysis and/or Orn by th e ac ti on of ADC and ODC whi ch showed that H6H is abundant in plant roots, but involves the symmetric diamine Puts th at is converted absent in leaf, stem, calyx, cultured cell s and cultured to N-methyl Put with the help of Put N-methyl roots. Immunohistoc hemi cal studies using transferase (PMT, EC 2. 1.1 .53). This is the first monoclonal antibody and immunogo ld -silver committed step in alkaloid biosynth esis whi ch drives enhancement studi es detected H6H onl y in the the flov,: of ni trogen away from PA biosynthesis to pericycle cell s of the you ng root in several 18 1 alkaloid biosynthesis. N-methyl Put can also be scopolami ne-produci ng plants . Hartmann produced through di rect meth ylation of Put or demonstrated a close relati onship between the decarboxylation of !-methyl Orn . N- met hyl Put is biosynthesis of PAs and senceionine N-oxide, the then oxidatively deaminated by diamine ox idase major pyrrolizidine alk aloids produced in root (DAO, EC 1.4.3.6) and cyc li sed spontaneously to th e cu ltures of Solanum vulgaris. 9 10 1-met hyi-A-pyrro linum via 4-met hylaminob utano1 · . It is then condensed with ni cotinic ac id or its Molecular cloning of polyamine and alkaloid 10 derivati ves by an unknown enzyme to form ni cotine . biosynthetic genes SPDS transfers the aminopropyl moiety of dSAM to The eDNA clone representing ODC from Datura 8 Put whereas PMT transfers the methy l moiety of has been obtained recentl / . ADC gene ha s bee n 1088 INDIAN 1 EXP BIOL, NOVEMBER 2000 19 20 2 1 b .d . ?? c I oned f rom oat , tomato , pea , Ara t opsl.!;-- and which was expressed as a galactosidase fusion protein 23 31 soyabean . The cloning of eDNA encoding the in E. coli • enzyme nicotiana PMTs is generated by subtrac ti on 24 hybridi zation , the deduced aminoacid sequence of Regulation of alkaloid biosynthetic gene expression PMT is hi ghly homol ogous to the sequence of SPDS Like other pl ant genes, expression of the genes from human (73 % identical), mouse (70% identi cal) encoding biosyntheti c enzymes fo r alkaloids are 5 and E.coli (58 % identicali . Nicotiana PMT is more regulated spatially and temporally by plant hormones, homologous to the peptide fragments (73% identity li ght and stress.2 Ni cotine is synthesised in response and 88% homology in 66 amin o acid res idu es) to wounding. PAs are not only essenti al for cell encoded by a parti al eDNA sequence of ri ce SPDS divi sion ,but also play an import:m t role in the 5 (GenBank accession No.
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