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NEWLY DISCOVERED HORMONES
Polyamines (Putrescine, Spermidine, Sperrmine, Cadaverine ) Brassinosteroids Salicylic acid (cut flowers and leafy vegetables) Jasmonates (inhibitors) Systemin Alpha Tocopherols (antioxidants) Fusicoccin (from Fusariutn amygdali) Triacontanol (growth promoter extracted from alfalfa) Turgorins Batasins (causes dormancy in bulbils. Extracted from yam.)
Polyamines
POLYAMINES
Definition Those hormones or compounds which possess
two or more than two amino groups.
These are the polyvalent cation compounds that contain two or more amino groups.
found ubiquitously in all organisms (plants and animals as well as bacteria)
Because of their positive charge they can bind to many macromolecules including DNA, RNA and protein (Kusano et al., 2008)
POLYAMINES The diamine putrescine, the triamine spermidine
and the tetramine spermine are ubiquitous in plant cells (Smith et al, 1979; Bagni and Pistocchi, 1992).
They occur as free cations and as conjugates with phenolic acids and macromolecules (Galston and Sawnhey, 1990).
Their levels increase greatly in response to environmental stresses, most notably under conditions of potassium deficiency, water deficits, salinity stress, anaerobiosis and acid stress (Flores et al, 1989).
Because polyamines are synthesized by amino acid decarboxylation reactions which consume H+, polyamine accumulation may function as part of a homeostatic mechanism to keep intracellular pH at a constant value (Flores et al, 1985).
Polyamines may also play a role in the regulation of DNA replication and cell division, and are implicated in the control of senescence and morphogenesis (Evans and Malmberg, 1989; Galston and Sawnhey, 1990).
It has been proposed that polyamines could be part of an intrinsic signaling network and membrane stabilization (Kusano et al., 2008).
Polyamines also serve as precursors of several classes of alkaloids (Smith et al, 1979; Flores et al, 1989; Hashimoto and Yamada, 1994) which may play important roles in plant defense against herbivores.
Plant-based foods containing polyamines have considerable impact on human health (Lima et al., 2011). Organic foods contain markedly more polyamines than crops grown using conventional procedures
POLYAMINES
Types of polyamines Among the most abundant and
physiologically active polyamines are
Putrescine Spermidine Spermine Cadaverine
COMMON AND UNCOMMON DIAMINES AND POLYAMINES FOUND IN PLANTS
PUTRESCINE
Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine) formed by and having the smell of rotting flesh.
It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms. Putrescine and cadaverine were first described by the Berlin physician Ludwig Brieger in 1885.
Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.
Putrescine
Chemical name 1,4-Diaminobutane
Other names TetramethylenediamineButane-1,4-diamine
Chemical formula C4H12N2
Molecular mass 88.15 g/mol
Density 0.877 g/cm³
Melting point 27 °C
Boiling point 158-160 °C
PUTRESCINE SYNTHESIS
ARGININE DECARBOXYLASE (ADC)
Arginine decarboxylase (ADC) (a chloroplast localized enzyme (Borrell et al, 1995) is induced by a variety of stresses (most notably potassium deficiency; Watson and Malmberg, 1996) and is thought to be the enzyme primarily responsible for environmental stress-induced putrescine accumulation (Galston and Sawnhey, 1990):
PHYSIOLOGICAL ROLES OF PUTRESCINE Loss of regeneration capacity of rice in long term culture is
associated with massive accumulation of putrescine due to an increase in arginine decarboxylase activity. Difluoromethylarginine, an inhibitor or arginine decarboxylase, restored regeneration capacity to long-term cultures (Bajaj and Rajam, 1996). Spermidine treatment also caused a reduction in putrescine content and arginine decarboxylase activity and restoration of plant regeneration ability (Bajaj and Rajam, 1996). In contrast, putrescine promotes and difluoromethylarginine inhibits somatic embryogenesis in eggplant (Yadav and Rajam, 1998).
The alternative, more direct pathway of synthesis of putresine via ornithine decarboxylation catalyzed by cytosolic ornithine decarboxylase (ODC) [EC 4.1.1.17] is proposed to be of little importance in stress-induced putrescine accumulation, but may be critical in regulation of developmental processes (Galston and Sawhney, 1990; Walden et al, 1997). Increased putrescine biosynthesis catalyzed by ornithine decarboxylase promotes somatic embryogenesis in carrots (Bastola and Minocha, 1995).
Levels of putrescine are higher in a drought tolerant wheat cultivar in comparison to a drought susceptible wheat cultivar. These wheat cultivars also differ for oxidant stress resistance as assayed by resistance to paraquat (Ye et al, 1997). Constitutively elevated levels of Arg decarboxylase and Orn decarboxylase are correlated with paraquat resistance in Conzya bonariensis (Ye et al, 1997). Arg decarboxylase and Orn decarboxylase are differentially regulated in Conzya bonariensis, with only the former detectable in 2 week-old plants. Orn decarboxylase becomes more abundant than Arg decarboxylase in 10 week-old plants (Ye et al, 1997). Exogenously supplied putrescine prevents oxidative damage in paraquat-resistant C. bonariensis (Ye et al, 1997). In part this may be due to inhibition of paraquat uptake by putrescine (Hart et al, 1993). Ye et al (1997) suggest that putrescine and other polyamines could function directly or indirectly as free radical scavengers.
CADAVERINE
Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine Cadaverine is the decarboxylation product of the amino acid lysine.
However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive smell of urine and semen.
Cadaverine
Chemical name 1,5-diaminopentane
Other names pentamethylenediaminepentane-1,5-diamine
Chemical formula C5H14N2
Molecular mass 102.18 g/mol
Density 0.870 g/cm³
Melting point 9 °C
Boiling point 178-180 °C
BIOSYNTHESIS OF PUTRESCINE & CADAVERINE
The diamine cadaverine is derived from the amino acid lysine by decarboxylation. Its synthesis is catalyzed by lysine decarboxylase [EC 4.1.1.18]. Cadaverine may play an important role in root development (Gamarnik and Frydman, 1991).
SPERMINE
Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses.
Crystals of spermine phosphate were first described in 1678, in human semen, by Anton van Leeuwenhoek. The name spermin [sic] was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede. et al).
Spermine
Systematic name N,N'-bis(3-aminopropyl)butane-1,4-diamine
Other names gerontine, musculamine and neuridine
Chemical formula
C10H26N4
Molecular mass 202.34 g/mol
Density x.xxx g/cm3
Melting point 29°C
Boiling point xx.x °C
SPERMIDINE
Spermidine is a polyamine involved in cellular metabolism that can be used to stimulate the enzyme, T7 RNA polymerase, a type of RNA polymerase.
Inhibits neuronal nitric oxide synthase (nNOS).
Binds and precipitates DNA. May be used for purification of DNA binding
proteins. Stimulates T4 polynucleotide kinase (This
enzyme transfers gamma phosphate from ATP to DNA or RNA) activity.
Spermidine
Systematic name N-(3-aminopropyl)butane-1,4-diamineN-(3-aminopropyl)-1,4-diaminobutane
Chemical formula C7H19N3
Molecular mass 145.25 g/mol
Properties
Density 0.925 g/mL at 25 °C
Melting point xx.x °C
Boiling point xx.x °C
Refractive index n20/D 1.479(lit.)
Foreign activity DNase, RNase, and protease, none detected
Storage temp. 2-8°C
BIOSYNTHESIS OF SPERMIDINE & SPERMINE
Spermidine, and spermine are synthesized from L-arginine and L-ornithine. Synthesis of spermidine and spermine requires an aminopropyl group derived from SAM, and there may be competition between the ethylene and polyamine biosynthesis pathways when concentrations of SAM are limited. The primary (terminal) amines of polyamines are oxidized by diamine oxidases, the secondary amines by polyamine oxidases.
SPERMIDINE AND SPERMINE SYNTHESIS
The condensation of decarboxylated SAM and putrescine is catalyzed by spermidine synthase (putrescine aminopropyltransferase) [EC 2.5.1.16]. Further condensation of spermidine with decarboxylated SAM, catalyzed by spermine synthase [EC 2.5.1.22], produces the tetramine, spermine (Flores et al, 1989).
METABOLISM OF POLYAMINES
METABOLISM OF POLYAMINES
In addition to serving as a precursor of spermidine and spermine, putrescine has three other metabolic fates; conjugation with hydroxycinnamic acids, metabolism to gamma-aminobutyrate (GABA), and utilization in alkaloid biosynthesis.
(see also discussion of GABA metabolism under Aminotransferase reactions)
GABA can be derived from putrescine (via gamma-aminobutyraldehyde) through the reactions catalyzed by diamine oxidase [EC 1.4.3.6] and gamma-aminobutyraldehyde dehydrogenase (Flores et al, 1989). As noted in the discussion of Quaternary ammonium and tertiary sulfonium compounds, the latter enzyme may be the same as BADH involved in glycinebetaine synthesis (Trossat et al, 1997).
Putrescine serves as precursor of the nicotine and tropane alkaloids (Smith et al, 1979; Flores et al, 1989; Hashimoto and Yamada, 1994), which may play important roles in plant defense against herbivores.
MODE OF ACTION OF POLYAMINES Bonding
In polyamine, amino group contains +ve charge on NH+
3 Which helps to bind with –vely charged phosphate group of DNA and RNA. As a result of this combination, they often increase transcription of DNA and translation of RNA. They enhance or stimulate protein synthesis.
Cell cycle regulation Polyamines cause phosphorylation of proteins,
they are involved in the regulation of cell cycle by controlling the phosphorylation of proteins that take part in cell cycle.
HYDROXYCINNAMIC ACID CONJUGATES OF POLYAMINES
Hydroxycinnamic amide (HCA) conjugates of polyamines accumulate markedly in the floral apex during flower development, and are implicated in the development of competence to flower; certain mutants of tobacco which are deficient in HCAs are unable to flower, and male sterile mutants of maize lack HCA accumulation in anthers (Flores et al, 1989). A novel polyamine conjugate, N4-hexanoylspermidine, has been identified in senescing pea ovaries and petals (Perez-Amador et al, 1996).
PHYSIOLOGICAL FUNCTIONS OF POLYAMINES Membrane Stabilization – Stabilize Membrane Structure and
Function e.g. Thylakoid DNA Stabilization – Interaction with Nucleic acid Spm-DNA
complexes stabilize DNAs against thermal denaturation. Spd also has same effects.
Enzyme Activity – Stimulate enzyme activity e.g. Kinases in animals and and F 1,6 bisphosphate in plant
Cell Division – Enhance Cell Division but polyamines are not involved in Cell Elongation
Buffering of Cellular pH – The reversible protonation of multiple amino groups of PAs, serves as buffer in the cells
Role in Flowering – Floral axis synthesizes large quantities of conjugate PAs de novo
Development of Ovary and Ovule – The development of the ovary and ovules and ovules during maturation seems highly sensitive to PAs.
Embryogenesis – Increases embryogenesis Senescence – At the time of senescence, there is low amount of
PAs. Abiotic Stress Tolerance – Play significant role in abiotic stresses
tolerance like chilling, drought and salinity. Auxin Correlation -Since auxin application increases PAs in plants,
it is proposed that auxins act through PAs to promote growth Tuber formation, Root initiation Fruit ripening