Putrescine: Difference between revisions

{{Short description|Foul-smelling organic chemical compound}}

{{Chembox

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|Watchedfields = changed

|verifiedrevid = 408973251

|ImageFile1=.

|ImageFile1_Ref = {{chemboximage|correct|??}}

|ImageSize1 = 160

|ImageName1 = Skeletal formula of putrescine

|ImageCaption1 = [[Skeletal formula]]

|ImageFile2 = Putrescine-3D-balls.png

| = {{|correct|}}

|ImageSize2 = 160

|ImageName2 = Ball and stick model of putrescine

|ImageCaption2 = [[Ball-and-stick model]]<ref>{{ Cite journal | url = https://dx.doi.org/10.5517/cc4g850 | title = CSD Entry: QATWAJ : 1,4-Butanediamine | website = [[Cambridge Structural Database]]: Access Structures | year = 2001 | publisher = [[Cambridge Crystallographic Data Centre]] | doi = 10.5517/cc4g850 |access-date = 2021-11-07 | last1 = Thalladi | first1 = V.R. | last2 = Boese | first2 = R. | last3 = Weiss | first3 = H.-C. }}</ref><ref>{{ cite journal | title = The Melting Point Alternation in ''α'',''ω''-Alkanediols and ''α'',''ω''-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions | first1 = V. R. | last1 = Thalladi | first2 = R. | last2 = Boese | first3 = H.-C. | last3 = Weiss | journal = [[Angewandte Chemie International Edition|Angew. Chem. Int. Ed.]] | year = 2000 | volume = 39 | issue = 5 | pages = 918–922 | doi = 10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E | pmid = 10760893 }}</ref>

| = -14-

|OtherNames = 1,4-Diaminobutane, 1,4-Butanediamine

|Section1={{Chembox Identifiers

|CASNo = 110-60-1

| = {{|correct|}}

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = V10TVZ52E4

|PubChem = 1045

|ChemSpiderID = 13837702

| = {{|correct|}}

|EINECS = 203-782-3

|UNNumber = 2928

|DrugBank = DB01917

|DrugBank_Ref = {{drugbankcite|changed|drugbank}}

|KEGG = C00134 <!--C02896-->

|KEGG_Ref = {{keggcite|correct|kegg}}

|MeSHName = Putrescine

|ChEBI = 17148

|ChEBI_Ref = {{ebicite|changed|EBI}}

|ChEMBL = 46257

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|IUPHAR_ligand = 2388

|RTECS = EJ6800000

|Beilstein = 605282

|Gmelin = 1715

|3DMet = B00037

|SMILES = NCCCCN

|StdInChI = 1S/C4H12N2/c5-3-1-2-4-6/h1-6H2

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = KIDHWZJUCRJVML-UHFFFAOYSA-N

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|Section2={{Chembox Properties

|C=4 | H=12 | N=2

|Appearance = Colourless crystals

|Odor = fishy-ammoniacal, pungent

|Density = 0.877 g/mL

|MeltingPtC = 27.5

|BoilingPtK = 431.7

|Solubility = Miscible

|LogP = −0.466

|VaporPressure = 2.33 mm Hg at 25 deg C (est)

|HenryConstant = 3.54x10⁻¹⁰ atm-cu m/mol at 25 deg C (est)

|RefractIndex = 1.457

}}

|Section3={{Chembox Hazards

|GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}}

|GHSSignalWord = '''DANGER'''

|HPhrases = {{H-phrases|228|302|312|314|331}}

|PPhrases = {{P-phrases|210|261|280|305+351+338|310}}

|FlashPtC = 51

|ExploLimits = 0.98–9.08%

|LD50 = {{Unbulleted list|463 mg kg⁻¹ <small>(oral, rat)</small>|1.576 g kg⁻¹ <small>(dermal, rabbit)</small>}}

}}

|Section4={{Chembox Related

|OtherFunction_label = alkanamines

|OtherFunction = {{Unbulleted list|[[Propylamine]]|[[Isopropylamine]]|[[1,2-Diaminopropane]]|[[1,3-Diaminopropane]]|[[Isobutylamine]]|[[tert-Butylamine|''tert''-Butylamine]]|[[n-Butylamine|''n''-Butylamine]]|[[sec-Butylamine|''sec''-Butylamine]]|[[1-Aminopentane]]|[[Cadaverine]]}}

|OtherCompounds = {{Unbulleted list|[[2-Methyl-2-nitrosopropane]]|[[Nylon 46]] }}

}}

}}

'''Putrescine''' is an [[organic compound]] with the formula (CH₂)₄(NH₂)₂. It is a colorless solid that melts near room temperature. It is classified as a [[diamine]].<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1=Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}</ref> Together with [[cadaverine]], it is largely responsible for the foul odor of [[Putrefaction|putrefying]] flesh, but also contributes to other unpleasant odors.

Putrescine is produced on industrial scale by [[hydrogenation]] of [[succinonitrile]].<ref name=Ullmann>

Biotechnological production of putrescine from renewable feedstock . A metabolically engineered strain of Escherichia coli that produces putrescine at high in glucose mineral salts medium has been described.<ref name=Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine>{{cite

| year = 2009| journal = Biotechnology and Bioengineering | last1 = Qian | first1 = Zhi-Gang | last2 = Xia | first2 = Xiao-Xia | last3 = Yup Lee | first3 = Sang| volume = 104| issue = 4| pages = 651–662| pmid = 19714672| doi-access = free}}</ref>

[[File:Polyamine synthesis.svg|left|thumb|400x400px|Biosynthesis of spermidine and spermine from putrescine. Ado = 5'-adenosyl.]]

[[Spermidine synthase]] uses putrescine and [[S-Adenosylmethioninamine|''S''-adenosylmethioninamine]] (decarboxylated [[S-Adenosyl methionine|''S''-adenosyl methionine]]) to produce [[spermidine]]. Spermidine in turn is combined with another ''S''-adenosylmethioninamine and gets converted to [[spermine]].

Putrescine is synthesized in small quantities by healthy living cells by the action of [[ornithine decarboxylase]].

Putrescine is synthesized biologically via two different pathways, both starting from [[arginine]].

* In one pathway, arginine is converted into [[agmatine]]. The conversion is catalyzed by the enzyme [[arginine decarboxylase]] (ADC). Agmatine is transformed into N-carbamoylputrescine by [[Agmatine deiminase|agmatine imino hydroxylase]] (AIH). Finally, N-carbamoylputrescine is hydrolyzed to give putrescine.<ref>{{cite journal|pmid=6895223|title=Enzymic conversion of agmatine to putrescine in Lathyrus sativus seedlings. Purification and properties of a multifunctional enzyme (putrescine synthase). | volume=256 | issue=18|date=September 1981|pages=9532–41|author=Srivenugopal KS, Adiga PR|journal=J. Biol. Chem.|doi=10.1016/S0021-9258(19)68795-8 |doi-access=free}}</ref>

* In the second pathway, arginine is converted into [[ornithine]] and then ornithine is converted into putrescine by [[ornithine decarboxylase]] (ODC).

Putrescine, via [[metabolic intermediate]]s including [[monoacetylputrescine]] and [[gamma-Aminobutyraldehyde|γ-aminobutyraldehyde]] (GABAL) and [[biotransformation]]s mediated by [[diamine oxidase]] (DAO), [[monoamine oxidase]] (MAO), and [[aminobutyraldehyde dehydrogenase]] (ABALDH), can act as a minor [[precursor (biochemistry)|biological precursor]] of [[γ-aminobutyric acid]] (GABA) in the [[brain]] and elsewhere.<ref name="RashmiZananJohn2018">{{cite book | last=Rashmi | first=Deo | last2=Zanan | first2=Rahul | last3=John | first3=Sheeba | last4=Khandagale | first4=Kiran | last5=Nadaf | first5=Altafhusain | title=Studies in Natural Products Chemistry | chapter=γ-Aminobutyric Acid (GABA): Biosynthesis, Role, Commercial Production, and Applications | publisher=Elsevier | volume=57 | date=2018 | isbn=978-0-444-64057-4 | doi=10.1016/b978-0-444-64057-4.00013-2 | page=413–452 | url=https://www.researchgate.net/profile/Carla-Varela-2/publication/324580560_Phenolic_Derivatives_From_Medicinal_Herbs_and_Plant_Extracts_Anticancer_Effects_and_Synthetic_Approaches_to_Modulate_Biological_Activity/links/5e4668ce458515072d9ab1a4/Phenolic-Derivatives-From-Medicinal-Herbs-and-Plant-Extracts-Anticancer-Effects-and-Synthetic-Approaches-to-Modulate-Biological-Activity.pdf#page=432 | quote=Alternate pathways of GABA synthesis from putrescine and other polyamines have also been reported [207–211]. Here, γ-aminobutyraldehyde, an intermediate from polyamine degradation reaction via combined activities of diamine oxidase (DAO, E.C. 1.4.3.6) and 4-aminobutyraldehyde dehydrogenase (ABALDH), leads to the synthesis of GABA [205,212,213]. In response to abiotic stresses, GABA is also reported to be synthesized from proline via D1-pyrroline intermediate formation [47,205,214] and also by a nonenzymatic reaction [214]. However, GABA synthesis from polyamine pathways is minor in the brain, [215] although they play a significant role in the developing brain [216] and retina [217]. But GABA can be formed from putrescine in the mammalian brain [218].}}</ref><ref name="ShelpBozzoTrobacher2012">{{cite journal | vauthors = Shelp BJ, Bozzo GG, Trobacher CP, Zarei A, Deyman KL, Brikis CJ | title = Hypothesis/review: contribution of putrescine to 4-aminobutyrate (GABA) production in response to abiotic stress | journal = Plant Sci | volume = 193-194 | issue = | pages = 130–135 | date = September 2012 | pmid = 22794926 | doi = 10.1016/j.plantsci.2012.06.001 | url = }}</ref><ref name="BenedettiDostert1994">{{cite journal | vauthors = Benedetti MS, Dostert P | title = Contribution of amine oxidases to the metabolism of xenobiotics | journal = Drug Metab Rev | volume = 26 | issue = 3 | pages = 507–535 | date = 1994 | pmid = 7924902 | doi = 10.3109/03602539408998316 | url = | quote = MAO also catalyses the deamination of a natural brain constituent, monoacetyl-putrescine, producing y-acetylaminobutyraldehyde, which in turn participates in the formation of brain GABA [13].}}</ref>

==Occurrence==

Putrescine is found in all [[organism]]s.<ref name=":0">{{Cite journal |last1=Cui |first1=Jing |last2=Pottosin |first2=Igor |last3=Lamade |first3=Emmanuelle |last4=Tcherkez |first4=Guillaume |date=June 2020 |title=What is the role of putrescine accumulated under potassium deficiency? |url=https://onlinelibrary.wiley.com/doi/10.1111/pce.13740 |journal=Plant, Cell & Environment |language=en |volume=43 |issue=6 |pages=1331–1347 |doi=10.1111/pce.13740 |pmid=32017122 |s2cid=211023002 |issn=0140-7791}}</ref> Putrescine is widely found in plant tissues,<ref name=":0"/> often being the most common polyamine present within the organism. Its role in development is well documented, but recent studies have suggested that putrescine also plays a role in stress responses in plants, both to biotic and abiotic stressors.<ref>{{Cite journal |last1=González-Hernández |first1=Ana Isabel |last2=Scalschi |first2=Loredana |last3=Vicedo |first3=Begonya |last4=Marcos-Barbero |first4=Emilio Luis |last5=Morcuende |first5=Rosa |last6=Camañes |first6=Gemma |date=January 2022 |title=Putrescine: A Key Metabolite Involved in Plant Development, Tolerance and Resistance Responses to Stress |journal=International Journal of Molecular Sciences |language=en |volume=23 |issue=6 |pages=2971 |doi=10.3390/ijms23062971 |issn=1422-0067 |pmc=8955586 |pmid=35328394|doi-access=free}}</ref> The absence of putrescine in plants is associated with an increase in both parasite and fungal population in plants.

Putrescine serves an important role in a multitude of ways, which include: a [[Ion|cation]] substitute, an [[osmolyte]], or a transport protein.<ref name=":0" /> It also serves as an important regulator in a variety of surface proteins, both on the cell surface and on organelles, such as the mitochondria and chloroplasts. A recorded increase of ATP production has been found in mitochondria and ATP synthesis by chloroplasts with an increase in mitochondrial and chloroplastic putrescine, but putrescine has also been shown to function as a developmental inhibitor in some plants, which can be seen as [[dwarfism]] and late flowering in ''Arabiadopsis'' plants.<ref name=":0" />

Putrescine production in plants can also be promoted by fungi in the soil.<ref>{{Cite journal |last=Copeland |first=Charles |date=2022-04-01 |title=The feeling is mutual: Increased host putrescine biosynthesis promotes both plant and endophyte growth |url=https://doi.org/10.1093/plphys/kiac001 |journal=Plant Physiology |volume=188 |issue=4 |pages=1939–1941 |doi=10.1093/plphys/kiac001 |issn=0032-0889 |pmc=8968283 |pmid=35355052}}</ref> [[Piriformospora indica]] (''P.&nbsp;indica'') is one such fungus, found to promote putrescine production in ''[[Arabidopsis]]'' and common garden tomato plants. In a 2022 study it was shown that the presence of this fungus had a promotional effect on the growth of the root structure of plants. After [[gas chromatography]] testing, putrescine was found in higher amounts in these root structures.<ref name=":1">{{Cite journal |last1=Ioannidis |first1=Nikolaos E. |last2=Cruz |first2=Jeffrey A. |last3=Kotzabasis |first3=Kiriakos |last4=Kramer |first4=David M. |date=2012-01-12 |title=Evidence That Putrescine Modulates the Higher Plant Photosynthetic Proton Circuit |journal=PLOS ONE |language=en |volume=7 |issue=1 |pages=e29864 |doi=10.1371/journal.pone.0029864 |issn=1932-6203 |pmc=3257247 |pmid=22253808|bibcode=2012PLoSO...729864I |doi-access=free }}</ref>

Plants that had been inoculated with ''P.&nbsp;indica'' had presented an excess of arginine decarboxylase.<ref name=":1" /> This is used in the process of making putrescine in plant cells. One of the downstream effects of putrescine in root cells is the production of [[auxin]]. That same study found that putrescine added as a fertilizer showed the same results as if it was inoculated with the fungus, which was also shown in ''Arabidopsis'' and [[barley]]. The evolutionary foundations of this connection and putrescine are still unclear.

Putrescine is a component of [[bad breath]] and [[bacterial vaginosis]].<ref>{{cite journal|author1=Yeoman, CJ |author2=Thomas, SM |author3=Miller, ME |author4=Ulanov, AV |author5=Torralba, M |author6=Lucas, S |author7=Gillis, M |author8=Cregger, M |author9=Gomez, A |author10=Ho, M |author11=Leigh, SR |author12=Stumpf, R |author13=Creedon, DJ |author14=Smith, MA |author15=Weisbaum, JS |author16=Nelson, KE |author17=Wilson, BA |author18=White, BA |title=A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.|journal=PLOS ONE|year=2013|volume=8|issue=2|pages=e56111|doi=10.1371/journal.pone.0056111|pmid=23405259|pmc=3566083|bibcode=2013PLoSO...856111Y|doi-access=free}}</ref> It is also found in [[semen]] and some microalgae, together with [[spermine]] and [[spermidine]].

== Uses ==

Putrescine reacts with [[adipic acid]] to yield the [[polyamide]] [[nylon 46]], which is marketed by [[Envalior]] (formerly [[DSM (company)|DSM]]) under the trade name Stanyl.<ref>{{cite web |url=http://www.dsm.com/products/stanyl/en_US/home.html|archive-url=https://web.archive.org/web/20170925055608/http://www.dsm.com/products/stanyl/en_US/home.html |title=Stanyl® |publisher=[[DSM (company)|DSM]] |archive-date= 25 September 2017}}</ref><ref>{{cite web |url=https://www.envalior.com/en-us/products/stanyl.html |title=PA46 - Stanyl® |publisher=[[Envalior]] |access-date= 28 August 2024}}</ref>

Application of putrescine, along with other polyamines, can be used to extend the shelf life of fruits by delaying the ripening process.<ref>{{Cite journal|last1=Abbasi|first1=Nadeem Akhtar|last2=Ali|first2=Irfan|last3=Hafiz|first3=Ishfaq Ahmad|last4=Alenazi|first4=Mekhled M.|last5=Shafiq|first5=Muhammad|date=January 2019|title=Effects of Putrescine Application on Peach Fruit during Storage|journal=Sustainability|language=en|volume=11|issue=7|pages=2013|doi=10.3390/su11072013|doi-access=free}}</ref> Pre-harvest application of putrescine has been shown to increase plant resistance to high temperatures and drought.<ref>{{Cite journal|last1=Todorov|first1=D.|last2=Alexieva|first2=V.|last3=Karanov|first3=E.|date=1998-12-01|title=Effect of Putrescine, 4-PU-30, and Abscisic Acid on Maize Plants Grown under Normal, Drought, and Rewatering Conditions|url=https://doi.org/10.1007/PL00007035|journal=Journal of Plant Growth Regulation|language=en|volume=17|issue=4|pages=197–203|doi=10.1007/PL00007035|pmid=9892742|s2cid=20062811|issn=1435-8107}}</ref> Both of these effects seem to result from lowered ethylene production following exogenous putrescine exposure.<ref>{{Cite journal|last1=Khan|first1=A.S.|last2=Z. Singh|title=Influence of Pre and Postharvest Applications of Putrescine on Ethylene Production, Storage Life and Quality of 'Angelino' Plum|date=May 2008|url=https://www.actahort.org/books/768/768_14.htm|journal=Acta Horticulturae|issue=768|pages=125–133|doi=10.17660/ActaHortic.2008.768.14|issn=0567-7572}}</ref>

Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing.<ref>{{Cite journal|last1=Pelletti|first1=Guido|last2=Garagnani|first2=Marco|last3=Barone|first3=Rossella|last4=Boscolo-Berto|first4=Rafael|last5=Rossi|first5=Francesca|last6=Morotti|first6=Annalisa|last7=Roffi|first7=Raffaella|last8=Fais|first8=Paolo|last9=Pelotti|first9=Susi|date=2019-04-01|title=Validation and preliminary application of a GC–MS method for the determination of putrescine and cadaverine in the human brain: a promising technique for PMI estimation|url=https://www.sciencedirect.com/science/article/pii/S0379073819300283|journal=Forensic Science International|language=en|volume=297|pages=221–227|doi=10.1016/j.forsciint.2019.01.025|pmid=30831414|s2cid=73461335|issn=0379-0738}}</ref>

Putrescine together with [[chitosan]] has been successfully used in [[postharvest]] physiology as a natural fruit coating.<ref name="FH">{{cite journal |first1= R |last1= Bahmani | first2= F |last2= Razavi | first3= S|last3= Mortazavi | first4= A |last4= Juárez-Maldonado | first5= G |last5= Gohari | title = Chitosan–putrescine nanoparticle coating attenuates postharvest decay and maintains ROS scavenging system activity of strawberry cv. ‘Camarosa’ during cold storage | url = https://sciendo.com/article/10.2478/fhort-2024-0009 | journal = [[Folia Horticulturae]] | volume = 36 | issue = 1 | pages = 149-160 | date = February 2024 | pmid = | doi = 10.2478/fhort-2024-0009 | publisher = Polish Society of Horticultural Science | s2cid = 19887643 | doi-access = free }}</ref> Putrescine with chitosan treated fruits had higher antioxidant capacity and [[enzyme]] activities than untreated fruits. Fresh [[strawberry|strawberries]] coated have lower [[decomposition|decay]] percentage, higher tissue firmness, contents of [[total soluble solids]]. Nanoparticles of putrescine with chitosan are effective in preserving the nutritional quality and prolonging the post-harvest life of strawberries during storage up to 12 days.<ref name="FH"/>

==History==

Putrescine and [[cadaverine]] were first described in 1885 by the [[Berlin]] physician Ludwig Brieger (1849–1919).<ref>Brief biography of [http://www.sammlungen.hu-berlin.de/dokumente/14948/ Ludwig Brieger] {{Webarchive|url=https://web.archive.org/web/20111003041704/http://www.sammlungen.hu-berlin.de/dokumente/14948/ |date=2011-10-03}} (in German). Biography of [http://jewishencyclopedia.com/articles/3708-brieger-ludwig Ludwig Brieger] in English.</ref><ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), [https://archive.org/details/weitereuntersuc00briegoog/page/n49 page 43]. From page 43: Ich nenne dasselbe Putrescin, von putresco, faul werden, vermodern, verwesen. (I call this [compound] "putrescine", from [the Latin word] ''putresco'', to become rotten, decay, rot.)</ref><ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), [https://archive.org/details/weitereuntersuc00briegoog/page/n45 page 39].</ref>

In rats a low [[Acute toxicity|acute oral toxicity]] of 2000 mg/kg body weight<ref>..==Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats</ref>

==Further reading==

* {{cite book | last =Haglund | first =William | title =Forensic taphonomy: The Postmortem Fate of Human Remains | publisher =CRC Press | year =1996 | isbn =0-8493-9434-1 | pages =[https://archive.org/details/forensictaphonom0000unse/page/100 100] | url-access =registration | url =https://archive.org/details/forensictaphonom0000unse/page/100}}

{{}}

==External links==

* [http://gmd.mpimp-golm.mpg.de/Spectrums/cf58e7b1-7e8f-4734-90e3-965149b9f6ac.aspx Putrescine MS Spectrum]

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[[Category:NMDA receptor antagonists]]

[[Category:1,4-Butanediyl compounds]]

[[Category:Substances discovered in the 19th century]]