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Putrescine

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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.[3] Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Names
Preferred IUPAC name
Butane-1,4-diamine
Other names
1,4-Diaminobutane, 1,4-Butanediamine
Identifiers
3D model (JSmol)
3DMet
605282
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.440 Edit this at Wikidata
EC Number
  • 203-782-3
1715
KEGG
MeSH Putrescine
RTECS number
  • EJ6800000
UNII
UN number 2928
  • InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2 checkY
    Key: KIDHWZJUCRJVML-UHFFFAOYSA-N checkY
  • NCCCCN
Properties
C4H12N2
Molar mass 88.154 g·mol−1
Appearance Colourless crystals
Odor fishy-ammoniacal, pungent
Density 0.877 g/mL
Melting point 27.5 °C (81.5 °F; 300.6 K)
Boiling point 158.6 °C; 317.4 °F; 431.7 K
Miscible
log P −0.466
Vapor pressure 2.33 mm Hg at 25 deg C (est)
3.54x10−10 atm-cu m/mol at 25 deg C (est)
1.457
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Danger
H228, H302, H312, H314, H331
P210, P261, P280, P305+P351+P338, P310
Flash point 51 °C (124 °F; 324 K)
Explosive limits 0.98–9.08%
Lethal dose or concentration (LD, LC):
  • 463 mg kg−1 (oral, rat)
  • 1.576 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Production

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Putrescine is produced on an industrial scale by the hydrogenation of succinonitrile.[3]

Biotechnological production of putrescine from a renewable feedstock has been investigated. A metabolically engineered strain of Escherichia coli that produces putrescine at high concentrations in glucose mineral salts medium has been described.[4]

Biochemistry

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Biosynthesis of spermidine and spermine from putrescine. Ado = 5'-adenosyl.

Spermidine synthase uses putrescine and S-adenosylmethioninamine (decarboxylated 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.

Putrescine, via metabolic intermediates including N-acetylputrescine, γ-aminobutyraldehyde (GABAL), N-acetyl-γ-aminobutyric acid (N-acetyl-GABAL), and N-acetyl-γ-aminobutyric acid (N-acetyl-GABA), biotransformations mediated by diamine oxidase (DAO), monoamine oxidase B (MAO-B), aminobutyraldehyde dehydrogenase (ABALDH), and other enzymes, can act as a minor biological precursor of γ-aminobutyric acid (GABA) in the brain and elsewhere.[6][7][8][9][10][11] In 2021, it was discovered that MAO-B does not mediate dopamine catabolism in the rodent striatum but instead participates in striatal GABA synthesis and that synthesized GABA in turn inhibits dopaminergic neurons in this brain area.[12][11] It has been found that MAO-B, via the putrescine pathway, importantly mediates GABA synthesis in astrocytes in various brain areas, including in the hippocampus, cerebellum, striatum, cerebral cortex, and substantia nigra pars compacta (SNpc).[12][11]

Occurrence

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Putrescine is found in all organisms.[13] Putrescine is widely found in plant tissues,[13] 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.[14] 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 cation substitute, an osmolyte, or a transport protein.[13] 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.[13]

Putrescine production in plants can also be promoted by fungi in the soil.[15] Piriformospora indica (P. 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.[16]

Plants that had been inoculated with P. indica had presented an excess of arginine decarboxylase.[16] 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.[17] It is also found in semen and some microalgae, together with spermine and spermidine.

Uses

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Putrescine reacts with adipic acid to yield the polyamide nylon 46, which is marketed by Envalior (formerly DSM) under the trade name Stanyl.[18][19]

Application of putrescine, along with other polyamines, can be used to extend the shelf life of fruits by delaying the ripening process.[20] Pre-harvest application of putrescine has been shown to increase plant resistance to high temperatures and drought.[21] Both of these effects seem to result from lowered ethylene production following exogenous putrescine exposure.[22]

Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing.[23]

Putrescine together with chitosan has been successfully used in postharvest physiology as a natural fruit coating.[24] Putrescine with chitosan treated fruits had higher antioxidant capacity and enzyme activities than untreated fruits. Fresh strawberries coated have lower 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.[24]

History

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Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[25][26][27]

Toxicity

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In rats, putrescine has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).[28]

Further reading

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  • Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. pp. 100. ISBN 0-8493-9434-1.

References

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  1. ^ Thalladi, V.R.; Boese, R.; Weiss, H.-C. (2001). "CSD Entry: QATWAJ : 1,4-Butanediamine". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc4g850. Retrieved 2021-11-07.
  2. ^ Thalladi, V. R.; Boese, R.; Weiss, H.-C. (2000). "The Melting Point Alternation in α,ω-Alkanediols and α,ω-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions". Angew. Chem. Int. Ed. 39 (5): 918–922. doi:10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E. PMID 10760893.
  3. ^ a b Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 3527306730.
  4. ^ Qian, Zhi-Gang; Xia, Xiao-Xia; Yup Lee, Sang (2009). "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Biotechnology and Bioengineering. 104 (4): 651–662. doi:10.1002/bit.22502. PMID 19714672.
  5. ^ Srivenugopal KS, Adiga PR (September 1981). "Enzymic conversion of agmatine to putrescine in Lathyrus sativus seedlings. Purification and properties of a multifunctional enzyme (putrescine synthase)". J. Biol. Chem. 256 (18): 9532–41. doi:10.1016/S0021-9258(19)68795-8. PMID 6895223.
  6. ^ Rashmi, Deo; Zanan, Rahul; John, Sheeba; Khandagale, Kiran; Nadaf, Altafhusain (2018). "γ-Aminobutyric Acid (GABA): Biosynthesis, Role, Commercial Production, and Applications". Studies in Natural Products Chemistry. Vol. 57. Elsevier. pp. 413–452. doi:10.1016/b978-0-444-64057-4.00013-2. ISBN 978-0-444-64057-4. 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].
  7. ^ Shelp BJ, Bozzo GG, Trobacher CP, Zarei A, Deyman KL, Brikis CJ (September 2012). "Hypothesis/review: contribution of putrescine to 4-aminobutyrate (GABA) production in response to abiotic stress". Plant Sci. 193–194: 130–135. Bibcode:2012PlnSc.193..130S. doi:10.1016/j.plantsci.2012.06.001. PMID 22794926.
  8. ^ Benedetti MS, Dostert P (1994). "Contribution of amine oxidases to the metabolism of xenobiotics". Drug Metab Rev. 26 (3): 507–535. doi:10.3109/03602539408998316. PMID 7924902. 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].
  9. ^ Watanabe M, Maemura K, Kanbara K, Tamayama T, Hayasaki H (2002). "GABA and GABA Receptors in the Central Nervous System and Other Organs". A Survey of Cell Biology. International Review of Cytology. Vol. 213. pp. 1–47. doi:10.1016/s0074-7696(02)13011-7. ISBN 978-0-12-364617-0. PMID 11837891.
  10. ^ Seiler N (June 2004). "Catabolism of polyamines". Amino Acids. 26 (3): 217–233. doi:10.1007/s00726-004-0070-z. PMID 15221502.
  11. ^ a b c Cho HU, Kim S, Sim J, Yang S, An H, Nam MH, Jang DP, Lee CJ (July 2021). "Redefining differential roles of MAO-A in dopamine degradation and MAO-B in tonic GABA synthesis". Exp Mol Med. 53 (7): 1148–1158. doi:10.1038/s12276-021-00646-3. PMC 8333267. PMID 34244591.
  12. ^ a b Nam MH, Sa M, Ju YH, Park MG, Lee CJ (April 2022). "Revisiting the Role of Astrocytic MAOB in Parkinson's Disease". Int J Mol Sci. 23 (8): 4453. doi:10.3390/ijms23084453. PMC 9028367. PMID 35457272.
  13. ^ a b c d Cui, Jing; Pottosin, Igor; Lamade, Emmanuelle; Tcherkez, Guillaume (June 2020). "What is the role of putrescine accumulated under potassium deficiency?". Plant, Cell & Environment. 43 (6): 1331–1347. doi:10.1111/pce.13740. ISSN 0140-7791. PMID 32017122. S2CID 211023002.
  14. ^ González-Hernández, Ana Isabel; Scalschi, Loredana; Vicedo, Begonya; Marcos-Barbero, Emilio Luis; Morcuende, Rosa; Camañes, Gemma (January 2022). "Putrescine: A Key Metabolite Involved in Plant Development, Tolerance and Resistance Responses to Stress". International Journal of Molecular Sciences. 23 (6): 2971. doi:10.3390/ijms23062971. ISSN 1422-0067. PMC 8955586. PMID 35328394.
  15. ^ Copeland, Charles (2022-04-01). "The feeling is mutual: Increased host putrescine biosynthesis promotes both plant and endophyte growth". Plant Physiology. 188 (4): 1939–1941. doi:10.1093/plphys/kiac001. ISSN 0032-0889. PMC 8968283. PMID 35355052.
  16. ^ a b Ioannidis, Nikolaos E.; Cruz, Jeffrey A.; Kotzabasis, Kiriakos; Kramer, David M. (2012-01-12). "Evidence That Putrescine Modulates the Higher Plant Photosynthetic Proton Circuit". PLOS ONE. 7 (1): e29864. Bibcode:2012PLoSO...729864I. doi:10.1371/journal.pone.0029864. ISSN 1932-6203. PMC 3257247. PMID 22253808.
  17. ^ Yeoman, CJ; Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M; Gomez, A; Ho, M; Leigh, SR; Stumpf, R; Creedon, DJ; Smith, MA; Weisbaum, JS; Nelson, KE; Wilson, BA; White, BA (2013). "A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease". PLOS ONE. 8 (2): e56111. Bibcode:2013PLoSO...856111Y. doi:10.1371/journal.pone.0056111. PMC 3566083. PMID 23405259.
  18. ^ "Stanyl®". DSM. Archived from the original on 25 September 2017.
  19. ^ "PA46 - Stanyl®". Envalior. Retrieved 28 August 2024.
  20. ^ Abbasi, Nadeem Akhtar; Ali, Irfan; Hafiz, Ishfaq Ahmad; Alenazi, Mekhled M.; Shafiq, Muhammad (January 2019). "Effects of Putrescine Application on Peach Fruit during Storage". Sustainability. 11 (7): 2013. doi:10.3390/su11072013.
  21. ^ Todorov, D.; Alexieva, V.; Karanov, E. (1998-12-01). "Effect of Putrescine, 4-PU-30, and Abscisic Acid on Maize Plants Grown under Normal, Drought, and Rewatering Conditions". Journal of Plant Growth Regulation. 17 (4): 197–203. doi:10.1007/PL00007035. ISSN 1435-8107. PMID 9892742. S2CID 20062811.
  22. ^ Khan, A.S.; Z. Singh (May 2008). "Influence of Pre and Postharvest Applications of Putrescine on Ethylene Production, Storage Life and Quality of 'Angelino' Plum". Acta Horticulturae (768): 125–133. doi:10.17660/ActaHortic.2008.768.14. ISSN 0567-7572.
  23. ^ Pelletti, Guido; Garagnani, Marco; Barone, Rossella; Boscolo-Berto, Rafael; Rossi, Francesca; Morotti, Annalisa; Roffi, Raffaella; Fais, Paolo; Pelotti, Susi (2019-04-01). "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". Forensic Science International. 297: 221–227. doi:10.1016/j.forsciint.2019.01.025. ISSN 0379-0738. PMID 30831414. S2CID 73461335.
  24. ^ a b Bahmani, R; Razavi, F; Mortazavi, S; Juárez-Maldonado, A; Gohari, G (February 2024). "Chitosan–putrescine nanoparticle coating attenuates postharvest decay and maintains ROS scavenging system activity of strawberry cv. 'Camarosa' during cold storage". Folia Horticulturae. 36 (1). Polish Society of Horticultural Science: 149–160. doi:10.2478/fhort-2024-0009. S2CID 19887643.
  25. ^ Brief biography of Ludwig Brieger Archived 2011-10-03 at the Wayback Machine (in German). Biography of Ludwig Brieger in English.
  26. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), 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.)
  27. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
  28. ^ Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology. 35 (3–4): 337–348. doi:10.1016/S0278-6915(97)00121-X. ISSN 0278-6915. PMID 9207896.
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