Chemistry:Spermidine

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Spermidine
Skeletal formula of spermidine
Ball and stick model of spermidine
Names
Preferred IUPAC name
N1-(3-Aminopropyl)butane-1,4-diamine
Identifiers
3D model (JSmol)
3DMet
1698591
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 204-689-0
454510
KEGG
MeSH Spermidine
RTECS number
  • EJ7000000
UNII
UN number 2735
Properties
C7H19N3
Molar mass 145.250 g·mol−1
Appearance Colourless liquid
Odor Ichtyal, ammoniacal
Density 925 mg mL−1
Melting point 22 to 25 °C (72 to 77 °F; 295 to 298 K)
145 g L−1 (at 20 °C)
log P −0.504
UV-vis (λmax) 260 nm
Absorbance 0.1
1.479
Hazards
GHS pictograms GHS05: Corrosive
GHS Signal word DANGER
H314
P280, P305+351+338, P310
Flash point 112 °C (234 °F; 385 K)
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Spermidine is a polyamine compound (C7H19N3) found in ribosomes and living tissues and having various metabolic functions within organisms. It was originally isolated from semen.[1]

Function

Spermidine is an aliphatic polyamine. Spermidine synthase (SPDS) catalyzes its formation from putrescine. It is a precursor to other polyamines, such as spermine and its structural isomer thermospermine.

Spermidine synchronizes an array of biological processes, (such as Ca2+, Na+, K+ -ATPase) thus maintaining membrane potential and controlling intracellular pH and volume. Spermidine regulates biological processes, such as Ca2+ influx by glutamatergic N-methyl-D-aspartate receptor (NMDA receptor), which has been associated with nitric oxide synthase (NOS) and cGMP/PKG pathway activation and a decrease of Na+,K+-ATPase activity in cerebral cortex synaptosomes.

Spermidine is a longevity agent in mammals due to various mechanisms of action, which are just beginning to be understood. Autophagy is the main mechanism at the molecular level, but evidence has been found for other mechanisms, including inflammation reduction, lipid metabolism, and regulation of cell growth, proliferation, and death.[2][3] Spermidine has been theorized to promote autophagy via the MAPK pathway by inhibiting phosphorylation of raf,[2] or possibly by inhibiting cytosolic autophagy-related protein acetylation by EP300 and thereby increasing acetylation of tubulin.[3]

Spermidine is known to regulate plant growth, assisting the in vitro process of transcribing RNA, and inhibition of NOS. Also, spermidine is a precursor to other polyamines, such as spermine and thermospermine, some of which contribute to tolerance against drought and salinity in plants.

Spermidine has been tested and discovered to encourage hair shaft elongation and lengthen hair growth. Spermidine has also been found to “upregulate expression of the epithelial stem cell-associated keratins K15 and K19, and dose-dependently modulated K15 promoter activity in situ and the colony forming efficiency, proliferation and K15 expression of isolated human K15-GFP+ cells in vitro.”[4]

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

Biochemical actions

Spermidine's known actions include:

Sources

Good dietary sources of spermidine are aged cheese, mushrooms, soy products, legumes, corn, and whole grains.[14] Spermidine is plentiful in a Mediterranean diet.[3] For comparison: The spermidine content in human seminal plasma varies between approx. 15 and 50 mg/L (mean 31 mg/L).[15]

Food Spermidine
mg/kg		 notes & refs
Wheat germ 243 [16]
Soybean, dried 207 Japanese[14]
Cheddar, 1yr old 199 [14]
Soybean, dried 128 German[14]
Mushroom 89 Japanese[14]
Rice bran 50 [14]
Chicken liver 48 [14]
Green peas 46 [14]
Mango 30 [14]
Chickpea 29 [14]
Cauliflower (cooked) 25 [14]
Broccoli (cooked) 25 [14]

Note: spermidine content varies by source and age. See ref for details.

In grains, the endosperm contains most of the spermidine. One of the best known grain dietary sources is wheat germ, containing as much as 243 mg/kg.[16]

Uses

  • Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse. May be used for purification of DNA-binding proteins.
  • Spermidine is also used, along with calcium chloride, for precipitating DNA onto microprojectiles for bombardment with a gene gun.[17]
  • Spermidine has also been reported to protect the heart from aging and prolong the lifespan of mice, while in humans it was correlated with lower blood pressure.[18] It also was found to reduce the amount of aging in yeast, flies, worms, and human immune cells by inducing autophagy.[19]
  • Spermidine may play a role in male and female fertility.[20] Fertile men have higher spermidine levels than men who are infertile,[21] and spermidine supplementation has been shown to help maintain a healthy hormone balance and reduce oxidative stress.[22]
  • Spermidine is commonly used for in vitro molecular biology reactions, particularly, in vitro transcription by phage RNA polymerases,[23] in vitro transcription by human RNA polymerase II,[24] and in vitro translation.
  • Spermidine increases specificity and reproducibility of Taq-mediated PCR by neutralizing and stabilizing the negative charge on DNA phosphate backbone.

See also

References

  1. ↑ American Heritage Dictionary Retrieved 2014-11-18.
  2. ↑ 2.0 2.1 Minois, Nadège (28 January 2014). "Molecular Basis of the "Anti-Aging" Effect of Spermidine and Other Natural Polyamines – A Mini-Review". Gerontology 60 (4): 319–326. doi:10.1159/000356748. PMID 24481223. http://www.karger.com/Article/Pdf/356748. 
  3. ↑ 3.0 3.1 3.2 "Spermidine in health and disease". Science 359 (6374): eaan2788. 2018. doi:10.1126/science.aan2788. PMID 29371440. 
  4. ↑ Ramot, Yuval; Tiede, Stephan; Bíró, Tamás; Abu Bakar, Mohd Hilmi; Sugawara, Koji; Philpott, Michael P.; Harrison, Wesley; Pietilä, Marko et al. (27 July 2011). "Spermidine Promotes Human Hair Growth and Is a Novel Modulator of Human Epithelial Stem Cell Functions". PLOS ONE 6 (7): e22564. doi:10.1371/journal.pone.0022564. ISSN 1932-6203. PMID 21818338. Bibcode: 2011PLoSO...622564R. 
  5. ↑ Hu, J; Mahmoud, MI; El-Fakahany, EE (1994). "Polyamines inhibit nitric oxide synthase in rat cerebellum". Neuroscience Letters 175 (1–2): 41–5. doi:10.1016/0304-3940(94)91073-1. PMID 7526294. 
  6. ↑ Wan, CY; Wilkins, TA (1993). "Spermidine facilitates PCR amplification of target DNA". PCR Methods and Applications 3 (3): 208–10. doi:10.1101/gr.3.3.208. PMID 8118404. 
  7. ↑ Cull, M; McHenry, CS (1990). "Preparation of extracts from prokaryotes". Guide to Protein Purification. Methods in Enzymology. 182. pp. 147–53. doi:10.1016/0076-6879(90)82014-S. ISBN 978-0-12-182083-1. 
  8. ↑ Blethen, SL; Boeker, EA; Snell, EE (1968). "Arginine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme". The Journal of Biological Chemistry 243 (8): 1671–7. doi:10.1016/S0021-9258(18)93498-8. PMID 4870599. 
  9. ↑ Wu, WH; Morris, DR (1973). "Biosynthetic arginine decarboxylase from Escherichia coli. Subunit interactions and the role of magnesium ion". The Journal of Biological Chemistry 248 (5): 1696–9. doi:10.1016/S0021-9258(19)44246-4. PMID 4571774. 
  10. ↑ Tabor, CW; Tabor, H (1984). "Polyamines". Annual Review of Biochemistry 53: 749–90. doi:10.1146/annurev.bi.53.070184.003533. PMID 6206782. 
  11. ↑ Krug, MS; Berger, SL (1987). "First-strand cDNA synthesis primed with oligo(dT)". Guide to Molecular Cloning Techniques. Methods in Enzymology. 152. pp. 316–25. doi:10.1016/0076-6879(87)52036-5. ISBN 978-0-12-182053-4. 
  12. ↑ Karkas, JD; Margulies, L; Chargaff, E (1975). "A DNA polymerase from embryos of Drosophila melanogaster. Purification and properties". The Journal of Biological Chemistry 250 (22): 8657–63. doi:10.1016/S0021-9258(19)40721-7. PMID 241752. 
  13. ↑ Bouché, JP (1981). "The effect of spermidine on endonuclease inhibition by agarose contaminants". Analytical Biochemistry 115 (1): 42–5. doi:10.1016/0003-2697(81)90519-4. PMID 6272602. 
  14. ↑ 14.00 14.01 14.02 14.03 14.04 14.05 14.06 14.07 14.08 14.09 14.10 14.11 Ali, Mohamed Atiya; Poortvliet, Eric; Strömberg, Roger; Yngve, Agneta (2011). "Polyamines in foods: development of a food database". Food Nutr Res. 55: 5572. doi:10.3402/fnr.v55i0.5572. PMID 21249159. 
  15. ↑ "Sperma" (in de), Wissenschaftliche Tabellen Geigy (Basel: CIBA-GEIGY Limited) Teilband Körperflüssigkeiten: pp. 181-189, 1977 
  16. ↑ 16.0 16.1 "Brochure on Polyamines, rev. 2". Japan: Oryza Oil & Fat Chemocial Co., Ltd.. 2011-12-26. http://www.oryza.co.jp/html/english/pdf/polyamine_vol.2.pdf. 
  17. ↑ T.M. Klein; T. Gradziel; M.E. Fromm; J.C. Sanford (1988). "Factors influencing gene delivery into Zea mays cells by high–velocity microprojectiles". Nature Biotechnology 6 (5): 559–63. doi:10.1038/nbt0588-559. 
  18. ↑ Eisenberg, Tobias; Abdellatif, Mahmoud; Schroeder, Sabrina; Primessnig, Uwe; Stekovic, Slaven; Pendl, Tobias; Harger, Alexandra; Schipke, Julia et al. (2016). "Cardioprotection and lifespan extension by the natural polyamine spermidine". Nature Medicine 22 (12): 1428–1438. doi:10.1038/nm.4222. PMID 27841876. 
  19. ↑ "Induction of autophagy by spermidine promotes longevity". Nat. Cell Biol. 11 (11): 1305–14. November 2009. doi:10.1038/ncb1975. PMID 19801973. https://www.openaccessrepository.it/record/23132. 
  20. ↑ "The Ultimate Spermidine Guide: Benefits, Side Effects & How To Take" (in en). https://pro-hormones.co.uk/blogs/news/the-ultimate-spermidine-supplement-guide-2022. 
  21. ↑ "Polyamines on the Reproductive Landscape". https://academic.oup.com/edrv/article/32/5/694/2354766. 
  22. ↑ Li, Bo; Hu, Xiaopeng; Yang, Yanzhou; Zhu, Mingyan; Zhang, Jiong; Wang, Yanrong; Pei, Xiuying; Zhou, Huchen et al. (2019-09-06). "GAS5/miR-21 Axis as a Potential Target to Rescue ZCL-082-Induced Autophagy of Female Germline Stem Cells In Vitro". Molecular Therapy. Nucleic Acids 17: 436–447. doi:10.1016/j.omtn.2019.06.012. ISSN 2162-2531. PMID 31319247. 
  23. ↑ "Synthetic polyamines stimulate in vitro transcription by T7 RNA polymerase". Nucleic Acids Res. 22 (14): 2784–90. July 1994. doi:10.1093/nar/22.14.2784. PMID 8052534. 
  24. ↑ "Purification and some properties of a soluble DNA-dependent RNA polymerase from nuclei of human placenta". Eur. J. Biochem. 9 (3): 311–8. June 1969. doi:10.1111/j.1432-1033.1969.tb00610.x. PMID 5795512. 

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