Spermidine

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Spermidine
Skeletal formula of spermidine
Ball and stick model of spermidine
Identifiers
CAS number 124-20-9 YesY
PubChem 1102
ChemSpider 1071 N
EC number 204-689-0
UN number 2735
DrugBank DB03566
KEGG C00315 N
MeSH Spermidine
ChEBI CHEBI:16610 N
ChEMBL CHEMBL19612 N
IUPHAR ligand 2390
RTECS number EJ7000000
Beilstein Reference 1698591
Gmelin Reference 454510
3DMet B01214
Jmol-3D images Image 1
Properties
Molecular formula C7H19N3
Molar mass 145.25 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)
Solubility in water 145 g L−1 (at 20 °C)
log P −0.504
λmax 260 nm
Absorbance 0.1
Refractive index (nD) 1.479
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H314
GHS precautionary statements P280, P305+351+338, P310
EU classification Corrosive C
R-phrases R34
S-phrases S26, S36/37/39
Flash point 112 °C (234 °F; 385 K)
Related compounds
Related amines
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Spermidine is a polyamine compound (C
7
H
19
N
3
) found in ribosomes and living tissues, and having various metabolic functions within organisms. It was originally isolated from semen.[1]

Function[edit]

Polyamines, such as spermidine, are polycationic aliphatic amines and are multifunctional. They serve vital roles in cell survival.

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 due to its impact on chromatin-mediated regulation of gene expression, however the mechanism is poorly understood. Spermidine synthase (SPDS) catalyzes the formation of spermidine. Spermidine helps further polyamines, this can include polyamines and thermospermine. These contribute to a resistance of dry climate and salinity.

It is known to regulate plant growth, assisting the in vitro process of transcribing RNA, and inhibition of NOS. Also, spermidine is a precursor to polyamines, such as spermine and thermospermine, most 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.”

Spermidine is synthesized from putrescine and is a precursor of spermine.

SPD SPM synthesis English.svg

Biochemical actions[edit]

Spermidine's known actions include:

Sources[edit]

Polyamines are ubiquitous in the animal, fungi, and plant kingdoms. Therefore, they appear in a wide array of foodstuff. There is a popular myth that grapefruits contain high amounts of spermidine, which probably relies on the confusion between spermidine and putrescine. While citrus fruits show high amounts of putrescine, they contain very little spermidine. Good dietary sources of spermidine are aged cheese, mushrooms, soy products, legumes, corn, and whole grains.[11] In grains, the endosperm contains most of the spermidine. The most concentrated known dietary source is wheat germ, containing as much as 243 mg/kg.[12]

Uses[edit]

  • 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 has also been found to reduce the amount of aging in yeast, flies, worms, and human immune cells by inducing autophagy.[13] Recently Tirupathi Pichiah et al., suggested that spermidine may be helpful for treating type 2 diabetes.[14]

See also[edit]

References[edit]

  1. ^ American Heritage Dictionary Retrieved 2014-11-18.
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Cull, M; McHenry, CS (1990). "Preparation of extracts from prokaryotes". Methods in enzymology. Methods in Enzymology 182: 147–53. doi:10.1016/0076-6879(90)82014-S. ISBN 978-0-12-182083-1. PMID 2107372. 
  5. ^ Blethen, SL; Boeker, EA; Snell, EE (1968). "Argenine decarboxylase from Escherichia coli. I. Purification and specificity for substrates and coenzyme". The Journal of Biological Chemistry 243 (8): 1671–7. PMID 4870599. 
  6. ^ 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. PMID 4571774. 
  7. ^ Tabor, CW; Tabor, H (1984). "Polyamines". Annual review of biochemistry 53: 749–90. doi:10.1146/annurev.bi.53.070184.003533. PMID 6206782. 
  8. ^ Krug, MS; Berger, SL (1987). "First-strand cDNA synthesis primed with oligo(dT)". Methods in enzymology. Methods in Enzymology 152: 316–25. doi:10.1016/0076-6879(87)52036-5. ISBN 978-0-12-182053-4. PMID 2443800. 
  9. ^ 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. PMID 241752. 
  10. ^ 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. 
  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. 
  12. ^ "Brochure on Polyamines, rev. 2". Japan: Oryza Oil & Fat Chemocial Co., Ltd. 2011-12-26. Retrieved 2013-11-06. 
  13. ^ Tobias Eisenberg, Heide Knauer, Alexandra Schauer, Sabrina Büttner, Christoph Ruckenstuhl, Didac Carmona-Gutierrez, Julia Ring, Sabrina Schroeder, Christoph Magnes, Lucia Antonacci, Heike Fussi, Luiza Deszcz, Regina Hart, Elisabeth Schraml, Alfredo Criollo, Evgenia Megalou, Daniela Weiskopf, Peter Laun, Gino Heeren, Michael Breitenbach, Beatrix Grubeck-Loebenstein, Eva Herker, Birthe Fahrenkrog, Kai-Uwe Fröhlich, Frank Sinner, Nektarios Tavernarakis, Nadege Minois, Guido Kroemer, Frank Madeo (4 October 2009). "Induction of autophagy by spermidine promotes longevity,". Nature Cell Biology 11 (11): 1305–14. doi:10.1038/ncb1975. PMID 19801973. 
  14. ^ Tirupathi Pichiah, PB; Suriyakalaa, U; Kamalakkannan, S; Kokilavani, P; Kalaiselvi, S; SankarGanesh, D; Gowri, J; Archunan, G; Cha, YS; Achiraman, S (October 2011). "Spermidine may decrease ER stress in pancreatic beta cells and may reduce apoptosis via activating AMPK dependent autophagy pathway". Medical hypotheses 77 (4): 677–9. doi:10.1016/j.mehy.2011.07.014. PMID 21831529. 

External links[edit]