Spermidine

Source: Wikipedia, the free encyclopedia.
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
ECHA InfoCard
 100.004.264 Edit this at Wikidata
EC Number
  • 204-689-0
454510
IUPHAR/BPS
KEGG
MeSH Spermidine
RTECS number
  • EJ7000000
UNII
UN number 2735
  • InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 ☒N
    Key: ATHGHQPFGPMSJY-UHFFFAOYSA-N ☒N
  • NCCCCNCCCN
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 labelling:
GHS05: Corrosive
Danger
H314
P280, P305+P351+P338, 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 checkY☒N ?)

Spermidine is a polyamine compound (C
7H
19N
3) 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

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. ^
    PMID 24481223
    .
  3. ^
    PMID 29371440
    .
  4. PMID 21818338
    .
  5. S2CID 37856308
    .
  6. PMID 8118404
    .
  7. PMID 2107372
    .
  8. PMID 4870599
    .
  9. PMID 4571774
    .
  10. PMID 6206782
    .
  11. PMID 2443800
    .
  12. PMID 241752
    .
  13. PMID 6272602
    .
  14. ^
    PMID 21249159
    .
  15. ^ Ciba-Geigy, ed. (1977), "Sperma", Wissenschaftliche Tabellen Geigy (in German), vol. Teilband Körperflüssigkeiten (8 ed.), Basel: CIBA-GEIGY Limited, pp. 181-189
  16. ^ a b "Brochure on Polyamines, rev. 2" (PDF). Japan: Oryza Oil & Fat Chemocial Co., Ltd. 2011-12-26. Archived from the original (PDF) on 2016-03-03. Retrieved 2013-11-06.
  17. S2CID 32178592
    .
  18. PMID 27841876
    .
  19. S2CID 3126330
    .
  20. ^ "The Ultimate Spermidine Guide: Benefits, Side Effects & How To Take". Prohormones. Retrieved 2022-07-29.
  21. ^ "Polyamines on the Reproductive Landscape". academic.oup.com. Retrieved 2022-07-29.
  22. PMID 31319247
    .
  23. PMID 8052534
    .
  24. PMID 5795512
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Spermidine&oldid=1212656836"