20-Hydroxyecdysone

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20-Hydroxyecdysone
Skeletal formula of 20-hydroxyecdysone
Ball-and-stick model of the 20-hydroxyecdysone molecule
Clinical data
Pregnancy
category
  • X
Routes of
administration		Oral
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
Elimination half-life4-9 hours
ExcretionUrinary:?%
Identifiers
  • (2β,3β,5β,22R)-2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one
JSmol)
  • O=C1\C=C3/[C@@H]([C@]2(C[C@H](O)[C@H](O)C[C@@H]12)C)CC[C@]4([C@@]3(O)CC[C@@H]4[C@](O)(C)[C@H](O)CCC(O)(C)C)C
  • InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1 checkY
  • Key:NKDFYOWSKOHCCO-YPVLXUMRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring

mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In humans, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein-coding gene.[1]

Sources in arthropods

The primary sources of 20-hydroxyecdysone in larvae are the prothoracic gland, ring gland, gut, and fat bodies. These tissues convert dietary cholesterol into the mature forms of the hormone 20-hydroxyecdysone.[2] For the most part these glandular tissues are lost in the adult with exception of the fat body, which is retained as a sheath of lipid tissue surrounding the brain and organs of the abdomen. In the adult female the ovary is a substantial source of 20-hydroxyecdysone production.[3] Adult males are left with, so far as is currently known, one source of 20-hydroxyecdysone which is the fat body tissue. These hormone producing tissues express the ecdysone receptor throughout development, possibly indicating a functional feedback mechanism.

Ecdysteroid activity in arthropods

An

intracellular protein
.

In humans and other mammals

Use as supplement

20-Hydroxyecdysone and other ecdysteroids are marketed as ingredients in nutritional supplements for various sports, particularly

promotional source?
]

Use as research tool

20-Hydroxyecdysone and other ecdysteroids are used in biochemistry research as inducers in transgenic animals, whereby a new gene is introduced into an animal so that its expression is under the control of an introduced ecdysone receptor. Adding or removing ecdysteroids from the animal's diet then gives a convenient way to turn the inserted gene on or off (see ecdysone receptor). At usual doses, 20-hydroxyecdysone appears to have little or no effect on animals that do not have extra genes inserted; it also has high bioavailability when taken orally, so it is useful for determining whether the transgene has been taken up effectively.[15]

External links

  • Ecdybase, The Ecdysone Handbook - a free online ecdysteroids database

References

  1. S2CID 163166547
    .
  2. PMID 12502734
    .
  3. PMID 6813165
    .
  4. PMID 32293681
    .
  5. PMID 18500969
    .
  6. ^ Simakin SY (1988). "The Combined Use of Ecdisten and the Product'Bodrost'during Training in Cyclical Types of Sport". Scientific Sports Bulletin: 2.
  7. PMID 8704590
    .
  8. PMID 18220764
    .
  9. ^ Smetanin BY (1986). The influence of preparations of plant origin on physical work capacity (Report). The Russian Ministry of Public Health.
  10. ^ Fadeev BG. Comments on the Results of Retibol in the Practice of Athletic Training and Rehabilitation (Report). Natural Sports Research Institute.
  11. PMID 9575416
    .
  12. S2CID 163166547
    .
  13. PMID 24974955
    .
  14. ^ "Ecdysterone: Definition, Benefits, & Side Effects". Turkesterone.com.
  15. PMID 11114195
    .
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