Turkesterone

Last updated

Turkesterone
Turkesterone.svg
Turkesterone3D.png
Identifiers
  • (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C27H44O8
Molar mass 496.641 g·mol−1
3D model (JSmol)
  • C[C@]12C[C@H]([C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)O
  • InChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+/m0/s1
  • Key:WSBAGDDNVWTLOM-XHZKDPLLSA-N

Turkesterone is a naturally occurring phytoecdysteroid, a subclass of ecdysteroids - steroidal compounds structurally related to invertebrate molting hormones. It is predominantly found in numerous plant species including Ajuga turkestanica , [1] various Vitex species, [2] [3] [4] Triticum aestivum , [5] Cyanotis arachnoidea and Rhaponticum acaule. [6]

Turkesterone possesses a polyhydroxylated structure with a cyclopentanoperhydrophenanthrene skeleton, typically consisting of 27 - 30 carbon atoms and a β-oriented side chain at C17, resembling cholesterol-derived steroids. [7] However, unlike anabolic-androgenic steroid, turkesterone does not bind to androgen receptor. Instead, it is hypothesized to exert its anabolic effects through the activation of the phosphoinositide 3-kinase (PI3K)/AKT signaling pathway, which regulates protein synthesis, cellular growth, and muscle hypertrophy. [8] Additionally, turkesterone has been implicated in promoting nitrogen retention, enhancing mitochondrial biogenesis of organelles, and modulating lipid and carbohydrate metabolism, contributing to improved physical performance and recovery. [9] Its bioactivity extends beyond muscle anabolism, demonstrating adaptogenic, antioxidant, and neuroprotective properties, making it a promising candidate for therapeutic applications in stress resilience, neurodegeneration, and metabolic disorders. [10]

Despite its potential, further research is needed to fully elucidate its pharmacokinetics, bioavailability, and long-term effects in humans.

See also

References

  1. ↑ Guibout L, Mamadalieva N, Balducci C, Girault JP, Lafont R (2015). "The minor ecdysteroids from Ajuga turkestanica" (PDF). Phytochemical Analysis. 26 (5): 293–300. Bibcode:2015PChAn..26..293G. doi:10.1002/pca.2563. PMID   25953625. S2CID   10373609.
  2. ↑ dos Santos TC, Delle Monache F, Leitão SG (March 2001). "Ecdysteroids from two Brazilian Vitex species". Fitoterapia. 72 (3): 215–220. doi:10.1016/s0367-326x(00)00304-x. PMID   11295296.
  3. ↑ Suksamrarn A, Kumpun S, Yingyongnarongkul BE (November 2002). "Ecdysteroids of Vitex scabra stem bark". Journal of Natural Products. 65 (11): 1690–1692. Bibcode:2002JNAtP..65.1690S. doi:10.1021/np020199o. PMID   12444704.
  4. ↑ Bunu MI, Ndinteh DT, Macdonald JR, Langat MK, Isyaka SM, Sadgrove NJ, et al. (August 2021). "Ecdysteroids from the Stem Bark of Vitex doniana Sweet (Lamiaceae; ex. Verbenaceae): A Geographically Variable African Medicinal Species". Antibiotics. 10 (8): 937. doi: 10.3390/antibiotics10080937 . PMC   8388959 . PMID   34438987.
  5. ↑ Janeczko A, Oklestkova J, Tarkowská D, Drygaś B (March 2021). "Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants". International Journal of Molecular Sciences. 22 (6): 2855. doi: 10.3390/ijms22062855 . PMC   7999220 . PMID   33799719.
  6. ↑ Zughdani M, Yusufoğlu HS, Ekiz G, Linden A, Çalış İ (December 2020). "Ecdysteroids from the underground parts of Rhaponticum acaule (L.) DC" (PDF). Phytochemistry. 180: 112530. Bibcode:2020PChem.180k2530Z. doi:10.1016/j.phytochem.2020.112530. PMID   33049649. S2CID   222353903.
  7. ↑ Dinan L (June 2001). "Phytoecdysteroids: biological aspects". Phytochemistry. 57 (3): 325–339. Bibcode:2001PChem..57..325D. doi:10.1016/S0031-9422(01)00078-4. PMID   11393511.
  8. ↑ Isenmann E, Ambrosio G, Joseph JF, Mazzarino M, de la Torre X, Zimmer P, et al. (July 2019). "Ecdysteroids as non-conventional anabolic agent: performance enhancement by ecdysterone supplementation in humans". Archives of Toxicology. 93 (7): 1807–1816. Bibcode:2019ArTox..93.1807I. doi:10.1007/s00204-019-02490-x. PMID   31123801.
  9. ↑ Cahlíková L, Macáková K, Chlebek J, Hošt'álková A, Kulhánková A, Opletal L (July 2011). "Ecdysterone and its Activity on some Degenerative Diseases". Natural Product Communications. 6 (5). doi:10.1177/1934578X1100600527. ISSN   1934-578X.
  10. ↑ Read H, Wilson ID, Lafont R (1990). "A Note on Overpressure Thin-Layer Chromatography of Ecdysteroids". Chromatography and Isolation of Insect Hormones and Pheromones. New York, NY: Springer US. pp. 127–130. doi:10.1007/978-1-4684-8062-7_12. ISBN   978-1-4684-8064-1.


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