Chemistry:Protodioscin

From HandWiki
Short description: Chemical compound
Protodioscin
Protodioscin.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC51H84O22
Molar mass1049.211 g·mol−1
3D model (JSmol)
  (verify)

Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, Trigonella Dioscorea and Trillium families.[1][2][3] It is best known as the putative active component of the herbal aphrodisiac plant Tribulus terrestris.[4][5]

Extracts from T. terrestris standardised for protodioscin content have been demonstrated to produce proerectile effects in isolated tissues and aphrodisiac action in several animal species.[6][7] It is thought protodioscin achieves this primarily through causing an increase in androgen receptor immunoreactivity, meaning it increases the concentration of androgen receptors in cells, causing the organism to become more sensitive to androgens like testosterone and dihydrotestosterone (DHT).[8] The mechanism for these effects has not been clearly established, and while protodioscin has been demonstrated to trigger release of nitric oxide in corpus cavernosum tissue,[9] and also to produce statistically significant increases in the levels of the hormones testosterone, dihydrotestosterone and dehydroepiandrosterone in animal studies,[10] studies in humans have failed to show efficacy and its use remains controversial.[11][12]

References

  1. "Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection". Journal of Pharmaceutical Sciences 90 (11): 1752–8. November 2001. doi:10.1002/jps.1124. PMID 11745732. 
  2. "Protodioscin isolated from fenugreek (Trigonella foenumgraecum L.) induces cell death and morphological change indicative of apoptosis in leukemic cell line H-60, but not in gastric cancer cell line KATO III". International Journal of Molecular Medicine 11 (1): 23–6. January 2003. doi:10.3892/ijmm.11.1.23. PMID 12469212. 
  3. "Steroidal saponins from Dioscorea panthaica and their cytotoxic activity". Die Pharmazie 59 (4): 294–6. April 2004. PMID 15125576. 
  4. "Distribution of steroidal saponins in Tribulus terrestris from different geographical regions". Phytochemistry 69 (1): 176–86. January 2008. doi:10.1016/j.phytochem.2007.07.003. PMID 17719068. Bibcode2008PChem..69..176D. 
  5. "Govanoside B, a new steroidal saponin from rhizomes of Trillium govanianum". Natural Product Research (6): 1–9. May 2020. 
  6. "Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats". Life Sciences 71 (12): 1385–96. August 2002. doi:10.1016/S0024-3205(02)01858-1. PMID 12127159. 
  7. "Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model". Journal of Alternative and Complementary Medicine 9 (2): 257–65. April 2003. doi:10.1089/10755530360623374. PMID 12804079. 
  8. "Effect of Tribulus terrestris on nicotinamide adenine dinucleotide phosphate-diaphorase activity and androgen receptors in rat brain". Journal of Ethnopharmacology 96 (1–2): 127–32. January 2005. doi:10.1016/j.jep.2004.08.030. PMID 15588660. 
  9. "Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum". Annals of the Academy of Medicine, Singapore 29 (1): 22–6. January 2000. PMID 10748960. 
  10. "The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat". Phytomedicine 15 (1–2): 44–54. January 2008. doi:10.1016/j.phymed.2007.11.011. PMID 18068966. 
  11. "A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions". Journal of Sex & Marital Therapy 29 (3): 185–205. 2003. doi:10.1080/00926230390155096. PMID 12851124. 
  12. "Nutrients and botanicals for erectile dysfunction: examining the evidence". Alternative Medicine Review 9 (1): 4–16. March 2004. PMID 15005641.