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Protopanaxadiol

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Ginseng plant extract
Protopanaxadiol
Names
IUPAC name Dammar-24-ene-3β,12β,20-triol
Systematic IUPAC name (1S,3aR,3bR,5aR,7S,9aR,9bR,11R,11aR)-1--3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopentaphenanthene-7,11-diol
Identifiers
CAS Number
3D model (JSmol)
Abbreviations PPD
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30+/m0/s1Key: PYXFVCFISTUSOO-VUFVRDRTSA-N
  • InChI=1/C30H52O3/c1-19(2)10-9-14-30(8,33)20-11-16-29(7)25(20)21(31)18-23-27(5)15-13-24(32)26(3,4)22(27)12-17-28(23,29)6/h10,20-25,31-33H,9,11-18H2,1-8H3/t20-,21+,22-,23+,24-,25-,27-,28+,29+,30+/m0/s1Key: PYXFVCFISTUSOO-VUFVRDRTBZ
SMILES
  • CC(=CCC(C)(1CC2(1(C32(CC43(CC(C4(C)C)O)C)C)O)C)O)C
Properties
Chemical formula C30H52O3
Molar mass 460.743 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

The health effect of protopanaxadiol inside the human body is still unclear. One study suggests it has rapid, non-genomic effects on endothelial cells, binding to the glucocorticoid and oestrogen beta receptors. The study also showed an increase in intracellular calcium ion concentration.

Shanghai Innovative Research Center of Traditional Chinese Medicine (SIRC-TCM) is trying to develop an antidepressant based on this substance under the brand name Yoxintine. The drug has finished phase II trials as of May 2023. Results were published in November 2024.

A pharmacokinetic study done on phase IIa human volunteers reports the relationship between oral dose and blood plasma concentration, but no data is given for oral bioavailbility, half life, or volume of distribution. In rats, the oral bioavailbility is about 48% and the half-life is 6.25 hours when given as an extract containing both PPD and PPT. When given alone, reported bioavailbility values are lower, at 20.7–36.8%.

See also

References

  1. Shibata, S.; Tanaka, O.; Sado, M.; Tsushima, S. (1963). "The genuine sapogenin of ginseng". Tetrahedron Letters. 4 (12): 795–800. doi:10.1016/S0040-4039(01)90718-X.
  2. Tanaka, O.; Nagai, M.; Shibata, S. (1964). "Stereochemistry of protopanaxadiol, a genuine sapogenin of ginseng". Tetrahedron Letters. 5 (33–34): 2291–7. doi:10.1016/S0040-4039(00)71705-9.
  3. Leung; et al. (2009). "Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells". British Journal of Pharmacology. 156 (4): 626–637. doi:10.1111/j.1476-5381.2008.00066.x. PMC 2697710. PMID 19226254.
  4. 文汇 (2023-05-23). "全球首个单分子抗抑郁中药进入临床Ⅲ期研究，由人参开发而来" [World's first single-molucule antidepressant TCM enters phase III clinical study, is developed from ginseng]. news.qq.com (in Chinese (China)).
  5. Dong, Z; Shen, Q; Zhu, H; Yang, Z; Lv, J; Feng, R; Bai, X; Huang, G; Hu, Y; Pan, L; Zhao, G; Jia, W; Wang, X (14 November 2024). "Efficacy and safety of YOXINTINE for depression: A double-blinded, randomized, placebo-controlled, phase 2 clinical trial". Phytomedicine : international journal of phytotherapy and phytopharmacology. 136: 156204. doi:10.1016/j.phymed.2024.156204. PMID 39580994.
  6. Ling, J; Yu, Y; Zhu, J; Li, Y; Ling, L; Wang, L; Xu, C; Duan, G (15 September 2016). "A highly sensitive HPLC-MS/MS method for quantification of 20(S)-protopanaxadiol in human plasma and its application in phase IIa clinical trial of a novel antidepressant agent". Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 1031: 214–220. doi:10.1016/j.jchromb.2016.07.044. PMID 27507666.
  7. Kong, LT; Wang, Q; Xiao, BX; Liao, YH; He, XX; Ye, LH; Liu, XM; Chang, Q (April 2013). "Different pharmacokinetics of the two structurally similar dammarane sapogenins, protopanaxatriol and protopanaxadiol, in rats". Fitoterapia. 86: 48–53. doi:10.1016/j.fitote.2013.01.019. PMID 23391424.


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