Protopanaxadiol

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).[1][2]

Protopanaxadiol
Names
IUPAC name
Dammar-24-ene-3β,12β,20-triol
Systematic IUPAC name
(1S,3aR,3bR,5aR,7S,9aR,9bR,11R,11aR)-1-[(2S)-2-Hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthene-7,11-diol
Identifiers
3D model (JSmol)
Abbreviations PPD
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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/s1 ☒N
    Key: PYXFVCFISTUSOO-VUFVRDRTSA-N ☒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/s1
    Key: PYXFVCFISTUSOO-VUFVRDRTBZ
  • CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)O)C)O)C
Properties
C30H52O3
Molar mass 460.743 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The health effects 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.[3]

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.


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