Misplaced Pages

Protopanaxadiol

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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.

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.


Stub icon

This article about an alcohol is a stub. You can help Misplaced Pages by expanding it.

Categories: