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Protopanaxadiol information


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
CAS Number
  • 7755-01-3 checkY
3D model (JSmol)
  • Interactive image
Abbreviations PPD
ChEBI
  • CHEBI:76237 ☒N
ChEMBL
  • ChEMBL375563 ☒N
ChemSpider
  • 8095918 ☒N
KEGG
  • C20715 checkY
PubChem CID
  • 9920281
UNII
  • P6717R7BP8 ☒N
CompTox Dashboard (EPA)
  • DTXSID10952905 Edit this at Wikidata
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/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
SMILES
  • 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
Chemical formula
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).
☒N verify (what is checkY☒N ?)
Infobox references

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]

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]

  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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Protopanaxadiol

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Protopanaxadiol (PPD) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene...

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Panax notoginseng

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Dammarane-type ginsenosides includes 2 classifications: the 20(S)-protopanaxadiol (ppd) and 20(S)-protopanaxatriol (ppt) classifications. P. notoginseng...

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Ginsenoside

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family. The dammaranes further subdivided into 2 main groups, the protopanaxadiols and protopanaxatriols, with other smaller groups such as the ocotillol-type...

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American ginseng

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constituents. Dammarane-type ginsenosides include two classifications: 20(S)-protopanaxadiol (PPD) and 20(S)-protopanaxatriol (PPT). American ginseng contains high...

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Dammarane

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triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol). Compounds of the series were first isolated from and named after...

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Dammarene

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These compounds are often composed of saponins, examples include Protopanaxadiol and triol, Dammarenediol I and II. Dammarenediol II synthase Chun JH...

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M1

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Sphagnum auriculatum bog pool community 20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol, a ppd-type monoglucoside ginsenoside metabolized by intestinal bacteria...

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Yunnan Baiyao

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alkaloids, and calcium phosphate – all components of Chinese yam. Protopanaxadiol and panaxatriol, sapogenins found in ginseng (Panax ginseng) and notoginseng...

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Panaxatriol

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pseudoginseng). It is formed by the dehydration of protopanaxatriol. Protopanaxadiol Kang, Soo Yeon; Schini-Kerth, Valérie B.; Kim, Nak Doo (1995). "Ginsenosides...

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Protopanaxatriol

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(Panax ginseng) and in notoginseng (Panax pseudoginseng). Panaxatriol Protopanaxadiol Kang, Soo Yeon; Schini-Kerth, Valérie B.; Kim, Nak Doo (1995). "Ginsenosides...

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depressant, a chemical added to crude oil to lower its "pour point" ppd, Protopanaxadiol, a molecule Psychogenic polydipsia, excessive water intake with a psychiatric...

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The constituents of ginseng include triterpene saponins, aglycone protopanaxadiol, aglycone protopanaxytriol, aglycone oleanolic acid and water-soluble...

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Ginsenoside Rb1

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synthase (DS) as the catalyst. The dammarenediol-II is converted to protopanaxadiol and then to ginsenoside Rd. Finally, GRb1 is synthesized from ginsenoside...

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Zhang, W (March 2013). "Two novel hydroperoxylated products of 20(S)-protopanaxadiol produced by Mucor racemosus and their cytotoxic activities against...

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Paraptosis

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"potently kill colorectal cancer cells". Specifically, derivatives of protopanaxadiol Rg3 and Rh2, are the key ginsenosides found in the extract. In colorectal...

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