Protopanaxatriol

Protopanaxatriol
Names
IUPAC name
(20R)-Dammar-24-ene-3β,6α,12β,20-tetrol
Systematic IUPAC name
(1S,3aR,3bR,5S,5aR,7S,9aR,9bR,11R,11aR)-1-[(2R)-2-Hydroxy-6-methylhept-5-en-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene-5,7,11-triol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1 ☒N
    Key: SHCBCKBYTHZQGZ-DLHMIPLTSA-N ☒N
  • InChI=1/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-15-28(6)24(19)20(31)16-22-27(5)14-12-23(33)26(3,4)25(27)21(32)17-29(22,28)7/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21-,22+,23-,24-,25-,27+,28+,29+,30+/m0/s1
    Key: SHCBCKBYTHZQGZ-DLHMIPLTBT
  • O[C@H]4[C@@H]1[C@H](CC[C@]1([C@]2([C@@H]([C@]3(C)[C@@H]([C@@H](O)C2)C(C)(C)[C@@H](O)CC3)C4)C)C)[C@@](O)(C)CC\C=C(/C)C
Properties
C30H52O4
Molar mass 476.742 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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Protopanaxatriol (PPT) is an organic compound that is an aglycone of ginsenosides, a group of steroid glycosides.[1] It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (Panax ginseng) and in notoginseng (Panax pseudoginseng).

In rats, the oral bioavailbility is about 3.7% and the half-life is 0.80 hours (when given as a PPD-PPT mixture). PPT is unstable in acid, showing 40% degradation after 4 hours at 37°C both in pH 1.2 buffer solution and rat stomach contents.[2] It is extensively metabolized in mice.[3]

See also

References

  1. ^ Kang, Soo Yeon; Schini-Kerth, Valérie B.; Kim, Nak Doo (1995). "Ginsenosides of the protopanaxatriol group cause endothelium-dependent relaxation in the rat aorta". Life Sciences. 56 (19): 1577–1586. doi:10.1016/0024-3205(95)00124-o. PMID 7723586.
  2. ^ 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.
  3. ^ Wang, YZ; Wang, YS; Chu, SF; Chen, NH; Zhang, JT (April 2010). "Protopanaxatriol metabolites identified by LC-MS/MS after oral administration in mice". International journal of clinical pharmacology and therapeutics. 48 (4): 282–90. doi:10.5414/cpp48282. PMID 20353750.


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