An active ginsenoside metabolite
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20(S)-Protopanaxatriol

Item No. 29073

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,6α,12β)-dammar-24-ene-3,6,12,20-tetrol
CAS Number
34080-08-5
Synonyms
  • 20(S)-APPT
  • 20(S)-PPT
Molecular Formula
C30H52O4
Formula Weight
476.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
CC1(C)[C@@H](O)CC[C@@]2(C)[C@@]1([H])[C@@H](O)C[C@]3(C)[C@]2([H])C[C@@H](O)[C@@]4([H])[C@@]3(C)CC[C@]4([H])[C@@](C)(O)CC/C=C(C)/C
InChi Code
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
InChi Key
SHCBCKBYTHZQGZ-CJPZEJHVSA-N
Origin
Plant/Ginseng Radix et Rhizoma
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    20(S)-Protopanaxatriol is an active aglycone metabolite of various panaxatriol ginsenosides, including ginsenoside Re (Item No. 15330), ginsenoside Rf (Item No. 23667), ginsenoside Rg1 (Item No. 15315), ginsenoside Rg2 (Item No. 15331), and ginsenoside Rh1 (Item No. 27318).1 It is cytotoxic to HL-60 cancer cells (IC50 = 16 µM).2 20(S)-Protopanaxatriol inhibits the proliferation of human umbilical vein endothelial cells (HUVECs; EC50 = 6.64 µg/ml).3 It inhibits LPS-induced increases in the protein levels of COX-2 and inducible nitric oxide synthase (iNOS) and decreases LPS-induced NF-κB activity in RAW 264.7 cells when used at concentrations ranging from 1 to 20 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Helms, S. Cancer prevention and therapeutics: Panax ginseng. Altern. Med. Rev. 9(3), 259-274 (2004).

    2. Tian, Y., Guo, H., Han, J., et al. Microbial transformation of 20(S)-protopanaxatriol by Mucor spinosus. J. Nat. Prod. 68(5), 678-680 (2005).

    3. Usami, Y., Liu, Y.-N., Lin, A.-S., et al. Antitumor agents. 261. 20(S)-Protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of 1H NMR spectra. J. Nat. Prod. 71(3), 478-481 (2008).

    4. Oh, G.S., Pae, H.O., Choi, B.M., et al. 20(S)-Protopanaxatriol, one of ginsenoside metabolites, inhibits inducible nitric oxide synthase and cyclooxygenase-2 expressions through inactivation of nuclear factor-κB in RAW 264.7 macrophages stimulated with lipopolysaccharide. Cancer Lett. 205(1), 23-29 (2004).