A quassinoid with diverse biological activities
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Eurycomanone

Item No. 30896

Technical Information
Formal Name
(1β,11β,12α,15β)-11,20-epoxy-1,11,12,14,15-pentahydroxy-picrasa-3,13(21)-diene-2,16-dione
CAS Number
84633-29-4
Synonyms
  • NSC 339187
  • Pasakbumin A
Molecular Formula
C20H24O9
Formula Weight
Purity
≥95%
A solid
DMSO: slightly soluble
SMILES
C=C1[C@]([C@]([C@]2([H])[C@]3(O)[C@@H]1O)(CO3)[C@@](O4)([H])C[C@@]([C@]2(C)[C@@H]5O)([H])C(C)=CC5=O)(O)[C@@H](O)C4=O
InChi Code
InChI=1S/C20H24O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,9,11-14,16,22-24,26-27H,2,5-6H2,1,3H3/t9-,11+,12+,13+,14-,16+,17+,18+,19-,20-/m0/s1
InChi Key
UCUWZJWAQQRCOR-OKNZMGBLSA-N
Origin
Plant/Tongkat Ali
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Eurycomanone is a quassinoid originally isolated from E. longifolia that has diverse biological activities.1 It is active against the W2 and D6 clones of P. falciparum (IC50s = 0.015 and 0.026 µg/ml, respectively).2 Eurycomanone induces lipolysis in 3T3-L1 adipocytes with an EC50 value of 14.6 µM, an effect that can be blocked by the protein kinase A (PKA) inhibitor H-89 (Item No. 10010556).3 It induces cell cycle arrest at the G2/M phase and apoptosis in HepG2 cells when used at a concentration of 5 µg/ml.4 It reduces estrogen release and increases testosterone release in isolated rat Leydig cell-rich testicular interstitial cell preparations when used at concentrations of 1 and 10 µM.5 Eurycomanone (1 mg/kg, i.p.) decreases gastric acid secretion and lesion size in rat models of indomethacin-, water immersion stress-, or pyloric ligation-induced ulcer formation.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Darise, M., Kohda, H., Mizutani, K., et alEurycomanone and eurycomanol, quassinoids from the roots of Eurycoma longifolia. Phytochemistry 21(8), 2091-2093 (1982).

    2. Kuo, P.-C., Damu, A.G., Lee, K.-H., et alCytotoxic and antimalarial constituents from the roots of Eurycoma longifolia. Bioorg. Med. Chem. 12(3), 537-544 (2004).

    3. Lahrita, L., Hirosawa, R., Kato, E., et alIsolation and lipolytic activity of eurycomanone and its epoxy derivative from Eurycoma longifolia. Bioorg. Med. Chem. 25(17), 4829-4834 (2017).

    4. Zakaria, Y., Rahmat, A., Pihie, A.H.L., et alEurycomanone induce apoptosis in HepG2 cells via up-regulation of p53. Cancer Cell Int. 9, (2009).

    5. Low, B.-S., Choi, S.-B., Wahab, H.A., et alEurycomanone, the major quassinoid in Eurycoma longifolia root extract increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesis. J. Ethnopharmacol. 149(1), 201-207 (2013).

    6. Tada, H., Yasuda, F., Otani, K., et alNew antiulcer quassinoids from Eurycoma longifolia. Eur. J. Med. Chem. 26(3), 345-349 (1991).