Eurycomanone

Names

[ Name ]:
Eurycomanone

[Synonym ]:
(1β,11α,12α,15β)-1,11,12,14,15-Pentahydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione dihydrate
pasakbumin-a
EURYCOMANONE
Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12,14,15-pentahydroxy-, (1β,11α,12α,15β)-, hydrate (1:2)

Biological Activity

[Description]:

Eurycomanone could increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesis.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Endocrinology

Natural Products >> Others

[In Vitro]

Eurycomanone (EN) significantly increased testosterone production dose-dependently at 0.1, 1.0 and 10.0 μM, but the two lower doses when combined with 3-isobutyl-1-methylxanthine (IBMX), the phosphodiesterase inhibitor were not significantly higher than EN or IBMX alone, except at a higher concentration. The molecular docking studies indicated EN and IBMX were binding at different sites of the enzyme. EN has no reversal of inhibition by aminoglutethimide, ketoconazole or nifedipine at the respective steroid oogenesis enzyme. The quassinoid was also non-responsive to the inhibition of oestrogen receptor by tamoxifen, but displayed improved for mestane inhibition of aromatase in reducing oestrogen production. The molecular docking studies further supported that EN and formestane bound to aromatase with similar orientations and free energy binding values[1].

[References]

[1]. Low BS, et al. Eurycomanone, the major quassinoid in Eurycoma longifolia root extract increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesis. J Ethnopharmacol. 2013 Aug 26;149(1):201-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
273-285℃ (methanol ethyl ether )

[ Molecular Formula ]:
C₂₀H₂₄O₉

[ Molecular Weight ]:
408.40

[ PSA ]:
172.21000

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TJ7862500

CHEMICAL NAME :: Picrasa-3,13(21)-diene-2,16-dione, 11,2O-epoxy-1,11,12,14,15-pentahydroxy-, (1-beta,11- beta,12-alpha,15-beta)-, dihydrate

CAS REGISTRY NUMBER :: 84633-29-4

LAST UPDATED :: 199303

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H24-O9.2H2-O

MOLECULAR WEIGHT :: 444.48

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 26,345,1991