Eurycomanone Chemical Properties

Melting point:

273-285℃ (methanol ethyl ether )

Boiling point:

669.5±55.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

Solid

pka

11.29±0.70(Predicted)

color 

Off-White to Pale Beige

InChIKey

RRXCMOJNEHOTBC-OHYAWSEYNA-N

SMILES

[C@]123CO[C@@]4(O)[C@H](O)C(=C)[C@]1(O)[C@@H](O)C(=O)O[C@]2([H])C[C@@]1([H])C(C)=CC(=O)[C@@H](O)[C@]1(C)[C@]34[H].O.O |&1:0,3,5,9,11,16,19,26,28,30,r|

Eurycomanone Usage And Synthesis

Uses

Eurycomanone is known as a cytotoxic compound found in Eurycoma Longifolia Jack. Previous studies had noted its cytotoxic effects against various cancer cell lines. More recent research demonstrated the ability of Eurycomanone to suppress the expression of lung cancer cell tumor markers, prohibitin, annexin 1 and endoplasmic reticulum protein 28. Eurycomanone was shown to also exerts the ability to induce apoptosis through the up-regulation of p53 in human cervical carcinoma cells.

Definition

ChEBI: A quassinoid isolated from Eurycoma longifolia and has been shown to exhibit antineoplastic and antimalarial activties.

Manufacturing Process

The extraction and purification process of eurycomanone in a kind of Tongkat Ali plant:
The preparation of the first medicinal extract: Tongkat Ali tree root meal is gone out eurycomanone with solvent extraction, extracting solution, concentrating under reduced pressure obtains Tongkat Ali medicinal extract.
Second degreasing: by Tongkat Ali medicinal extract with petroleum ether extraction, leaves standstill, layering. The low-pole compositions include removing fat-soluble pigment.
3rd extracting and separating: the medicinal extract after petroleum ether degreasing with extraction into ethyl acetate, obtain the ethyl acetate solution of eurycomanone.
4th pillar layer separation: the ethyl acetate solution of eurycomanone is separated with silica gel column chromatography, obtaining the elutriant containing eurycomanone.
5th decolouring: the composition containing eurycomanone is activated carbon decolorizing.
6th concentrates and crystallization: the destainer concentrates under reduced pressure of eurycomanone, and crystallization obtains the crude product eurycomanone.
7th purifying: add sherwood oil in crude product eurycomanone, then drip a little ethyl acetate, by the impurity pigment washing removing on crystallisate, obtain the xln of white.
8th filters, dry: by the vacuum-drying of eurycomanone xln.

Biological Activity

Eurycomanone, the major quassinoid in the E. longifolia root extract, significantly increased testosterone production in a dose-dependent manner at 0.1, 1.0 and 10.0 μM (p < 0.05). It enhanced testosterone steroidogenesis at the rat testicular Leydig’s cells by inhibiting the aromatase conversion of testosterone to oestrogen and may also involve phosphodiesterase inhibition at a high concentration. Also, standardized extracts of E. longifolia Jack containing a high concentration of quassinoids (20% eurycomanone and 4% of 13α,21-dihydroeurycomanone) may have potential anti-estrogenic effects[1].

References

[1] Shaheed Ur Rehman, Hye Hyun Yoo, Kevin Choe. “Review on a Traditional Herbal Medicine, Eurycoma longifolia Jack (Tongkat Ali): Its Traditional Uses, Chemistry, Evidence-Based Pharmacology and Toxicology.” Molecules 21 3 (2016): 331.

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