| Identification | Back Directory | [Name]
EURYCOMANONE | [CAS]
84633-29-4 | [Synonyms]
NSC 339187
EURYCOMANONE
pasakbumin-a
Eurycoma longifolia
Eurycomanone (~90%)
EurycomalongifoliaJack
Extract of Orion nigrum
Eurycomanone (Pasakbumin A)
Extract of amaryllis asiatica l
Eurycomanone (Synonyms: Pasakbumin A)
11-beta,12-alpha,15-beta)-betdihydrate
Eurycomanone, 98%, from Eurycoma longifolia
11,2o-epoxy-1,11,12,14,15-pentahydroxy-13(21)-diene-(1-picrasa-16-dione
11β,20-Epoxy-1β,11,12α,14,15β-pentahydroxypicrasa-3,13(21)-diene-2,16-dione
Picrasa-3,13(21)-diene-2,16-dione,11,20-epoxy-1,11,12,14,15-pentahydroxy-, (1b,11b,12a,15b)-
Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12,14,15-pentahydroxy-, (1β,11β,12α,15β)-
(1beta,8xi,11beta,12alpha,15beta)-1,11,12,14,15-pentahydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione | [Molecular Formula]
C20H28O11 | [MDL Number]
MFCD01704311 | [MOL File]
84633-29-4.mol | [Molecular Weight]
444.43 |
| Chemical Properties | Back Directory | [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 | [biological source]
plant | [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| |
| Hazard Information | Back Directory | [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]. | [storage]
Store at -20°C | [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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