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A quassinoid isolated from Tongkat Ali (Eurycoma longifolia) extract and has been shown to exhibit antineoplastic and antimalarial activties.
Tongkat Ali (Eurycoma longifolia) extract is known as a cytotoxic compound found in Eurycoma Longifolia Jack.
Previous studies had noted Tongkat Ali (Eurycoma longifolia) extract's cytotoxic effects against various cancer cell lines.
CAS: 84633-29-4
MF: C20H24O9
MW: 408.4
Synonyms
;EURYCOMANONE;11,2o-epoxy-1,11,12,14,15-pentahydroxy-13(21)-diene-(1-picrasa-16-dione;11-beta,12-alpha,15-beta)-betdihydrate;pasakbumin-a;11β,20-Epoxy-1β,11,12α,14,15β-pentahydroxypicrasa-3,13(21)-diene-2,16-dione;NSC 339187;(1beta,8xi,11beta,12alpha,15beta);1,11,12,14,15-pentahydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione;Eurycoma longifolia;Eurycomanone;84633-29-4;Pasakbumin-A;X7F43HL2HB;pasakbumin A;(1R,4R,5R,7R,8R,11R,13S,17S,18S,19R)-4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-;3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione;4,5,7,8,17-Pentahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo;[9.8.0.01,7.04,19.013,18]nonadec-14-ene-9,16-dione;NSC-339187;UNII-X7F43HL2HB;DTXSID101004921;GLXC-14855;HY-N5012;AKOS030530160;Eurycomanone (Synonyms: Pasakbumin A);NSC 339187;AC-34394;AS-78621;DA-53072;CS-0032073;(1.BETA.,11.BETA.,12.ALPHA.,15.BETA.)-11,20-EPOXY-1,11,12,14,15-PENTAHYDROXYPICRASA-3,13(21)-DIENE-2,16-DIONE;(1R,4R,5R,7R,8R,11R,13S,17S,18S,19R)-4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-;3,10-dioxapentacyclo[9.8.0.0(1),?.0?,(1)?.0(1)(3),(1)?]nonadec-14-ene-9,16-dione;PICRASA-3,13(21)-DIENE-2,16-DIONE, 11,20-EPOXY-1,11,12,14,15-PENTAHYDROXY-, ;(1.BETA.,11.BETA.,12.ALPHA.,15.BETA.)-;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
More recent research demonstrated the ability of Tongkat Ali (Eurycoma longifolia) extract to suppress the expression of lung cancer cell tumor markers, prohibitin, annexin 1 and endoplasmic reticulum protein 28.
Tongkat Ali (Eurycoma longifolia) extract was shown to also exerts the ability to induce apoptosis through the up-regulation of p53 in human cervical carcinoma cells.
Tongkat Ali (Eurycoma longifolia) extract is a natural product that belongs to the group of quassinoids.
Tongkat Ali (Eurycoma longifolia) extract is obtained from the plant Eurycoma longifolia, which grows in tropical Asia and Africa.
The extract has been shown to have clinical properties such as body formation, protein target, and surface methodology.
3T3-L1 preadipocytes were used for the in vitro assays of Tongkat Ali (Eurycoma longifolia) extract.
Group P2 cells were used for histological analysis and pharmacological agents were found to be chemical stable.
Tongkat Ali (Eurycoma longifolia) extract is known as a cytotoxic compound found in Eurycoma Longifolia Jack.
Previous studies had noted Tongkat Ali (Eurycoma longifolia) extract's cytotoxic effects against various cancer cell lines.
More recent research demonstrated the ability of Tongkat Ali (Eurycoma longifolia) extract to suppress the expression of lung cancer cell tumor markers, prohibitin, annexin 1 and endoplasmic reticulum protein 28.
Tongkat Ali (Eurycoma longifolia) extract was shown to also exerts the ability to induce apoptosis through the up-regulation of p53 in human cervical carcinoma cells.
Tongkat Ali (Eurycoma longifolia) extract 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
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 Tongkat Ali (Eurycoma longifolia) extract 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 Tongkat Ali (Eurycoma longifolia) extract, 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
Tongkat Ali (Eurycoma longifolia) extract, the major quassinoid in the Tongkat Ali (Eurycoma longifolia) extract root extract, significantly increased testosterone production in a dose-dependent manner at 0.1, 1.0 and 10.0 μM (p < 0.05).
Tongkat Ali (Eurycoma longifolia) extract 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 Tongkat Ali (Eurycoma longifolia) extract Jack containing a high concentration of quassinoids (20% eurycomanone and 4% of 13α,21-dihydroeurycomanone) may have potential anti-estrogenic effects.
