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Phytoandrogenic properties of Eurycoma longifolia as natural alternative to testosterone replacement therapy

George A, Henkel R

Andrologia, 2014 Sep;46(7):708-21.
PMID: 24386995 DOI: 10.1111/and.12214

The testosterone deficiency syndrome (TDS) is characterised by numerous symptoms, including low libido, increased fat mass, fatigue, erectile dysfunction or osteoporosis, and up to 80% of men will experience some kind of ageing males' symptoms. This is caused by the age-depending decline in serum testosterone levels with concentrations being about 40-50% lower in men older than 60 years compared with young men. This significant decline in testosterone levels is further closely linked with medical conditions such as obesity, metabolic syndrome, diabetes or hypertension. The conventional way of treating TDS is the testosterone replacement therapy (TRT), for which preparations are on the market. Apart from the beneficial effects of TRT, significant adverse side effects have been described, and prostate cancer (PCa) as absolute contraindication is debated. Eurycoma longifolia (Tongkat Ali; TA) is natural alternative to TRT and has been shown to restore serum testosterone levels, thus significantly improving sexual health. This includes significant positive effects on bone health and physical condition of patients. In addition, a significant antihyperglycaemic effect and cytotoxicity against PCas cells has been shown. Thus far, at therapeutic concentrations, no significant side effects of the treatment were obvious. Therefore, TA might be a safe alternative to TRT.

Matched MeSH terms: Eurycoma/chemistry*
Standardised water-soluble extract of Eurycoma longifolia, Tongkat ali, as testosterone booster for managing men with late-onset hypogonadism?

Tambi MI, Imran MK, Henkel RR

Andrologia, 2012 May;44 Suppl 1:226-30.
PMID: 21671978 DOI: 10.1111/j.1439-0272.2011.01168.x

In most countries, millions of people are relying on herbal medicines as remedy for numerous ailments. In South-East Asia, Eurycoma longifolia Jack, also known as 'Malaysian ginseng' or Tongkat ali, is used to combat stress and disease and to improve physical strength. Moreover, the compounds of the roots of this plant are reported to have aphrodisiac and testosterone enhancing effects in the rat. Considering that human studies are not available, 76 of 320 patients suffering from late-onset hypogonadism (LOH) were given 200 mg of a standardised water-soluble extract of Tongkat ali for 1 month. The Ageing Males' Symptoms (AMS) according to the standardised rating scale and the serum testosterone concentration were taken. Results show that treatment of LOH patients with this Tongkat ali extract significantly (P < 0.0001) improved the AMS score as well as the serum testosterone concentration. While before treatment only 10.5% of the patients did not show any complaint according to the AMS scale and 35.5% had normal testosterone levels, after the completed treatment 71.7% and 90.8% of the patients showed normal values, respectively. Thus, Tongkat ali extract appears to be useful as a supplement in overcoming the symptoms of LOH and for the management of hypogonadism.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext F16, a fraction from Eurycoma longifolia jack extract, induces apoptosis via a caspase-9-independent manner in MCF-7 cells

Tee TT, Cheah YH, Hawariah LP

Anticancer Res, 2007 Sep-Oct;27(5A):3425-30.
PMID: 17970090

F16 is a plant-derived pharmacologically active fraction extracted from Eurycoma longifolia Jack. Previously, we have reported that F16 inhibited the proliferation of MCF-7 human breast cancer cells by inducing apoptotic cell death while having some degree of cytoselectivity on a normal human breast cell line, MCF-10A. In this study, we attempted to further elucidate the mode of action of F16. We found that the intrinsic apoptotic pathway was invoked, with the reduction of Bcl-2 protein. Then, executioner caspase-7 was cleaved and activated in response to F16 treatment. Furthermore, apoptosis in the MCF- 7 cells was accompanied by the specific proteolytic cleavage of poly(ADP-ribose) polymerase-1 (PARP-1). Surprisingly, caspase-9 and p53 were unchanged with F16 treatment. We believe that the F16-induced apoptosis in MCF-7 cells occurs independently of caspase-9 and p53. Taken together, these results suggest that F16 from E. longifolia exerts anti-proliferative action and growth inhibition on MCF-7 cells through apoptosis induction and that it may have anticancer properties.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext Induction of apoptosis by Eurycoma longifolia jack extracts

Tee TT, Azimahtol HL

Anticancer Res, 2005 May-Jun;25(3B):2205-13.
PMID: 16158965

Extracts of the plant Eurycoma longifolia have been shown to possess cytotoxic, antimalarial, anti-ulcer, antipyretic and plant growth inhibition activities. The present study investigated the effects of extracts and their chromatographic fractions from the root of E. longifolia on the growth of a human breast cancer cell line, MCF-7. Our data indicated that E. longifolia extracts and fractions exert a direct antiproliferative activity on MCF-7. The bioassay-guided root fractionation resulted in the isolation of three active fractions, F5, F6 and F7, which displayed IC50 values of (6.17+/-0.38) microg/ml, (4.40+/-0.42) microg/ml and (20.00+/-0.08) microg/ml, respectively. The resultant from F7 purification, F16, exhibited a higher cytotoxic activity towards MCF-7, (IC50=15.23+/-0.66 microg/ml) and a certain degree of selectivity against a normal breast cell line, MCF-10A (IC50=66.31-0.47 microg/ml). F16 significantly increased apoptosis in MCF-7 cells, as evaluated by the Tdt-mediated dUTP nick end labelling assay and nuclear morphology. Western blotting revealed down-regulation of the anti-apoptotic Bcl-2 protein expression. F16, however, did not affect the expression of the pro-apoptotic protein, Bax. These results, therefore, suggest that F16 has antiproliferative effects on MCF-7 cells by inducing apoptosis through the modulation of Bcl-2 protein levels.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext Eurycoma longifolia Jack in managing idiopathic male infertility

Tambi MI, Imran MK

Asian J Androl, 2010 May;12(3):376-80.
PMID: 20348942 DOI: 10.1038/aja.2010.7

This study investigated the effect of treatment with the proprietary standardized, water-soluble extract of the root of the Malaysian plant, Eurycoma longifolia Jack, which is thought to enhance male fertility with regard to higher semen volumes, sperm concentrations, the percentage of normal sperm morphology and sperm motility in male partners of sub-fertile couples with idiopathic infertility. A total of 350 patients were given 200 mg of the extract daily and follow-up semen analyses were performed every 3 months for 9 months. Of these 350 patients, 75 patients completed one full cycle of 3 months. Follow-up semen analyses in these patients showed significant improvement in all semen parameters. The proprietary extract of Eurycoma longifolia Jack significantly improved the sperm quality in these patients, allowing for 11 (14.7%) spontaneous pregnancies.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext Eurycoma longifolia upregulates osteoprotegerin gene expression in androgen- deficient osteoporosis rat model

Shuid AN, El-arabi E, Effendy NM, Razak HS, Muhammad N, Mohamed N, et al.

BMC Complement Altern Med, 2012;12:152.
PMID: 22967165 DOI: 10.1186/1472-6882-12-152

Eurycoma longifolia (EL) has been shown recently to protect against bone calcium loss in orchidectomised rats, the model for androgen-deficient osteoporosis. The mechanism behind this is unclear but it may be related to its ability to elevate testosterone levels or it may directly affect bone remodeling. The aim of this study is to determine the mechanism involved by investigating the effects of EL extract on serum testosterone levels, bone biomarkers, biomechanical strength and gene expression of Receptor Activator of Nuclear Factor kappa-B ligand (RANKL), Osteoprotegerin (OPG) and Macrophage-Colony Stimulating Factor (MCSF) in orchidectomised rats.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext In vitro anti-Toxoplasma gondii activity of root extract/fractions of Eurycoma longifolia Jack

Kavitha N, Noordin R, Chan KL, Sasidharan S

BMC Complement Altern Med, 2012;12:91.
PMID: 22781137 DOI: 10.1186/1472-6882-12-91

Toxoplasma gondii infection causes toxoplasmosis, an infectious disease with worldwide prevalence. The limited efficiency of drugs against this infection, their side effects and the potential appearance of resistant strains make the search of novel drugs an essential need. We examined Eurycoma longifolia root extract and fractions as potential sources of new compounds with high activity and low toxicity. The main goal of this study was to investigate the anti-T. gondii activity of crude extract (TACME) and four fractions (TAF 273, TAF 355, TAF 191 and TAF 401) from E. longifolia, with clindamycin as the positive control.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext Effect of herbal extract Eurycoma longifolia (Physta®) on female reproductive hormones and bone biochemical markers: an ovariectomised rat model study

M Chinnappan S, George A, Ashok G, Choudhary YK

BMC Complement Med Ther, 2020 Feb 05;20(1):31.
PMID: 32024514 DOI: 10.1186/s12906-020-2814-z

BACKGROUND: Each year 1.5 million women experience menopause when menstrual cycles cease resulting from the loss of ovarian function and oestrogen deprivation, a hormone that helps prevent bone loss. This study investigated the effects of Physta®, a standardized herbal extract of Eurycoma longifolia Jack (PEL), on hormonal balance and parameters associated with hormonal imbalance, namely body and uterus weight and bone biochemical markers relevant in menopausal symptoms.
METHODS: Forty-eight Sprague Dawley rats were randomly divided into six groups of eight rats each: (A) Sham operated; control (B) Untreated (ovariectomised (OVX) with vehicle), (C) PEL 100 (OVX + 100 mg/kg body weight (bw)), (D) PEL 300 (OVX + 300 mg/kg bw), (E) PEL 500 (OVX + 500 mg/kg bw) and (F) Positive control, testosterone undecanoate (TU) (OVX+ 10 mg/kg bw). Group A and B received daily oral administrations of the vehicle, Group C-E received daily oral administration of PEL and Group F received testosterone undecanoate intramuscularly weekly. At the end of 8 weeks, serum calcium, phosphate, bone alkaline phosphatase (BALP), osteocalcin, follicle stimulating hormone (FSH), luteinising hormone (LH), oestrogen, progesterone and testosterone were measured, then the animals were sacrificed and uterus was isolated, while weight was recorded in all experimental groups.
RESULTS: Treatment of OVX rats with PEL at a dose of 500 mg/kg showed decreased serum FSH (P

Matched MeSH terms: Eurycoma/chemistry*
Fulltext First Report of Eurycoma longifolia Jack Root Extract Causing Relaxation of Aortic Rings in Rats

Tee BH, Hoe SZ, Cheah SH, Lam SK

Biomed Res Int, 2016;2016:1361508.
PMID: 27800486 DOI: 10.1155/2016/1361508

Although Eurycoma longifolia has been studied for erectile function, the blood pressure- (BP-) lowering effect has yet to be verified. Hence, this study aims at investigating the BP-lowering properties of the plant with a view to develop an antihypertensive agent that could also preserve erectile function. Ethanolic root extract was partitioned by hexane, dichloromethane (DCM), ethyl acetate, butanol, and water. The DCM fraction, found to be potent in relaxing phenylephrine- (PE-) precontracted rat aortic rings, was further purified by column chromatography. Subfraction DCM-II, being the most active in relaxing aortae, was studied for effects on the renin-angiotensin and kallikrein-kinin systems in aortic rings. The effect of DCM-II on angiotensin-converting enzyme (ACE) activity was also evaluated in vitro. Results showed that DCM-II reduced (p < 0.05) the contractions evoked by angiotensin I and angiotensin II (Ang II). In PE-precontracted rings treated with DCM-II, the Ang II-induced contraction was attenuated (p < 0.05) while bradykinin- (BK-) induced relaxation enhanced (p < 0.001). In vitro, DCM-II inhibited (p < 0.001) the activity of ACE. These data demonstrate that the vasodilatory effect of DCM-II appears to be mediated via inhibition of Ang II type 1 receptor and ACE as well as enhancement of Ang II type 2 receptor activation and BK activity.

Matched MeSH terms: Eurycoma/chemistry*
Fulltext The effect of eurycoma longifolia Jack on spermatogenesis in estrogen-treated rats

Wahab NA, Mokhtar NM, Halim WN, Das S

Clinics (Sao Paulo), 2010;65(1):93-8.
PMID: 20126351 DOI: 10.1590/S1807-59322010000100014

There is little data concerning the ability of Eurycoma longifolia Jack (EL) to reverse the inhibitory effects of estrogen on testosterone production and spermatogenesis. The aim of the present study was to determine the effect of EL on testicular histology and sperm count in estrogen-treated male rats.

Matched MeSH terms: Eurycoma/chemistry*
Efficacy of Tongkat Ali (Eurycoma longifolia) on erectile function improvement: systematic review and meta-analysis of randomized controlled trials

Kotirum S, Ismail SB, Chaiyakunapruk N

Complement Ther Med, 2015 Oct;23(5):693-8.
PMID: 26365449 DOI: 10.1016/j.ctim.2015.07.009

OBJECTIVE: To determine the efficacy of Tongkat Ali (Eurycoma longifolia) herbal extract on erectile function improvement.
METHODS: Comprehensive electronic databases were searched from inception through October 2014. Randomized controlled trials investigating Tongkat Ali compared to placebo were included. Outcome of interest was the improvement of erectile dysfunction. The difference of changes from baseline of the outcome between Tongkat Ali and placebo was pooled using weighted mean difference (WMD). Methodological quality of included studies was assessed using Jadad's quality scale and Cochrane's risk of bias.
RESULTS: Of the 342 articles identified, 2 studies involving a total of 139 participants were analyzed. No significance between group difference was found in the mean WMD of the change in the 5- item version of the international index of erectile function (IIEF-5) at week-12 (0.91; 95% CI: -1.50 to 3.33 with I(2)=89.5%, P-value=0.002) with statistical heterogeneity. Based on the subgroup analysis, significant improved IIEF-5 score of 2.15 (95% CI 1.03-3.27) was found in subjects with lower baseline IIEF-5 score, but this was not seen among those with higher baseline IIEF-5 score.
CONCLUSION: Based on current evidence, the herbal extract of Tongkat Ali may have clinical effect on erectile function. However, more efficacy trials are warranted to further support current evidence.
KEYWORDS: Alternative medicine; Erectile dysfunction; Eurycoma longifolia; Extract; Root; Tongkat Ali

Matched MeSH terms: Eurycoma/chemistry*
Eurycoma longifolia, A Potential Phytomedicine for the Treatment of Cancer: Evidence of p53-mediated Apoptosis in Cancerous Cells

Thu HE, Hussain Z, Mohamed IN, Shuid AN

Curr Drug Targets, 2018;19(10):1109-1126.
PMID: 28721818 DOI: 10.2174/1389450118666170718151913

BACKGROUND: Eurycoma longifolia is a well-documented herbal medicine that has gained widespread recognition due to its versatile pharmacological activities including anticancer, antimalarial, antimicrobial, antioxidant, aphrodisiac, anti-inflammatory, anxiolytic, anti-diabetic, antirheumatism and anti-ulcer. Plethora of in vitro and in vivo studies evidenced their excellent antiproliferative and anticancer efficacy against various types of human cancers.
OBJECTIVE: This review was aimed to critically analyze the therapeutic viability and anticancer efficacy of Eurycoma longifolia in the treatment of cancer and also to propose its molecular and translational mechanism of cytotoxicity against cancerous cells.
RESULTS: Among a range of medicinally active compounds isolated from various parts (roots, stem, bark and leaves) of Eurycoma longifolia, 16 compounds have shown promising anti-proliferative and anticancer efficacies. Eurycomanone, one of the most active medicinal compounds of Eurycoma longifolia, displayed a strong dose-dependent anticancer efficacy against lung carcinoma (A-549 cells) and breast cancer (MCF-7 cells); however, showed moderate efficacy against gastric (MGC-803 cells) and intestinal carcinomas (HT-29 cells). The prime mode of cytotoxicity of Eurycoma longifolia and its medicinal compounds is the induction of apoptosis (programmed cell death) via the up-regulation of the expression of p53 (tumor suppressor protein) and pro-apoptotic protein (Bax) and downregulation of the expression of anti-apoptotic protein (Bcl-2). A remarkable alleviation in the mRNA expression of various cancer-associated biomarkers including heterogeneous nuclear ribonucleoprotein (hnRNP), prohibitin (PHB), annexin-1 (ANX1) and endoplasmic reticulum protein-28 (ERp28) has also been evidenced.
CONCLUSION: Eurycoma longifolia and its medicinal constituents exhibit promising anticancer efficacy and thus can be considered as potential complementary therapy for the treatment of various types of human cancers.

Matched MeSH terms: Eurycoma/chemistry*
Recent Advances in Antibacterial, Antiprotozoal and Antifungal Trends of Eurycoma longifolia: A Review of Therapeutic Implications and Future Prospects

Thu HE, Hussain Z, Mohamed IN, Shuid AN

Curr Drug Targets, 2018;19(14):1657-1671.
PMID: 29468964 DOI: 10.2174/1389450119666180219123815

BACKGROUND: Eurycoma longifolia (E. longifolia) has gained widespread recognition due to its versatile pharmacological activities including aphrodisiac, anticancer, antimicrobial, antioxidant, anti-inflammatory, anxiolytic, anti-diabetic, ergogenic, insecticidal, anti-rheumatism, bone protection, and anti-ulcer effects.
OBJECTIVE: This review was aimed to critically overview the literature and summarizes the antibacterial, antiprotozoal, and antifungal trends of E. longifolia and its medicinally active components.
RESULTS: Besides its well-documented safety, efficacy, and tolerability, a plethora of in vitro, in vivo, and human clinical studies has evidenced the antimicrobial efficacy of E. longifolia and its bioactive constituents. Phytochemical screening of various types of extracts (methanolic, ethyl acetate, and nbutanolic) from different parts (roots, stem, and leaves) of E. longifolia displayed a dose-dependent antibacterial, antiprotozoal, and antifungal responses. Comparative analysis revealed that the root extract of E. longifolia exhibited the highest antimicrobial efficacy compared to other parts of the plant. Bioactivity-guided fractionation identified that among all of the medicinal compounds isolated/ extracted from different parts of E. longifolia, eurycomanone displayed the strongest antibacterial, antiprotozoal and antifungal activities.
CONCLUSION: Based on the critical analysis of the literature, we identified that E. longifolia exhibits promising antibacterial, antiprotozoal, and antifungal efficacies against various pathogenic microbes and thus can be considered as a potential complementary and alternative antimicrobial therapy.

Matched MeSH terms: Eurycoma/chemistry*
Contamination of mercury in tongkat Ali hitam herbal preparations

Ang HH, Lee KL

Food Chem Toxicol, 2006 Aug;44(8):1245-50.
PMID: 16567029 DOI: 10.1016/j.fct.2006.01.014

The DCA (Drug Control Authority), Malaysia has implemented the phase three registration of traditional medicines on 1 January 1992. As such, a total of 100 products in various pharmaceutical dosage forms of a herbal preparation found in Malaysia, containing tongkat Ali hitam, either single or combined preparations, were analyzed for the presence of a heavy toxic metal, mercury, using atomic absorption spectrophotometer, after performing a simple random sampling to enable each sample an equal chance of being selected in an unbiased manner. Results showed that 26% of these products possessed 0.53-2.35 ppm of mercury, and therefore, do not comply with the quality requirement for traditional medicines in Malaysia. The quality requirement for traditional medicines in Malaysia is not exceeding 0.5 ppm for mercury. Out of these 26 products, four products have already registered with the DCA, Malaysia whilst the rest, however, have not registered with the DCA, Malaysia.

Matched MeSH terms: Eurycoma/chemistry*
Determination of mercury by cold vapor atomic absorption spectrophotometer in Tongkat Ali preparations obtained in Malaysia

Ang HH, Lee EL, Cheang HS

Int J Toxicol, 2004 Jan-Feb;23(1):65-71.
PMID: 15162849 DOI: 10.1080/10915810490269654

The DCA (Drug Control Authority), Malaysia, has implemented the phase 3 registration of traditional medicines on 1 January 1992, with special emphasis on the quality, efficacy, and safety (including the presence of heavy metals) in all pharmaceutical dosage forms of traditional medicine preparations. As such, a total of 100 products in various pharmaceutical dosage forms of a herbal preparation, containing Tongkat Ali, were analyzed for mercury content using cold vapor atomic absorption spectrophotometer. Results showed that 36% of the above products possessed 0.52 to 5.30 ppm of mercury and, therefore, do not comply with the quality requirement for traditional medicines in Malaysia. Out of these 36 products, 5 products that possessed 1.05 to 4.41 ppm of mercury were in fact have already registered with the DCA, Malaysia. However, the rest of the products that contain 0.52 to 5.30 ppm of mercury still have not registered with the DCA, Malaysia. Although this study showed that only 64% of the products complied with the quality requirement for traditional medicines in Malaysia pertaining to mercury, they cannot be assumed safe from mercury contamination because of batch-to-batch inconsistency.

Matched MeSH terms: Eurycoma/chemistry*
Eurycoma longifolia Jack enhances sexual motivation in middle-aged male mice

Ang HH, Lee KL, Kiyoshi M

J Basic Clin Physiol Pharmacol, 2003;14(3):301-8.
PMID: 14964739 DOI: 10.1515/jbcpp.2003.14.3.301

Eurycoma longifolia Jack was investigated for sexual motivation activity in adult, middle-aged male mice and in retired breeders, using the modified open field and the modified runway choice methods. Each mouse received 500 mg/kg of one of 4 fractions of E. longifolia Jack, viz. chloroform, methanol, butanol, and water, whereas the mice in the control and yohimbine groups received 3 ml/kg of normal saline and 30 mg/kg of yohimbine daily respectively for 10 d. The results show a transient increase in the percentage of male mice responding to the right choice after chronic consumption of the fractions with 50 percent of the adult middle-aged male mice treated with E. longifolia Jack and yohimbine scoring the right choice after 8 and 5 days post-treatment respectively. In conclusion, this study has shown that E. longifolia Jack continues to enhance sexual motivation in adult, middle-aged male mice and in retired breeders.

Matched MeSH terms: Eurycoma/chemistry*
Effect of Eurycoma longifolia Jack on libido in middle-aged male rats

Ang HH, Lee KL

J Basic Clin Physiol Pharmacol, 2002;13(3):249-54.
PMID: 12670032 DOI: 10.1515/jbcpp.2002.13.3.249

The effect of increasing doses of various fractions of Eurycoma longifolia Jack extracts on libido was examined in middle-aged male rats. The results showed that a high dose (800 mg/kg) of all E. longifolia Jack extracts significantly increased mount frequency (MF) (P < 0.05) over that of untreated controls, but had no effect on the frequency of intromission or ejaculation. Methanol, chloroform, water, and butanol fractions exhibited MF of 2.5 +/- 0.1, 2.6 +/- 0.3, 2.5 +/- 0.1 and 2.6 +/- 0.2, respectively, in adult, middle-aged male rats, and retired breeders versus 2.3 +/- 0.1 in untreated controls. This translated to a minor increase in MF of 8.7%, 13.0%, 8.7%, and 13.0% for these fractions, respectively, during the 20-minute observation period. The results of this study show that E. longifolia Jack extracts can increase libido in middle-aged male rats.

Matched MeSH terms: Eurycoma/chemistry*
LC-PDA-MS/MS-Based Characterization of Key Phytochemicals in Eurycoma Longifolia Roots

Chua LS, Segaran A, Wong HJ

J Chromatogr Sci, 2021 Jun 21;59(7):659-669.
PMID: 33876232 DOI: 10.1093/chromsci/bmab041

The objective of the study was to fractionate the crude extract of Eurycoma longifolia (E. longifolia) roots and identify the intense peaks using HPLC-PDA-MS/MS, UPLC-MS/MS and H-NMR. Column chromatography was used to fractionate the crude extract into individual fractions using six solvent systems ranged from ethyl acetate, methanol and water in increasing polarity. Two fractions with nearly pure and intense peaks were selected for compound identification. Chromenone (coumarin) and chromone derivatives were putatively identified, besides several previously reported quassinoid glycosides (eurycomanone derived glycoside, 2,3-dehydro-4α-hydroxylongilactone glucoside, eurycomanol glycoside and eurycomanol trimer) in the fraction 11 of 100% methanol. A newly reported compound, namely hydroxyl glyyunanprosapogenin D (838 g/mol) was proposed to be the compound detected in the fraction 11 of 50% ethyl acetate and 50% methanol. This is also the first study to report the identification of chromenones and chromones in E. longifolia extract.

Matched MeSH terms: Eurycoma/chemistry*
Developing a validated liquid chromatography-mass spectrometric method for the simultaneous analysis of five bioactive quassinoid markers for the standardization of manufactured batches of Eurycoma longifolia Jack extract as antimalarial medicaments

Teh CH, Murugaiyah V, Chan KL

J Chromatogr A, 2011 Apr 8;1218(14):1861-77.
PMID: 21367427 DOI: 10.1016/j.chroma.2011.02.014

An extensive comparative study on the electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) mass spectrometry using automated flow injection analysis (FIA), was performed on eurycomanone (1), 13α(21)-epoxyeurycomanone (2), eurycomanol (3), eurycomanol-2-O-β-d-glucopyranoside (4), and 13,21-dihydroeurycomanone (5), the bioactive markers isolated from Eurycoma longifolia. The effects of eluent mixture (methanol or acetonitrile in water) and acidic modifiers (acetic acid, formic acid and trifluoroacetic acid) on the ionization efficiency of the markers were also investigated. The ESI in the positive ion mode with methanol containing 0.1% (v/v) acetic acid was selected for the subsequent optimization of nebulizer pressure, dry gas flow, dry gas temperature and capillary voltage to improve the sensitivity of the total ion chromatogram (TIC). Fragmentation of the analytes was further investigated by varying the capillary exit offset voltage and fragmentation amplitude in positive mode of ESI. The detection limits (LODs) were determined in isolation mode (selected ion monitoring, SIM). Their limits of detection (LODs) ranged between 0.03 and 0.1μgmL(-1) while the intra-day and inter-day precisions were less than 5.72% and 4.82%, respectively. The method was next applied for the simultaneous analysis of the markers to standardize various batches of manufactured extracts of E. longifolia for potential use as antimalarial products. Multiple Reaction Monitoring (MRM) mode was used for the quantification of analytes which gave protonated molecular ion, [M+H](+). For those without pseudo-molecular ions, SIM mode was used to quantify the analytes. The batches contained 5.65-9.95% of eurycomanone (1), 5.21-19.75% of eurycomanol (3) and 7.59-19.95% of eurycomanol-2-O-β-d-glucopyranoside (4) as major quassinoids whereas, 13α(21)-epoxyeurycomanone (2), and 13,21-dihydroeurycomanone (5) were much lower in concentrations of 0.78-3.90% and 0.47-1.76%, respectively.

Matched MeSH terms: Eurycoma/chemistry*
LC-MS/MS-based metabolites of Eurycoma longifolia (Tongkat Ali) in Malaysia (Perak and Pahang)

Chua LS, Amin NA, Neo JC, Lee TH, Lee CT, Sarmidi MR, et al.

J Chromatogr B Analyt Technol Biomed Life Sci, 2011 Dec 15;879(32):3909-19.
PMID: 22119436 DOI: 10.1016/j.jchromb.2011.11.002

A number of three LC-MS/MS hybrid systems (QTof, TripleTof and QTrap) has been used to profile small metabolites (m/z 100-1000) and to detect the targeted metabolites such as quassinoids, alkaloids, triterpene and biphenylneolignans from the aqueous extracts of Eurycoma longifolia. The metabolite profiles of small molecules showed four significant clusters in the principle component analysis for the aqueous extracts of E. longifolia, which had been collected from different geographical terrains (Perak and Pahang) and processed at different extraction temperatures (35°C and 100°C). A small peptide of leucine (m/z 679) and a new hydroxyl methyl β-carboline propionic acid have been identified to differentiate E. longifolia extracts that prepared at 35°C and 100°C, respectively. From the targeted metabolites identification, it was found that 3,4ɛ-dihydroeurycomanone (quassinoids) and eurylene (squalene-type triterpene) could only be detected in the Pahang extract, whereas canthin-6-one-3N-oxide could only be detected in the Perak extract. Overall, quassinoids were present in the highest concentration, particularly eurycomanone and its derivatives compared to the other groups of metabolites. However, the concentration of canthin-6-one and β-carboline alkaloids was significantly increased when the roots of the plant samples were extracted at 100°C.

Matched MeSH terms: Eurycoma/chemistry*

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