Comparative X‐Ray and Conformational Analysis of a New Crystal of 13<i>α</i>,21-Dihydroeurycomanone with Eurycomanone from<i>Eurycoma longifolia</i>and Their Anti-Estrogenic Activity Using the Uterotrophic Assay

Teh, Chin-Hoe; Abdulghani, Mahfoudh; Morita, Hiroshi; Shiro, Motoo; Hussin, Abas Hj; Chan, Kit‐Lam

doi:10.1055/s-0030-1250159

Cited by 20 publications

(14 citation statements)

References 27 publications

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“…The known constituents were identified as eurycomalactone ( 2 ), 19 7α-hydroxyeurycomalactone ( 3 ), 20 5,6-dehydroeurycomalactone ( 4 ), 4 eurycolactone E ( 5 ), 21 longilactone ( 6 ), 22 14,15β-dihydroklaieanone ( 7 ), 23 11-dehydroklaieanone ( 8 ), 24 eurycomanone ( 9 ), 22,25,26 13,21-dehydroeurycomanone ( 10 ), 22 laurycolactone A ( 11 ), 5 laurycolactone B ( 12 ), 5 1-methoxycarbonyl-β-carboline ( 13 ), 27 9-hydroxycanthin-6-one ( 14 ), 28 9-methoxycanthin-6-one ( 15 ), 28 9,10-dimethoxycanthin-6-one ( 16 ), 9 5-methoxy-4-hydroxycanthin-6-one ( 17 ), 29 canthin-6-one 9- O -β- d -glucoside ( 18 ), 30 scopoletin ( 19 ), 31 fraxidin ( 20 ), 31 eurylene ( 21 ), 12 pedunculoside ( 22 ), 32 vanillic acid ( 23 ), vanillic aldehyde ( 24 ), syringic acid ( 25 ), 1,1′-biphenyl-3,3′-dicarboxylic acid ( 26 ), isoaloeresin D ( 27 ), 33 and 3,5,6,7,8,3′,4′-heptamethoxyflavone ( 28 ). 34 Compound identification was carried out by means of mass spectrometry and NMR spectroscopy as well as by comparison of physical and spectroscopic data with those of reference compounds reported in the literature.…”

Section: Results and Discussionmentioning

confidence: 99%

NF-κB Inhibitors from Eurycoma longifolia

et al. 2014

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The roots of Eurycoma longifolia have been used in many countries of Southeast Asia to alleviate various diseases including malaria, dysentery, sexual insufficiency, and rheumatism. Although numerous studies have reported the pharmacological properties of E. longifolia, the mode of action of the anti-inflammatory activity has not been elucidated. Bioguided isolation of NF-κB inhibitors using an NF-κB-driven luciferase reporter gene assay led to the identification of a new quassinoid, eurycomalide C (1), together with 27 known compounds including 11 quassinoids (2–12), six alkaloids (13–18), two coumarins (19, 20), a squalene derivative (21), a triterpenoid (22), and six phenolic compounds (23–28) from the extract of E. longifolia. Evaluation of the biological activity revealed that C19-type and C20-type quassinoids, β-carboline, and canthin-6-one alkaloids are potent NF-κB inhibitors, with IC50 values in the low micromolar range, while C18-type quassinoids, phenolic compounds, coumarins, the squalene derivative, and the triterpenoid turned out to be inactive when tested at a concentration of 30 μM. Eurycomalactone (2), 14,15β-dihydroklaieanone (7), and 13,21-dehydroeurycomanone (10) were identified as potent NF-κB inhibitors with IC50 values of less than 1 μM.

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Section: Results and Discussionmentioning

confidence: 99%

NF-κB Inhibitors from Eurycoma longifolia

et al. 2014

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“…The eurycomanone ( 1 ; Purity > 96%), eurycomanol ( 2 ; Purity > 95%), 13α,21‐dihydroeurycomanone ( 3 ; Purity > 95%) and 13α(21)‐epoxyeurycomanone ( 4 ; Purity > 95%) (Fig. ) were isolated and purified following the protocol described previously (Teh et al ., , , ). The purity of the compounds was determined with Empower 2 workstation software (Waters, Milford, MA, USA) operated in a Waters Delta Prep HPLC system equipped with a Waters 2996 photodiode array detector.…”

Section: Methodsmentioning

confidence: 99%

“…The eurycomanone (1; Purity > 96%), eurycomanol (2; Purity > 95%), 13α,21dihydroeurycomanone (3; Purity > 95%) and 13α(21)epoxyeurycomanone (4; Purity > 95%) ( Fig. 1) were isolated and purified following the protocol described previously (Teh et al, 2010(Teh et al, , 2011a(Teh et al, , 2011b 13 C NMR (C 5 D 5 N, 175 MHz): 10.9 (C-19), 23 (C-18), 26.2 (C-6), 42.7 (C-5), 46.5 (C-10), 48.3 (C-9), 53.1 (C-8), 68.2 (C-20), 72.3 (C-15), 76.4 (C-7), 79.9 (C-14), 81.5 (C-12), 85 (C-1), 110.1 (C-11), 119.9 (C-21), 126.6 (C-3), 148.5 (C-13), 163.1 (C-4), 174.4 (C-16), 198 (C-2). Analysis of chemical content in E. longifolia extract by HPLC.…”

Section: Methodsmentioning

confidence: 99%

Acute, Reproductive Toxicity and Two‐generation Teratology Studies of a Standardized Quassinoid‐rich Extract of Eurycoma longifolia Jack in Sprague–Dawley Rats

Low

Das²,

Chan

2013

Phytotherapy Research

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The roots of Eurycoma longifolia Jack are popularly sought as herbal medicinal supplements to improve libido and general health amongst the local ethnic population. The major quassinoids of E. longifolia improved spermatogenesis and fertility but toxicity studies have not been well documented. The reproductive toxicity, two generation of foetus teratology and the up-and-down acute toxicity were investigated in Sprague-Dawley rats orally treated with quassinoid-rich E. longifolia extract (TAF273). The results showed that the median lethal dose (LD50 ) of TAF273 for female and male rats was 1293 and >2000 mg/kg, respectively. Fertility index and litter size of the TAF273 treated were significantly increased when compared with those of the non-treated animals. The TAF273-treated dams decreased in percentage of pre-implantation loss, post-implantation loss and late resorption. No toxic symptoms were observed on the TAF273-treated pregnant female rats and their foetuses were normal. The no-observed adverse effect level (NOAEL) obtained from reproductive toxicity and teratology studies of TAF273 in rats was 100 mg/kg body weight/day, being more than 10-fold lower than the LD50 value. Thus, any human dose derived from converting the rat doses of 100 mg/kg and below may be considered as safe for further clinical studies.

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“…Eurycomanone is the major quassinoid found in E. longifolia extracts, and it is supposed to be primarily responsible for the pharmacological or biological activities of E. longifolia , as mentioned earlier (Chan, Choo, Morita, & Itokawa, ; Chua et al, ; Han, Kim, Rehman, Choe, & Yoo, ; Han, Jang, Kim, Kim, & Yoo, ; Low, Choi, Wahab, Das, & Chan, ; Low et al, ; Miyake, Tezuka, Awale, Li, & Kadota, ; Teh et al, ; Wong et al, ; Zakaria, Rahmat, Pihie, Abdullah, & Houghton, ). It has been reported that the content of eurycomanone in E. longifolia root extracts reaches 9.95% (Han et al, , ; Teh, Murugaiyah, & Chan, ).…”

Section: Introductionmentioning

confidence: 82%

Determination of eurycomanone in rat plasma using hydrophilic interaction liquid chromatography–tandem mass spectrometry for pharmacokinetic study

Rehman

Choi

Han

et al. 2016

Biomedical Chromatography

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In this study, a rapid, sensitive, and reliable hydrophilic interaction liquid chromatography-tandem mass spectrometry (HILIC-MS/MS) method for the determination of eurycomanone in rat plasma was developed and validated. Plasma samples were pretreated with a protein precipitation method and quercitrin was used as an internal standard (IS). A HILIC silica column (2.1 × 100 mm, 3 μm) was used for hydrophilic-based chromatographic separation, using the mobile phase of 0.1% formic acid with acetonitrile in gradient elution at a flow rate of 0.25 mL/min. Precursor-product ion pairs for multiple-reaction monitoring were m/z 409.1 → 391.0 for eurycomanone and m/z 449.1 → 303.0 for IS. The linear range was 2-120 ng/mL. The intra- and inter-day accuracies were between 95.5 and 103.4% with a precision of <4.2%. The developed method was successfully applied to the pharmacokinetic analysis of eurycomanone in rat plasma after oral dosing with pure compound and E. longifolia extract. The C and AUC , respectively, were 40.43 ± 16.08 ng/mL and 161.09 ± 37.63 ng h/mL for 10 mg/kg eurycomanone, and 9.90 ± 3.97 ng/mL and 37.15 ± 6.80 ng h/mL for E. longifolia extract (2 mg/kg as eurycomanone). The pharmacokinetic results were comparable with each other, based on the dose as eurycomanone.

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Comparative X‐Ray and Conformational Analysis of a New Crystal of 13α,21-Dihydroeurycomanone with Eurycomanone fromEurycoma longifoliaand Their Anti-Estrogenic Activity Using the Uterotrophic Assay

Cited by 20 publications

References 27 publications

NF-κB Inhibitors from Eurycoma longifolia

NF-κB Inhibitors from Eurycoma longifolia

Acute, Reproductive Toxicity and Two‐generation Teratology Studies of a Standardized Quassinoid‐rich Extract of Eurycoma longifolia Jack in Sprague–Dawley Rats

Determination of eurycomanone in rat plasma using hydrophilic interaction liquid chromatography–tandem mass spectrometry for pharmacokinetic study

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