Eurycomanone (Pasakbumin A)
(Synonyms: 宽缨酮,Pasakbumin A) 目录号 : GC32430
A quassinoid with diverse biological activities
Cas No.:84633-29-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Eurycomanone is a quassinoid originally isolated from E. longifolia that has diverse biological activities.1 It is active against the W2 and D6 clones of P. falciparum (IC50s = 0.015 and 0.026 ?g/ml, respectively).2 Eurycomanone induces lipolysis in 3T3-L1 adipocytes with an EC50 value of 14.6 ?M, an effect that can be blocked by the protein kinase A (PKA) inhibitor H-89 .3 It induces cell cycle arrest at the G2/M phase and apoptosis in HepG2 cells when used at a concentration of 5 ?g/ml.4 It reduces estrogen release and increases testosterone release in isolated rat Leydig cell-rich testicular interstitial cell preparations when used at concentrations of 1 and 10 ?M.5 Eurycomanone (1 mg/kg, i.p.) decreases gastric acid secretion and lesion size in rat models of indomethacin-, water immersion stress-, or pyloric ligation-induced ulcer formation.6
1.Darise, M., Kohda, H., Mizutani, K., et al.Eurycomanone and eurycomanol, quassinoids from the roots of Eurycoma longifoliaPhytochemistry21(8)2091-2093(1982) 2.Kuo, P.-C., Damu, A.G., Lee, K.-H., et al.Cytotoxic and antimalarial constituents from the roots of Eurycoma longifoliaBioorg. Med. Chem.12(3)537-544(2004) 3.Lahrita, L., Hirosawa, R., Kato, E., et al.Isolation and lipolytic activity of eurycomanone and its epoxy derivative from Eurycoma longifoliaBioorg. Med. Chem.25(17)4829-4834(2017) 4.Zakaria, Y., Rahmat, A., Pihie, A.H.L., et al.Eurycomanone induce apoptosis in HepG2 cells via up-regulation of p53Cancer Cell Int.9(2009) 5.Low, B.-S., Choi, S.-B., Wahab, H.A., et al.Eurycomanone, the major quassinoid in Eurycoma longifolia root extract increases spermatogenesis by inhibiting the activity of phosphodiesterase and aromatase in steroidogenesisJ. Ethnopharmacol.149(1)201-207(2013) 6.Tada, H., Yasuda, F., Otani, K., et al.New antiulcer quassinoids from Eurycoma longifoliaEur. J. Med. Chem.26(3)345-349(1991)
| Cas No. | 84633-29-4 | SDF | |
| 别名 | 宽缨酮,Pasakbumin A | ||
| Canonical SMILES | O[C@@]1([C@H]2O)[C@@]34[C@@]([C@](OC4)(O)[C@H](O)C1=C)([H])[C@]([C@@](C(C)=CC5=O)([H])C[C@@]3([H])OC2=O)([C@@H]5O)C | ||
| 分子式 | C20H24O9 | 分子量 | 408.4 |
| 溶解度 | DMSO: 16.67 mg/mL (40.82 mM) | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4486 mL | 12.2429 mL | 24.4858 mL |
| 5 mM | 0.4897 mL | 2.4486 mL | 4.8972 mL |
| 10 mM | 0.2449 mL | 1.2243 mL | 2.4486 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The botanical Eurycomanone is a potent growth regulator of the diamondback moth
Ecotoxicol Environ Saf 2021 Jan 15;208:111647.PMID:33396167DOI:10.1016/j.ecoenv.2020.111647.
Eurycomanone is a quassinoid compound that is derived from Eurycoma longifolia, and it is often used as an indicator to evaluate the active ingredients of Eurycoma longifolia. However, Eurycomanone has rarely been reported to have biological activity toward pests. In this study, we evaluated the antifeedant activity of Eurycomanone against the diamondback moth(Plutella xylostella), with a non-selective AFC50(the concentration that corresponds to 50% antifeedant action) value and selective AFC50 of 17.5 mg/L and 14.2 mg/L, respectively, which were 2.1-fold (36.9 mg/L) and 2-fold (28.5 mg/L) lower than that of azadirachtin, respectively. In addition, Eurycomanone was used to treat the roots of Brassica chinensis L. at a concentration of 100 碌g/g for 72 h. The antifeedant index was found to reach 93% by tracking the leaves. After feeding with 20 碌g/g Eurycomanone, no pupae or eclosion were observed. To explore this mechanism, we used scanning electron microscopy to discover that Eurycomanone could prevent the development of taste receptors on the maxillary palp of diamondback moth larvae. Additional electrophysiological measurements showed that Eurycomanone exhibited excitatory action to the central taste neurons of diamondback moth and significantly inhibited the GABAA receptor current. Eurycomanone exhibited significant activity as an antifeedant, inhibited growth and excelled at systemic absorption.
Pasakbumin A controls the growth of Mycobacterium tuberculosis by enhancing the autophagy and production of antibacterial mediators in mouse macrophages
PLoS One 2019 Mar 13;14(3):e0199799.PMID:30865638DOI:10.1371/journal.pone.0199799.
Tuberculosis (TB) is a chronic infectious disease caused by Mycobacterium tuberculosis (Mtb) and remains a major health problem worldwide. Thus, identification of new and more effective drugs to treat emerging multidrug-resistant TB (MDR-TB) and to reduce the side effects of anti-TB drugs, such as liver toxicity and other detrimental changes, is urgently needed. In this study, to develop a novel candidate drug for effective TB treatment with few side effects in the host, we selected Pasakbumin A isolated from Eurycoma longifolia (E. longifolia) Jack, which protected host cells against Mtb infection-induced death. Pasakbumin A significantly inhibited intracellular Mtb growth by inducing the autophagy via the ERK1/2-mediated signaling pathway in Mtb-infected macrophages. We further investigated whether Pasakbumin A could be used as a potential adjuvant for TB treatment. Treatment with Pasakbumin A and anti-TB drug rifampicin (RMP) potently suppressed intracellular Mtb killing by promoting autophagy as well as TNF-伪 production via the ERK1/2- and NF-魏B-mediated signaling pathways in Mtb-infected cells. Our results suggest that Pasakbumin A could be developed as a novel anti-TB drug or host-directed therapeutic (HDT) strategy to protect against host cell death and improve host defense mechanisms against Mtb infection in macrophages.
Bioavailability of Eurycomanone in Its Pure Form and in a Standardised Eurycoma longifolia Water Extract
Pharmaceutics 2018 Jul 11;10(3):90.PMID:29997335DOI:10.3390/pharmaceutics10030090.
Eurycoma longifolia is one of the commonly consumed herbal preparations and its major chemical compound, Eurycomanone, has been described to have antimalarial, antipyretic, aphrodisiac, and cytotoxic activities. Today, the consumption of E. longifolia is popular through the incorporation of its extract in food items, most frequently in drinks such as tea and coffee. In the current study, the characterisation of the physicochemical and pharmacokinetic (PK) attributes of Eurycomanone were conducted via a series of in vitro and in vivo studies in rats and mice. The solubility and chemical stability of Eurycomanone under the conditions of the gastrointestinal tract environment were determined. The permeability of Eurycomanone was investigated by determining its distribution coefficient in aqueous and organic environments and its permeability using the parallel artificial membrane permeability assay system and Caco-2 cultured cells. Eurycomanone's stability in plasma and its protein-binding ability were measured by using an equilibrium dialysis method. Its stability in liver microsomes across species (mice, rat, dog, monkey, and human) and rat liver hepatocytes was also investigated. Along with the PK evaluations of Eurycomanone in mice and rats, the PK parameters for the Malaysian Standard (MS: 2409:201) standardised water extract of E. longifolia were also evaluated in rats. Both rodent models showed that Eurycomanone in both the compound form and extract form had a half-life of 0.30 h. The differences in the bioavailability of Eurycomanone in the compound form between the rats (11.8%) and mice (54.9%) suggests that the PK parameters cannot be directly extrapolated to humans. The results also suggest that Eurycomanone is not readily absorbed across biological membranes. However, once absorbed, the compound is not easily metabolised (is stable), hence retaining its bioactive properties, which may be responsible for the various reported biological activities.
A Quassinoid Diterpenoid Eurycomanone from Eurycoma longifolia Jack Exerts Anti-Cancer Effect through Autophagy Inhibition
Molecules 2022 Jul 8;27(14):4398.PMID:35889271DOI:10.3390/molecules27144398.
Eurycomanone (EN) is one of the representative quassinoid diterpenoids from roots of Eurycoma longifolia Jack, a natural medicine that is widely distributed in Southeast Asia. Previous studies showed that EN induces cancer cell apoptosis and exhibits anti-cancer activity, but the molecular mechanism of EN against cancer has still not been elucidated. In this study, we examined the regulatory effect of EN on autophagy to reveal the mechanism of EN-mediated colon cancer growth inhibition. First, we found that EN is able to inhibit colon cancer cell proliferation and colony formation. The angiogenesis level in cancer cells was inhibited as well. Next, the treatment of EN led to the suppression of autophagy, which was characterized by the downregulation of the LC3-II level and the formation of GFP-LC3 puncta under EN treatment in colon cancer. Moreover, we revealed that the mTOR signaling pathway was activated by EN in a time- and concentration-dependent manner. Finally, autophagy induction protected colon cancer cells from EN treatment, suggesting that autophagy improves cell survival. Taken together, our findings revealed the mechanism of EN against colon cancer through inhibiting autophagy and angiogenesis in colon cancer, supporting that the autophagy inhibitor EN could be developed to be a novel anti-cancer agent.
Antiadipogenic effects of a standardized quassinoids-enriched fraction and Eurycomanone from Eurycoma longifolia
Phytother Res 2018 Jul;32(7):1332-1345.PMID:29520860DOI:10.1002/ptr.6065.
Bioactive compounds of Eurycoma longifolia (EL) jack were previously shown to reduce omentum fat mass and oestradiol-induced fatty uterine adhesion in rats. However, the exact role of EL on adipogenesis remains unknown. This study sought to investigate the effects of an EL standardized quassinoids-enriched fraction (SQEL) and the pure compound, Eurycomanone, on adipogenesis in 3T3-L1 preadipocyte cells. 3T3-L1 cells were induced to differentiate and treated for 8 days. The treatment reduced intracellular accumulation of lipid droplets and triglycerides in the differentiating adipocytes and induced lipolysis in matured adipocytes. The expressions of adipogenic transcription factors and markers were also significantly downregulated during the early stage of differentiation. Furthermore, SQEL also suppressed body weight gain, decreased epididymal and perirenal fat pad mass and size, and reduced the accumulation of fat in the livers of C57BL/6J mice fed with normal or high-fat diet that were concurrently given 5 mg/kg and 10 mg/kg (i.p) of SQEL for 12 weeks. SQEL also improved glucose intolerance and decreased the elevated total cholesterol and triglyceride levels in these mice groups. These findings suggest that SQEL could be explored as an alternative pharmacologic agent inhibiting adipogenesis for the prevention of obesity.