Eurycomalactone | CAS# 23062-24-0 | NF-κB inhibitor

MedKoo Cat#: 414159 | Name: Eurycomalactone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eurycomalactone is a natural product found in Eurycoma longifolia Jack., acts as a potent NF-κB inhibitor, with an IC50 of 0.5 μM. Eurycomalactone inhibits protein synthesis, depletes cyclin D1, but does not affect TNFα-induced degradation of IκBα or the phosphorylation of IKKα/β and IκBα.

Chemical Structure

Eurycomalactone

CAS#23062-24-0

Theoretical Analysis

MedKoo Cat#: 414159

Name: Eurycomalactone

CAS#: 23062-24-0

Chemical Formula: C19H24O6

Exact Mass: 348.1573

Molecular Weight: 348.39

Elemental Analysis: C, 65.50; H, 6.94; O, 27.55

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 420.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Eurycomalactone

IUPAC/Chemical Name

(1R,2R,5S,5aR,7aS,11S,11aS,11bR,12R)-1,11-dihydroxy-5a,8,11a,12-tetramethyl-1,5,5a,7,7a,11,11a,11b-octahydro-2,5-methanonaphtho[1,2-d]oxepine-4,6,10(2H)-trione

InChi Key

OGHYZHNTIINXEO-MGBQOKOWSA-N

InChi Code

InChI=1S/C19H24O6/c1-7-5-10(20)16(23)18(3)9(7)6-11(21)19(4)12-8(2)14(25-17(12)24)13(22)15(18)19/h5,8-9,12-16,22-23H,6H2,1-4H3/t8-,9+,12-,13+,14-,15-,16-,18+,19+/m1/s1

SMILES Code

C[C@]12[C@@]([C@H]([C@@]3([H])[C@@H]([C@]2([H])C(O3)=O)C)O)([H])[C@@]4([C@@](C(C)=CC([C@H]4O)=O)([H])CC1=O)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Eurycomalactone is a natural product found in Eurycoma longifolia Jack., acts as a potent NF-κB inhibitor, with an IC50 of 0.5 μM.

In vitro activity:

To determine the effect of ECL (eurycomalactone) on NSCLC cell viability in vitro, human lung cancer A549 (adenocarcinoma) and Calu-1 (squamous cell carcinoma) cells were incubated with various concentrations of ECL (0–160 µM) for 24 or 48 h, and cell viability was then examined by MTT assay. As revealed in Fig. 1B and C, ECL treatment significantly reduced the cell viability of both NSCLC cell lines in a concentration- and time-dependent manner. The ECL concentrations required for a 50% inhibition of cell viability (IC50) of A549 cells at 24 and 48 h (20.81±1.86 and 3.15±0.36 µM, respectively) were markedly lower compared with those required for the same inhibition of cell viability in Calu-1 cells (151.87±4.75 and 12.95±0.85 µM, respectively), indicating that ECL has a higher toxicity in A549 than Calu-1 cells. Table I summarizes the ECL concentrations at IC20, IC40 and IC50 after 24 and 48 h of incubation. The IC20, IC40 and IC50 concentrations of ECL at 24 h (2, 12 and 20 µM for A549 cells, and 10, 80 and 150 µM for Calu-1 cells) were used for subsequent experiments. Reference: Oncol Rep. 2020 Oct; 44(4): 1441–1454. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7448543/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 348.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Dukaew N, Chairatvit K, Pitchakarn P, Imsumran A, Karinchai J, Tuntiwechapikul W, Wongnoppavich A. Inactivation of AKT/NF‑κB signaling by eurycomalactone decreases human NSCLC cell viability and improves the chemosensitivity to cisplatin. Oncol Rep. 2020 Oct;44(4):1441-1454. doi: 10.3892/or.2020.7710. Epub 2020 Jul 31. PMID: 32945500; PMCID: PMC7448543. 2. Malainer C, Schachner D, Sangiovanni E, Atanasov AG, Schwaiger S, Stuppner H, Heiss EH, Dirsch VM. Eurycomalactone Inhibits Expression of Endothelial Adhesion Molecules at a Post-Transcriptional Level. J Nat Prod. 2017 Dec 22;80(12):3186-3193. doi: 10.1021/acs.jnatprod.7b00503. Epub 2017 Nov 17. PMID: 29148754; PMCID: PMC5744186.

In vitro protocol:

In vivo protocol:

TBD

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Enhancement of Radiosensitivity by Eurycomalactone in Human NSCLC Cells Through G₂/M Cell Cycle Arrest and Delayed DNA Double-Strand Break Repair. Oncol Res. 2020 Mar 27;28(2):161-175. doi: 10.3727/096504019X15736439848765. Epub 2019 Nov 14. PMID: 31727206; PMCID: PMC7851521. 5: Yunos NM, Wahab HA, Al-Thiabat MG, Sallehudin NJ, Jauri MH. In Vitro and In Silico Analysis of the Anticancer Effects of Eurycomanone and Eurycomalactone from Eurycoma longifolia. Plants (Basel). 2023 Jul 31;12(15):2827. doi: 10.3390/plants12152827. PMID: 37570981; PMCID: PMC10421158. 6: Dukaew N, Chairatvit K, Pitchakarn P, Imsumran A, Karinchai J, Tuntiwechapikul W, Wongnoppavich A. Inactivation of AKT/NF‑κB signaling by eurycomalactone decreases human NSCLC cell viability and improves the chemosensitivity to cisplatin. Oncol Rep. 2020 Oct;44(4):1441-1454. doi: 10.3892/or.2020.7710. Epub 2020 Jul 31. PMID: 32945500; PMCID: PMC7448543. 7: Miyake K, Tezuka Y, Awale S, Li F, Kadota S. Quassinoids from Eurycoma longifolia. J Nat Prod. 2009 Dec;72(12):2135-40. doi: 10.1021/np900486f. PMID: 19919052. 8: Tran TV, Malainer C, Schwaiger S, Atanasov AG, Heiss EH, Dirsch VM, Stuppner H. NF-κB inhibitors from Eurycoma longifolia. J Nat Prod. 2014 Mar 28;77(3):483-8. doi: 10.1021/np400701k. Epub 2014 Jan 27. PMID: 24467387; PMCID: PMC3971761. 9: Khanijo T, Jiraungkoorskul W. Review Ergogenic Effect of Long Jack, Eurycoma Longifolia. Pharmacogn Rev. 2016 Jul-Dec;10(20):139-142. doi: 10.4103/0973-7847.194041. PMID: 28082797; PMCID: PMC5214558. 10: Bhat R, Karim AA. Tongkat Ali (Eurycoma longifolia Jack): a review on its ethnobotany and pharmacological importance. Fitoterapia. 2010 Oct;81(7):669-79. doi: 10.1016/j.fitote.2010.04.006. Epub 2010 Apr 29. PMID: 20434529. 11: Bräuer P, Anielski P, Schwaiger S, Stuppner H, Tran TVA, Vollmer G, Zierau O, Thieme D, Keiler AM. In vitro metabolism of selected bioactive compounds of Eurycoma longifolia root extract to identify suitable markers in doping control. Drug Test Anal. 2019 Jan;11(1):86-94. doi: 10.1002/dta.2449. Epub 2018 Aug 9. PMID: 29975460. 12: Ezzat SM, Okba MM, Ezzat MI, Aborehab NM, Mohamed SO. Rho-Kinase II Inhibitory Potential of Eurycoma longifolia New Isolate for the Management of Erectile Dysfunction. Evid Based Complement Alternat Med. 2019 May 15;2019:4341592. doi: 10.1155/2019/4341592. PMID: 31223329; PMCID: PMC6541974. 13: Ang HH, Hitotsuyanagi Y, Fukaya H, Takeya K. Quassinoids from Eurycoma longifolia. Phytochemistry. 2002 Apr;59(8):833-7. doi: 10.1016/s0031-9422(01)00480-0. PMID: 11937162. 14: Han YM, Jang M, Kim IS, Kim SH, Yoo HH. Simultaneous quantitation of six major quassinoids in Tongkat Ali dietary supplements by liquid chromatography with tandem mass spectrometry. J Sep Sci. 2015 Jul;38(13):2260-6. doi: 10.1002/jssc.201500207. Epub 2015 Jun 11. PMID: 25914245. 15: Chan KL, Choo CY, Abdullah NR, Ismail Z. Antiplasmodial studies of Eurycoma longifolia Jack using the lactate dehydrogenase assay of Plasmodium falciparum. J Ethnopharmacol. 2004 Jun;92(2-3):223-7. doi: 10.1016/j.jep.2004.02.025. PMID: 15138004. 16: Effah Z, Li L, Xie J, Karikari B, Xu A, Wang L, Du C, Duku Boamah E, Adingo S, Zeng M. Widely untargeted metabolomic profiling unearths metabolites and pathways involved in leaf senescence and N remobilization in spring-cultivated wheat under different N regimes. Front Plant Sci. 2023 May 16;14:1166933. doi: 10.3389/fpls.2023.1166933. PMID: 37260937; PMCID: PMC10227437. 17: Choonong R, Ruangdachsuwan S, Churod T, Palabodeewat S, Punyahathaikul S, Juntarapornchai S, Ketsuwan K, Komaikul J, Masrinoul P, Kitisripanya T, Juengwatanatrakul T, Yusakul G, Kanchanapoom T, Putalun W. Evaluating the in Vitro Efficacy of Quassinoids from Eurycoma longifolia and Eurycoma harmandiana against Common Cold Human Coronavirus OC43 and SARS- CoV-2 Using In-Cell Enzyme-Linked Immunosorbent Assay. J Nat Prod. 2022 Dec 23;85(12):2779-2788. doi: 10.1021/acs.jnatprod.2c00736. Epub 2022 Nov 18. PMID: 36399766. 18: Chan KL, Choo CY, Morita H, Itokawa H. High performance liquid chromatography in phytochemical analysis of Eurycoma longifolia. Planta Med. 1998 Dec;64(8):741-5. doi: 10.1055/s-2006-957570. PMID: 17253320. 19: Miyake K, Li F, Tezuka Y, Awale S, Kadota S. Cytotoxic activity of quassinoids from Eurycoma longifolia. Nat Prod Commun. 2010 Jul;5(7):1009-12. PMID: 20734929.