Episilvestrol
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MedKoo CAT#: 333063

CAS#: 697235-39-5

Description: Episilvestrol, a derivative of silvestrol, is isolated from the fruits and twigs of Aglaia silvestris, Episilvestrol exhibited potent in vitro cytotoxic activity


Chemical Structure

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Episilvestrol
CAS# 697235-39-5

Theoretical Analysis

MedKoo Cat#: 333063
Name: Episilvestrol
CAS#: 697235-39-5
Chemical Formula: C34H38O13
Exact Mass: 654.2312
Molecular Weight: 654.665
Elemental Analysis: C, 62.38; H, 5.85; O, 31.77

Price and Availability

Size Price Availability Quantity
25.0mg USD 6450.0 2 Weeks
50.0mg USD 9450.0 2 Weeks
100.0mg USD 14950.0 2 Weeks
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Synonym: Episilvestrol

IUPAC/Chemical Name: methyl (1R,2R,3S,3aR,8bS)-6-(((2S,3R,6R)-6-((S)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate

InChi Key: GVKXFVCXBFGBCD-JRPGFILLSA-N

InChi Code: InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25+,26+,27+,29+,31+,32+,33-,34-/m0/s1

SMILES Code: O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=CC(O[C@@H]6O[C@@H]([C@@H](O)CO)CO[C@H]6OC)=CC(OC)=C35)OC

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

Product Data:

Biological target: Apoptosis Inducer
In vitro activity: Episilvestrol has limited plasma membrane permeability and is metabolized in liver microsomes in a manner consistent with that reported for Silvestro In addition, a series of analogues of these compounds were prepared where the complex pseudo-sugar at C6 has been replaced with chemically simpler moieties to improve drug-likeness. Selected compounds from this work possess excellent activity in biochemical and cellular translation assays with potent activity against leukemia cell lines. Reference: Hawkins BC, Lindqvist LM, Nhu D, Sharp PP, Segal D, Powell AK, Campbell M, Ryan E, Chambers JM, White JM, Rizzacasa MA, Lessene G, Huang DC, Burns CJ. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul;9(7):1556-66. doi: 10.1002/cmdc.201400024. Epub 2014 Mar 27. PMID: 24677741.
In vivo activity: It is demonstrated that eukaryotic initiation factors eIF4AI/II were the only proteins detected to bind silvestrol (1) and biotinylated episilvestrol (9) by affinity purification. This study demonstrates the remarkable selectivity of these promising chemotherapeutics. Reference: Chambers JM, Lindqvist LM, Webb A, Huang DC, Savage GP, Rizzacasa MA. Synthesis of biotinylated episilvestrol: highly selective targeting of the translation factors eIF4AI/II. Org Lett. 2013 Mar 15;15(6):1406-9. doi: 10.1021/ol400401d. Epub 2013 Mar 5. PMID: 23461621.

Preparing Stock Solutions

The following data is based on the product molecular weight 654.665 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.

Recalculate based on batch purity %
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: Hawkins BC, Lindqvist LM, Nhu D, Sharp PP, Segal D, Powell AK, Campbell M, Ryan E, Chambers JM, White JM, Rizzacasa MA, Lessene G, Huang DC, Burns CJ. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul;9(7):1556-66. doi: 10.1002/cmdc.201400024. Epub 2014 Mar 27. PMID: 24677741.
In vitro protocol: Hawkins BC, Lindqvist LM, Nhu D, Sharp PP, Segal D, Powell AK, Campbell M, Ryan E, Chambers JM, White JM, Rizzacasa MA, Lessene G, Huang DC, Burns CJ. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul;9(7):1556-66. doi: 10.1002/cmdc.201400024. Epub 2014 Mar 27. PMID: 24677741.
In vivo protocol: Chambers JM, Lindqvist LM, Webb A, Huang DC, Savage GP, Rizzacasa MA. Synthesis of biotinylated episilvestrol: highly selective targeting of the translation factors eIF4AI/II. Org Lett. 2013 Mar 15;15(6):1406-9. doi: 10.1021/ol400401d. Epub 2013 Mar 5. PMID: 23461621.

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1: Burgers LD, Fürst R. Natural products as drugs and tools for influencing core processes of eukaryotic mRNA translation. Pharmacol Res. 2021 May 29;170:105535. doi: 10.1016/j.phrs.2021.105535. Epub ahead of print. PMID: 34058326.

2: Huang DN, Wang S, Sooranna SR, Miao JH. The efficacy of natural bioactive compounds for the treatment of nasopharyngeal carcinoma. Mini Rev Med Chem. 2021 Jan 4. doi: 10.2174/1389557521666210105113831. Epub ahead of print. PMID: 33402084.

3: Agarwal G, Wilson JR, Kurina SJ, Anaya-Eugenio GD, Ninh TN, Burdette JE, Soejarto DD, Cheng X, Carcache de Blanco EJ, Rakotondraibe LH, Kinghorn AD. Structurally Modified Cyclopenta[b]benzofuran Analogues Isolated from Aglaia perviridis. J Nat Prod. 2019 Oct 25;82(10):2870-2877. doi: 10.1021/acs.jnatprod.9b00631. Epub 2019 Oct 17. PMID: 31621322; PMCID: PMC6819999.

4: Li X, Li M, Ruan H, Qiu W, Xu X, Zhang L, Yu J. Co-targeting translation and proteasome rapidly kills colon cancer cells with mutant RAS/RAF via ER stress. Oncotarget. 2017 Feb 7;8(6):9280-9292. doi: 10.18632/oncotarget.14063. Erratum in: Oncotarget. 2018 Jan 22;9(6):7271. PMID: 28030835; PMCID: PMC5354731.

5: Daker M, Yeo JT, Bakar N, Abdul Rahman AS, Ahmad M, Yeo TC, Khoo AS. Inhibition of nasopharyngeal carcinoma cell proliferation and synergism of cisplatin with silvestrol and episilvestrol isolated from Aglaia stellatopilosa. Exp Ther Med. 2016 Jun;11(6):2117-2126. doi: 10.3892/etm.2016.3201. Epub 2016 Mar 29. PMID: 27284293; PMCID: PMC4887938.

6: Othman N, Pan L, Mejin M, Voong JC, Chai HB, Pannell CM, Kinghorn AD, Yeo TC. Cyclopenta[b]benzofuran and Secodammarane Derivatives from the Stems of Aglaia stellatopilosa. J Nat Prod. 2016 Apr 22;79(4):784-91. doi: 10.1021/acs.jnatprod.5b00810. Epub 2016 Mar 14. PMID: 26974604; PMCID: PMC4841703.

7: Hawkins BC, Lindqvist LM, Nhu D, Sharp PP, Segal D, Powell AK, Campbell M, Ryan E, Chambers JM, White JM, Rizzacasa MA, Lessene G, Huang DC, Burns CJ. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul;9(7):1556-66. doi: 10.1002/cmdc.201400024. Epub 2014 Mar 27. PMID: 24677741.

8: Chambers JM, Lindqvist LM, Webb A, Huang DC, Savage GP, Rizzacasa MA. Synthesis of biotinylated episilvestrol: highly selective targeting of the translation factors eIF4AI/II. Org Lett. 2013 Mar 15;15(6):1406-9. doi: 10.1021/ol400401d. Epub 2013 Mar 5. PMID: 23461621.

9: Chambers JM, Huang DC, Lindqvist LM, Savage GP, White JM, Rizzacasa MA. Total synthesis of 2''',5'''-diepisilvestrol and its C1''' epimer: key structure activity relationships at C1''' and C2'''. J Nat Prod. 2012 Aug 24;75(8):1500-4. doi: 10.1021/np300376f. Epub 2012 Jul 20. PMID: 22817615.

10: Pan L, Kardono LB, Riswan S, Chai H, Carcache de Blanco EJ, Pannell CM, Soejarto DD, McCloud TG, Newman DJ, Kinghorn AD. Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re- collection of Aglaia foveolata. J Nat Prod. 2010 Nov 29;73(11):1873-8. doi: 10.1021/np100503q. Epub 2010 Oct 12. PMID: 20939540; PMCID: PMC2993763.

11: Adams TE, El Sous M, Hawkins BC, Hirner S, Holloway G, Khoo ML, Owen DJ, Savage GP, Scammells PJ, Rizzacasa MA. Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4'-desmethoxyepisilvestrol. J Am Chem Soc. 2009 Feb 4;131(4):1607-16. doi: 10.1021/ja808402e. PMID: 19140688.

12: El Sous M, Khoo ML, Holloway G, Owen D, Scammells PJ, Rizzacasa MA. Total synthesis of (-)-episilvestrol and (-)-silvestrol. Angew Chem Int Ed Engl. 2007;46(41):7835-8. doi: 10.1002/anie.200702700. PMID: 17823902.

13: Hwang BY, Su BN, Chai H, Mi Q, Kardono LB, Afriastini JJ, Riswan S, Santarsiero BD, Mesecar AD, Wild R, Fairchild CR, Vite GD, Rose WC, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD. Silvestrol and episilvestrol, potential anticancer rocaglate derivatives from Aglaia silvestris. J Org Chem. 2004 May 14;69(10):3350-8. doi: 10.1021/jo040120f. Erratum in: J Org Chem. 2004 Sep 3;69(18):6156. PMID: 15132542.