(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester
- Product Name
- (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester
- CAS No.
- 697235-38-4
- Chemical Name
- (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester
- Synonyms
- Silvestrol;(-)-Silvestrol;(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester;1H-Cyclopenta[b]benzofuran-2-carboxylic acid, 6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-Methoxy-1,4-dioxan-2-yl]o xy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-Methoxy-3a-(4-Methoxypheny l)-3-phenyl-, Methyl ester, (1R,2R,3S,3aR,8bS)-
- CBNumber
- CB22565895
- Molecular Formula
- C34H38O13
- Formula Weight
- 654.66
- MOL File
- 697235-38-4.mol
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester Property
- Melting point:
- 120-122℃
- Boiling point:
- 800.8±65.0 °C(Predicted)
- Density
- 1.45
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 11.57±0.70(Predicted)
- color
- White to off-white
N-Bromosuccinimide Price
- Product number
- CS-0543
- Product name
- Silvestrol
- Purity
- 98.00%
- Packaging
- 1mg
- Price
- $840
- Updated
- 2021/12/16
- Product number
- CS-0543
- Product name
- Silvestrol
- Purity
- 98.00%
- Packaging
- 2mg
- Price
- $1500
- Updated
- 2021/12/16
- Product number
- A3818
- Product name
- Silvestrol
- Packaging
- 1mg
- Price
- $1559
- Updated
- 2021/12/16
- Product number
- A3818
- Product name
- Silvestrol
- Packaging
- 2mg
- Price
- $2599
- Updated
- 2021/12/16
- Product number
- CS-0543
- Product name
- Silvestrol
- Purity
- 98.00%
- Packaging
- 5mg
- Price
- $3200
- Updated
- 2021/12/16
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester Chemical Properties,Usage,Production
Uses
Silvestrol is a eukaryotic translation initiation factor 4A (eIF4A) inhibitor isolated from Agave americana Linn.. Silvestrol induces autophagy and caspase-mediated apoptosis[1][2][3].
Definition
ChEBI: An organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phen l group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia si vestris, it exhibits antineoplastic activity.
Anticancer Research
It is a natural flavogline compound from the group of cyclopenta[b]benzofurans,extracted from the fruits of Aglaila sylvestre, which shows anticancer activityagainst lung and breast cancers (Shoeb 2006). The plant extract is reported to bepotent against P-388 cells in in vivo experiments. In the hollow fiber in vivo assay,it shows cytotoxicity in a dose-dependent way. It works by altering the cell signal pathways that related to the cell survival as well as angiogenesis and exerts itseffects by inhibiting the translation of mRNA preferentially associated withmalignancy (Balunas and Kinghorn 2005; Cencic et al. 2009).
in vivo
Silvestrol (1.5 mg/kg, i.p.) does not adversely affect production of human IgG by xenografted B-lymphocytes in mice. Silvestrol significantly prolongs survival compared to vehicle. There is no such lymphocyte infiltration detected in the spleens of any of the Silvestrol-treated mice, and nor do these animals exhibit any other obvious signs of lymphoma upon necropsy[5].
IC 50
eIF4
References
[1] Chambers JM, et al. 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
[2] Kim S, et al. Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7. Anticancer Res. 2007 Jul-Aug;27(4B):2175-83. PMID:17695501
[3] Chen WL, et al. Silvestrol induces early autophagy and apoptosis in human melanoma cells. BMC Cancer. 2016 Jan 13;16:17. DOI:10.1186/s12885-015-1988-0
[4] Daker M, et al. Inhibition of nasopharyngeal carcinoma cell proliferation and synergism of CDDP with silvestrol and episilvestrol isolated from Aglaia stellatopilosa. Exp Ther Med. 2016 Jun;11(6):2117-2126. DOI:10.3892/etm.2016.3201
[5] Patton JT, et al. The translation inhibitor silvestrol exhibits direct anti-tumor activity while preserving innate and adaptive immunity against EBV-driven lymphoproliferative disease. Oncotarget. 2015 Feb 20;6(5):2693-708. DOI:10.18632/oncotarget.2098
[6] Wolfe AL, et al. RNA G-quadruplexes cause eIF4A-dependent oncogene translation in cancer. Nature. 2014 Sep 4;513(7516):65-70. DOI:10.1038/nature13485
[7] Wiegering A, et al. Targeting Translation Initiation Bypasses Signaling Crosstalk Mechanisms That Maintain High MYC Levels in Colorectal Cancer. Cancer Discov. 2015 Jul;5(7):768-781. DOI:10.1158/2159-8290.CD-14-1040
[8] Todt D, et al. The natural compound silvestrol inhibits hepatitis E virus (HEV) replication in vitro and in vivo. Antiviral Res. 2018 Sep;157:151-158. DOI:10.1016/j.antiviral.2018.07.010
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
(1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-Dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxylic acid methyl ester Suppliers
- Tel
- +86-21-20908456
- Fax
- 021-58180499
- sales@BioChemBest.com
- Country
- China
- ProdList
- 6003
- Advantage
- 61
- Tel
- 1-631-485-4226; 16314854226
- info@bocsci.com
- Country
- United States
- ProdList
- 12952
- Advantage
- 65
- Tel
- 021-58950125
- Fax
- (86) 21-58955996
- info@chemexpress.com
- Country
- China
- ProdList
- 7552
- Advantage
- 61
- Tel
- 18149758185
- sales-cpd@caerulumpharma.com
- Country
- China
- ProdList
- 3506
- Advantage
- 58
- Tel
- Fax
- -
- xg01_gj@163.com
- Country
- China
- ProdList
- 9484
- Advantage
- 50
- Tel
- Fax
- -
- eric_feng1954@126.com
- Country
- China
- ProdList
- 9248
- Advantage
- 55
- Tel
- 400-1166-196 15982826727
- Fax
- QQ：800101999
- cdhxsj@163.com
- Country
- China
- ProdList
- 14603
- Advantage
- 60
- Tel
- 010-50973130 18101056239
- 3193328036@qq.com
- Country
- China
- ProdList
- 29760
- Advantage
- 68
- Tel
- 010-60605840 18892239720
- Fax
- 010-60605840
- psaitong@jm-bio.com
- Country
- China
- ProdList
- 12306
- Advantage
- 58
- Tel
- +1-800-259-7612
- Fax
- +1-800-259-7612
- info@musechem.com
- Country
- United States
- ProdList
- 4660
- Advantage
- 60