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| | ROCAGLAMIDE Basic information |
| Product Name: | ROCAGLAMIDE | | Synonyms: | ROCAGLAMIDE;(1R)-2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide;(1R)-N,N-Dimethyl-1α,8bβ-dihydroxy-3β-phenyl-3aβ-(4-methoxyphenyl)-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide;2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide;2,3,3a,8b-Tetrahydro-N,N-dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-1H-cyclopenta[b]benzofuran-2α-carboxamide;N,N-Dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide;(1R,2R,3S,3aR,8bS)-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide;NSC 326408 | | CAS: | 84573-16-0 | | MF: | C29H31NO7 | | MW: | 505.56 | | EINECS: | | | Product Categories: | | | Mol File: | 84573-16-0.mol |  |
| | ROCAGLAMIDE Chemical Properties |
| Melting point | 117-118 °C | | Boiling point | 667.3±55.0 °C(Predicted) | | density | 1.321±0.06 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | Soluble in DMSO or Ethanol | | form | film | | pka | 11.70±0.70(Predicted) | | color | colorless | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. Protect from exposure to light and moisture. |
| | ROCAGLAMIDE Usage And Synthesis |
| Description | Rocaglamide is an anti-inflammatory, insecticidal, and anticancer tetrahydrobenzofuran isolated from Aglaia species. It has been shown to inhibit both TNF-α and the activation of NF-κB in Jurkat T cells with IC50 values in the nanomolar range. At 25 nM, rocaglamide induces apoptosis in various human leukemia cell lines, activating p38 MAPK/JNK and suppressing ERK. Rocaglamide also reduces IFN-γ, TNF-α, IL-2, and IL-4 production in peripheral blood T cells at a concentration of 50 nM. Furthermore, rocaglamide can inhibit the T cell expression of the immune response transcription factor, nuclear factor of activated T cells. | | Uses | Rocaglamide is derived from a Chinese medicinal plant Aglaia. Rocaglamide induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells freshly isolated from patients. | | Definition | ChEBI: An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at
position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity. | | General Description | Rocaglamide is known to be derived from tetrahydro benzofuran and is also an active chemical compound of Aglaia plants. | | Biochem/physiol Actions | Rocaglamide is a potent anticancer agent isolated from the genus Aglaia. Rocaglamides inhibit protein synthesis without affecting DNA or RNA synthesis. Recent study shows that Rocaglamide binds to prohibitin (PHB) 1 and 2, which prevents interaction between PHB and CRaf and inhibits CRaf activation and subsequently CRaf-MEK-ERK signaling. Also, Rocaglamide is an immunosuppressant that inhibits activation of NF-kB and NF-AT. | | target | Bcl-2/Bax | Caspase | p53 | TNF-α | NF-kB | MEK | ERK | Chk | Raf | p38MAPK | | References | 1) Baumann?et al.?(2002),?Rocaglamide Derivatives Are Potent Inhibitors of NF-kB Activation in T-cells; J. Biol. Chem.?277?44791
2) Prolsch?et al.?(2005),?Rocaglamide Derivatives Are Immunosuppressive Phytochemicals That Target NF-AT Activity in T Cells; J. Immunol.?174?7075
3) Polier?et al.?(2012),?The natural anticancer compounds rocaglamides inhibit the Raf-MEK-ERK pathway by targeting prohibitin1 and 2; Chem. Biol.?19?1093
4) Neumann?et al.?(2014),?The natural anticancer compound rocaglamide selectively inhibits the G1-S phase transition in cancer cells through the ATM/ATR-mediated Chk1/2 cell cycle checkpoints; Int. J. Cancer?134?1991
5) Zhu?et al.?(2007),?The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities; Int. J. Cancer?121?1839 |
| | ROCAGLAMIDE Preparation Products And Raw materials |
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