Rocaglamide is a natural product which belongs to a class of molecules called flavaglines.[1][2] This compound was isolated in 1982 by Ming-Lu King (金明儒) and colleagues based on its antileukemic activity.[3] The name of Rocaglamide is named from two parts: Roc- and aglamide. Roc- means Republic of China (中華民國), where this product was first isolated; aglamide indicates this product is isolated from Large-leaved Aglaia (Scientific name: Aglaia rimosa[4]). Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. Rocaglamide A (RocA) inhibits eukaryotic translation initiation by binding to the translation initiation factor eIF4A and converting it into a translational repressor.[5]
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Names | |
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Preferred IUPAC name
(1R,2R,3S,3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide | |
Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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Properties | |
C29H31NO7 | |
Molar mass | 505.567 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rocaglamide was first synthesized by Barry Trost in 1990.[6] Although other syntheses have been described since, Trost’s remains the only one to afford rocaglamide in an enantio-specific manner.
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