Rocaglamide Explained

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]

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.

See also

• FL3 (flavagline)
• Eukaryotic translation
• eIF4A
• Silvestrol

Notes and References

1. Ebada SS, Lajkiewicz N, Porco JA, Li-Weber M, Proksch P . Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae) . Progress in the Chemistry of Organic Natural Products . Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. 94 . 1–58 . 2011 . 21833837 . 10.1007/978-3-7091-0748-5_1 . 978-3-7091-0747-8 . 4157394 .
2. Ribeiro N, Thuaud F, Nebigil C, Désaubry L . Recent advances in the biology and chemistry of the flavaglines . Bioorganic & Medicinal Chemistry . 20 . 6 . 1857–64 . March 2012 . 22071525 . 10.1016/j.bmc.2011.10.048 .
3. King ML, Chiang CC, Ling HC, Fujita E, Ochiai M, McPhail AT . X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia . Chem. Commun. . 20. 1150–1 . 1992 . 10.1039/c39820001150.
4. Iwasaki S, Floor SN, Ingolia NT . Rocaglates convert DEAD-box protein eIF4A into a sequence-selective translational repressor . Nature . 534 . 7608 . 558–61 . June 2016 . 27309803 . 10.1038/nature17978 . 4946961. 2016Natur.534..558I .
5. Web site: Aglaia rimosa (Blanco) Merr.. Plants of the World Online. en. 2022-12-14. ). 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.^[4]
6. Trost BM, Greenspan PD, Yang BV, Saulnier MG . An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (−)-rocaglamide . Journal of the American Chemical Society . 112 . 24 . 9022–4 . November 1990 . 10.1021/ja00180a081 .