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

pka

11.70±0.70(Predicted)

form 

film

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.

Safety Information

WGK Germany 

3

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] BERND BAUMANN. Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells.[J]. The Journal of Biological Chemistry, 2002, 277 47: 44791-44800. DOI:10.1074/jbc.m208003200
[2] PETER PROKSCH. Rocaglamide derivatives are immunosuppressive phytochemicals that target NF-AT activity in T cells.[J]. Journal of immunology, 2005, 174 11: 7075-7084. DOI:10.4049/jimmunol.174.11.7075
[3] GERNOT POLIER. The natural anticancer compounds rocaglamides inhibit the Raf-MEK-ERK pathway by targeting prohibitin 1 and 2.[J]. Chemistry & biology, 2012, 19 9: 1093-1104. DOI:10.1016/j.chembiol.2012.07.012
[4] JENNIFER NEUMANN. 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[J]. International Journal of Cancer, 2013, 134 8: 1991-2002. DOI:10.1002/ijc.28521
[5] JIA Y. ZHU. The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities[J]. International Journal of Cancer, 2007, 121 8: 1839-1846. DOI:10.1002/ijc.22883

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