Rocaglamide
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MedKoo CAT#: 406598

CAS#: 84573-16-0

Description: Rocaglamide is the first cyclopenta[b]benzofuran derivative (flavagline), isolated from Aglaia elliptifolia in 1982 by King and colleagues based on its antileukemic activity. Like other flavaglines, rocaglamide displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities.

Chemical Structure

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Rocaglamide
CAS# 84573-16-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406598
Name: Rocaglamide
CAS#: 84573-16-0
Chemical Formula: C29H31NO7
Exact Mass: 505.21
Molecular Weight: 505.560
Elemental Analysis: C, 68.90; H, 6.18; N, 2.77; O, 22.15

Price and Availability

Size Price Availability Quantity
1mg USD 150 Ready to ship
2mg USD 250 Ready to ship
5mg USD 565 Ready to ship
10mg USD 1015 Ready to ship
25mg USD 2285 Ready to ship
50mg USD 4115 Ready to ship
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Synonym: Rocaglamide; Rocaglamide A; RocA; NSC 326408.

IUPAC/Chemical 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]benzofuran-2-carboxamide

InChi Key: DAPAQENNNINUPW-IDAMAFBJSA-N

InChi Code: InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

SMILES Code: O=C([C@H]([C@H]1C2=CC=CC=C2)[C@@H](O)[C@]3(O)[C@@]1(C4=CC=C(OC)C=C4)OC5=CC(OC)=CC(OC)=C35)N(C)C

Appearance: White to off- white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:         

Biological target: Rocaglamide (RocA) is a heat shock factor 1 (HSF1) activation inhibitor with an IC50 of ~50 nM.
In vitro activity: This study concludes that combination treatment of rocaglamide and mitomycin C is a highly effective tumor therapy. A low concentration of mitomycin C combined rocaglamide ROC significantly promoted HCT116 and HT29 cell apoptosis and inhibited cell proliferation by downregulating the expression of Bcl-2 and c-FLIP, upregulating the expression of Bax, activating the caspase cascade, arresting cell cycle in G1 phase, and increasing the level of reactive oxygen species. Reference: Pathol Res Pract. 2023 Mar;243:154350. https://pubmed.ncbi.nlm.nih.gov/36780842/
In vivo activity: In post-heart transplant operated mice, rocaglamide was found to regulate oxidative stress response and reduce inflammatory cell infiltration and organ injury, which have been associated with the inhibition of NF-AT activation in T cells. Reference: Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. https://pubmed.ncbi.nlm.nih.gov/35087613/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.0 158.24
Ethanol 5.0 9.89

Preparing Stock Solutions

The following data is based on the product molecular weight 505.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Xie L, Cheng L, Wei Y. Mitomycin C enhanced the antitumor efficacy of Rocaglamide in colorectal cancer. Pathol Res Pract. 2023 Mar;243:154350. doi: 10.1016/j.prp.2023.154350. Epub 2023 Feb 4. PMID: 36780842. 2. So L, Obata-Ninomiya K, Hu A, Muir VS, Takamori A, Song J, Buckner JH, Savan R, Ziegler SF. Regulatory T cells suppress CD4+ effector T cell activation by controlling protein synthesis. J Exp Med. 2023 Mar 6;220(3):e20221676. doi: 10.1084/jem.20221676. Epub 2023 Jan 4. PMID: 36598533; PMCID: PMC9827529. 3. Dai C, Zhou X, Wang L, Tan R, Wang W, Yang B, Zhang Y, Shi H, Chen D, Wei L, Chen Z. Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. doi: 10.1155/2022/2048095. PMID: 35087613; PMCID: PMC8787457. 4. Wu Y, Giaisi M, Köhler R, Chen WM, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL-resistance in human multiple myeloma and acute T-cell leukemia in vivo in a mouse xenogtraft model. Cancer Lett. 2017 Mar 28;389:70-77. doi: 10.1016/j.canlet.2016.12.010. Epub 2016 Dec 18. PMID: 27998762.
In vitro protocol: 1. Xie L, Cheng L, Wei Y. Mitomycin C enhanced the antitumor efficacy of Rocaglamide in colorectal cancer. Pathol Res Pract. 2023 Mar;243:154350. doi: 10.1016/j.prp.2023.154350. Epub 2023 Feb 4. PMID: 36780842. 2. So L, Obata-Ninomiya K, Hu A, Muir VS, Takamori A, Song J, Buckner JH, Savan R, Ziegler SF. Regulatory T cells suppress CD4+ effector T cell activation by controlling protein synthesis. J Exp Med. 2023 Mar 6;220(3):e20221676. doi: 10.1084/jem.20221676. Epub 2023 Jan 4. PMID: 36598533; PMCID: PMC9827529.
In vivo protocol: 1. Dai C, Zhou X, Wang L, Tan R, Wang W, Yang B, Zhang Y, Shi H, Chen D, Wei L, Chen Z. Rocaglamide Prolonged Allograft Survival by Inhibiting Differentiation of Th1/Th17 Cells in Cardiac Transplantation. Oxid Med Cell Longev. 2022 Jan 17;2022:2048095. doi: 10.1155/2022/2048095. PMID: 35087613; PMCID: PMC8787457. 2. Wu Y, Giaisi M, Köhler R, Chen WM, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL-resistance in human multiple myeloma and acute T-cell leukemia in vivo in a mouse xenogtraft model. Cancer Lett. 2017 Mar 28;389:70-77. doi: 10.1016/j.canlet.2016.12.010. Epub 2016 Dec 18. PMID: 27998762.

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1: Luan Z, He Y, He F, Chen Z. Rocaglamide overcomes tumor necrosis factor-related apoptosis-inducing ligand resistance in hepatocellular carcinoma cells by attenuating the inhibition of caspase-8 through cellular FLICE-like-inhibitory protein downregulation. Mol Med Rep. 2015 Jan;11(1):203-11. doi: 10.3892/mmr.2014.2718. Epub 2014 Oct 21. PubMed PMID: 25333816; PubMed Central PMCID: PMC4237083.

2: Duong NT, Edrada-Ebel R, Ebel R, Lin W, Duong AT, Dang XQ, Nguyen NH, Proksch P. New rocaglamide derivatives from Vietnamese Aglaia species. Nat Prod Commun. 2014 Jun;9(6):833-4. PubMed PMID: 25115092.

3: Pan L, Woodard JL, Lucas DM, Fuchs JR, Kinghorn AD. Rocaglamide, silvestrol and structurally related bioactive compounds from Aglaia species. Nat Prod Rep. 2014 Jul;31(7):924-39. doi: 10.1039/c4np00006d. Epub 2014 May 2. Review. PubMed PMID: 24788392; PubMed Central PMCID: PMC4091845.

4: Becker MS, Schmezer P, Breuer R, Haas SF, Essers MA, Krammer PH, Li-Weber M. The traditional Chinese medical compound Rocaglamide protects nonmalignant primary cells from DNA damage-induced toxicity by inhibition of p53 expression. Cell Death Dis. 2014 Jan 16;5:e1000. doi: 10.1038/cddis.2013.528. PubMed PMID: 24434508; PubMed Central PMCID: PMC4040689.

5: Neumann J, Boerries M, Köhler R, Giaisi M, Krammer PH, Busch H, Li-Weber M. 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. 2014 Apr 15;134(8):1991-2002. doi: 10.1002/ijc.28521. Epub 2013 Oct 21. PubMed PMID: 24150948.

6: El-Neketi M, Ebrahim W, Duong NT, Gedara S, Badria F, Saad HE, Müller WE, Proksch P. Cytotoxic rocaglamide derivatives from Aglaia duppereana. Z Naturforsch C. 2013 Jul-Aug;68(7-8):269-74. PubMed PMID: 24066511.

7: Sadlish H, Galicia-Vazquez G, Paris CG, Aust T, Bhullar B, Chang L, Helliwell SB, Hoepfner D, Knapp B, Riedl R, Roggo S, Schuierer S, Studer C, Porco JA Jr, Pelletier J, Movva NR. Evidence for a functionally relevant rocaglamide binding site on the eIF4A-RNA complex. ACS Chem Biol. 2013 Jul 19;8(7):1519-27. doi: 10.1021/cb400158t. Epub 2013 May 7. PubMed PMID: 23614532; PubMed Central PMCID: PMC3796129.

8: Malona JA, Cariou K, Spencer WT 3rd, Frontier AJ. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization. J Org Chem. 2012 Feb 17;77(4):1891-908. doi: 10.1021/jo202366c. Epub 2012 Jan 26. PubMed PMID: 22283818; PubMed Central PMCID: PMC3306619.

9: Rodrigo CM, Cencic R, Roche SP, Pelletier J, Porco JA. Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies. J Med Chem. 2012 Jan 12;55(1):558-62. doi: 10.1021/jm201263k. Epub 2011 Dec 19. PubMed PMID: 22128783; PubMed Central PMCID: PMC3263355.

10: Giaisi M, Köhler R, Fulda S, Krammer PH, Li-Weber M. Rocaglamide and a XIAP inhibitor cooperatively sensitize TRAIL-mediated apoptosis in Hodgkin's lymphomas. Int J Cancer. 2012 Aug 15;131(4):1003-8. doi: 10.1002/ijc.26458. Epub 2011 Nov 8. PubMed PMID: 21952919.

11: Cai XH, Xie B, Guo H. Progress in the total synthesis of rocaglamide. ISRN Org Chem. 2011 Apr 4;2011:239817. doi: 10.5402/2011/239817. Review. PubMed PMID: 24052818; PubMed Central PMCID: PMC3767207.

12: Bleumink M, Köhler R, Giaisi M, Proksch P, Krammer PH, Li-Weber M. Rocaglamide breaks TRAIL resistance in HTLV-1-associated adult T-cell leukemia/lymphoma by translational suppression of c-FLIP expression. Cell Death Differ. 2011 Feb;18(2):362-70. doi: 10.1038/cdd.2010.99. Epub 2010 Aug 13. PubMed PMID: 20706274; PubMed Central PMCID: PMC3131883.

13: Malona JA, Cariou K, Frontier AJ. Nazarov cyclization initiated by peracid oxidation: the total synthesis of (+/-)-rocaglamide. J Am Chem Soc. 2009 Jun 10;131(22):7560-1. doi: 10.1021/ja9029736. PubMed PMID: 19445456; PubMed Central PMCID: PMC2732401.

14: Zhu JY, Giaisi M, Köhler R, Müller WW, Mühleisen A, Proksch P, Krammer PH, Li-Weber M. Rocaglamide sensitizes leukemic T cells to activation-induced cell death by differential regulation of CD95L and c-FLIP expression. Cell Death Differ. 2009 Sep;16(9):1289-99. doi: 10.1038/cdd.2009.42. Epub 2009 Apr 17. PubMed PMID: 19373244.

15: Giese MW, Moser WH. Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence. Org Lett. 2008 Oct 2;10(19):4215-8. doi: 10.1021/ol801435j. Epub 2008 Aug 28. PubMed PMID: 18754622.

16: Zhu JY, Lavrik IN, Mahlknecht U, Giaisi M, Proksch P, Krammer PH, Li-Weber M. The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities. Int J Cancer. 2007 Oct 15;121(8):1839-46. PubMed PMID: 17565740.

17: Chumkaew P, Kato S, Chantrapromma K. Potent cytotoxic rocaglamide derivatives from the fruits of Amoora cucullata. Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1344-6. PubMed PMID: 16946551.

18: Proksch P, Giaisi M, Treiber MK, Palfi K, Merling A, Spring H, Krammer PH, Li-Weber M. Rocaglamide derivatives are immunosuppressive phytochemicals that target NF-AT activity in T cells. J Immunol. 2005 Jun 1;174(11):7075-84. PubMed PMID: 15905551.

19: Bringmann G, Mühlbacher J, Messer K, Dreyer M, Ebel R, Nugroho BW, Wray V, Proksch P. Cyclorocaglamide, the first bridged cyclopentatetrahydrobenzofuran, and a related "open chain" rocaglamide derivative from Aglaia oligophylla. J Nat Prod. 2003 Jan;66(1):80-5. PubMed PMID: 12542350.

20: Baumann B, Bohnenstengel F, Siegmund D, Wajant H, Weber C, Herr I, Debatin KM, Proksch P, Wirth T. Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells. J Biol Chem. 2002 Nov 22;277(47):44791-800. Epub 2002 Sep 16. PubMed PMID: 12237314.