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SML0656

Rocaglamide

Name: Rocaglamide
Brand: SIGMA

≥96% (HPLC), anti-cancer agent, film

Synonym(s):

(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, Roc-A, Rocaglamide A

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₁NO₇

CAS Number:

84573-16-0

Molecular Weight:

505.56

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥96% (HPLC)

Form:

film

Quality level:

100

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Properties

Product Name

Rocaglamide, ≥96% (HPLC)

Quality Level

100

assay

≥96% (HPLC)

form

film

color

colorless

shipped in

wet ice

storage temp.

−20°C

SMILES string

N(C)(C)C(=O)[C@H]1[C@H]([C@@]2([C@@](Oc5c2c(cc(c5)OC)OC)([C@@H]1c4ccccc4)c3ccc(cc3)OC)O)O

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

InChI key

DAPAQENNNINUPW-IDAMAFBJSA-N

Description

General description

Rocaglamide is known to be derived from tetrahydro benzofuran and is also an active chemical compound of Aglaia plants.

Application

Rocaglamide has been used as an anticancer drug to treat enterovirus 71 neuropathogenesis and to study the role of prohibitin.

Biochem/physiol Actions

Rocaglamide is associated with osteoblast differentiation. In rheumatoid arthritis, rocaglamide might suppress inflammation, by preventing the expression of cytokines involved in it.

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.

Rocaglamide is a potent anticancer agent.

Features and Benefits

This compound is featured on the MAPKKKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

017M4708V

043M4761V

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Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

1H-cyclopenta[b]benzofuran lignans from Aglaia species inhibit cell proliferation and alter cell cycle distribution in human monocytic leukemia cell lines.

F I Bohnenstengel et al.

Zeitschrift fur Naturforschung. C, Journal of biosciences, 54(12), 1075-1083 (2000-02-24)

Thirteen naturally occurring 1H-cyclopenta[b]benzofuran lignans of the rocaglamide type as well as one naturally occurring aglain congener all of them isolated from three Aglaia species (Aglaia duperreana, A. oligophylla and A. spectabilis) collected in Vietnam were studied for their antiproliferative

Rocaglamide derivatives are potent inhibitors of NF-kappa B activation in T-cells.

Bernd Baumann et al.

The Journal of biological chemistry, 277(47), 44791-44800 (2002-09-19)

Crude extracts from different Aglaia species are used as anti-inflammatory remedies in the traditional medicine of several countries from Southeast Asia. Because NF-kappaB transcription factors represent key regulators of genes involved in immune and inflammatory responses, we supposed that the

Rocaglamide derivatives are immunosuppressive phytochemicals that target NF-AT activity in T cells.

Peter Proksch et al.

Journal of immunology (Baltimore, Md. : 1950), 174(11), 7075-7084 (2005-05-21)

Aglaia (family Meliaceae) plants are used in traditional medicine (e.g., in Vietnam) for the treatment of inflammatory skin diseases and allergic inflammatory disorders such as asthma. Inflammatory diseases arise from inappropriate activation of the immune system, leading to abnormal expression

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Global Trade Item Number

SKU	GTIN
SML0656-100UG	04061832450490