An amide with diverse biological activities
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Asperglaucide

Item No. 28499

Technical Information
Formal Name
N-[(1S)-1-[(acetyloxy)methyl]-2-phenylethyl]-αS-(benzoylamino)-benzenepropanamide
CAS Number
56121-42-7
Synonyms
  • Aurantiamide Acetate
Molecular Formula
C27H28N2O4
Formula Weight
Purity
≥70%
A solid
DMSO: solubleEthanol: soluble
SMILES
O=C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](CC2=CC=CC=C2)COC(C)=O)=O)C3=CC=CC=C3
InChi Code
InChI=1S/C27H28N2O4/c1-20(30)33-19-24(17-21-11-5-2-6-12-21)28-27(32)25(18-22-13-7-3-8-14-22)29-26(31)23-15-9-4-10-16-23/h2-16,24-25H,17-19H2,1H3,(H,28,32)(H,29,31)/t24-,25-/m0/s1
InChi Key
VZPAURMDJZOGHU-DQEYMECFSA-N
Origin
Fungus/Aspergillus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Asperglaucide is an amide originally isolated from P. aurantiacum that has diverse biological activities, including anti-inflammatory, antibacterial, antioxidant, and anticancer properties.1,2,3,4 Asperglaucide inhibits production of nitric oxide (NO), prostaglandin E2 (PGE2; Item No. 14010), and IL-1β in LPS-stimulated BV-2 microglial cells (IC50s = 49.7, 51.5, and 40.4 µM, respectively).2 It is active against Gram-negative bacteria (MICs = 0.05-0.10 mg/ml) and has antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and Trolox equivalent antioxidant capacity (TEAC) assays (EC50s = 9.51-78.81 µg/ml).3 Asperglaucide decreases viability of U87 and U251 cancer cells in vitro when used at concentrations ranging from 10 to 100 µM and reduces tumor growth when administered at a dose of 1 mg via intratumoral injection in a U87 mouse xenograft model.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Banerji, A., and Ray, R. Aurantiamides: A new class of modified dipeptides from Piper aurantiacum. Phytochemistry 20(9), 2217-2220 (1981).

    2. Yoon, C.S., Kim, D.C., Lee, D.S., et alAnti-neuroinflammatory effect of aurantiamide acetate from the marine fungus Aspergillus sp. SF-5921: Inhibition of NF-κB and MAPK pathways in lipopolysaccharide-induced mouse BV2 microglial cells. Int. Immunopharmacol. 23(2), 568-574 (2014).

    3. Tamokou, J.D., Simo Mpetga, D.J., Keilah Lunga, P., et alAntioxidant and antimicrobial activities of ethyl acetate extract, fractions and compounds from stem bark of Albizia adianthifolia (Mimosoideae). BMC Complement. Altern. Med. 12, 99 (2012).

    4. Yang, Y., Zhang, L.H., Yang, B.X., et alAurantiamide acetate suppresses the growth of malignant gliomas in vitro and in vivo by inhibiting autophagic flux. J. Cell. Mol. Med. 19(5), 1055-1064 (2015).