A β-carboline alkaloid
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Manzamine A

Item No. 21444

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-tetradecahydro-24-(9H-pyrido[3,4-b]indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino[1',2':1,5]pyrrolo[3,2-e]azacyclopentadecin-13(13aH)-ol
CAS Number
104196-68-1
Synonyms
  • Keramamine A
Molecular Formula
C36H44N4O
Formula Weight
548.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
[H][C@@]1(N2CCCC/C=C\1)C[C@@]3(C4)[C@]2([H])[C@]5(O)CC/C=C/CCCC[N@@]4CC[C@@]3([H])C(C6=C(NC7=C8C=CC=C7)C8=CC=N6)=C5
InChi Code
InChI=1S/C36H44N4O/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2/b4-1+,13-7-/t26-,30-,34+
InChi Key
FUCSLKWLLSEMDQ-SHIWRGCWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $173

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    Product Description

    Manzamine A is a β-carboline alkaloid with diverse activities that has been found in marine sponges, including X. ashmorica.1 It is an inhibitor of glycogen synthase kinase 3β (GSK3β) and cyclin-dependent kinase 5 (CDK5; IC50s = 10.2 and 1.5 μM, respectively).2 It inhibits the growth of L5178y mouse lymphoma cells with an ED50 value of 1.8 μg/mL.1 In an agar diffusion assay, manzamine A inhibits the growth of B. subtilis and S. aureus, but not E. coli bacteria. It reduces the reverse transcriptase (RT) activity in supernatant from HIV-1-infected peripheral blood mononuclear cells (PBMCs; EC50 = 4.2 μM).3 In vivo, manzamine A (100 μmol/kg, i.p.) has antimalarial activity and reduces the amount of P. berghei in infected mice by over 90% relative to the control.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Edrada, R.A., Proksch, P., Wray, V., et al. Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica. J. Nat. Prod. 59(11), 1056-1060 (1996).

    2. Hamann, M., Alonso, D., Martín-Aparicio, E., et al. Glycogen synthase kinase-3 (GSK-3) inhibitory activity and structure-activity relationship (SAR) studies of the manzamine alkaloids. Potential for Alzheimer’s disease. J. Nat. Prod. 70(9), 1397-1405 (2007).

    3. Rao, K.V., Donia, M.S., Peng, J., et al. Manzamine B and E and ircinal A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer’s diseases. J. Nat. Prod. 69(7), 1034-1040 (2006).

    4. Ang, K.K., Holmes, M.J., Higa, T., et al. In vivo antimalarial activity of the beta-carboline alkaloid manzamine A. Antimicrob. Agents Chemother. 44(6), 1645-1649 (2000).