A plant growth and plant circadian rhythm regulator
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Brevicompanine B

Item No. 27962

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,5aS,10bR,11aS)-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
CAS Number
215121-47-4
Molecular Formula
C22H29N3O2
Formula Weight
367.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C([C@@]1([H])N2[C@@]3([H])[C@@](C(C=CC=C4)=C4N3)(C(C)(C)C=C)C1)N[C@H](CC(C)C)C2=O
InChi Code
InChI=1S/C22H29N3O2/c1-6-21(4,5)22-12-17-18(26)23-16(11-13(2)3)19(27)25(17)20(22)24-15-10-8-7-9-14(15)22/h6-10,13,16-17,20,24H,1,11-12H2,2-5H3,(H,23,26)/t16-,17+,20+,22-/m1/s1
InChi Key
HAXPBJUEOMQIJN-HBCLNWRISA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Brevicompanine B is a fungal metabolite originally isolated from P. brevicompactum that has plant growth and circadian rhythm regulatory activity.1 It inhibits hypocotyl elongation in lettuce seedlings when used at a concentration of 100 mg/L but does not inhibit elongation in rice seedlings at a concentration of 300 mg/L. Brevicompanine B (100 µM) inhibits primary root growth in Arabidopsis seedlings and disrupts the transcription of various genes involved in the regulation of plant circadian rhythm.2 It is active against P. falciparum with an IC50 value of 35 mg/ml.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kusano, M., Sotoma, G., Koshino, H., et al. Brevicompanines A and B: New plant growth regulators produced by the fungus, Penicillium brevicompactum. J. Chem. Soc. Perkin 1 2823-2826 (1998).

    2. de Montaigu, A., Oeljeklaus, J., Krahn, J.H., et al. The root growth-regulating brevicompanine natural products modulate the plant circadian clock. ACS Chem. Biol. 12(6), 1466-1471 (2017).

    3. Sprogøe, K., Manniche, S., Larsen, T.O., et al. Janoxepin and brevicompanine B: Antiplasmodial metabolites from the fungus Aspergillus janus. Tetrahedron 61(36), 8718-8721 (2005).