| Identification | Back Directory | [Name]
BrevicoMpanine B | [CAS]
215121-47-4 | [Synonyms]
BrevicoMpanine B
2H-Pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-, (3R,5aS,10bR,11aS)- | [Molecular Formula]
C22H29N3O2 | [MDL Number]
MFCD14635378 | [MOL File]
215121-47-4.mol | [Molecular Weight]
367.48 |
| Hazard Information | Back Directory | [Description]
Brevicompanine B is a fungal metabolite originally isolated from P. brevicompactum that has plant growth and circadian rhythm regulatory activity. 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. It is active against P. falciparum with an IC50 value of 35 mg/ml. | [Uses]
Brevicompanine B is a diketopiperazine-related metabolite produced by Penicillium and Aspergillus species. Brevicompanine B is active against the malaria parasite, Plasmodium falciparum, and shows pronounced plant growth regulatory activity but is devoid of antifungal or antibacterial activity. | [References]
[1] M. KUSANO. Brevicompanines A and B: new plant growth regulators produced by the fungus, Penicillium brevicompactum[J]. Journal of The Chemical Society-perkin Transactions 1, 1998, 69 1: 2823-2826. DOI: 10.1039/a803880e
[2] AMAURY DE MONTAIGU. The Root Growth-Regulating Brevicompanine Natural Products Modulate the Plant Circadian Clock[J]. ACS Chemical Biology, 2017, 12 6: 1466-1471. DOI: 10.1021/acschembio.6b00978
[3] KENNETT SPROGOEE. Janoxepin and Brevicompanine B: Antiplasmodial Metabolites from the Fungus Aspergillus janus.[J]. ChemInform, 2005, 36 51. DOI: 10.1002/chin.200551180 |
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