| Identification | Back Directory | [Name]
ambuic acid | [CAS]
340774-69-8 | [Synonyms]
ambuic acid
(2E)-4-[(1R,5R,6R)-3-(1E)-1-Hepten-1-yl-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methyl-2-butenoic acid
2-Butenoic acid, 4-[(1R,5R,6R)-3-(1E)-1-hepten-1-yl-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methyl-, (2E)- | [Molecular Formula]
C19H26O6 | [MDL Number]
MFCD28898930 | [MOL File]
340774-69-8.mol | [Molecular Weight]
350.41 |
| Hazard Information | Back Directory | [Description]
Ambuic acid is a cyclohexanone originally isolated from Pestalotiopsis and Monochaetia species that has phytopathogenic antifungal, quorum sensing inhibitory, and antibacterial activities. It is active against P. ultimum (MIC = 7.5 μg/ml) and inhibits the growth of a variety of other phytopathogenic fungi, including F. solani, H. sativum, and C. gramineum, but not P. oryzae, R. solani, or B. cinerea. Ambuic acid inhibits the biosynthesis of cyclic peptides involved in quorum sensing, including gelatinase biosynthesis-activating pheromone (GBAP) in E. faecalis, autoinducing peptide I (AIP-I) in S. aureus, and LsrD698 and LsrD826 in L. innocua. It suppresses abcess formation in a mouse model of skin infection induced by methicillin-resistant S. aureus (MRSA) when administered at a dose of 5 μg and decreases the activity of the agr quorum sensing system in an in vivo reporter assay. | [Uses]
Ambuic acid exhibits antimicrobial activity against Staphylococcus aureus, with IC50 of 43.9 μM for strain ATCC 6538. Ambuic acid is an inhbitor for the biosynthesis of cyclic peptide quorum sensing molecules (quormones) in gram-positive bacteria. Ambuic acid exhibits anti-inflammatory activity through ERK/JNK/MAPK signaling pathway[1][2][3]. | [storage]
Store at -20°C | [References]
[1] Zhang Q, et al., Anti-inflammatory action of ambuic acid, a natural product isolated from the solid culture of Pestalotiopsis neglecta, through blocking ERK/JNK mitogen-activated protein kinase signaling pathway. Exp Ther Med. 2018 Aug;16(2):1538-1546. DOI:10.3892/etm.2018.6294
[2] Nakayama J, et al., Ambuic acid inhibits the biosynthesis of cyclic peptide quormones in gram-positive bacteria. Antimicrob Agents Chemother. 2009 Feb;53(2):580-6. DOI:10.1128/AAC.00995-08
[3] Ding G, et al., Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp. J Nat Prod. 2009 Jan;72(1):182-6. DOI:10.1021/np800733y |
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