Ambuic acid
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| Category | Antibiotics |
| Catalog number | BBF-04511 |
| CAS | 340774-69-8 |
| Molecular Weight | 350.41 |
| Molecular Formula | C19H26O6 |
| Purity | ≥95% |
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Description
Ambuic acid is a cyclohexanone originally isolated from Pestalotiopsis and Monochaetia species. Antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. It is active against P. ultimum (MIC = 7.5 µg/ml) and inhibits the growth of a variety of other phytopathogenic fungi. Ambuic acid inhibits the biosynthesis of cyclic peptides involved in quorum sensing, including gelatinase biosynthesis-activating pheromone (GBAP).
Specification
| Synonyms | (+)-Ambuic acid; (2E,5R,6R,7R,8E,10E)-2-Methyl-5,9-carbonyl-5,6-epoxy-7-hydroxy-8-(hydroxymethyl)-2,8,10-hexadecatrienoic acid |
| Storage | Store at -20°C |
| IUPAC Name | (E)-4-[(1R,5R,6R)-3-[(E)-hept-1-enyl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid |
| Canonical SMILES | CCCCCC=CC1=C(C(C2C(C1=O)(O2)CC=C(C)C(=O)O)O)CO |
| InChI | InChI=1S/C19H26O6/c1-3-4-5-6-7-8-13-14(11-20)15(21)17-19(25-17,16(13)22)10-9-12(2)18(23)24/h7-9,15,17,20-21H,3-6,10-11H2,1-2H3,(H,23,24)/b8-7+,12-9+/t15-,17-,19+/m1/s1 |
| InChI Key | UDSQZJMGPSRCEM-HDKVZZTHSA-N |
Properties
| Appearance | Off-white Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 607.3±55.0°C at 760 mmHg |
| Melting Point | 223.49°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO, Ethanol, Methanol |
Reference Reading
1. Anti-proliferative ambuic acid derivatives from Hawaiian endophytic fungus Pestalotiopsis sp. FT172
Bao-Jun Yang, Shugeng Cao, Chun-Shun Li, James Turkson Phytochemistry . 2017 Aug;140:77-82. doi: 10.1016/j.phytochem.2017.04.017.
Five previously undescribed ambuic acid derivatives, pestallic acids A-E and three known analogs were isolated from the cultured broth of Pestalotiopsis sp. FT172. The structures of the pestallic acids A-E were determined through the analysis of HRMS and NMR spectroscopic data. The absolute configurations (ACs) of pestallic acids B-E were assigned by comparison of the experimental electric circular dichroism (ECD) spectra or the optical rotations with those in the literature. All compounds were tested against A2780 and cisplatin resistant A2780 (A2780CisR) cell lines. Pestallic acid E and (+)-ambuic acid showed potent activities with IC50values from 3.3 to 17.0 μM.
2. Ambuic acid inhibits the biosynthesis of cyclic peptide quormones in gram-positive bacteria
Jiro Nakayama, Kenji Sonomoto, Yasuhiro Igarashi, Norito Yoshimura, Yumi Uemura, Kenzo Nishiguchi Antimicrob Agents Chemother . 2009 Feb;53(2):580-6. doi: 10.1128/AAC.00995-08.
Quorum sensing is a cell-density-dependent regulatory system in gram-positive bacteria and is often regulated by cyclic peptides called "quormones," which function as extracellular communication signals. With an aim to discover an antipathogenic agent targeting quorum sensing in gram-positive bacteria, we screened 153 samples of fungal butanol extracts with the guidance of the inhibition of quorum-sensing-mediated gelatinase production in Enterococcus faecalis. Following the screenings, we found that ambuic acid, a known secondary fungal metabolite, inhibited the quorum-sensing-mediated gelatinase production without influencing the growth of E. faecalis. We further demonstrated that ambuic acid targeted the biosynthesis of a cyclic peptide quormone called gelatinase biosynthesis-activating pheromone. Furthermore, ambuic acid also inhibited the biosynthesis of the cyclic peptide quormones of Staphylococcus aureus and Listeria innocua. These results suggest the potential use of ambuic acid as a lead compound of antipathogenic drugs that target the quorum-sensing-mediated virulence expression of gram-positive bacteria.
3. Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp
Gang Ding, Yongsheng Che, Shuchun Liu, Shaobin Fu, Yan Li, Jiangchun Wei J Nat Prod . 2009 Jan;72(1):182-6. doi: 10.1021/np800733y.
Six new ambuic acid (1) derivatives (2-7) and a new torreyanic acid analogue (8) have been isolated from the crude extract of endophytic fungus Pestalotiopsis sp. inhabiting the lichen Multiclavula [corrected] sp. The structures of these compounds were elucidated primarily by NMR and MS methods, and their absolute configurations were assigned by application of the CD excitation chirality method. Compounds 1 and 2 displayed antimicrobial activity against the Gram-positive bacterium Staphylococcus aureus.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
