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MedKoo Cat#: 574244 | Name: Ambuic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ambuic acid is a cyclohexanone that has phytopathogenic antifungal, quorum sensing inhibitory, and antibacterial activities. 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.

Chemical Structure

Ambuic acid
Ambuic acid
CAS#340774-69-8

Theoretical Analysis

MedKoo Cat#: 574244

Name: Ambuic acid

CAS#: 340774-69-8

Chemical Formula: C19H26O6

Exact Mass: 350.1729

Molecular Weight: 350.41

Elemental Analysis: C, 65.13; H, 7.48; O, 27.39

Price and Availability

Size Price Availability Quantity
1mg USD 480.00 2 Weeks
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Related CAS #
No Data
Synonym
(+)-Ambuic Acid, Ambuic acid
IUPAC/Chemical Name
(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
InChi Key
UDSQZJMGPSRCEM-HDKVZZTHSA-N
InChi Code
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
SMILES Code
OCC1=C(/C=C/CCCCC)C([C@@]2(C/C=C(C)/C(O)=O)[C@H](O2)[C@@H]1O)=O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 350.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Li DY, Zhang XL, Li ZL. Two ambuic acid dimers derived from homo-endo Diels-Alder reaction from Pestalotiopsis versicolor. J Asian Nat Prod Res. 2022 Oct 20:1-9. doi: 10.1080/10286020.2022.2132480. Epub ahead of print. PMID: 36264599. 2: Ding G, Li Y, Fu S, Liu S, Wei J, Che Y. 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. Erratum in: J Nat Prod. 2009 Jul;72(7):1368. PMID: 19117486. 3: Nakayama J, Uemura Y, Nishiguchi K, Yoshimura N, Igarashi Y, Sonomoto K. 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. Epub 2008 Nov 17. PMID: 19015326; PMCID: PMC2630657. 4: Todd DA, Parlet CP, Crosby HA, Malone CL, Heilmann KP, Horswill AR, Cech NB. Signal Biosynthesis Inhibition with Ambuic Acid as a Strategy To Target Antibiotic-Resistant Infections. Antimicrob Agents Chemother. 2017 Jul 25;61(8):e00263-17. doi: 10.1128/AAC.00263-17. PMID: 28607020; PMCID: PMC5527603. 5: Li CS, Yang BJ, Turkson J, Cao S. Anti-proliferative ambuic acid derivatives from Hawaiian endophytic fungus Pestalotiopsis sp. FT172. Phytochemistry. 2017 Aug;140:77-82. doi: 10.1016/j.phytochem.2017.04.017. PMID: 28463686; PMCID: PMC5542815. 6: Zhang Q, Luan R, Li H, Liu Y, Liu P, Wang L, Li D, Wang M, Zou Q, Liu H, Matsuzaki K, Zhao F. 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. Epub 2018 Jun 12. PMID: 30116402; PMCID: PMC6090306. 7: Qi QY, Li EW, Han JJ, Pei YF, Ma K, Bao L, Huang Y, Zhao F, Liu HW. New ambuic acid derivatives from the solid culture of Pestalotiopsis neglecta and their nitric oxide inhibitory activity. Sci Rep. 2015 May 19;5:9958. doi: 10.1038/srep09958. PMID: 25989228; PMCID: PMC4437027. 8: Li JY, Harper JK, Grant DM, Tombe BO, Bashyal B, Hess WM, Strobel GA. Ambuic acid, a highly functionalized cyclohexenone with antifungal activity from Pestalotiopsis spp. and Monochaetia sp. Phytochemistry. 2001 Mar;56(5):463-8. doi: 10.1016/s0031-9422(00)00408-8. PMID: 11261579. 9: Jung SH, Hwang GS, Lee SI, Ryu DH. Total synthsis of (+)-ambuic acid: α-bromination with 1,2-dibromotetrachloroethane. J Org Chem. 2012 Mar 2;77(5):2513-8. doi: 10.1021/jo202357s. Epub 2012 Feb 16. PMID: 22280015. 10: Parthasarathy R, Sruthi D, Jayabaskaran C. Isolation and purifications of an ambuic acid derivative compound from marine algal endophytic fungi Talaromyces flavus that induces apoptosis in MDA-MB-231 cancer cells. Chem Biol Drug Des. 2023 May 29. doi: 10.1111/cbdd.14271. Epub ahead of print. PMID: 37246452. 11: Li J, Xie J, Yu FX, Chen YH, Zhao PJ. Pestalotic acids A-I, antibacterial ambuic acid analogues, from a mycoparasite (Pestalotipsis sp. cr014) of Cronartium ribicola. Arch Pharm Res. 2016 Sep 19. doi: 10.1007/s12272-016-0837-2. Epub ahead of print. PMID: 27645625. 12: Harper JK, Barich DH, Hu JZ, Strobel GA, Grant DM. Stereochemical analysis by solid-state NMR: structural predictions in ambuic acid. J Org Chem. 2003 Jun 13;68(12):4609-14. doi: 10.1021/jo020377i. PMID: 12790563. 13: Kurnia D, Ramadhanty ZF, Ardani AM, Zainuddin A, Dharsono HDA, Satari MH. Bio-Mechanism of Catechin as Pheromone Signal Inhibitor: Prediction of Antibacterial Agent Action Mode by In Vitro and In Silico Study. Molecules. 2021 Oct 22;26(21):6381. doi: 10.3390/molecules26216381. PMID: 34770790; PMCID: PMC8587927. 14: Guo W, Zhang Z, Zhu T, Gu Q, Li D. Penicyclones A-E, Antibacterial Polyketides from the Deep-Sea-Derived Fungus Penicillium sp. F23-2. J Nat Prod. 2015 Nov 25;78(11):2699-703. doi: 10.1021/acs.jnatprod.5b00655. Epub 2015 Nov 5. PMID: 26540093. 15: Harper JK, Grant DM, Zhang Y, Lee PL, Von Dreele R. Characterizing challenging microcrystalline solids with solid-state NMR shift tensor and synchrotron X-ray powder diffraction data: structural analysis of ambuic acid. J Am Chem Soc. 2006 Feb 8;128(5):1547-52. doi: 10.1021/ja055570j. PMID: 16448125. 16: Todd DA, Zich DB, Ettefagh KA, Kavanaugh JS, Horswill AR, Cech NB. Hybrid Quadrupole-Orbitrap mass spectrometry for quantitative measurement of quorum sensing inhibition. J Microbiol Methods. 2016 Aug;127:89-94. doi: 10.1016/j.mimet.2016.05.024. Epub 2016 May 26. PMID: 27237773; PMCID: PMC5226215. 17: Li C, Johnson RP, Porco JA Jr. Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade. J Am Chem Soc. 2003 Apr 30;125(17):5095-106. doi: 10.1021/ja021396c. PMID: 12708860. 18: Strobel GA. Rainforest endophytes and bioactive products. Crit Rev Biotechnol. 2002;22(4):315-33. doi: 10.1080/07388550290789531. PMID: 12487423. 19: Apriyanti E, Satari MH, Kurnia D. Potential of MurA Enzyme and GBAP in Fsr Quorum Sensing System as Antibacterial Drugs Target: In vitro and In silico Study of Antibacterial Compounds from Myrmecodia pendans. Comb Chem High Throughput Screen. 2021;24(1):109-118. doi: 10.2174/1386207323666200628111348. PMID: 32598250; PMCID: PMC8778655. 20: Wu X, Wang Y, Liu S, Liu X, Guo L. Microsporols A-C from the Plant Endophytic Fungus Pestalotiopsis microspore. Nat Prod Commun. 2015 Oct;10(10):1643-6. PMID: 26669093.