Quinolactacin A2
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02164 |
| CAS | |
| Molecular Weight | 270.33 |
| Molecular Formula | C16H18N2O2 |
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Description
Quinolactacin A2 is the dominant analogue of a family of quinolone metabolites produced by penicillium citrinum, inhibits acetylcholinesterase and TNF production.
Specification
| Synonyms | ZINC14684865 |
| IUPAC Name | (3S)-3-[(2S)-butan-2-yl]-4-methyl-2,3-dihydropyrrolo[3,4-b]quinoline-1,9-dione |
| Canonical SMILES | CCC(C)C1C2=C(C(=O)C3=CC=CC=C3N2C)C(=O)N1 |
| InChI | InChI=1S/C16H18N2O2/c1-4-9(2)13-14-12(16(20)17-13)15(19)10-7-5-6-8-11(10)18(14)3/h5-9,13H,4H2,1-3H3,(H,17,20)/t9-,13-/m0/s1 |
| InChI Key | FLHQAMWKNPOTDV-ZANVPECISA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Quinolactacin Biosynthesis Involves Non-Ribosomal-Peptide-Synthetase-Catalyzed Dieckmann Condensation to Form the Quinolone-γ-lactam Hybrid
Fanglong Zhao, Zhiwen Liu, Shuyuan Yang, Ning Ding, Xue Gao Angew Chem Int Ed Engl. 2020 Oct 19;59(43):19108-19114. doi: 10.1002/anie.202005770. Epub 2020 Aug 20.
Quinolactacins are novel fungal alkaloids that feature a quinolone-γ-lactam hybrid, which is a potential pharmacophore for the treatment of cancer and Alzheimer's disease. Herein, we report the identification of the quinolactacin A2 biosynthetic gene cluster and elucidate the enzymatic basis for the formation of the quinolone-γ-lactam structure. We reveal an unusual β-keto acid (N-methyl-2-aminobenzoylacetate) precursor that is derived from the primary metabolite l-kynurenine via methylation, oxidative decarboxylation, and amide hydrolysis reactions. In vitro assays reveal two single-module non-ribosomal peptide synthetases (NRPs) that incorporate the β-keto acid and l-isoleucine, followed by Dieckmann condensation, to form the quinolone-γ-lactam. Notably, the bioconversion from l-kynurenine to the β-keto acid is a unique strategy employed by nature to decouple R*-domain-containing NRPS from the polyketide synthase (PKS) machinery, expanding the paradigm for the biosynthesis of quinolone-γ-lactam natural products via Dieckmann condensation.
2. Quinolactacins revisited: from lactams to imide and beyond
Ben Clark, Robert J Capon, Ernest Lacey, Shaun Tennant, Jennifer H Gill Org Biomol Chem. 2006 Apr 21;4(8):1512-9. doi: 10.1039/b600959j. Epub 2006 Mar 16.
Chemical analysis of a solid phase fermentation of an Australian Penicillium citrinum strain has returned all known examples of a rare class of N-methyl quinolone lactams, quinolactacins A2 (1), B2 (2), C2 (3) and A1 (4), together with the new quinolactacins B1 (5), C1 (6), D1 (7) and D2 (8), and the novel derivatives quinolonimide (9) and quinolonic acid (10). Complete stereostructures were assigned to all these compounds by detailed spectroscopic analysis and chemical interconversion. Carefully controlled and monitored decomposition studies have confirmed that quinolactacins readily undergo C-3 epimerization and oxidation, and under appropriate conditions convert to quinolonimide and quinolonic acid. Mechanisms for key transformations are proposed. The decomposition studies suggested that only quinolactacins A2 (1) and B2 (2) are genuine natural products, with all other isolated compounds being decomposition artefacts. Quinolactacins C1 (6), C2 (3), and the racemic mixture of quinolactacins D1/D2 (8/7) all displayed notable cytotoxic activity.
3. Alkaloids from Xylariaceae sp., a marine-derived fungus
Xu-Hua Nong, Xiao-Yong Zhang, Xin-Ya Xu, Yun-Lin Sun, Shu-Hua Qi Nat Prod Commun. 2014 Apr;9(4):467-8.
A new pyridine derivative, 5-(2'-hydroxypropyl)pyridin-3-ol (1), with seven known alkaloids, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (2), penicillenol A1 (3), penicillenol A2 (4), a mixture of quinolactacin AI (5a) and quinolactacin A2 (5b), and a mixture of quinolactacin C1 (6a) and quinolactacin C2 (6b), were isolated from the culture broth of a marine-derived fungus Xylariaceae sp. SCSGAF0086. Their structures were elucidated by spectroscopic methods. Compound 2 showed weak antimicrobial activity against Bacillus subtilis, and a mixture of 6a and 6b exhibited strong antifouling activity toward Bugula neritina larval settlement.
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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 ╳
