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Journal articles on the topic 'Tetramic Acid'

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Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Jiang, Minghua, Senhua Chen, Jing Li, and Lan Liu. "The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms." Marine Drugs 18, no. 2 (February 15, 2020): 114. http://dx.doi.org/10.3390/md18020114.

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Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids, N-acylated tetramic acids, α-cyclopiazonic acid-type tetramic acids, and other tetramic acids) from marine-derived microbes, including fungi, actinobacteria, bacteria, and cyanobacteria, as reported in 195 research studies up to 2019.

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2

Ueda, Chihiro, Kazuhiro Tateda, Manabu Horikawa, Soichiro Kimura, Yoshikazu Ishii, Kaoru Nomura, Kanako Yamada, et al. "Anti-Clostridium difficile Potential of Tetramic Acid Derivatives from Pseudomonas aeruginosa Quorum-Sensing Autoinducers." Antimicrobial Agents and Chemotherapy 54, no. 2 (November 16, 2009): 683–88. http://dx.doi.org/10.1128/aac.00702-09.

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ABSTRACT We have examined the potential bactericidal activities of several tetramic acids derived from Pseudomonas autoinducers against Clostridium difficile, a cause of antibiotic-associated pseudomembranous colitis. Clinical isolates of C. difficile (n = 4) were incubated in broth with a chemically synthesized Pseudomonas autoinducer and its tetramic acid derivatives. The structure-activity relationship and the mechanisms of action were examined by a time-killing assay and by determination of the morphological/staining characteristics. The use of some tetramic acids derived from N-3-oxododecanoyl l-homoserine lactone resulted in more than 3-log reductions in the viability of C. difficile within 30 min at 30 μM. The outer membrane was suggested to be one of the targets for the bactericidal activity of tetramic acid, because disturbance of the bacterial outer surface was demonstrated by alteration of the Gram-staining characteristic and electron microscopy. The data for the tetramic acid derivatives demonstrate that the keto-enol structure and the length of the acyl side chain of tetramic acid may be essential for the antibacterial activity of this molecule. These results suggest the potential for tetramic acid derivatives to be novel agents with activity against C. difficile.

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3

Stachel, Hans-Dietrich, and Josef Schachtner. "Synthese von Heteroanaloga der Penicillsäure / Synthesis of Hetero Analogues of Penicillic Acid." Zeitschrift für Naturforschung B 51, no. 9 (September 1, 1996): 1334–38. http://dx.doi.org/10.1515/znb-1996-0919.

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4

Neumann, Kerstin, Stefan Kehraus, Michael Gütschow, and Gabriele M. König. "Cytotoxic and HLE-Inhibitory Tetramic Acid Derivatives from Marine-Derived Fungi." Natural Product Communications 4, no. 3 (March 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400308.

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Tetramic acid derivatives are an important class of nitrogen heterocycles with a pyrrolidine-2,4-dione core as a key structural motif. From the sponge-derived fungus Beauveria bassiana, a new equisetin-like tetramic acid derivative, beauversetin (1), was isolated. The sea weed-derived fungus Microdiplodia sp. produced the tetramic acid derivative 2 (Sch210972) which was shown to inhibit human leucocyte elastase (HLE) with an IC50 of 1.04 μg mL−1.

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5

Li, Yong, Zheng Huang, Jia Xu, Yong Ding, Dian-Yong Tang, Jie Lei, Hong-yu Li, Zhong-Zhu Chen, and Zhi-Gang Xu. "Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction." Beilstein Journal of Organic Chemistry 16 (April 9, 2020): 663–69. http://dx.doi.org/10.3762/bjoc.16.63.

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A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods.

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6

Myrtle, J. D., A. M. Beekman, and R. A. Barrow. "Ravynic acid, an antibiotic polyeneyne tetramic acid from Penicillium sp. elucidated through synthesis." Organic & Biomolecular Chemistry 14, no. 35 (2016): 8253–60. http://dx.doi.org/10.1039/c6ob00938g.

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7

Unten, Yufu, Masatoshi Murai, Katsuyuki Sakai, Yukihiro Asami, Takenori Yamamoto, Takahiro Masuya, and Hideto Miyoshi. "Natural tetramic acids elicit multiple inhibitory actions against mitochondrial machineries presiding over oxidative phosphorylation." Bioscience, Biotechnology, and Biochemistry 85, no. 12 (October 8, 2021): 2368–77. http://dx.doi.org/10.1093/bbb/zbab176.

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ABSTRACT The mitochondrial machineries presiding over ATP synthesis via oxidative phosphorylation are promising druggable targets. Fusaramin, a 3-acyl tetramic acid isolated from Fusarium concentricum FKI-7550, is an inhibitor of oxidative phosphorylation in Saccharomyces cerevisiae mitochondria, although its target has yet to be identified. Fusaramin significantly interfered with [3H]ADP uptake by yeast mitochondria at the concentration range inhibiting oxidative phosphorylation. A photoreactive fusaramin derivative (pFS-5) specifically labeled voltage-dependent anion channel 1 (VDAC1), which facilitates trafficking of ADP/ATP across the outer mitochondrial membrane. These results strongly suggest that the inhibition of oxidative phosphorylation by fusaramin is predominantly attributable to the impairment of VDAC1 functions. Fusaramin also inhibited FoF1-ATP synthase and ubiquinol-cytochrome c oxidoreductase (complex III) at concentrations higher than those required for the VDAC inhibition. Considering that other tetramic acid derivatives are reported to inhibit FoF1-ATP synthase and complex III, natural tetramic acids were found to elicit multiple inhibitory actions against mitochondrial machineries.

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8

Poncet, Jo�l, Patrick Jouin, Bertrand Castro, Louisette Nicolas, Mohamed Boutar, and Alain Gaudemer. "Tetramic acid chemistry. Part 1. Reinvestigation of racemisation during the synthesis of tetramic acids via Dieckmann cyclisation." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1990): 611. http://dx.doi.org/10.1039/p19900000611.

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9

Marfori, Eufrocinio C., Shin' ichiro Kajiyama, Ei-ichiro Fukusaki, and Akio Kobayashi. "Phytotoxicity of the tetramic acid metabolite trichosetin." Phytochemistry 62, no. 5 (March 2003): 715–21. http://dx.doi.org/10.1016/s0031-9422(02)00629-5.

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10

Spatz, Julia H., Sebastian J. Welsch, David-Emmanuel Duhaut, Nadine Jäger, Thomas Boursier, Martin Fredrich, Lars Allmendinger, et al. "Tetramic acid derivatives via Ugi–Dieckmann-reaction." Tetrahedron Letters 50, no. 15 (April 2009): 1705–7. http://dx.doi.org/10.1016/j.tetlet.2009.01.124.

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11

Poschenrieder, Hermann, Eduard Eckl, Hans-Dietrich Stachel, Andreas Windt, and Kurt Polborn. "Ring enlargement reactions of tetramic acid derivatives." Journal of Heterocyclic Chemistry 37, no. 4 (July 2000): 839–46. http://dx.doi.org/10.1002/jhet.5570370428.

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12

HENNING, H. G., and A. GLEBIN. "ChemInform Abstract: Advances in Tetramic Acid Chemistry." ChemInform 25, no. 22 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199422296.

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13

Zhao, Huaping, Zhipeng Cui, Yucheng Gu, Yuxiu Liu, and Qingmin Wang. "The phytotoxicity of natural tetramic acid derivatives." Pest Management Science 67, no. 9 (June 8, 2011): 1059–61. http://dx.doi.org/10.1002/ps.2210.

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14

Grunwald, Alyssa L., Fabrice Berrué, David P. Overy, and Russell G. Kerr. "Isolation of iqalisetins A and B from a Tolypocladium sp. isolated from marine sediment from Frobisher Bay in Canada’s arctic." Canadian Journal of Chemistry 94, no. 4 (April 2016): 444–48. http://dx.doi.org/10.1139/cjc-2015-0439.

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Two new decalin-tetramic acid compounds, iqalisetin A (1) and iqalisetin B (2), were identified from a Tolypocladium sp. isolated from a marine sediment sample collected from Frobisher Bay, Nunavut, in Canada’s arctic. The structures of the new compounds were elucidated by NMR experiments. The relative stereochemistry of the decalin skeleton was determined by NOESY experiments and confirmed that 1 and 2 contained a trans-decalin ring system. The absolute stereochemistry of the tetramic acid was determined using Marfey’s method. Compounds 1 and 2 did not exhibit any significant antimicrobial or cytotoxic activity.

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15

Iwata, Yasuhiro, Naomi Maekawara, Keiji Tanino, and Masaaki Miyashita. "Tetramic Acid Antibiotics: Stereoselective Synthesis of Streptolic Acid and Tirandalydigin." Angewandte Chemie International Edition 44, no. 10 (February 25, 2005): 1532–36. http://dx.doi.org/10.1002/anie.200462300.

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16

Iwata, Yasuhiro, Naomi Maekawara, Keiji Tanino, and Masaaki Miyashita. "Tetramic Acid Antibiotics: Stereoselective Synthesis of Streptolic Acid and Tirandalydigin." Angewandte Chemie 117, no. 10 (February 25, 2005): 1556–60. http://dx.doi.org/10.1002/ange.200462300.

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17

Zhao, Zhilong, Ting Shi, Min Xu, Nelson L. Brock, Yi-Lei Zhao, Yemin Wang, Zixin Deng, Xiuhua Pang, and Meifeng Tao. "Hybrubins: Bipyrrole Tetramic Acids Obtained by Crosstalk between a Truncated Undecylprodigiosin Pathway and Heterologous Tetramic Acid Biosynthetic Genes." Organic Letters 18, no. 3 (January 22, 2016): 572–75. http://dx.doi.org/10.1021/acs.orglett.5b03609.

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18

Fustero, Santos, Marta García de la Torre, Juan F. Sanz-Cervera, Carmen Ramírez de Arellano, Julio Piera, and Antonio Simón. "A Concise, Asymmetric Synthesis of Tetramic Acid Derivatives." Organic Letters 4, no. 21 (October 2002): 3651–54. http://dx.doi.org/10.1021/ol026599k.

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19

Marfori, Eufrocinio C., Takeshi Bamba, Shin 'ichiro Kajiyama, Ei-ichiro Fukusaki, and Akio Kobayashi. "Biosynthetic studies of the tetramic acid antibiotic trichosetin." Tetrahedron 58, no. 33 (August 2002): 6655–58. http://dx.doi.org/10.1016/s0040-4020(02)00689-0.

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20

Liu, Zhanxiang, Xiuxiu Ruan, and Xian Huang. "A facile solid phase synthesis of tetramic acid." Bioorganic & Medicinal Chemistry Letters 13, no. 15 (August 2003): 2505–7. http://dx.doi.org/10.1016/s0960-894x(03)00502-x.

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21

SHIMSHOCK, S. J., and P. DESHONG. "ChemInform Abstract: Synthesis of the Tetramic Acid Antibiotics." ChemInform 26, no. 1 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199501281.

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22

Pelkey, Erin, Fernando Banales Mejia, Megan Lafferty, Sophia Melvin, Nathanyal Truax, and Maeve Kean. "Lewis Acid Mediated Addition of Indoles and Alcohols to Tetronic Acid and Tetramic Acids." Synlett 28, no. 02 (October 13, 2016): 260–64. http://dx.doi.org/10.1055/s-0036-1588335.

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23

Sengoku, Tetsuya, Yusuke Murata, Chihiro Suzuki, Masaki Takahashi, and Hidemi Yoda. "Synthesis of new chiral lactam-fused pyridine derivatives." RSC Advances 5, no. 90 (2015): 73562–65. http://dx.doi.org/10.1039/c5ra16896a.

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An acid promoted cyclisation of benzylidene-modified tetramic acid and various enamines followed by MnO₂ oxidation afforded the corresponding C₂-symmetric and unsymmetric lactam-fused pyridines in enantiomerically pure forms.

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24

Mo, Xuhua, Qinglian Li, and Jianhua Ju. "Naturally occurring tetramic acid products: isolation, structure elucidation and biological activity." RSC Adv. 4, no. 92 (2014): 50566–93. http://dx.doi.org/10.1039/c4ra09047k.

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Natural products containing the tetramic acid core scaffold have been isolated from an assortment of terrestrial and marine species and often display wide ranging and potent biological activities including antibacterial, antiviral and antitumoral activities.

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25

Liang, Xiao, Zhong-Hui Huang, Xuan Ma, and Shu-Hua Qi. "Unstable Tetramic Acid Derivatives from the Deep-Sea-Derived Fungus Cladosporium sphaerospermum EIODSF 008." Marine Drugs 16, no. 11 (November 15, 2018): 448. http://dx.doi.org/10.3390/md16110448.

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Seven new unstable tetramic acid derivatives, cladosporiumins I-O (1–7), together with the known analogue cladodionen (8) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound 4 was a Mg complex of tetramic acid derivative. In acidic solvent, 4 could change to 1 and 6, and 7 could change to 5. In addition, 1, 5 and 8 existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of 1–8 were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.

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26

Boeckman, Robert K., Joan C. Potenza, and Eric J. Enholm. "Synthetic studies directed toward naturally occurring tetramic acids. 3. Synthesis of (-)-methyl ydiginate and the tetramic acid subunit for streptolydigin." Journal of Organic Chemistry 52, no. 3 (February 1987): 469–72. http://dx.doi.org/10.1021/jo00379a036.

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27

Loke, Inga, Guillaume Bentzinger, Julia Holz, Aruna Raja, Aman Bhasin, Florenz Sasse, Andreas Köhn, Rainer Schobert, and Sabine Laschat. "Synthesis of the AB ring system of clifednamide utilizing Claisen rearrangement and Diels–Alder reaction as key steps." Organic & Biomolecular Chemistry 14, no. 3 (2016): 884–94. http://dx.doi.org/10.1039/c5ob01491c.

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A synthesis to the functionalized AB ring system of clifednamide, member of macrocyclic tetramic acid lactams, was developed involving an Ireland–Claisen rearrangement and an intramolecular Diels–Alder reaction.

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28

Matiadis, Dimitrios, Dimitrios Tsironis, Valentina Stefanou, Olga Igglessi–Markopoulou, Vickie McKee, Yiannis Sanakis, Katerina N. Lazarou, Athanassios Chrissanthopoulos, Spyros N. Yannopoulos, and John M. Markopoulos. "X-Ray Crystallographic Analysis, EPR Studies, and Computational Calculations of a Cu(II) Tetramic Acid Complex." Bioinorganic Chemistry and Applications 2017 (2017): 1–10. http://dx.doi.org/10.1155/2017/7895023.

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In this work we present a structural and spectroscopic analysis of a copper(II) N-acetyl-5-arylidene tetramic acid by using both experimental and computational techniques. The crystal structure of the Cu(II) complex was determined by single crystal X-ray diffraction and shows that the copper ion lies on a centre of symmetry, with each ligand ion coordinated to two copper ions, forming a 2D sheet. Moreover, the EPR spectroscopic properties of the Cu(II) tetramic acid complex were also explored and discussed. Finally, a computational approach was performed in order to obtain a detailed and precise insight of product structures and properties. It is hoped that this study can enrich the field of functional supramolecular systems, giving place to the formation of coordination-driven self-assembly architectures.

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29

Shang, Zhuo, Li Li, Breno P. Espósito, Angela A. Salim, Zeinab G. Khalil, Michelle Quezada, Paul V. Bernhardt, and Robert J. Capon. "New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp." Organic & Biomolecular Chemistry 13, no. 28 (2015): 7795–802. http://dx.doi.org/10.1039/c5ob01058f.

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30

Whitt, James, Suzanne M. Shipley, David J. Newman, and Karina M. Zuck. "Tetramic Acid Analogues Produced by Coculture ofSaccharopolyspora erythraeawithFusarium pallidoroseum." Journal of Natural Products 77, no. 1 (January 14, 2014): 173–77. http://dx.doi.org/10.1021/np400761g.

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31

Petermichl, Markus, and Rainer Schobert. "Total Synthesis of the Diglycosidic Tetramic Acid Ancorinoside A." Chemistry - A European Journal 23, no. 59 (October 6, 2017): 14743–46. http://dx.doi.org/10.1002/chem.201704379.

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32

Poschenrieder, Hermann, Eduard Eckl, Hans-Dietrich Stachel, Andreas Windt, and Kurt Polborn. "ChemInform Abstract: Ring Enlargement Reactions of Tetramic Acid Derivatives." ChemInform 32, no. 2 (January 9, 2001): no. http://dx.doi.org/10.1002/chin.200102049.

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33

Dixon, Darren J., Steven V. Ley, and Deborah A. Longbottom. "Total synthesis of the plasmoidal pigment physarorubinic acid, a polyenoyl tetramic acid." Journal of the Chemical Society, Perkin Transactions 1, no. 16 (1999): 2231–32. http://dx.doi.org/10.1039/a904921e.

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34

Michael, Adam P., Emily J. Grace, Mike Kotiw, and Russell A. Barrow. "Ravenic Acid, a New Tetramic Acid Isolated from a Cultured Microfungus,Penicilliumsp." Journal of Natural Products 65, no. 9 (September 2002): 1360–62. http://dx.doi.org/10.1021/np0200358.

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35

Schütznerová, Eva, Anna Krchňáková, and Viktor Krchňák. "Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives." Molecules 24, no. 7 (April 10, 2019): 1406. http://dx.doi.org/10.3390/molecules24071406.

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In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones.

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36

Lin, Xiaojing, Siwen Yuan, Senhua Chen, Bin Chen, Hui Xu, Lan Liu, Huixian Li, and Zhizeng Gao. "Heterologous Expression of Ilicicolin H Biosynthetic Gene Cluster and Production of a New Potent Antifungal Reagent, Ilicicolin J." Molecules 24, no. 12 (June 18, 2019): 2267. http://dx.doi.org/10.3390/molecules24122267.

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Ilicicolin H is a broad-spectrum antifungal agent targeting mitochondrial cytochrome bc1 reductase. Unfortunately, ilicicolin H shows reduced activities in vivo. Here, we report our effort on the identification of ilicicolin H biosynthetic gene cluster (BGC) by genomic sequencing a producing strain, Neonectria sp. DH2, and its heterologous production in Aspergillus nidulans. In addition, a shunt product with similar antifungal activities, ilicicolin J, was uncovered. This effort would provide a base for future combinatorial biosynthesis of ilicicolin H analogues. Bioinformatics analysis suggests that the backbone of ilicicolin H is assembled by a polyketide-nonribosomal peptide synthethase (IliA), and then offloaded with a tetramic acid moiety. Similar to tenellin biosynthesis, the tetramic acid is then converted to pyridone by a putative P450, IliC. The decalin portion is most possibly constructed by a S-adenosyl-l-methionine (SAM)-dependent Diels-Alderase (IliD).

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37

De Tommaso, Gaetano, Maria Michela Salvatore, Rosario Nicoletti, Marina DellaGreca, Francesco Vinale, Assunta Bottiglieri, Alessia Staropoli, et al. "Bivalent Metal-Chelating Properties of Harzianic Acid Produced by Trichoderma pleuroticola Associated to the Gastropod Melarhaphe neritoides." Molecules 25, no. 9 (May 4, 2020): 2147. http://dx.doi.org/10.3390/molecules25092147.

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Harzianic acid is a secondary metabolite of Trichoderma, structurally belonging to the dienyltetramic acid subgroup of the tetramic acids. Biological activities of harzianic acid are of great interest for its antimicrobial and plant growth-promoting activities, which might be related to its chelating properties. In the present work harzianic acid, isolated from cultures of a strain of Trichoderma pleuroticola associated to the gastropod Melarhaphe neritoides, was studied as a complexant agent of a number of biologically relevant transition metals (i.e., Zn2+, Fe2+, Cu2+, and Mn2+), using UV-VIS, potentiometry, MS and NMR techniques. Our findings show the coordination capacity of harzianic acid toward the above cations through the formation of neutral or charged complexes in a variable ratio depending on the metal and pH conditions.

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38

El Kaïm, Laurent, Rocío Gámez-Montaño, Nancy Alvarez-Rodríguez, and Aurélie Dos Santos. "The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives." Synlett 26, no. 16 (August 12, 2015): 2253–56. http://dx.doi.org/10.1055/s-0035-1560050.

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39

Wang, Shuangshuang, Longzhu Bao, Di Song, Jingjing Wang, Xiufang Cao, and Shaoyong Ke. "Amino acid-oriented poly-substituted heterocyclic tetramic acid derivatives as potential antifungal agents." European Journal of Medicinal Chemistry 179 (October 2019): 567–75. http://dx.doi.org/10.1016/j.ejmech.2019.06.078.

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40

Shephard, G. S., P. G. Thiel, E. W. Sydenham, R. Vleggaar, and W. F. O. Marasas. "Reversed-phase high-performance liquid chromatography of tenuazonic acid and related tetramic acids." Journal of Chromatography B: Biomedical Sciences and Applications 566, no. 1 (May 1991): 195–205. http://dx.doi.org/10.1016/0378-4347(91)80124-u.

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41

DeShong, Philip, Joseph A. Cipollina, and Nancy K. Lowmaster. "A general method for the synthesis of tetramic acid derivatives." Journal of Organic Chemistry 53, no. 7 (April 1988): 1356–64. http://dx.doi.org/10.1021/jo00242a003.

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42

Vassilikou-dova, A., I. M. Kalogeras, M. Petroliagi, O. Igglessi-markopoulou, and J. Markopoulos. "IR, NMR and dielectric characterization of a novel tetramic acid." Radiation Effects and Defects in Solids 150, no. 1-4 (November 1999): 409–14. http://dx.doi.org/10.1080/10420159908226266.

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43

Cherian, Philip T., Martin N. Cheramie, Ravi K. R. Marreddy, Dinesh M. Fernando, Julian G. Hurdle, and Richard E. Lee. "New β-lactam – Tetramic acid hybrids show promising antibacterial activities." Bioorganic & Medicinal Chemistry Letters 28, no. 18 (October 2018): 3105–12. http://dx.doi.org/10.1016/j.bmcl.2018.07.018.

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44

Fukuda, Takao, Yuri Sudoh, Yuki Tsuchiya, Toru Okuda, Nobuyasu Matsuura, Atsuko Motojima, Tsutomu Oikawa, and Yasuhiro Igarashi. "Tolypoalbin, a new tetramic acid from Tolypocladium album TAMA 479." Journal of Antibiotics 68, no. 6 (January 28, 2015): 399–402. http://dx.doi.org/10.1038/ja.2014.165.

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45

Lang, Gerhard, Anthony L. J. Cole, John W. Blunt, and Murray H. G. Munro. "An Unusual Oxalylated Tetramic Acid from the New Zealand BasidiomyceteChamonixiapachydermis." Journal of Natural Products 69, no. 1 (January 2006): 151–53. http://dx.doi.org/10.1021/np050488n.

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46

Marfori, Eufrocinio C., Takeshi Bamba, Shin 'ichiro Kajiyama, Ei-ichiro Fukusaki, and Akio Kobayashi. "ChemInform Abstract: Biosynthetic Studies of the Tetramic Acid Antibiotic Trichosetin." ChemInform 33, no. 50 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200250205.

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47

Dixon, Darren J., Steven V. Ley, and Deborah A. Longbottom. "ChemInform Abstract: Total Synthesis of the Plasmoidal Pigment Physarorubinic Acid, a Polyenoyl Tetramic Acid." ChemInform 30, no. 44 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199944189.

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48

Schlenk, Andrea, Randi Diestel, Florenz Sasse, and Rainer Schobert. "A Selective 3-Acylation of Tetramic Acids and the First Synthesis of Ravenic Acid." Chemistry - A European Journal 16, no. 8 (February 22, 2010): 2599–604. http://dx.doi.org/10.1002/chem.200902544.

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Soliga, Kevin J., Sofia I. Bär, Natalie Oberhuber, Haoxuan Zeng, Hedda Schrey, and Rainer Schobert. "Synthesis and Bioactivity of Ancorinoside B, a Marine Diglycosyl Tetramic Acid." Marine Drugs 19, no. 10 (October 19, 2021): 583. http://dx.doi.org/10.3390/md19100583.

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Abstract:

The sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a β-d-galactopyranosyl-(1→4)-β-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected d-lactose derived thioglycoside, its attachment to a C20-aldehyde spacer, functionalization of the latter with a terminal N-(β-ketoacyl)-d-aspartate, and a basic Dieckmann cyclization to close the pyrrolidin-2,4-dione ring with concomitant global deprotection. Ancorinoside B exhibited multiple biological effects of medicinal interest. It inhibited the secretion of the cancer metastasis-relevant matrix metalloproteinases MMP-2 and MMP-9, and also the growth of Staphylococcus aureus biofilms by ca 87% when applied at concentrations as low as 0.5 µg/mL. This concentration is far below its MIC of ca 67 µg/mL and thus unlikely to induce bacterial resistance. It also led to a 67% dispersion of preformed S. aureus biofilms when applied at a concentration of ca 2 µg/mL. Ancorinoside B might thus be an interesting candidate for the control of the general hospital, catheter, or joint protheses infections.

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Lou, Lili, Guoliang Qian, Yunxuan Xie, Jiliang Hang, Haotong Chen, Kathia Zaleta-Rivera, Yaoyao Li, et al. "Biosynthesis of HSAF, a Tetramic Acid-Containing Macrolactam from Lysobacter enzymogenes." Journal of the American Chemical Society 133, no. 4 (February 2, 2011): 643–45. http://dx.doi.org/10.1021/ja105732c.

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