Oxysporizoline, an antibacterial polycyclic quinazoline alkaloid from the marine-mudflat-derived fungus Fusarium oxysporum

Nenkep, Viviane N.; Yun, Keumja; Son, Byeng Wha

doi:10.1038/ja.2015.137

Cited by 30 publications

(24 citation statements)

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“…2) with specific correlations between the α-protons of the amino acid residues (Phe 6 , Tyr 1 , HICA 2 ) and carbonyl carbons of the neighboring residues, suggesting the presence of a Phe 6 -Tyr 1 -HICA 2 -Phe 3 fragment. In addition, the HMBC correlation between amide protons of the amino acid residues (Phe 3 , Phe 4 , Phe 5 ) and carbonyl carbons of the adjacent residues disclosed another fragment, i.e., Phe 3 -Phe 4 -Phe 5 -Phe 6 . Conse-quently, compound 1 was deduced to be cyclo (Tyr-HICA-Phe-Phe-Phe-Phe).…”

Section: Resultsmentioning

confidence: 98%

“…5.3 was then subjected to a Sephadex LH-20 column (100 × 2 cm, 100 µm) using MeOH as the mobile phase, yielding compound 3 (10 mg), while Fr. 5…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…Fusarium (Nectriaceae) is a genus of filamentous fungi that are widely distributed in soil and are associated with plants [3]. Most species are harmless saprophytic fungi that produce diverse bioactive secondary metabolites, including fusarubin, which has antitubercular activity [4], oxysporizoline, which has antibacterial activity [5], fusaric acid derivatives, which inhibit dopamine-β-hydroxylase and have phytotoxic activities [6], and trichothecenes, which inhibit protein synthesis in humans and animals [7].…”

Section: Introductionmentioning

confidence: 99%

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Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

et al. 2018

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Two novel cyclic hexadepsipeptides, fusarihexin A (1: ) and fusarihexin B (2: ), and two known compounds, cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Val) (3: ) and cyclo-(L-Leu-L-Leu-D-Leu-L-Leu-L-Ile) (4: ), were isolated from the marine mangrove endophytic fungus sp. R5. Their chemical structures were elucidated on the basis of spectroscopic data and Marfey's analysis. In an bioassay, fusarihexin A (1: ) remarkably inhibited three plant pathogenic fungi: (Penz.) Sacc., which causes anthracnose in many fruits and vegetables, (Berk. and M. A. Curtis) Arx, which causes crown rot and anthracnose in bananas, and Schlecht. f. sp. lycopersici (Sacc.) W. C. Snyder et H. N. Hansen, which causes Fusarium wilt and fruit rot in tomatoes. Fusarihexin B (2: ) strongly inhibited and . The compounds were more potent than carbendazim, which is widely used as an agricultural and horticultural fungicide worldwide.

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Section: Resultsmentioning

confidence: 98%

“…5.3 was then subjected to a Sephadex LH-20 column (100 × 2 cm, 100 µm) using MeOH as the mobile phase, yielding compound 3 (10 mg), while Fr. 5…”

Section: Extraction and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

et al. 2018

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“…Liu et al [29] recently (2019) detected a new antimicrobial quinazoline in Aspergillus sydowii SW9, living in China's seawater. They named the compound 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin- Oxysporizoline (21) was discovered by Nenkep et al (2016) [27] in the marine fungus F. oxysporum in Suncheon Bay, Korea. In an antimicrobial assay, it showed weak antibacterial activity against the Gram + , clinically relevant MRSA and multidrug-resistant S. aureus (MDRSA).…”

Section: Quinazolinesmentioning

confidence: 99%

“…Of the 35 novel alkaloids discussed in this review, three belong to the quinazoline alkaloids. Oxysporizoline (21) and thielaviazoline (22) are respectively a tris-anhydrotetramer and a trimer of anthranilic acid, for which no biochemical information is available [27,28]. On the other hand, self-condensation of anthranilic acid and chemical synthesis of polycyclic quinazoline derivatives like oxysporizoline complexed with metals were reported, and the latter implied several interesting bioactivities [91].…”

Section: Quinazolinesmentioning

confidence: 99%

Alkaloids from Marine Fungi: Promising Antimicrobials

et al. 2020

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Resistance of pathogenic microorganisms against antimicrobials is a major threat to contemporary human society. It necessitates a perpetual influx of novel antimicrobial compounds. More specifically, Gram− pathogens emerged as the most exigent danger. In our continuing quest to search for novel antimicrobial molecules, alkaloids from marine fungi show great promise. However, current reports of such newly discovered alkaloids are often limited to cytotoxicity studies and, moreover, neglect to discuss the enigma of their biosynthesis. Yet, the latter is often a prerequisite to make them available through sufficiently efficient processes. This review aims to summarize novel alkaloids with promising antimicrobial properties discovered in the past five years and produced by marine fungi. Several discovery strategies are summarized, and knowledge gaps in biochemical production routes are identified. Finally, links between the structure of the newly discovered molecules and their activity are proposed. Since 2015, a total of 35 new antimicrobial alkaloids from marine fungi were identified, of which 22 showed an antibacterial activity against Gram− microorganisms. Eight of them can be classified as narrow-spectrum Gram− antibiotics. Despite this promising ratio of novel alkaloids active against Gram− microorganisms, the number of newly discovered antimicrobial alkaloids is low, due to the narrow spectrum of discovery protocols that are used and the fact that antimicrobial properties of newly discovered alkaloids are barely characterized. Alternatives are proposed in this review. In conclusion, this review summarizes novel findings on antimicrobial alkaloids from marine fungi, shows their potential as promising therapeutic candidates, and hints on how to further improve this potential.

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Chemical Constituents of a Marine‐derived Fungus Fusarium oxysporum F0888 and their Antibacterial Activity

Zhao,

Cen,

et al. 2024

Chemistry & Biodiversity

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Six new compounds, including four hydroxyphenylacetic acid derivatives, stachylines H–K (1–4), a derivative of hydroxyphenylethanol (5), and one new amide (6), as well as 6 known compounds were obtained from a marine‐derived fungus Fusarium oxysporum F0888 isolated from sediments in the South China Sea. The structures and absolute configurations of new compounds were determined by spectroscopic (IR, NMR, and HR‐ESI‐MS) analyses, comparison of optical rotations, and the modified Mosher’s MTPA ester method. Antimicrobial and anti‐inflammatory activities of compounds 1–12 were tested. Unfortunately, all of isolated compounds were inactivity.

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Oxysporizoline, an antibacterial polycyclic quinazoline alkaloid from the marine-mudflat-derived fungus Fusarium oxysporum

Cited by 30 publications

References 4 publications

Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

Fusarihexins A and B: Novel Cyclic Hexadepsipeptides from the Mangrove Endophytic Fungus Fusarium sp. R5 with Antifungal Activities

Alkaloids from Marine Fungi: Promising Antimicrobials

Chemical Constituents of a Marine‐derived Fungus Fusarium oxysporum F0888 and their Antibacterial Activity

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