Genome- and MS-based mining of antibacterial chlorinated chromones and xanthones from the phytopathogenic fungus Bipolaris sorokiniana strain 11134

Han, Jackie; Zhang, Jingyu; Song, Zhijun; Liu, Miaomiao; Hu, Jiansen; Hou, Chengjian; Zhu, Guoliang; Jiang, Lan; Xia, Xuekui; Quinn, Ronald J.; Feng, Yunjiang; Zhang, Lixin; Hsiang, Tom; Liu, Xueting

doi:10.1007/s00253-019-09821-z

Cited by 22 publications

(15 citation statements)

References 83 publications

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“…Nevertheless, the chlorinated xanthones with simple skeleton were mainly isolated from lichens [52]. Examples of such fungal chlorinated xanthones are 4-chloropinselin from Monilinia fructicola and Bipolaris sorokiniana [40,42], chloroisosulochrin dehydrate from P. theae [49], 3,6,8-trihydroxy-5-chlorin-1-methylxanthone from Stachybotrys sp. [53], 4-chlorofischexanthone from Alternaria sp.…”

Section: Discussionmentioning

confidence: 99%

“…The biosynthetic pathway of 9 to 8, via 5 and 3, involves hydroxylation and chlorination of the phenolic nucleus, ring closure of the benzophenone structure to a xanthone type [41]. Recently, Han et al isolated new related compounds from phytopathogenic fungus B. sorokiniana and characterized the gene cluster encoding halogenated polyketides [42]. A similar range of halogenated metabolites and their pre-cursors isolated from A. sonchi, M. fructicola, and B. sorokiniana indicates that their biosynthesis proceeds in a similar way.…”

Section: Discussionmentioning

confidence: 99%

“…An example of such xanthone derivatives is 8-hydroxy-3-methylxanthone-1-carboxylate from Apiospora montagnei [56]. Therefore, 1 was suggested to be derived from chrysophanol [42]. The production of 5-chloromoniliphenone was predicted in B. sorokiniana as a biosynthetic intermediate of 4-chloropinselin and chloromonilicin [42].…”

Section: Discussionmentioning

confidence: 99%

“…This led us to revise structures of alternethanoxins A and B (Figure 4). All the isolated compounds from A. sonchi xanthones, chromones, and benzophenones are structurally and biosynthetically related [42]. Moreover, it was noted that UV-and MS-spectra of 5 and 9 are identical to alternethanoxins A and B (5a and 9a), respectively [24,39,40].…”

Section: Structure Elucidationmentioning

confidence: 94%

“…Eleven known compounds were identified comparing original and literature spectroscopy data: 4-chloropinselin (3) [41], methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) [42], pinselin (5) [39], methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) [43], methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (7) [40], chloromonilicin (8) [27], moniliphenone (9) [40], chloromonilinic acids B (10), C (12), and D (11) [44,45], and α-, β-diversolonic esters (13) [46] (Figure 1). Among them, compounds 4-7, 9, 11, and 13 were first reported for A. sonchi.…”

Section: Structure Elucidationmentioning

confidence: 99%

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Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

et al. 2020

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The fungus, Alternaria sonchi is considered to be a potential agent for the biocontrol of perennial sowthistle (Sonchus arvensis). A new chlorinated xanthone, methyl 8-hydroxy-3-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (1) and a new benzophenone derivative, 5-chloromoniliphenone (2), were isolated together with eleven structurally related compounds (3–13) from the solid culture of the fungus, which is used for the production of bioherbicidal inoculum of A. sonchi. Their structures were determined by spectroscopic (mostly by NMR and MS) methods. Alternethanoxins A and B, which were reported in A. sonchi earlier, were re-identified as moniliphenone and pinselin, respectively. The isolated compounds were tested for phytotoxic, antimicrobial, insecticidal, cytotoxic and esterase-inhibition activities. They did not demonstrate high phytotoxicity (lesions up to 2.5 mm in diameter/length at a concentration of 2 mg/mL) when tested on leaf disks/segments of perennial sowthistle (Sonchus arvensis) and couch grass (Elytrigia repens). They did not possess acute toxicity to Paramecium caudatum, and showed moderate to low cytotoxicity (IC50 > 25 µg/mL) for U937 and K562 tumor cell lines. However, chloromonilicin and methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) were shown to have antimicrobial properties with MIC 0.5–5 µg/disc. Compound 4 and chloromonilinic acid B were found to have contact insecticidal activity to wheat aphid (Schizaphis graminum) at 1 mg/mL. Compounds 2 and methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate displayed selective carboxylesterase inhibition activity at concentration of 100 µg/mL. Therefore, the waste solid substrate for production of A. sonchi spores can be re-utilized for the isolation of a number of valuable natural products.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Structure Elucidationmentioning

confidence: 94%

Section: Structure Elucidationmentioning

confidence: 99%

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Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

et al. 2020

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Synthetic and Natural Xanthones as Antibacterial Agents—Review

Prathiksha,

Murali,

Nayak

2024

ChemistrySelect

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Xanthones, a class of polyketide derivatives characterized by a dibenzo‐γ‐pyrone core structure, are aromatic oxygenated cyclic compounds extensively found in nature. They are known for their diverse biological activities, including anti‐Alzheimer, antitumor, and antidiabetic properties, which have spurred extensive research into their therapeutic potential. One of the most significant challenges facing mankind currently is the development of antibiotic resistance in pathogenic microbes making microbial infections increasingly difficult to treat. The formation of biofilms enhances bacterial resistance to antibiotics, immune defenses, and environmental stresses. In this review, we have categorized xanthones, both of biological origin and synthesized, based on their structure and summarized the recent studies on their ability to inhibit Gram‐positive and ‐negative bacteria as well as the various underlying mechanisms that contribute to their microbicidal activity. These mechanisms include inhibition of virulence factors and biofilm formation, interaction with cell membranes, and interference with cell wall synthesis and DNA replication. In addition, we have listed the various methods involved in biofilm inhibition and the structure‐activity relationship of various xanthone molecules, highlighting how xanthone derivatives exhibit increased antibacterial activity. With the growing concern of antibiotic resistance, exploring natural compounds like xanthones to study their interaction with bacterial cells is crucial for identifying new treatment options.

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Naturally Occurring Organohalogen Compounds—A Comprehensive Review

Gribble

2023

Progress in the Chemistry of Organic Natural Products

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Genome- and MS-based mining of antibacterial chlorinated chromones and xanthones from the phytopathogenic fungus Bipolaris sorokiniana strain 11134

Cited by 22 publications

References 83 publications

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi

Synthetic and Natural Xanthones as Antibacterial Agents—Review

Naturally Occurring Organohalogen Compounds—A Comprehensive Review

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