Heptacyclic oligophenalenones from the soil fungus Talaromyces bacillisporus BCC17645

Dramae, Aibrohim; Intaraudom, Chakapong; Bunbamrung, Nantiya; Saortep, Wacharee; Srichomthong, Kitlada; Pittayakhajonwut, Pattama

doi:10.1016/j.tet.2020.130980

Cited by 12 publications

(33 citation statements)

References 14 publications

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“…Although only the EtOAc extract was active against Pseudomonas aeruginosa [minimum inhibitory concentration (MIC) value of 128 µg/mL], all extracts were studied due to overlapping spots on their TLC profiles. Herein, we report the isolation, structural elucidation, and biological evaluation of three new compounds (1-3) together with fourteen known compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) from T. trachyspermus (▶ Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…Some species are used as biocontrol agents for soil-borne pathogens in the food industry, and for biotechnological and medical purposes [1]. Many classes of secondary metabolites have been reported from Talaromyces including alkaloids [2,3], peptides [2], esters [2,[4][5][6][7][8][9], phenyl derivatives [2,10], polyketides [2,[11][12][13][14][15][16], pyranones [2,17], quinones [2,18], steroids [2,19], and terpenoids [2,18,[20][21][22][23]. They have shown a wide range of bioactive activities such as cytotoxicity against human cancer cell lines [2,6,24], antibacterial [2-5, 8, 9, 14, 23], anti-inflammatory [15,16,20,21], inhibitory activities of several enzymes [6,10,13,17], antioxidative [11], and antiviral [22] properties.…”

Section: Introductionmentioning

confidence: 99%

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New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

et al. 2021

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Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A – C (1 – 3), together with fourteen known compounds (4 – 17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1 – 3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1 – 3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

et al. 2021

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“…Genera Penicillium and Talaromyces produce a wide range of polyketide-derived secondary metabolites with diverse bioactivities. These compounds are promising antitumor and antibacterial agents, leading to their applications in agriculture, environment, forestry, and pharmaceutical sectors ( Cao et al, 2015 ; Chaudhary et al, 2020 ; Dramae et al, 2020 ; Jimenez-Arreolaa et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

“…Duclauxin ( 1 ) was first isolated from the cultures of fungus Talaromyces duclauxii in 1965 ( Shibata et al, 1965 ). After that, a growing number of duclauxin derivatives were isolated from the genera Talaromyces and Penicillium ( Yamazaki and Okuyama, 1980 ; Wu et al, 2015 ; Zang et al, 2016a ; Chaiyosang et al, 2019 ; Wang et al, 2019 ; Chaudhary et al, 2020 ; Dramae et al, 2020 ; Jimenez-Arreolaa et al, 2020 ). Duclauxins have attracted particular attention as they have great potential to become remedies against multiple diseases.…”

Section: Introductionmentioning

confidence: 99%

“…Duclauxins have attracted particular attention as they have great potential to become remedies against multiple diseases. These compounds possess a wide range of biological properties, including antitumor ( Cao et al, 2015 ), antibacterial ( Dramae et al, 2020 ), cytotoxic ( Dethoup et al, 2006 ), antimalarial ( Chaiyosang et al, 2019 ), and enzyme inhibition ( Wu et al, 2015 ; Wang et al, 2019 ; Jimenez-Arreolaa et al, 2020 ). Some of these compounds have been identified as novel inhibitors of cancer cell lines ( Shiojiri et al, 1983 ) and pathogens ( Chaiyosang et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

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Duclauxin Derivatives From Fungi and Their Biological Activities

et al. 2021

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Duclauxin is a heptacyclic oligophenalenone dimer consisting of an isocoumarin and a dihydroisocoumarin unit. These two tricyclic moieties are joined by a cyclopentane ring to form a unique hinge or castanets-like structure. Duclauxin is effective against numerous tumor cell lines because it prevents adenosine triphosphate (ATP) synthesis by inhibiting mitochondrial respiration. There are about 36 reported natural duclauxin analogs mainly produced by 9 Penicillium and Talaromyces species (T. duclauxii, T. aculeatus, T. stipitatus, T. bacillisporus, T. verruculosus, T. macrosporus, P. herquei, P. manginii, and Talaromyces sp.). These metabolites exhibit remarkable biological activities, including antitumor, enzyme inhibition, and antimicrobial, showing tremendous potential in agricultural and medical applications. This review highlights the chemical structures and biological activities of fungal duclauxins, together with biosynthesis, absolute configuration, and mode of action for important duclauxins. Furthermore, phylogenetic analysis and correct names of Penicillium and Talaromyces species producing duclauxins are presented in this review.

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Polyketides with potential bioactivities from the mangrove-derived fungus Talaromyces sp. WHUF0362

Xue

et al. 2023

Mar Life Sci Technol

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Metabolites of microorganisms have long been considered as potential sources for drug discovery. In this study, five new depsidone derivatives, talaronins A-E (1–5) and three new xanthone derivatives, talaronins F–H (6–8), together with 16 known compounds (9–24), were isolated from the ethyl acetate extract of the mangrove-derived fungus Talaromyces species WHUF0362. The structures were elucidated by analysis of spectroscopic data and chemical methods including alkaline hydrolysis and Mosher’s method. Compounds 1 and 2 each attached a dimethyl acetal group at the aromatic ring. A putative biogenetic relationship of the isolated metabolites was presented and suggested that the depsidones and the xanthones probably had the same biosynthetic precursors such as chrysophanol or rheochrysidin. The antimicrobial activity assay indicated that compounds 5, 9, 10, and 14 showed potent activity against Helicobacter pylori with minimum inhibitory concentration (MIC) values in the range of 2.42–36.04 μmol/L. While secalonic acid D (19) demonstrated significant antimicrobial activity against four strains of H. pylori with MIC values in the range of 0.20 to 1.57 μmol/L. Furthermore, secalonic acid D (19) exhibited cytotoxicity against cancer cell lines Bel-7402 and HCT-116 with IC50 values of 0.15 and 0.19 μmol/L, respectively. The structure–activity relationship of depsidone derivatives revealed that the presence of the lactone ring and the hydroxyl at C-10 was crucial to the antimicrobial activity against H. pylori. The depsidone derivatives are promising leads to inhibit H. pylori and provide an avenue for further development of novel antibiotics.

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Heptacyclic oligophenalenones from the soil fungus Talaromyces bacillisporus BCC17645

Cited by 12 publications

References 14 publications

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Duclauxin Derivatives From Fungi and Their Biological Activities

Polyketides with potential bioactivities from the mangrove-derived fungus Talaromyces sp. WHUF0362

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