Bioactive oxaphenalenone dimers from the fungus Talaromyces macrosporus KKU-1NK8

Chaiyosang, Boonyanoot; Kanokmedhakul, Kwanjai; Sanmanoch, Wareerat; Boonlue, Sophon; Hadsadee, Sarinya; Jungsuttiwong, Siriporn; Kanokmedhakul, Somdej

doi:10.1016/j.fitote.2019.03.015

Cited by 13 publications

(34 citation statements)

References 25 publications

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“…Afterwards, bacillisporin A (2) was re-isolated from T. stipitatus grown on polished rice medium (Zang et al, 2016b). In another report, bacillisporins A (2) and B (3) were produced by fungus T. macrosporus KKU-1NK8 (Chaiyosang et al, 2019). Interestingly, bacillisporins A (2) and B (3) were isolated from a mangrove-derived endophytic fungus T. aculeatus No.…”

Section: Heptacyclic Duclauxin Derivativesmentioning

confidence: 99%

“…The 1 H and 13 C NMR spectroscopic data of compound 33 were similar to those of compound 32, except that the hydroxyl group at C-9 was replaced by an acetoxyl group (δ C carbonyl ester group 170.6 and methyl group δ H/C 1.99 (s)/20.8). Macrosporusone C (34) is the first oxaphenalenone dimer reported with a chlorine atom in the molecule (Chaiyosang et al, 2019). Talaromycesone B (35) was isolated as a brown powder from the culture broth and mycelia of a marine fungus Talaromyces sp.…”

Section: Asymmetrical Duclauxin Derivativesmentioning

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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Section: Heptacyclic Duclauxin Derivativesmentioning

confidence: 99%

Section: Asymmetrical Duclauxin Derivativesmentioning

confidence: 99%

Duclauxin Derivatives From Fungi and Their Biological Activities

et al. 2021

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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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Palladium‐Catalyzed C8‐Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

Berrou

Prévost

2021

Adv Synth Catal

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Herein, a direct C8‐oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium‐catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to the synthesis of variously substituted naphtholactones.

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Bioactive oxaphenalenone dimers from the fungus Talaromyces macrosporus KKU-1NK8

Cited by 13 publications

References 25 publications

Duclauxin Derivatives From Fungi and Their Biological Activities

Duclauxin Derivatives From Fungi and Their Biological Activities

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Palladium‐Catalyzed C8‐Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton

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