Chlorinated Coumarins from the Polypore Mushroom <i>Fomitopsis officinalis</i> and Their Activity against <i>Mycobacterium tuberculosis</i>

Hwang, Chang Hwa; Jaki, Birgit U.; Klein, Larry L.; Lankin, David C.; McAlpine, James B.; Napolitano, José G.; Fryling, Nicole A.; Franzblau, Scott G.; Cho, Sang Hyun; Stamets, Paul; Wang, Yuehong; Pauli, Guido F.

doi:10.1021/np400497f

Cited by 45 publications

(35 citation statements)

References 26 publications

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“…Based on the observations obtained from the four molecules in assays to Mycobacterium tuberculosis (anti-TB), the authors concluded that the anti-TB activity is higher when the ethyl ester introduces chlorine in position 6, while coumarins with a chlorine substituted at the 7-position are less active (Hwang et al 2013). Mammalian cell cytotoxicity using Vero cells was observed by the authors at a similar concentration that causes significant inhibition against M. tuberculosis and Mycobacterium bovis.…”

Section: Fungal Coumarins Basidiomycetes Fungimentioning

confidence: 95%

“…This compound is used as a choleretic to improve bile secretion and regulate the pressure of the bile duct to ease inflammation and adjust liver function (Wang et al 2007). Hwang et al (2013) isolated two new coumarins (Fig. 2), 6-chloro-4-phenyl-2H-chromen-2-one (1) molecular formula C 15 H 9 ClO 2 , with 0.5 mg when isolated, and ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate, with 0.2 mg when isolated, from an EtOH extract of the mushroom Fomitopsis officinalis, aimed for the application in tuberculosis treatment (anti-TB).…”

Section: Fungal Coumarins Basidiomycetes Fungimentioning

confidence: 99%

“…More than 1300 coumarins have been identified as secondary metabolites from plants, bacteria, and fungi (Hwang et al 2013;Venugopala et al 2013;Wang et al 2013;Islam et al 2015). The name coumarin comes from a French term for the Tonka bean, coumarou (Dipteryx odorata), isolated by Vogel, 1820 (Venugopala et al 2013;Rohini and Srikumar 2014;Matos et al 2015).…”

Section: Introductionmentioning

confidence: 99%

“…Several bacteria and fungi are known to synthesize coumarin (Aslam et al 2010;Nikhil et al 2012;Rohini and Srikumar 2014), e.g., Agaricus sp. (Mogland and Saadabi 2012), Armillariella tabenscens (Wang et al 2007), Aspergillus (Rohini and Srikumar 2014), Fomitopsis officinalis (Hwang et al 2013), Ganoderma lucidum (Islam et al 2015), Macrolepiota mastoidea (Shirmila and Radhamany 2013), Penicillium, Pestalotiopsis sp. , Phellinus sp.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.

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Section: Fungal Coumarins Basidiomycetes Fungimentioning

confidence: 95%

Section: Fungal Coumarins Basidiomycetes Fungimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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“…Positive results were also obtained with extracts of ethanol, hexane and water of F. lilacinogilva against B. cereus, Escherichia coli and S. aureus (Bala et al 2011(Bala et al , 2012. Ethanolic compounds from F. officinalis exhibited bioactivity against Mycobacterium tuberculosis (Hwang et al 2013).…”

Section: Discussionmentioning

confidence: 99%

Antibacterial activity of Ethyl Acetate Extract of Agaricomycetes collected in Northeast Brazil

Ferreira-Silva¹

2017

CREAM

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Agaricomycetes produce bioactive substances with antibiotic, antiallergic, antiinflammatory, antioxidant, cytotoxic, antiatherogenic, hepatoprotective, hypoglycemic antiimmunoprotective properties. However, there have been few studies on material collected in Brazil. Thus, the current study aimed to improve the knowledge concerning the antibacterial potential of Agaricomycetes in the country by researching material collected in Northeast Brazil. Twenty one cultures deposited in Micoteca URM of UFPE and nine extracts from fresh basidiomata were tested. Extracts of the basidiomata and the cultures were obtained with ethyl acetate, which were solubilized at a concentration (1:10 v/v). The preliminary tests with the 30 samples (21 cultures and nine extracts of fresh basidiomata) were performed against eleven strains of Staphylococcus aureus, seven of which were resistant to oxacillin (ORSA), using block agar. Thirteen samples showed antibacterial activity, with inhibition between 9-24 mm and minimum inhibitory concentration (MIC) from 0.18-147 µg/mL, Fomitopsis cupreorosea (URM 6830), Ganoderma multiplicatum (URM 6975), G. parvulum (URM 2948), G. orbiforme (URM87741), Grammothele lineata (URM6827), Rigidoporus lineatus (URM 6828), R. microporus (URM 6878), Stereum ostrea (URM 6973, URM 87848) being the most significant.

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Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids

Banik,

Saikiran,

Permula

et al. 2024

Chemistry An Asian Journal

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The present work reports a novel methodology for the selective arylation of coumarin‐3‐carboxylates with arylboronic acids via a photochemical route, marking the first‐ever attempt for the direct alkenyl C‐H arylation using rose bengal as a photocatalyst, which is a readily available and cost‐effective alternative to transition metal catalysis. The reaction proceeds smoothly in MeOH/H2O solvent media in the presence of radical initiator affording the arylated products in good yields (60‐80%). The reaction parameters such as visible light, radical initiator, oxidant, anhydrous solvent, and inert atmosphere play a crucial role for the success of this methodology. The substituents present on the substrate show a significant effect on the conversion. This study provides a valuable contribution to the field of organic synthesis offering a new and efficient approach to the arylation of coumarin‐3‐carboxylic acid esters with a broad substrate scope and high functional group tolerance. It is a versatile method and provides a direct access to biologically relevant 4‐arylcoumarin‐3‐carboxylates.

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Chlorinated Coumarins from the Polypore Mushroom Fomitopsis officinalis and Their Activity against Mycobacterium tuberculosis

Cited by 45 publications

References 26 publications

Fungi as a source of natural coumarins production

Fungi as a source of natural coumarins production

Antibacterial activity of Ethyl Acetate Extract of Agaricomycetes collected in Northeast Brazil

Visible Light‐Induced Metal‐free Arylation of Coumarin‐3‐carboxylates with Arylboronic Acids

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