Colletotrilactam A–D, novel lactams from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla

Wei, Bo; Yang, Zhiwei; Chen, Xiaowei; Zhou, Shuangyan; Yu, Hongwei; Sun, Jing-Yun; Yao, Xiaojun; Wang, Yonggang; Xue, Hongyan

doi:10.1016/j.fitote.2016.08.005

Cited by 20 publications

(10 citation statements)

References 24 publications

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“…HMC is known to have several biological activities, such as antifungal and phytotoxicity [42], and an inhibition of Saccharomyces cerevisiae growth and the formation of soybean callus [37]. Mellein, an isochromane, is known to inhibit monoamine oxidase [43], HCV protease [44], hepatitis C virus protease [45], and human DNA polymerase lambda [46]. The potency of HMC for MAO-B is much higher than that of mellein (IC 50 = 8.93 µg/mL, 50.16 µM)) [43].…”

Section: Discussionmentioning

confidence: 99%

Selective Inhibition of Human Monoamine Oxidase B by 5-hydroxy-2-methyl-chroman-4-one Isolated from an Endogenous Lichen Fungus Daldinia fissa

Jeong

Kang

Han

et al. 2021

JoF

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Inhibitory activities against monoamine oxidases (MAOs) and cholinesterases (ChEs) and antioxidant activity were evaluated for 195 extracts from Ukraine-derived endogenous lichen fungi (ELF). Among them, an ELF13 (identified as Daldinia fissa) extract showed the highest inhibitory activity against MAO-B, and 5-hydroxy-2-methyl-chroman-4-one (HMC) was isolated as a ~ 4-fold selective inhibitor of MAO-B (IC50 = 3.23 µM) compared to MAO-A (IC50 = 13.97 µM). HMC is a reversible competitive inhibitor with a Ki value of 0.896 µM. No cytotoxicity was observed in normal and cancer cells at 50 µM of HMC. HMC showed blood–brain barrier permeability and high gastrointestinal absorption in silico pharmacokinetics. The docking simulation results showed that the binding affinity of HMC for MAO-B (−7.3 kcal/mol) was higher than that of MAO-A (−6.1 kcal/mol) and that HMC formed a hydrogen bond interaction with Cys172 of MAO-B (distance: 3.656 Å), whereas no hydrogen bonding was predicted with MAO-A. These results suggest that HMC can be considered a candidate for the treatment of neurodegenerative diseases, such as Alzheimer’s disease and Parkinson’s disease.

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Section: Discussionmentioning

confidence: 99%

Selective Inhibition of Human Monoamine Oxidase B by 5-hydroxy-2-methyl-chroman-4-one Isolated from an Endogenous Lichen Fungus Daldinia fissa

Jeong

Kang

Han

et al. 2021

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“…Three new azaphilones with an unusual methylene bridge, named mycoleptones A, B, and C (122)(123)(124), were obtained from cultures of Mycoleptodiscus indicus (Magnaporthaceae), a fungus isolated from South American medicinal plant Borreria verticillate ( Figure 10) [124]. Besides, other polyketides, austidiol (125), eugenitin (126), 6-methoxieugenin (127), and 9-hydroxyeugenin (128), were also produced ( Figure 10) [124,125]. Their structures contain a 12-carbon atoms polyketide skeleton unit-linked, through an amide bond, with a derivative of L-isoleucine, a rare compound class [116].…”

Section: J Fungi 2020 6 X For Peer Review 3 Of 31mentioning

confidence: 99%

“…A fungus endophyte from Uncaria rhynchophylla , C. gloeosporioides (Glomerellaceae), produced four novel lactams in culture broth, colletotrilactam A–D ( 129 – 132 ); colletotrichine A ( 133 ) and B ( 134 ); and eleven more compounds: 2-isopropyl-5-methyl-2,4-cyclohexadien-1-ol ( 135 ), cis-4-hydroxymellein ( 9 ), 8-methyl-mellein( 10 ), hederagonic acid ( 136 ), mellein ( 137 ) and blumenol A ( 138 ), aspergiketone ( 139 ), djalonenol ( 140 ), (4S)-(+)-ascochin ( 141 ), 12,13-dihydroxyfumitremorgin C ( 142 ) and fumitremorgin C ( 143 ) [ 124 , 125 , 126 ]. On the other hand, when grown in wheat bran medium, C. gloeosporioides produced nine compounds: 4-epi-14-hydroxy-10, 23-dihydro-24, 25-dehydroaflavinine ( 144 ), 10, 23-dihydro-24,25-dehydro-21–oxoaflavinine ( 145 ), ergosterol ( 146 ), ergosterol peroxide ( 147 ), mellein ( 137 ), 4, 5-dihydroblumenol A ( 148 ), cyclo(L-leucyl-L-leucyl) ( 149 ), and brevianamide F ( 150 ).…”

Section: Secondary Metabolites Produced By Endophytic Fungi From Rmentioning

confidence: 99%

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Natural Products from Endophytic Fungi Associated with Rubiaceae Species

Cruz

Silva

Hamerski

2020

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This review presents the chemical diversity and pharmacological properties of secondary metabolites produced by endophytic fungi associated with various genera of Rubiaceae. Several classes of natural products are described for these endophytes, although, this study highlights the importance of some metabolites, which are involved in antifungal, antibacterial, anti-protozoal activities; neurodegenerative diseases; cytotoxic activity; anti-inflammatory and antioxidant activity; and hyperglycemic control.

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“…A maize seed-borne endophyte Sarocladium zeae (formerly Acremonium zeae ) was found to produce γ-lactam compounds, named pyrrocidine A and B ( He et al, 2002 ). Further, the cytotoxic awajanomycin from Acremonium species, cytochalasins from Rhinocladiella , and colletotrilactams A–D from endophytic Colletotrichum gloeosporioides all exemplify fungal production of higher order lactams ( Wagenaar et al, 2000 ; Jang et al, 2006 ; Wei et al, 2016 ). Such lactam production among fungi diversifies xenobiotic composition in soil and may contribute to the discovery of new valuable antibiotics.…”

Section: Lactams—the Archetypical Class Of Antibioticsmentioning

confidence: 99%

Fungal Lactamases: Their Occurrence and Function

et al. 2017

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Fungi are absorptive feeders and thus must colonize and ramify through their substrate to survive. In so doing they are in competition, particularly in the soil, with myriad microbes. These microbes use xenobiotic compounds as offensive weapons to compete for nutrition, and fungi must be sufficiently resistant to these xenobiotics. One prominent mechanism of xenobiotic resistance is through production of corresponding degrading enzymes. As typical examples, bacterial β-lactamases are well known for their ability to degrade and consequently confer resistance to β-lactam antibiotics, a serious emerging problem in health care. We have identified many fungal genes that putatively encode proteins exhibiting a high degree of similarity to β-lactamases. However, fungal cell walls are structurally different from the bacterial peptidoglycan target of β-lactams. This raises the question, why do fungi have lactamases and what are their functions? Previously, we identified and characterized one Fusarium verticillioides lactamase encoding gene (FVEG_08291) that confers resistance to the benzoxazinoid phytoanticipins produced by maize, wheat, and rye. Since benzoxazinoids are γ-lactams with five-membered rings rather than the four-membered β-lactams, we refer to the predicted enzymes simply as lactamases, rather than β-lactamases. An overview of fungal genomes suggests a strong positive correlation between environmental niche complexity and the number of fungal lactamase encoding genes, with soil-borne fungi showing dramatic amplification of lactamase encoding genes compared to those fungi found in less biologically complex environments. Remarkably, Fusarium species frequently possess large (>40) numbers of these genes. We hypothesize that many fungal hydrolytic lactamases are responsible for the degradation of plant or microbial xenobiotic lactam compounds. Alignment of protein sequences revealed two conserved patterns resembling bacterial β-lactamases, specifically those possessing PFAM domains PF00753 or PF00144. Structural predictions of F. verticillioides lactamases also suggested similar catalytic mechanisms to those of their bacterial counterparts. Overall, we present the first in-depth analysis of lactamases in fungi, and discuss their potential relevance to fitness and resistance to antimicrobials in the environment.

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Colletotrilactam A–D, novel lactams from Colletotrichum gloeosporioides GT-7, a fungal endophyte of Uncaria rhynchophylla

Cited by 20 publications

References 24 publications

Selective Inhibition of Human Monoamine Oxidase B by 5-hydroxy-2-methyl-chroman-4-one Isolated from an Endogenous Lichen Fungus Daldinia fissa

Selective Inhibition of Human Monoamine Oxidase B by 5-hydroxy-2-methyl-chroman-4-one Isolated from an Endogenous Lichen Fungus Daldinia fissa

Natural Products from Endophytic Fungi Associated with Rubiaceae Species

Fungal Lactamases: Their Occurrence and Function

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