Bioactive metabolites from Alternaria brassicicola ML-P08, an endophytic fungus residing in Malus halliana
23 May 2009-World Journal of Microbiology & Biotechnology (Springer Netherlands)-Vol. 25, Iss: 9, pp 1677-1683
TL;DR: A total of 48 strains were isolated from the normal tissues of Malus halliana and the EtOAc extracts of their cultures were subjected to primary antimicrobial screening against four test bacteria and three fungi, and 22 strains exhibited antimicrobial activity against at least one test microbe.
Abstract: A total of 48 strains were isolated from the normal tissues of Malus halliana and the EtOAc extracts of their cultures were subjected to primary antimicrobial screening against four test bacteria and three fungi. As a result, 22 strains exhibited antimicrobial activity against at least one test microbe. Among them, Alternaria brassicicola ML-P08 showing strong activity (MICs: 0.31–2.50 mg/ml) was selected for further investigation on its secondary metabolites. Bioassay-guided fractionation of the EtOAc extract of its liquid culture afforded seven compounds, which were identified as alternariol (1), alternariol 9-methyl ether (2), altechromone A (3), herbarin A (4), cerevisterol (5), 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (6) and 3β-hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one (7), respectively, by spectral means (MS, IR, 1H- and 13C-NMR). In vitro antimicrobial assay showed that compound 3 was substantially active against Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Candida albicans with the MICs of 3.9, 3.9, 1.8, and 3.9 μg/ml, respectively. Compound 4 also showed pronounced antifungal activity against Trichophyton rubrum and C. albicans with MICs of both 15.6 μg/ml. In addition, compound 1 exhibited strong xanthine oxidase inhibitory activity with the IC50 of 15.5 μM, comparable to that of positive control, allopurinol (IC50: 10.7 μM).
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TL;DR: This work is intended to provide the foundation for updating the ascomycete component of the “Without prejudice list of generic names of Fungi” published in 2013, which will be developed into a list of protected generic names.
Abstract: Knowledge of the relationships and thus the classification of fungi, has developed rapidly with increasingly widespread use of molecular techniques, over the past 10–15 years, and continues to accelerate. Several genera have been found to be polyphyletic, and their generic concepts have subsequently been emended. New names have thus been introduced for species which are phylogenetically distinct from the type species of particular genera. The ending of the separate naming of morphs of the same species in 2011, has also caused changes in fungal generic names. In order to facilitate access to all important changes, it was desirable to compile these in a single document. The present article provides a list of generic names of Ascomycota (approximately 6500 accepted names published to the end of 2016), including those which are lichen-forming. Notes and summaries of the changes since the last edition of ‘Ainsworth & Bisby’s Dictionary of the Fungi’ in 2008 are provided. The notes include the number of accepted species, classification, type species (with location of the type material), culture availability, life-styles, distribution, and selected publications that have appeared since 2008. This work is intended to provide the foundation for updating the ascomycete component of the “Without prejudice list of generic names of Fungi” published in 2013, which will be developed into a list of protected generic names. This will be subjected to the XIXth International Botanical Congress in Shenzhen in July 2017 agreeing to a modification in the rules relating to protected lists, and scrutiny by procedures determined by the Nomenclature Committee for Fungi (NCF). The previously invalidly published generic names Barriopsis, Collophora (as Collophorina), Cryomyces, Dematiopleospora, Heterospora (as Heterosporicola), Lithophila, Palmomyces (as Palmaria) and Saxomyces are validated, as are two previously invalid family names, Bartaliniaceae and Wiesneriomycetaceae. Four species of Lalaria, which were invalidly published are transferred to Taphrina and validated as new combinations. Catenomycopsis Tibell & Constant. is reduced under Chaenothecopsis Vain., while Dichomera Cooke is reduced under Botryosphaeria Ces. & De Not. (Art. 59).
243 citations
TL;DR: This review aims to briefly summarize the structurally different metabolites produced by Alternaria fungi, as well as their occurrences, biological activities and functions.
Abstract: Alternaria is a cosmopolitan fungal genus widely distributing in soil and organic matter. It includes saprophytic, endophytic and pathogenic species. At least 268 metabolites from Alternaria fungi have been reported in the past few decades. They mainly include nitrogen-containing metabolites, steroids, terpenoids, pyranones, quinones, and phenolics. This review aims to briefly summarize the structurally different metabolites produced by Alternaria fungi, as well as their occurrences, biological activities and functions. Some considerations related to synthesis, biosynthesis, production and applications of the metabolites from Alternaria fungi are also discussed.
195 citations
Cites background from "Bioactive metabolites from Alternar..."
...Metabolite class Metabolite name Alternaria species Reference Cyclo-(L-Phe-trans-4hydroxy-L-Pro-) (44) A. alternata [44] Cyclo-(L-Ala-trans-4hydroxy-L-Pro-) (45) A. alternata [44] AM-toxin I (46) A. mali (A. alternata) [39] AM-toxin II (47) A. mali (A. alternata) [39] AM-toxin III (48) A. mali (A. alternata) [39] Destruxin A (49) A. linicola [31] Destruxin B (50) A. brassicae [45] A. linicola [31] Homodestruxin B (51) A. brassicae [46] Desmethyldestruxin B (52) A. brassicae [46] Tentoxin (53) A. alternata [47] A. citri [29] A. linicola [31] A. porri [48] Isotentoxin (54) A. porri [48] Dihydrotentoxin (55) A. citri [29] A. porri [47,48] Uridine (56) A. alternata [49] Adenosine (57) A. alternata [49] Brassicicolin A (58) A. brassicicola [50,51] Fumitremorgin B (59) Alternaria sp. FL25 [52] Fumitremorgin C (60) Alternaria sp. FL25 [52] Paclitaxel = Taxol (61) A. alternata var. monosporus [53] Steroids Ergosterol (62) A. alternata [27,54] Ergosta-4,6,8(14),22-tetraen- 3-one (63) A. alternata [27,54] Ergosta-4,6,8(9),22-tetraen- 3-one (64) A. alternata [49] Ergosta-7,24(28)-dien-3-ol (65) A. alternata [49] 3β-Hydroxy-ergosta- 5,8(9),22-trien-7-one (66) A. brassicicola ML-P08 [55] 3β,5α-Dihydroxy-ergosta- 7,22-dien-6-one (67) A. brassicicola ML-P08 [55] Cerevisterol (68) A. brassicicola ML-P08 [55] Terpenoids Bicycloalternarene 1 (69) A. alternata [56] Bicycloalternarene 11 (70) A. alternata [56] Bicycloalternarene 2 (71) A. alternata [56] Bicycloalternarene 3 = ACTG toxin A (72) A. alternata [56] Bicycloalternarene 4 (73) A. alternata [56] Bicycloalternarene 10 (74) A. alternata [56] Molecules 2013, 18 5895 Table 1....
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...Four monobenzopyranones namely tenuissimassatin (150), altechromone A (151), 2,5-dimethyl-7hydroxychromone (152) and phomapyrone F (153) were isolated from Alternaria fungi [22,55,79]....
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...brassicicola ML-P08 [55] 2,5-Dimethyl-7hydroxychromone (152) Alternaria sp....
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...brassicicola ML-P08 [55] 3β,5α-Dihydroxy-ergosta7,22-dien-6-one (67) A....
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...Herbarin A (132) and altechromone A (151) from A. brassicicola ML-P08 exhibited antimicrobial activity on Trichophyton rubrum, Candida albicans, Apergillus niger, Bacillus subtilis, Escherichia Molecules 2013, 18 5922 coli, Pseudomonas fluorescens with MICs ranged from 1.8 to 62.5 μg/mL [55]....
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TL;DR: The present review article compiles recent (2006-2016) literature to provide an update on endophyte research aimed at finding metabolites with antibiotic activities to show that endophytes that produce bioactive compounds have been collected globally.
168 citations
01 Jan 2012
TL;DR: Recently, the endophytic Corynespora cassiicola was found to produce potent antioxidant compounds corynesidones A and B, and corynether A, together with a known diaryl ether (LL-V125α) (Fig 18), as revealed by oxygen radical absorbance capacity (ORAC) assay.
Abstract: ion; it is believed to have antioxidant activity 11 times greater than trolox, a vitamin E derivative (Strobel et al. 2002, Harper et al. 2003). The endophytic Cephalosporium sp. IFB-E001 and Microsphaeropsis olivacea were isolated from host plants Trachelospermum jasminoides and Pilgerodendron uviferum respectively; both produced a phenolic metabolite graphislactone A (Fig18), which displayed potent in vitro antioxidant and free radical-scavenging activity stronger than the standards, butylated hydroxytoluene (BHT) and ascorbic acid (Hormazabal et al. 2005, Song et al. 2005). Huang et al. (2007) investigated the antioxidant capacities of endophytic fungal cultures of medicinal Chinese plants and its correlation to their total phenolic contents. They suggested that the phenolic content were the major antioxidant constituents of the endophytes (Huang et al. 2008a). The methanol extract of an endophyte Xylaria sp. isolated from the medicinal plant Ginkgo biloba exhibited strong antioxidant capacity due to the presence of “phenolics” and “flavonoids” among identified compounds (Liu et al. 2007). Recently, the endophytic Corynespora cassiicola was found to produce potent antioxidant compounds corynesidones A and B, and corynether A, together with a known diaryl ether (LL-V125α) (Fig 18), as revealed by oxygen radical absorbance capacity (ORAC) assay with units ranging between 4.35.9. Corynesidone B could also scavenge 2,2diphenyl-1-picrylhydrazyl (DPPH) free radicals with an IC50 22.4 μM, at the same activity as that of ascorbic acid. Beside antioxidant activity of corynesidone A, its exhibit aromatase inhibitory activity with an IC50 value of 5.30 μM; this activity magnitude is comparable to the first generation aromatase inhibitor drug, aminoglutethimide. Both antiaromatase and antioxidant activities of corynesidone A are interesting functions because this dual biological activity may be useful for cancer chemoprevention, particularly for breast cancer (Chomcheon et al. 2009). Also, the endophyte fungus Phyllosticta sp. isolated from Guazuma tomentosa was also found to exhibit strong antioxidant activity (Srinivasan et al. 2010). Zeng et al. (2011) Current Research in Environmental & Applied Mycology Doi 10.5943/cream/2/1/3 60 reported many of endophytic fungi as potential novel source of natural antioxidants from medicinal plant Scapania verrucosa. Antiviral Activities of Endophytic Fungi Many reports demonstrated the importance of endophytic fungi in production of antiviral agents, such as, cytonic acids A and B, novel human cytomegalovirus (hCMV) protease inhibitors, which had been isolated from solid-state fermentation of the endophytic fungus Cytonaema sp., )Guo et al. 2000). Investigation of endophytes associated with leaves of Quercus coccifera lead to isolation of the endophyte with the ability to synthesize hinnuliquinone, a potent inhibitor of human immunodeficiency virus type 1 (HIV-1) protease (Singh et al. 2004). Endophytic isolates (582) with 360 morphologically distinct fungi were obtained from 81 Thai medicinal plant species. Extracts of 92 isolates could inhibit Mycobacterium tuberculosis, while 6 extracts inhibited Plasmodium falciparum, and strong anti-viral activity against Herpes simplex virus type 1 was observed in 40 isolates (Wiyakrutta et al. 2004). Mellisol and 1,8-dihydroxynaphthol 1O-a-glucopyranoside were isolated from endophytic fungus Xylaria mellisii, which possess activity against herpes simplex virustype 1 (Pittayakhajonwut et al. 2005). Florke et al. (2006) reported antihepatitis C virus (HCV) activity of dihydroisocoumarin (R)-(-)-mellein (Fig 19). It inhibits HCV protease with an IC50 value of 35 mM. This compound had been isolated from a number of endophytic fungi, such as Pezicula livida, Plectophomella sp., and Cryptosporiopsis malicoticis (Krohn et al. 1997). Pullularins A (Fig 19), which had been isolated from ethyl acetate extract of endophytic fungus Pullularia sp., was also shown to have antiviral activity against herpes simplex virus type 1(HSV-1) with IC50 3.3 mg/ml (Isaka et al. 2007). Pestalotheol C (Fig 19), which was isolated from the endophyte Pestalotiopsis theae, was found to have anti-HIV properties (Li et al. 2008b). The aryl tetralin lignans, such as podophyllotoxin and its analogs showed antiviral and cytotoxicity activities and used as the precursor for many drugs for treatment cancer and viral infections, like etoposide, teniposide, and etopophos phosphate. Podophyllotoxin was found to produced by many endophytes: Trametes hirsute, Aspergillus fumigates, Phialocephala fortinii, and Fusarium oxysporum ( Eyberger et al. 2006, Puri et al. 2006, Kour et al. 2008, Kusari et al. 2009a). Arunpanichlert et al. (2010) investigated the secondary metabolites of endophytic fungus Penicillium sclerotiorum, and isolated the known compound (+)Sclerotiorin. (+)-Sclerotiorin (Fig 19) was evaluated for its inhibitory effect on human immunodeficiency virus HIV-1 integrase and protease and for antifungal activity, and found to exhibit anti-HIV-1 integrase and protease activities with IC50 values of 45.88 and 198.41μM, respectively, and showed weak anti-fungal activity against Candida albicans and Cryptococcus neoformans with MIC values of 202.53 and 101.26 μM, respectively. The endophyte Phomopsis sp., isolated from Musa acuminata, was found to produce hexaketide γ-lactones. Oblongolides Z, and 2deoxy-4α-hydroxyoblongolide X (Fig 19) showed anti-herpes simplex virus type 1 (HSV1) activity IC50 values of 14 μM and 76 μM, respectively. Oblongolides Z exhibited comparable cytotoxic activity against KB, BC, NCI-H187, and nonmalignant Vero cell lines with IC50 values of 37, 26, 32, and 60μM, respectively (Bunyapaiboonsri et al. 2010). New chlorinated pupukeananes possessing a unique spiroketal peroxide skeleton, named chloropupukeanolides A (Fig 19), were isolated from endophytic Pestalotiopsis fici. This compound was found to inhibit HIV-1 replication in vitro in C8166 cells with an IC50 value of 6.9 μM, and showed cytotoxicity against human cancer cell lines HeLa, MCF-7 and MDA-MB-231 with IC50 values of 16.9, 15.5 and 15.9μM, respectively (Liu et al. 2010a). Zhang et al. (2011) reported isolation and structure elucidation of Emerimidine A, and B (Fig 19) from culture of endophytic fungus Emericella sp., both of them showed moderate inhibition to Influenza virus H1 N1 with IC50 values of 42.07 mg/ml and 62.05 mg/ml respectively. Current Research in Environmental & Applied Mycology Doi 10.5943/cream/2/1/3 61 Fig. 19 – Structure of Antiviral Compounds isolated from some Endophytic Fungi Other Biological Activities of Endophytic Fungi Endophytic fungi are also known as producers of many other metabolites of biological interest, such as anti-inflammatory, anti-diabetic, anti-malarial and immunesuppressant agents, as well as insecticidal and antinematodes agents. Immunosuppressive drugs are used to prevent allograft rejection in organ transplantation, and could be used to treat autoimmune diseases such as rheumatoid arthritis and insulin-dependent diabetes. Lee et al. (1995a) reported endophytic Fusarium subglutinans can produce compounds (Subglutinol A and B) that can influence the immune system of animals. Subglutinol A (Fig 20) and B are noncytotoxic diterpene pyrones; both of compounds have IC50 values of 0.1 μM and were roughly as potent as the immunosuppressant drug cyclosporin A. The lack of toxicity associated with subglutinols A and B suggests that they could be use as immunosuppressant agents. Recently, the endophytic Pestalotiopsis leucothes isolated from Trypterygium wilfordii was found to produce compounds which have variable effects on Tand B-cells and monocyte, these compounds may represent a new source of immunomodulatory agents or for treatment of human immune mediated diseases (Kumar et al. 2005). A new compound named Collutelin A, has been isolated from endophytic Colletotrichum dematium and was shown to exhibit strong immunosuppressive activity as it inhibited CD4 (+) Tcell activation of Interleukin 2 production (Ren et al. 2008). Gliocladicillins A and B were reported as effective antitumor agents in vitro and in vivo, since they induced tumor cell apoptosis and showed significant inhibition on proliferation of melanoma B16 cells implanted into immunodeficient mice (Chen et al. 2009). Zhang et al. (1999) investigated the anti-diabetic activity of endophytic fungi by isolation of nonpeptidal L-783, 281 from an endophytic Pseudomassaria sp., this compound was found to act as insulin, with Current Research in Environmental & Applied Mycology Doi 10.5943/cream/2/1/3 62 advance that it is not destroyed in the digestive tract and may be given orally. Oral administration of L-783,281 in two mouse models of diabetes resulted in significant lowering of blood glucose levels, these results may lead to a new therapeutic agent for diabetes. Insulin-mimetic compound demethyl asterriquinone B-1 (Fig 20) has been isolated from culture of endophytic Pseudomassaria sp. (Salituro et al. 2001, Strobel 2002). Many reports indicated that endophytic fungi are capable of producting of antiinflammatory compounds, such as phomol and mevinic acid (Fig 20), which had been isolated from culture of the endophytic fungus Phomopsis. (Weber et al. 2004a). Both compounds showed strong anti-inflammatory activity. Phenylpropanoids compounds were reported to be isolated from endophytes; they have received more interest for medicinal applications as they have multifold activities, such as anticancer, antioxidant, antimicrobial, anti-inflammatory and immunosuppressive properties (Korkina 2007). Wang et al. (2010) reported isolation of four compounds (Epicoccins M & R, Entepicoccin G, and Diketopiperazine) that exhibited potent anti-inflammatory activities from cultures of endophytic Epicoccum nigrum. The compounds were found to inhibit the platelet activating factor-induced release of β-glucuronid
148 citations
TL;DR: The beneficial effects of one particular species of PGPR (Pseudomonas fluorescenceens) on plants through induced plant defense is focused on and a better understanding of the biotic factors modulating P. fluorescens–plant interactions will improve the effectiveness of introducing P.fluorescens to enhance plant production and defense.
Abstract: Plant growth-promoting rhizobacteria (PGPR) are increasingly appreciated for their contributions to primary productivity through promotion of growth and triggering of induced systemic resistance in plants. Here we focus on the beneficial effects of one particular species of PGPR (Pseudomonas fluorescens) on plants through induced plant defense. This model organism has provided much understanding of the underlying molecular mechanisms of PGPR-induced plant defense. However, this knowledge can only be appreciated at full value once we know to what extent these mechanisms also occur under more realistic, species-diverse conditions as are occurring in the plant rhizosphere. To provide the necessary ecological context, we review the literature to compare the effect of P. fluorescens on induced plant defense when it is present as a single species or in combination with other soil dwelling species. Specifically, we discuss combinations with other plant mutualists (bacterial or fungal), plant pathogens (bacterial or fungal), bacterivores (nematode or protozoa), and decomposers. Synergistic interactions between P. fluorescens and other plant mutualists are much more commonly reported than antagonistic interactions. Recent developments have enabled screenings of P. fluorescens genomes for defense traits and this could help with selection of strains with likely positive interactions on biocontrol. However, studies that examine the effects of multiple herbivores, pathogens, or herbivores and pathogens together on the effectiveness of PGPR to induce plant defenses are underrepresented and we are not aware of any study that has examined interactions between P. fluorescens and bacterivores or decomposers. As co-occurring soil organisms can enhance but also reduce the effectiveness of PGPR, a better understanding of the biotic factors modulating P. fluorescens–plant interactions will improve the effectiveness of introducing P. fluorescens to enhance plant production and defense.
118 citations
Cites background from "Bioactive metabolites from Alternar..."
...Other PGPR could also produce secondary metabolites which inhibit P. fluorescens (Figure 1; Gu, 2009)....
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...Circled numbers refer to articles describing the interactions: (1) Jin et al. (2010), (2) Gu (2009); Prieto et al. (2011), (3) Elsherif and Grossmann (1996); Pedersen et al. (2009), (4) Walker et al. (2012), (5) Combes-Meynet et al. (2011); Garbeva et al. (2011), (6) Elmer (2009); Troxler et al.…...
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References
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1,396 citations
TL;DR: In this paper, the authors investigated the role of the endophyte and its biologically active metabolites in its association with its host and found that a higher proportion of the fungal endophytes, in contrast to the soil isolates, inhibited at least one of the test organisms for antialgal and herbicidal activities.
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TL;DR: The review summarises natural products containing the 2-pyrone moiety and places an emphasis upon the biological activity associated with 2-pyrones, particularly with respect to potential therapeutic or anti-microbial agents.
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TL;DR: The study demonstrated that the effects for these medicinal plants used for the gout treatment were based, at least in part, on the xanthine oxidase inhibitory action.
239 citations
TL;DR: This is the first report on the antimicrobial potentials of endophytic fungi residing in Q. variabilis and isolation of brefeldin A produced by Cladosporium sp.
Abstract: Among 67 endophytic fungi isolated from Quercus variabilis, 53.7% of endophytic fungal fermentation broths displayed growth inhibition on at least one test microorganism, such as pathogenic fungi (Trichophyton rubrum, Candida albicans, Aspergillus niger, Epidermophyton floccosum, Microsporum canis) and bacteria (Escherichia coli, Bacillus subtilis, Pseudomonas fluorescens). Moreover, 19.4% of strains showed a broader antimicrobial spectrum, such as Aspergillus sp., Penicillium sp., Alternaria sp., 20.9% of strains showed strong inhibition (+++) to pathogenic bacteria, while only 7.5% displayed that to test fungi. The most active antifungal strain I(R)9-2, Cladosporium sp. was selected and fermented. From the broth, a secondary metabolite, brefeldin A was obtained. This is the first report on the antimicrobial potentials of endophytic fungi residing in Q. variabilis and isolation of brefeldin A produced by Cladosporium sp.
152 citations