Xylarkarynone A and B: Two Bioactive Eremophilane Sesquiterpenes from Xylaria sp. HHY-2.

A new compound xylarkarynone A (1), a first reported natural product compound xylarkarynone B (2) and eight known compounds (3-10) were isolated from Xylaria sp. HHY-2. Their structures were elucidated by spectroscopic methods, DP4+ probability analyses and electronic circular dichroism (ECD) calculations. The bioactivities of isolated compounds were assayed. Compound 1 exhibited obvious activity against A549 cells with an IC50 value of 6.12±0.28 µM. Additionally, compound 1 showed moderate antifungal activities against Plectosphaerella cucumerina and Aspergillus niger with minimum inhibitory concentrations (MICs) of both 16 µg/mL, which was at the same grade with positive control nystatin. Most compounds exhibited varying degrees of inhibitory activity against P. cucumerina, indicating that Xylaria sp. has potential as inhibitors against P. cucumerina.

First Report of Brown Leaf Rot Disease on Dendrobium nobile Caused by Xylaria flabelliformis in Guizhou Province, China.

Dendrobium nobile is the largest species of the Orchidaceae family and produces dendrobine, a compound with medicinal properties (Sarsaiya et al., 2020a; Sarsaiya et al., 2024; Qian et al., 2024). The accumulation of dendrobine in D. nobile is regulated by various pathogenic fungi, which directly and indirectly influence dendrobine biosynthesis (Sarsaiya et al., 2019a; Sarsaiya et al., 2019b). In a field planted with D. nobile in Guizhou Province, China, small lesions were initially observed on the upper part of the leaves from May to June 2019, which later developed into larger brown necrotic leaf lesions. Over time, these lesions greatly impacted the medicinal value (dendrobine) and productivity of the plant. A pure culture of Xylaria flabelliformis from infected wild D. nobile leaves was recovered and subsequently cultured on potato dextrose agar (PDA) at 25 °C for 5 days. Xylaria flabelliformis grew slowly and was composed of white mycelia. Colonies were initially white, with a regular margin, and formed stromata that consisted of mycelia sterilia without ascospores. We identified the strain as Xylaria flabelliformis based on its morphological characteristics (Liu et al., 2007) and by sequencing elongation factor-1α (EF-1α). The length of the DNA sequence of EF-1α that was used for the analysis of Xylaria flabelliformis was 1188 bp. BLASTx (nucleotide 6-frame translation-protein) analysis using the National Center for Biotechnology Information database showed that the obtained protein sequence (BLASTx protein accession no.: UTS95822.1, BLASTn nucleotide sequence accession no.: MW508334.1) had the highest similarity (98.21%) with the X. flabelliformis hypothetical protein (TRX95197.1) based on a thorough phylogenetic comparison with other Xylaria species. Healthy D. nobile seedlings were planted in pots and sterilized. The terminal leaves were excised from all pre-sterilised D. nobile seedlings and inoculated with Xylaria flabelliformis mycelial plugs, whereas sterile PDA plugs and moist cotton plugs were used as controls. All seedlings were maintained under optimum temperature and humidity conditions (25 °C and 80%, respectively) for seven days for observation and analysis. All experiments were performed in triplicate. After the incubation period, brown leaf rot lesions were observed for the first time on the inoculated D. nobile leaves, but no symptoms were observed on the leaves of the two control groups (sterile PDA plugs and moist cotton plugs). To complete Koch's postulates, Xylaria flabelliformis was re-isolated and identified from all diseased tissues by DNA sequencing of the EF-1α. It was determined for the first time that Xylaria flabelliformis can cause brown leaf lesions in D. nobile. Moreover, the pathogenicity of Xylaria flabelliformis in D. nobile has not been previously reported (Mead et al., 2019; Meng et al., 2019; Sarsaiya et al., 2019a; Sarsaiya et al., 2020b; Chen et al., 2023; Rinchen, 2023; Cao et al., 2024). To the best of our knowledge, this is the first report of BLRS lesions in D. nobile leaves caused by Xylaria flabelliformis in Guizhou Province, China. Identification of Xylaria flabelliformis as a pathogen of D. nobile is crucial for advancing effective management and control practices against brown leaf rot disease. This discovery provides valuable insights into the development of targeted strategies to mitigate the impact of Xylaria flabelliformis on D. nobile, safeguard medicinal properties such as dendrobine, and enhance overall productivity.

New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184.

The fungus Xylaria sp. Z184, harvested from the leaves of Fallopia convolvulus (L.) Á. Löve, has been isolated for the first time. Chemical investigation on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called fallopiaxylaresters A-C (1-3), and a new bisabolane-type sesquiterpenoid, named fallopiaxylarol A (4), along with the first complete set of spectroscopic data for the previously reported pestalotiopyrone M (5). Known pyranone derivatives (6-11), sesquiterpenoids (12-14), isocoumarin derivatives (15-17), and an aromatic allenic ether (18) were also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and α-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 ± 0.82% at a concentration of 50 µg/mL. The compounds 5, 7, and 8 displayed weak antibacterial activity against Staphylococcus areus subsp. aureus at a concentration of 100 µM.

Two New Compounds from the Fungus Xylaria nigripes.

In the process of discovering more neural-system-related bioactive compounds from Xylaria nigripes, xylariamino acid A (1), a new amino acid derivative, and a new isovaleric acid phenethyl ester (2) were isolated and identified. Their structures and absolute configurations were determined by analyses of IR, HRESIMS, NMR spectroscopic data, and gauge-independent atomic orbital (GIAO) NMR calculation, as well as electronic circular dichroism (ECD) calculation. The isolated compounds were evaluated for their neuroprotective effects against damage to PC12 cells by oxygen and glucose deprivation (OGD). Compounds 1 and 2 can increase the viability of OGD-induced PC12 cells at all tested concentrations. Moreover, compound 2 (1 µmol L-1) can significantly reduce the percentage of apoptotic cells.

[First evidence of nitrilase enzymatic activity of Xylaria sp. and its relationship with the biosynthesis of indole-3-acetic acid]. / Primera evidencia de actividad enzimática nitrilasa en Xylaria sp., y su relación con la biosíntesis de ácido indol-3-acético.

Endophytic fungi inhabit plant tissues internally and asymptomatically, and many of them are involved in the synthesis of bioactive metabolites of antifungal and therapeutic nature, as well as other compounds of biotechnological importance including indole derivatives, among many others. Ecologically, they provide some benefits to plants including protection against phytopathogens and promotion of root growth. In this sense, Xylaria sp. is a cellulose-decomposing fungus with biotechnological potential. It is worth mentioning that indole-3-acetic acid (IAA) also plays an extremely important role in plant-micro-organism interactions, as it is essential for physiology and proper plant morphological development. It is known that nitrile-hydrolytic enzymes (nitrilases) are involved in the synthesis of plant indole compounds; however, relatively little information is available concerning the nature of these enzymes in the fungal kingdom. In view of the above, through a biochemical and molecular-genetic approach, it has been demonstrated for the first time that Xylaria sp. carries out nitrile-hydrolytic enzyme activity using nitrogen and carbon-rich compounds as substrate. The studied strain increased its relative gene expression levels and showed mycelial growth, both in the presence of chemical compounds such as cyanobenzene and KCN. Thus, the results of this work suggest that the micro-organism is capable of degrading complex nitrogenous molecules. On the other hand, through fungal biofertilization, it was observed that Xylaria sp. promotes the development of the root system of Arabidopsis thaliana seedlings, in addition to synthesizing IAA.

Biotization of highbush blueberry with ericoid mycorrhizal and endophytic fungi improves plant growth and vitality.

Ecological methods are becoming increasingly popular. One of these methods is plant biotization. In our paper, we focus on selection of Vaccinium corymbosum hairy root-inhabiting fungi for plant growth promotion in a single microorganism inoculation setup and then composed a multiorganismal inoculum enriched with a representative of another group of fungi, leaf endophytes. The hairy roots of V. corymbosum hosted 13 fungal taxa. In single inoculation of the plant with fungal strains, the most beneficial for plant growth were Oidiodendron maius and Phialocephala fortinii. Additional inoculation of the plants with three root symbiotic fungi (O. maius, Hymenoscyphus sp. and P. fortinii) and with the endophytic fungus Xylaria sp. increased plant height in laboratory experiments. On a semi-industrial scale, inoculation improved plant biomass and vitality. Therefore, the amendment of root-associated fungal communities with a mixture of ericoid mycorrhizal and endophytic fungi may represent an alternative to conventional fertilization and pesticide application in large-scale blueberry production. KEY POINTS: • O. maius and P. fortinii significantly stimulated V. corymbosum growth in a single inoculation. • Multimicroorganismal inoculum increased plant biomass and vitality. • Blueberry biotization with ericoid and endophytic fungi is recommended.

[Secondary metabolites of endophyte fungi Xylaria sp. from Coptis chinensis].

Two new polyketides, lasobutone A(1) and lasobutone B(2), along with three known compounds, guignardianone C(3), guignardic acid(4), and 4-hydroxy-17R-methylincisterol(5), were isolated from the endophytic fungi Xylaria sp. by silica gel, MCI, and preparative HPLC, which was separated from the Chinese medicinal material Coptis chinensis and cultivated through solid fermentation with rice. Their structures were elucidated on the basis of spectroscopic methods, such as MS, NMR, IR, UV, and ECD. Compounds 2 and 4 showed inhibitory activities against the nitric oxide(NO) production in the LPS-induced macrophage RAW264.7 with IC_(50) values of 58.7 and 42.5 µmol·L~(-1) respectively, while compound 5 exhibited cytotoxic activities against HT-29 with IC_(50) value of 14.3 µmol·L~(-1).

Bioactive PKS-NRPS Alkaloids from the Plant-Derived Endophytic Fungus Xylaria arbuscula.

A novel hybrid PKS-NRPS alkaloid, xylarialoid A (1), containing a 13-membered macrocyclic moiety and [5,5,6] fused tricarbocyclic rings, together with ten known cytochalasins (2-11), was isolated from a plant-derived endophytic fungus, Xylaria arbuscula. The chemical structures of all compounds were elucidated using 1D and 2D NMR, HR ESIMS spectroscopic analyses, and electronic circular dichroism (ECD) calculation. Compounds 1-3 and 10 exhibited significant antitumor activities against A549 and Hep G2 cell lines, with IC50 values of 3.6-19.6 µM. In addition, compound 1 showed potent anti-inflammatory activity against LPS-induced nitric oxide (NO) production in macrophage RAW 264.7 cells (IC50, 6.6 µM).

Nematicidal Activity of Grammicin Biosynthesis Pathway Intermediates in Xylaria grammica KCTC 13121BP against Meloidogyne incognita.

Grammicin, a polyketide metabolite produced by the endolichenic fungus Xylaria grammica KCTC 13121BP, shows strong nematicidal activity against Meloidogyne incognita. This study was performed to elucidate the grammicin biosynthesis pathway of X. grammica KCTC 13121BP and to examine the nematicidal activity of the biosynthesis intermediates and derivatives against M. incognita. Two grammicin biosynthesis intermediates were isolated from a T-DNA insertion transformant (strain TR-74) of X. grammica KCTC 13121BP and identified as 2-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione (compound 1) and 2,5-dihydroxybenzaldehyde (compound 2), which were also reported to be intermediates in the biosynthesis pathway of patulin, an isomer of grammicin. This indicates that the grammicin biosynthesis pathway overlaps almost with that of patulin, except for the last few steps. Among 13 grammicin biosynthesis intermediates and their derivatives (except grammicin), toluquinol caused the highest M. incognita J2 mortality, with an LC50/72 h value of 11.13 µg/mL, which is similar to grammicin with an LC50/72 h value of 15.95 µg/mL. In tomato pot experiments, the wettable powder type formulations (WP) of toluquinol (17.78 µg/mL) and grammicin (17.78 µg/mL) also effectively reduced gall formation on the roots of tomato plants with control values of 72.22% and 77.76%, respectively, which are much higher than abamectin (16.67%), but lower than fosthiazate (100%). The results suggest that toluquinol can be used directly as a biochemical nematicide or as a lead molecule for the development of new synthetic nematicides for the control of root-knot nematode diseases.

Xyloneside A: A New Glycosylated Incisterol Derivative from Xylaria sp. FB.

Xylaria species are prolific natural product producers. Here, we report the characterization of a new glycosylated incisterol derivative, called xyloneside A (1) and two known lignans (2 and 3) from the ascomycetous Xylaria sp. FB. The structure of xyloneside A (1) was determined by 1D and 2D NMR spectroscopy, high-resolution electrospray ionization mass spectrometry and electronic circular dichroism measurements. Xyloneside A is composed of a 1,2,3,4,5,10,19-heptanorergosterane skeleton and a ß-D-mannopyranose moiety. This is the first report of an incisterol derivative from an Ascomycete. The biological effects of the isolated metabolites on cytotoxicity, autophagy, cell-migration, and angiogenesis were evaluated.

Mannosylxylarinolide, a new 3,4-seco-ergostane-type steroidal saponin featuring a ß-d-mannose from the endophytic fungus Xylaria sp.

Mannosylxylarinolide (1), a new 3,4-seco-ergostane-type steroidal saponin featuring a ß-d-mannose moiety, was isolated from the culture of the endophytic fungus Xylaria sp. that had been isolated from an ornamental plant of Hoya sp. The gross structure was determined by spectroscopic data, and the absolute configuration of the new 3,4-seco-ergostane-type steroidal saponin (1) was determined by X-ray diffraction analysis.

Diverse members of the Xylariales lack canonical mating-type regions.

A survey of genomes reported here for 10 isolates of Monosporascus species and an additional 25 genomes from other members of the Xylariales (representing 15 genera) available in public databases indicated that genes typically associated with MAT1-1 (mat A) or MAT1-2 (mat a) mating types are absent or have diverged greatly relative to counterparts in other Pezizomycotina. This was particularly surprising for isolates known to be homothallic, given that homothallic members of the Pezizomycotina typically possess a MAT1-1-1 (mat A-1) gene and one or both of two other closely-linked mating-type genes, MAT1-1-2 (mat A-2) and MAT1-1-3 (mat A-3), in addition to MAT1-2-1 (mat a-1). We failed to detect candidate genes for either MAT1-1-1 or MAT1-1-2 in any member of the Xylariales. Genes related to MAT1-2-1 and MAT1-1-3 are present in the genomes examined, but most appear to be orthologs of MATA_HMG (high-mobility group) genes with non-mating-type functions rather than orthologs of mating-type genes. Several MATA_HMG genes were found in genome positions that suggest they are derived from mating-type genes, but these genes are highly divergent relative to known MAT1-2-1 and MAT1-1-3 genes. The genomes examined represent substantial diversity within the order and include M. cannonballus, M. ibericus, Xylaria hypoxylon, X. striata, Daldinia eschscholzii, Eutypa lata, Rosellinia necatrix, Microdochium bolleyi and several others. We employed a number of avenues to search for homologs, including multiple BLAST approaches and examination of annotated genes adjacent to genes known to flank mating regions in other members of the Ascomycota. The results suggest that the mating regions have been lost from, or altered dramatically in, the Xylariales genomes examined and that mating and sexual development in these fungi are controlled differently than has been reported for members of the Pezizomycotina studied to date.

Isolation and enhancement of resveratrol production in Xylaria psidii by exploring the phenomenon of epigenetics: using DNA methyltransferases and histone deacetylase as epigenetic modifiers.

Resveratrol is an important stilbene which is having a high demand due to its therapeutic, cosmeceutical and nutraceutical activities. The current study mainly focuses on strategies to enhance the fungal potential to produce resveratrol via the activation of the cryptic biosynthetic pathway with their particular interest in the antioxidant application. The endophytic fungus Xylaria psidii was isolated from the surface sterilized leaf of Vitis vinifera. With the help of HPLC analysis it is found that resveratrol concentration was maximum and enhanced in case of treatment with 5 µm SAHA (52.32 µg/mL) and by 10 µm AZA (48.94 µg/mL) followed by 10 µm SAHA (41.10 µg/mL) and 5 µm AZA (37.72 µg/mL). After treatment with different concentration of epigenetic modifiers such as HDAC inhibitors (SAHA) and dMNTs (AZA) inhibitors, a significant increase in antioxidant potential was obtained. In the case of DPPH increase in scavenging potential was found as compared to wild strain. Treatment with 5 µm SAHA and by 10 µm AZA was showing strong antioxidant potential among all the epigenetic variants as compared to wild strain. In the case of TEAC also the same trend as in the case of DPPH was obtained.

Carbaryl biodegradation by Xylaria sp. BNL1 and its metabolic pathway.

Although ascomycetes occupy a vaster niche in soil than the well-studied basidiomycetes, they have received limited attention in studies related to bioremediation. In this study, the degradation of carbaryl by Xylaria sp. was studied in different culture conditions and its possible metabolic pathway was elucidated. In liquid culture, 99% of the added carbaryl was eliminated when cytochrome P450 (CYP450) was active, which was similar to the degradation rate of Pleurotus ostreatus, a fungus with strong bioremediation ability. Mn2+ is beneficial to the degradation of carbaryl. Compared to the 72.17% degradation rate in sterile soil, 59.0% carbaryl was eliminated in non-sterile soil, which suggested that Xylaria sp. BNL1 can resist microorganismal infection. Furthermore, the intracellular fractions containing laccase, CYP450, and carbaryl esterase efficiently degraded carbaryl. The presence of carbaryl metabolites suggested that Xylaria sp. BNL1 initiated its attack on carbaryl via carbaryl esterase to release α-naphthol, which was further degraded to 1,4-naphthoquinone and benzoic acid by CYP450 and laccase. Thus, our study highlights the potential of using Xylaria sp. for bioremediation.

Xylarianins A-D from the endophytic fungus Xylaria sp. SYPF 8246 as natural inhibitors of human carboxylesterase 2.

Eighteen secondary metabolites were isolated from the fermentation broth of the endophytic fungus Xylaria sp. SYPF 8246, including four new compounds, xylarianins A-D (1-4), three new natural products, 6-methoxycarbonyl-2'-methyl-3,5,4',6'-tetramethoxy-diphenyl ether (5), 2-chlor-6-methoxycarbonyl-2'-rnethyl-3,5,4',6'-tetramethoxy-diphenyl ether (6), and 2-chlor-4'-hydroxy-6-methoxy carbonyl-2'-methyl-3,5,6'-trimethoxy-diphenyl ether (7), and eleven known compounds (8-18). Their structural elucidations were conducted by using 1D and 2D NMR, HRESIMS, and Rh2(OCOCF3)4-induced electronic circular dichroism (ECD) spectra analyses. The integrated 1H and 13C NMR data of three new natural products 5-7 were reported for the first time. All the isolated compounds were assayed for their inhibitory activities against human carboxylesterase 2 (hCE 2). Compounds 1, 5-9, and 18 displayed significant inhibitory activities against hCE 2 with IC50 values of 10.43 ±â€¯0.51, 6.69 ±â€¯0.85, 12.36 ±â€¯1.27, 18.25 ±â€¯1.78, 29.78 ±â€¯0.48, 18.86 ±â€¯1.87, and 20.72 ±â€¯1.51 µM, respectively. The interactions between compounds 1 and 5 with hCE 2 were anaylzed by molecular docking.

Biosorption of copper by endophytic fungi isolated from Nepenthes ampullaria.

Copper (Cu) tolerance was observed by endophytic fungi isolated from the carnivorous plant Nepenthes ampullaria (collected at an anthropogenically affected site, Kuching city; and a pristine site; Heart of Borneo). The fungal isolates, capable of tolerating Cu up to 1000 ppm (11 isolates in total), were identified through molecular method [internal transcribed spacer 4+5 (ITS4+5); ITS1+NL4; ß-tubulin region using Bt2a + Bt2b], and all of them grouped with Diaporthe, Nigrospora, and Xylaria. A Cu biosorption study was then carried out using live and dead biomass of the 11 fungal isolates. The highest biosorption capacity of using live biomass was achieved by fungal isolates Xylaria sp. NA40 (73·26 ± 1·61 mg Cu per g biomass) and Diaporthe sp. NA41 (72·65 ± 2·23 mg Cu per g biomass), NA27 (59·81 ± 1·15 mg Cu per g biomass) and NA28 (56·85 ± 4·23 mg Cu per g biomass). The fungal isolate Diaporthe sp. NA41 also achieved the highest biosorption capacity of 59·33 ± 0·15 mg g-1 using dead biomass. The living biomass possessed a better biosorption capacity than the dead biomass (P < 0·05) and the roadside fungal strains showed higher Cu biosorption capacities using live biomass compared to the jungle fungal strains (P < 0·05). SIGNIFICANCE AND IMPACT OF THE STUDY: Our study highlights that fungal biosorption capacity is highly dependent on the sampling area (roadside vs jungle) with roadside fungal strains showing significantly higher copper (Cu) biosorption capacities using living biomass compared to fungal strains originating from plants collected in virgin jungle (P < 0·05). It also highlights that different biosorption mechanisms (alive - metabolic dependent and dead biomass - metabolic independent) result in different amounts of Cu being removed from the solutions. The living biomass possessed a better biosorption capacity than the dead biomass (P < 0·05).

Osteoclastogenesis Inhibitory Polyketides from the Sponge-Associated Fungus Xylaria feejeensis.

A new ten-membered macrolide (1) and a new α-pyrone derivative, (-)-annularin C (2), together with 14 known analogs (3-16) were isolated from the AcOEt extract of the fungus Xylaria feejeensis isolated from the South China Sea sponge Stylissa massa. The structures of the new compounds were elucidated by the spectroscopic analysis and by comparison with reported data. The absolute configuration was determined by the optical rotation and ECD experiments. In an in vitro test, compounds 1, 5 and 9 exhibited significant down-regulating activity of osteoclast cell differentiation at 0.5 and 1 µm. This is the first report of the fungus X. feejeensis from a marine sponge and of osteoclastogenesis inhibitory activity for the metabolites of these kinds.

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites.

Griseofulvin is a fungal metabolite and antifungal drug used for the treatment of dermatophytosis in both humans and animals. Recently, griseofulvin and its analogues have attracted renewed attention due to reports of their potential anticancer effects. In this study griseofulvin (1) and related analogues (2-6, with 4 being new to literature) were isolated from Xylaria cubensis. Six fluorinated analogues (7-12) were synthesized, each in a single step using the isolated natural products and Selectflour, so as to examine the effects of fluorine incorporation on the bioactivities of this structural class. The isolated and synthesized compounds were screened for activity against a panel of cancer cell lines (MDA-MB-435, MDA-MB-231, OVCAR3, and Huh7.5.1) and for antifungal activity against Microsporum gypseum. A comparison of the chemical space occupied by the natural and fluorinated analogues was carried out by using principal component analysis, documenting that the isolated and fluorinated analogues occupy complementary regions of chemical space. However, the most active compounds, including two fluorinated derivatives, were centered around the chemical space that was occupied by the parent compound, griseofulvin, suggesting that modifications must preserve certain attributes of griseofulvin to conserve its activity.

Three New Ergot Alkaloids from the Fruiting Bodies of Xylaria nigripes (Kl.) Sacc.

Three new ergot alkaloids, xylanigripones A - C (1 - 3) together with three known compounds, agroclavine (4), 8,9-didehydro-10-hydroxy-6,8-dimethylergolin (5), and (6S)-agroclavine N-oxide (6) were isolated from the fungus Xylaria nigripes (Kl.) Sacc. Their structures were elucidated by comprehensive spectroscopic analyses and high-resolution mass spectrometry as well as by comparison with the literature. The absolute configuration was determined by Density Functional Theory (DFT) calculation methods. In addition, all of the compounds were evaluated for bioactivity via a cytotoxicity assay, an acetylcholinesterase inhibition assay and a cholesterol ester transfer protein inhibition assay.

Secondary metabolites of endophytic Xylaria species with potential applications in medicine and agriculture.

Fungal endophytes are important sources of bioactive secondary metabolites. The genus Xylaria Hill (ex Schrank, 1789, Xylariaceae) comprises various endophytic species associated to both vascular and non vascular plants. The secondary metabolites produced by Xylaria species include a variety of volatile and non-volatile compounds. Examples of the former are sesquiterpenoids, esters, and alcohols, among others; and of the latter we find terpenoids, cytochalasins, mellein, alkaloids, polyketides, and aromatic compounds. Some of these metabolites have shown potential activity as herbicides, fungicides, and insecticides; others possess antibacterial, antimalarial, and antifungal activities, or α-glucosidase inhibitory activity. Thus metabolites from Xylaria are promising compounds for applications in agriculture for plague control as biopesticides, and biocontrol agents; and in medicine, for example as drugs for the treatment of infectious and non-infectious diseases. This review seeks to show the great value of the secondary metabolites of Xylaria, particularly in the agriculture and medicine fields.