A new phthalide from the endophytic fungus Xylaria sp. GDG-102

A new phthalide derivative, xylarphthalide A (1), along with two known compounds (-)-5-carboxylmellein (2) and (-)-5-methylmellein (3), were isolated from the endophytic fungus Xylaria sp. GDG-102 cultured from the Chinese medicinal plant Sophora tonkinensis. Their structures were identified by MS and NMR experiments, and the absolute configuration of 1 was further confirmed by single-crystal X-ray diffraction analysis. Compound 1–3 showed antibacterial activities against Bacillus megaterium, Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Shigella dysenteriae with MIC values of 12.5–25 μg/mL.     

Eremophilane sesquiterpenes from the endophytic fungus Xylaria sp. GDG-102

A new eremophilane sesquiterpene, xylareremophil (1), together with five known eremophilanes, 1α,10α-epoxy-3α-hydroxyeremophil-7(11)-en-12,8β-olide (2), 1,10α,13-trihydroxyeremophil-7(11)-en-12,8-olide (3), 1α,10α-epoxy-13-hydroxyeremophil-7(11)-en-12,8β-olide (4), mairetolides B (5) and G (6) were isolated from the endophytic fungus Xylaria sp. GDG-102 cultured from Sophora tonkinensis. Their structures were elucidated on the basis of spectroscopic data analysis. The absolute configurations of 1 was determined by comparing computed electronic circular dichroism (ECD) and optical rotation (OR) with experimental results. Compounds 1, 5 and 6 showed antibacterial activities against Proteus vulgaris, Micrococcus luteus, Micrococcus lysodeikticus and Bacillus subtilis with MIC values of 25–100 μg/mL.     

Secondary metabolites of Xylaria sp., an endophytic fungus from Taxus mairei

One new metabolite 3,7-dimethyl-9-(-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)nona-1,6-dien-3-ol, together with nine known compounds, were isolated from the strain Xylaria sp., an endophytic fungus of Taxus mairei. Their structures were deduced from 1D and 2D NMR data. In vitro cytotoxicity and antibacterial activity of these compounds were evaluated. Some of them exhibited substantial activity.     

Two new tetralone derivatives from the culture of Xylaria hypoxylon AT-028

Two new tetralone derivatives named xylariol A （1） and B （2） were isolated from the EtOAc extract of the culture broth of Xylaria hypoxylon AT-028 （Xylariaceae）, and their structures were elucidated by MS, 1R, 1D- and 2D-NMR spectra, and by X-ray diffraction analysis. 1 and 2 showed moderate cytotoxic activities against Hep G2 cells in the in vitro cytotoxic assay with IC50 values of 22.3 and 21.2 μg/mL, respectively.     

Three New Sesquiterpenoids from Xylaria sp. NCY2

Three new sesquiterpenoids, xylarenones A ( 1 ) and B ( 2 ), and xylarenic acid ( 3 ), were obtained from the endophytic fungal strain Xylaria sp. NCY2, which was isolated from Torreya jackii Chun . Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and by HR‐Q‐TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.     

Xylastriasan A,a new cytochalasan from the fungus Xylaria striata

Xylastriasan A (1), a new cytochalasan alkaloid with a rare 5/6/6/5/6 pentacyclic skeleton, and ergosterol (2) were isolated from the ethanol extract of fruiting bodies of the fungus Xylaria striata. Their structures were determined by analysis of their spectroscopic data. Compound 1 exhibited weak cytotoxic activity against HEPG2, B16 and A549 cell lines with IC₅₀ values of 93.61, 85.61 and 91.58 μM, respectively. Ergosterol (2) potentiated pentobarbital-induced sleep by not only increasing the number of falling asleep and prolonging sleeping time but also reducing sleep latency at a dosage of 5 mg/kg.     

1H and 13C NMR assignments for two new xanthones from the endophytic fungus Xylaria sp. FRR 5657

The complete 1H and 13C NMR assignments are reported for the new natural products, 7-hydroxy-3-(hydroxymethyl)-1-methoxy-9H-xanthen-9-one (1) and 2,5-dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene -1-carboxylic acid (2). Both of these secondary metabolites were isolated from the fermentation culture of the endophytic fungus Xylaria sp. FRR 5657. 1D and 2D NMR experiments that included 1H, gCOSY, gHSQC and gHMBC were used for the determination of the structure and assignment of these xanthones.     

Two new polyketides from the fungus Penicillium oxalicum MHZ153

Two new polyketides, penicilloxalones A (1) and B (2), together with 13 known compounds (3–15), were isolated from the ethyl acetate extract of the solid substrate fermentation cultures of the fungus Penicillium oxalicum MHZ153. The structures of the isolates were determined by spectroscopic analysis and comparison of their spectroscopic and physicochemical data with the literature values. Compounds 7 and 11 showed inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC₅₀ values of 0.9 ± 0.2 μM and 87.9 ± 0.7 μM, respectively.     

Secondary Metabolites from the Endophytic Fungus Xylaria cubensis

Seven new metabolites, including three sesquiterpenoids, 10‐hydroxythujopsene ( 1 ), akotriol ( 2 ), and xylaritriol ( 3 ), one diterpenoid, cubentriol ( 4 ), one aliphatic derivative, akoenic acid ( 5 ), one alkaloid, akodionine ( 6 ), and one isocoumarin, akolitserin ( 7 ), together with seven known compounds, 8 – 14 , were isolated from the AcOEt‐soluble fraction of the fermentation broth of the endophytic fungus Xylaria cubensis, derived from the leaves of Litsea akoensis Hayata (Lauraceae). Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and by HR‐ESI‐MS mass spectrometry. Among the isolates, (?)‐(R)‐7‐hydroxymellein showed IL‐6 inhibitory activity with an IC₅₀ value of 9.41 μM .     

Chemical Constituents from the Fermented Mycelia of the Medicinal Fungus Xylaria nigripes

Nineteen compounds mainly including pyrrole‐containing alkaloids and phytosterols were isolated from the EtOH extract of the fermented mycelia of Xylaria nigripes, a precious medicinal fungus known as Wuling Shen in Chinese. On the basis of spectroscopic methods, the structures of the new naturally occurring compounds were determined to be (4S)‐3,4‐dihydro‐4‐(4‐hydroxybenzyl)‐3‐oxo‐1H‐pyrrolo[2,1‐c][1,4]oxazine‐6‐carbaldehyde ( 1 ), methyl (2S)‐2‐[2‐formyl‐5‐(hydroxymethyl)‐1H‐pyrrol‐1‐yl]‐3‐(4‐hydroxyphenyl)propanoate ( 2 ), and 3‐{4‐[(2R)‐(2,3‐dihydroxy‐3‐methylbutoxy]phenyl}‐7‐hydroxy‐4H‐chromen‐4‐one ( 3 ), respectively. The absolute configurations of 1 and 2 were deduced by the observed Cotton effects in their circular dichroism (CD) spectra, whereas that of the 1,2‐diol moiety in 3 was determined using the Snatzke's method. Their biological activities such as neuroprotective, anti‐neuroinflammatory, and cytotoxic properties were also reported.     

A new amino amidine derivative from the wood-decaying fungus Xylaria cf. cubensis SWUF08-86

The secondary metabolites of Xylaria cf. cubensis SWUF08-86 fungus were investigated, and the chromatographic separation of the crude extracts yielded seventeen compounds. The structure elucidation by spectroscopic analysis including 1D and 2D NMR and the comparison of these data with literature, along with HREIMS spectrometry, revealed one new amino amidine derivative (1), together with five known simple cyclic dipeptide analogs, diketopiperazines (2–6) and eleven other known compounds, including one hemi-cycline (10), three aromatic derivatives (11–13), one sesquiterpene (14) and three sterols (15–17). The isolated compounds were screened for anticancer and anti-pathogenic bacterial and fungal activities. Based on this work, Xylaria cf. cubensis SWUF08-86 has proven to be a diverse secondary metabolites producer.     

A new chromene from the fruiting bodies of Chroogomphus rutilus

A new chromene, acetic acid 2R-(4,8-dimethylnona-3,7-dienyl)-8-hydroxy-2-methyl-2H-chromen-6-yl ester (1), was isolated from the fruiting bodies of Chroogomphus rutilus, together with six known compounds (2–7). The structures of these compounds were identified based on 1D and 2D NMR, including ¹H–¹H COSY, HMQC and HMBC spectroscopic methods. Of these seven compounds, 2 and 3 showed cytotoxicity against HSC-T6, SK-Hep1 and A549 cell lines.     

New Cytochalasins from the Marine‐Derived Fungus Xylaria sp. SCSIO 156

Two new cytochalasins, 18‐deoxycytochalasin Q ( 1 ) and 21‐O‐deacetylcytochalasin Q ( 2 ), together with four known analogues, cytochalasin Q ( 3 ), 19,20‐epoxycytochalasin Q ( 4 ), 21‐O‐deacetyl‐19,20‐epoxycytochalasin Q ( 5 ), and cytochalasin D ( 6 ), were isolated from the fungus Xylaria sp. SCSIO156 originated from the South China Sea marine sediment. The structures of 1 and 2 were elucidated by MS and 1D‐ and 2D‐NMR data analyses, and comparison with known compounds. The known compounds 3 – 6 were identified by comparison of their MS and NMR data with those reported in the literature. In the in vitro antitumor assay, compounds 2 – 6 showed mild cytotoxicity against three tumor cell lines (MCF‐7, SF‐268, and NCI‐H460).     

One new Lignan derivative from the fruiting bodies of Ganoderma lipsiense

One new lignan derivative 2,3-dimethyl-4-(4′-hydroxy-3′,5′-dimethoxyphenyl)-6-hydroxy-7-methoxy-naphthalene (1), together with four known analogues (2-5), were isolated from acetone extract of the fruiting bodies of Ganoderma lipsiense collected in the Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compound 1 showed insecticidal activity against newly hatched karvae of Helicoverpa armigera Hubner. Compounds 1-5 showed moderate antibacterial activity against Staphylococcus aureus with the same MIC value of 1.25?μg/mL.     

A new natural nucleotide and other antibacterial metabolites from an endophytic Nocardia sp.

Nine compounds were isolated from Nocardia sp. YIM 64630, and their structures were elucidated as 5′-O-acetyl-2′-deoxyuridine (1), 22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol (2), 22E,24R-5α,6α-epoxyergosta-8,22-diene-3β,7α-diol (3), 22E,24R-ergosta-7,22-diene-3β,5α,6β-triol (4), 5α,8α-epidioxyergosta-6,22-dien-3β-ol (5), 4′,5,6-trihydroxy-7-methoxyisoflavone (6), 2,4,4′-trihydroxy-deoxybenzoin (7), methyl [4-hydroxyphenyl]acetate (8) and daidzein by extensive spectroscopic analyses. Compound 1 was isolated from natural resources for the first time. The antimicrobial and antioxidant activities of compounds 1–8 were investigated.     

Two new polyketides from Hawaiian endophytic fungus Pestalotiopsis sp. FT172

Two new polyketides, pestalotiotones A (1) and B (2) were isolated from the cultured broth of Pestalotiopsis sp. FT172. The structures of compounds 1 and 2 were determined by analysis of HRMS and NMR spectroscopic data. The absolute configurations of compound 1 were assigned by Mosher reaction, J-based configuration analysis, and DP4 NMR calculations. Both compounds were tested against cancer cell lines, pathogenic fungi and bacteria.     

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).     

巴戟天内生真菌Trichoderma spirale A725中两个新的聚酮类化合物(英文)

综合运用硅胶柱色谱、反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及制备型高效液相色谱技术对药用植物巴戟天内生真菌Trichoderma spirale A725的次生代谢产物进行分离纯化,得到6个聚酮类化合物,采用多种现代波谱技术确定其结构,分别为:6-羟基-4-异丙基-1,8-二甲基螺环[4.5]癸-1,8-二烯-7-酮(1),2-羟基-2,5-二甲基-7-氧代-5,7-二氢-2H-呋喃[3,4-b]吡喃-4-羧酸(2), 3-乙基-4-羟基-6-甲基-二氢-吡喃-2-酮(3),苯乙内酯A (4), 3-羟基-5-(4-羟基苄基)二氢呋喃-2(3H)-酮(5), 4-乙酰-3-羟基-6-甲基吡喃-2-酮(6).其中化合物1和2为新化合物,化合物3为新天然产物.此外,利用四株肿瘤细胞株(Hep G-2、MCF-7、SF-268及A549)对化合物1~6细胞毒活性进行评估,结果表明化合物1~6对上述肿瘤细胞均无明显的细胞毒活性.     

Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508

(3R*,3aR*,9aR*)-3,9a-Dimethyl-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromene-5,7-diol (xyloketal H), a representative of a new family of xyloketals, was isolated from the marine-derived mangrove fungus Xylaria sp. 2508. Its structure was elucidated by spectroscopic data and single-crystal X-ray diffraction analysis. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1051–1052, June, 2006.     

Glaucopine C, a new diterpene from the fruiting bodies of Sarcodon glaucopus

In this work the mushroom Sarcodon glaucopus was studied. A new cyathane, glaucopine C (1), was isolated from the hexane extract and identified by 1H and 13C NMR spectra analysis. Glaucopine C showed anti-inflammatory acitvity.