Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha

The methanol extract of fruiting bodies of the ascomycete Xylaria polymorpha afforded three isopimarane diterpene glycosides, namely, 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (1), 15-hydroxy-16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (2), and 16-α-d-glucopyranosyloxyisopimar-7-en-19-oic acid (3). Their structures were determined by spectroscopic methods and by single-crystal X-ray analysis. They showed cytotoxicity against human cancer cell lines and exhibited IC₅₀ values ranging from 71 to 607 μM. Further studies on the cytotoxicity of these compounds against HL60 cells demonstrated that they induced apoptosis along with typical DNA fragmentation. It was observed that 2 was less active than 1 and 3.     

Bioluminescence characteristics of the fruiting body of Mycena chlorophos

Bioluminescent fungi are widely distributed on land and most belong to the class Basidomycetes. Light of about 530 nm wavelength maximum is emitted continuously. The molecular basis for the light‐emitting process remains unclear. We investigated the characteristics of the bioluminescence using cultivated fruiting bodies of M. chlorophos. Only fresh fruiting bodies exhibited long‐lasting light emission; rapid decay of light emission was observed with frozen and freeze‐dried samples. Freeze‐dried samples can be stored at room temperature under dry conditions and may be useful for the isolation of luciferin. The light emission of the fresh fruiting bodies was maintained in various buffers at varying pH; it could be stopped with pH 4 acetate buffer and could be recovered at pH 6. The isolation of luciferin from the fresh fruiting bodies might be possible by the control of buffer pH. The effect of temperature on the light emission of fruiting bodies indicated that bioluminescence in M. chlorophos may involve enzymatic reaction(s). The solubilization of bioluminescent components from the fruiting bodies could not be achieved with various surfactants. Copyright © 2011 John Wiley & Sons, Ltd.     

Structure of fomitellan A, a mannofucogalactan from the fruiting bodies of Fomitella fraxinea

Chemical structure of fomitellan A, a polysaccharide with a mitogenic effect isolated from the fruiting bodies of Fomitella fraxinea, has been assigned as a mannofucogalactan with a repeating unit of penta-saccharide, which was composed of a (1→6)-linked d-galactopyranosyl backbone having a C-2 position substituted with disaccharide units of 3-O-d-mannopyranosyl-l-fucopyranosyl residue. The ¹H and ¹³C NMR signals of fomitellan A have been completely assigned by extensive NMR experiments.     

Isolation and characterization of a lectin from Grifola frondosa fruiting bodies

An N-acetylgalactosamine-specific lectin (GFL) was isolated from Grifola frondosa fruiting bodies by affinity chromatographies on acid-treated Sepharose CL-4B and then GalNAc-Toyopearl. The isolated lectin agglutinated all types of erythrocytes equally. Molecular masses estimated by gel filtration under various buffers and matrices varied from 30 to 52 kDa. On the other hand, SDS-PAGE in the presence or absence of 2-mercaptoethanol showed three major bands of 33, 66 and 100 kDa and a faint band of 65 kDa. This lectin exhibited GalNAc-specificity. The protein was a glycoprotein containing 3.3% total sugar, and the amino acid analysis revealed a high content of acidic and hydroxy amino acids and a low content of methionine and histidine. GFL was cytotoxic against HeLa cells. The toxicity did not appear after preincubating the lectin with the haptenic sugar N-acetylgalactosamine.     

荷叶离褶伞子实体化学成分

本文对祁连山野生荷叶离褶伞Lyophyllum decastes子实体的化学成分和生物活性进行研究。采用硅胶色谱、高效液相色谱等多种方法进行分离纯化得到8个化合物,通过MS、NMR和电子圆二色谱 （ECD）等方法确定了化学结构,其中有4个为聚炔类化合物。化合物1作为天然产物系首次报道,其相绝对构型是通过比较ECD的方法确定。对所得聚炔类化合物应用细胞模型进行抗氧化活性（CAA）指标检测,化合物1-4均呈现一定抗氧化活性,其中化合物1的抗氧化活性最强,其EC₅₀为(24.73±6.12)μmol/L。聚炔类化合物1-4为荷叶离褶伞首次报道成分,可作为祁连山野生荷叶离褶伞HPLC-DAD化学表征参考化合物。     

Quantifying Hg within ectomycorrhizal fruiting bodies,from emergence to senescence

Ectomycorrhizal fruiting bodies (basidiomata) collected from forested areas in southwestern New Brunswick were analyzed for total mercury, sulphur, nitrogen, and carbon concentrations (THg, TS, TN, and TC, respectively). This analysis was done for caps and stalks and by development stage (emergent, mature, senescent) across 27 species associated with five classes, eight families, and 13 genera. Across the species, THg correlated positively with TN and TS, thereby implying N as well as S mitigated transfer of Hg from the mycelia into the basidiomata, with THg ranging from 3 to 10?457 ppb. TS, TN, and TC varied from 0.07 to 1, 1 to 11, and 43 to 53 %, respectively. Cap and stalk THg, TS, TN, and TC were also correlated to one another, with mean stalk/cap ratios of 0.59, 0.76, 0.71, and 0.98, respectively. Soil availability indexed by THg, TS, TN, and TC within the forest floor contributed to basidiomatal THg as well. THg, THg/TS, and THg/N varied strongly by species. These variations involved: (i) no growth dilution and no volatilization (Group I), (ii) growth dilution only (Group II), (iii) growth dilution followed by loss during senescence (Group III), and (iv) growth dilution combined with loss from emergence onward (Group IV). Depending on species, TN and TS remained the same or declined from 100 % at emergence to about 80 and 70 % at senescence. Lack of THg decline for the Group I species would be due to HgS encapsulation. Reanalyzing the freeze-dried samples revealed that THg continued to drop during the first year of air-dry storage for the Group II, II, and IV species, but TS, TN, and TC remained stable. The results were quantified by way of best-fitted regression models.     

Eryngin, a novel antifungal peptide from fruiting bodies of the edible mushroom Pleurotus eryngii

An antifungal peptide with a molecular mass of 10k Da was isolated from fruiting bodies of the mushroom Pleurotus eryngii. The peptide, designated as eryngin, inhibited mycelial growth in Fusarium oxysporum and Mycosphaerella arachidicola. It was unadsorbed on DEAE-cellulose and adsorbed on Affi-gel blue gel and S-Sepharose. Its N-terminal sequence demonstrated some similarity to the antifungal protein from the mushroom Lyophyllum shimeiji and little resemblance to thaumatin and thaumatin-like proteins.     

Adustin, a small translation-inhibiting polypeptide from fruiting bodies of the wild mushroom Polyporus adusta

A polypeptide, with a molecular mass of 16.5 kDa as determined by gel filtration and sodium dodecyl sulfate-polyacrylamide gel electrophoresis, has been isolated from the mushroom Polyporus adusta. The polypeptide, designated as adustin, inhibited translation in a cell-free rabbit reticulocyte lysate system with an IC50 of 0.34 microM. It was isolated using a protocol that involved ion exchange chromatography on DEAE-cellulose, affinity chromatography on Affi-gel blue gel, ion exchange chromatography on CM-Sepharose and fast protein liquid chromatography-gel filtration on Superdex 75. Adustin was unadsorbed on DEAE-cellulose, and adsorbed on Affi-gel blue gel and CM-Sepharose.     

灵芝子实体中的羊毛脂烷型灵芝酸酯类成分研究

目的系统研究灵芝子实体中的羊毛脂烷型灵芝酸酯类成分。方法通过氯仿对盐酸酸化的灵芝子实体提取物中的羊毛脂烷型三萜酸类成分进行萃取,结合硅胶柱层析、中压柱层析(RP C18色谱柱)、制备型HPLC(RP C18色谱柱)对提取物中的三萜酸酯类化学成分进行系统的分离、纯化。通过UV、ESIMS、HRESI-MS、1 H-NMR、13C-NMR、HSQC、HMBC、NOESY等波谱学手段结合文献数据对制备得到的三萜类单体成分进行准确的结构测定。结果从灵芝子实体的氯仿提取物中共分离鉴定了10个羊毛脂烷型灵芝酸酯类成分,分别为:(1)Ganoderic acid AP,(2)Methyl Ganoderate G,(3)Ganoderic acid H,(4)12β-Hydroxy-3,7,11,15,23-pentaoxo-5α-lanost-8-en-26-oic acid,(5)Ganoderic acid K,(6)Ganoderenic acid B,(7)Lucienic acid A,(8)Lucidenic acid B,(9)20(21)-Dehydrolucidenic acid A,(10)Lucidone D。结论灵芝子实体中极性较小的化学成分主要为羊毛脂烷型三萜及其降碳衍生物,该类成分多具有羧基或羧酸酯官能团,既而也称灵芝酸类,本文共分离鉴定了10个该系列成分,其中化合物1为新化合物。     

硬孔灵芝的化学成分研究

采用硅胶柱层析法进行分离纯化,从硬孔灵芝Ganoderma duropora的氯仿萃取物中分离得到甾类化合物8种。根据波谱数据,化合物1-8结构分别被鉴定为:麦角甾醇、麦角甾-7,22-二烯-3β-醇、麦角甾-7,22-二烯-3-酮、6,9-环氧麦角甾-7,22-二烯-3β-醇、过氧麦角甾醇、3,5-二羟基麦角甾-7,22-二烯-6-酮、β-谷甾醇和胡萝卜苷。     

Isolation of a ribonuclease from fruiting bodies of the wild mushroom Termitomyces globulus

A ribonuclease, with a molecular mass of 13 kDa and a ubiquitin-like N-terminal sequence, has been isolated from fruiting bodies of the mushroom Termitomyces globulus. The ribonuclease demonstrated ribonucleolytic activity toward poly A, poly C, poly G and poly U, with the activity toward poly A and poly C being much higher than that toward poly G and poly U. The ribonuclease was unadsorbed on DEAE-cellulose but adsorbed on Affi-gel blue gel and CM-Sepharose. The enzyme required a temperature of 70 degrees C for expression of maximal activity. However, the enzyme expressed nearly the same optimal activity over a wide pH range of 5.0-8.0.     

Structural characterization of a water-soluble beta-D-glucan from fruiting bodies of Agaricus blazei Murr

A beta-D-glucan, Ab2-2N, was isolated from the hot-water extract of fruiting bodies of Agaricus blazei Murr by ethanol precipitation, anion-exchange and gel-permeation chromatography. Its structure was investigated by composition analysis, methylation analysis, Smith degradation, mild hydrolysis, and NMR spectroscopy. It contains a (1-->6)-linked beta-D-glucopyranosyl backbone, with one side chain consisting of terminal and 3-substituted beta-D-glucopyranosyl residues attached at O-3 for every three backbone residues.     

Isolation and characterization of a lectin from Grifola frondosa fruiting bodies

An N-acetylgalactosamine-specific lectin (GFL) was isolated from Grifola frondosa fruiting bodies by affinity chromatographies on acid-treated Sepharose CL-4B and then GalNAc-Toyopearl. The isolated lectin agglutinated all types of erythrocytes equally. Molecular masses estimated by gel filtration under various buffers and matrices varied from 30 to 52 kDa. On the other hand, SDS-PAGE in the presence or absence of 2-mercaptoethanol showed three major bands of 33, 66 and 100 kDa and a faint band of 65 kDa. This lectin exhibited GalNAc-specificity. The protein was a glycoprotein containing 3.3% total sugar, and the amino acid analysis revealed a high content of acidic and hydroxy amino acids and a low content of methionine and histidine. GFL was cytotoxic against HeLa cells. The toxicity did not appear after preincubating the lectin with the haptenic sugar N-acetylgalactosamine.     

Meroterpenoids from the fruiting bodies of higher fungus Ganoderma resinaceum

Phytochemical investigation on the fruiting bodies of Ganoderma resinaceum led to the isolation of five new meroterpenoids, namely ganoresinains A–E (1–5), and four known analogues (6–9). The new compounds were identified by extensive analyses of spectroscopic data (NMR, MS, UV, and IR) and comparison with the literature data. Compound 1 and 6 were isolated as enantiomeric mixture, which were separated over analytical chiral HPLC chromatography. Compounds 6–9 were isolated from G. resinaceum for the first time.     

Two new nortriterpenoids from the fruiting bodies of Ganoderma daqingshanense

Two new nortriterpenoids named daqingshones A (1) and B (2), along with two known ganderic acids (3 and 4), were isolated from the fruiting bodies of Ganoderma daqingshanense. Their structures were elucidated by spectroscopic data including MS, 1D and 2D NMR. Compound 2 exhibited weak anti-acetylcholinesterase (AChE) activity with IC₅₀ value of 39.2 μM.