A new meroterpenoid and a new polyketide from Penicillium expansum GY618 Fungus

Two new compounds, including one meroterpenoid (1) and a polyketide derivative (2), along with six compounds (3−8), were isolated from the rice solid fermentation of Penicillium expansum GY618. The structures of these new compounds were elucidated through interpretations of spectroscopic data and highresolution electrospray ionization mass spectrometry. The absolute configurations of all new compounds were unambiguously established through the optical rotation or calculation of the ECD spectrum. All isolated compounds were evaluated for their antibacterial and antitumor activities. Compound 6 exhibited weak antitumor activity.     

泰国红树内生真菌土曲霉xy03菌株中新杂萜类成分

采用硅胶柱层析、SephadexLH-20凝胶柱层析和高效液相色谱(HPLC)等技术,从一株红树马六甲木果楝来源的土曲霉Aspergillus terreusxy03的发酵物中分离得到了7个杂萜类化合物:asptercin A(1)、(1R,4aR,6aR,12aR,12bS)-1,3,4,4a,5,6,6a,12,1...     

A new meroterpenoid, chrodrimanin C, from YO-2 of Talaromyces sp

The new meroterpenoid, chrodrimanin C (3), together with chrodrimanins A (2) and B (1) were isolated from okara (the insoluble residue of whole soybean) that had been fermented with strain YO-2 of Talaromyces sp. Their structures were elucidated by spectroscopic methods. The partial structures of 1 essential for exhibiting insecticidal activity were investigated by using a silkworm assay. The absolute configuration of 1 was also determined.     

Depsidones from Talaromyces stipitatus SK-4, an endophytic fungus of the mangrove plant Acanthus ilicifolius

An endophytic fungus (Talaromyces stipitatus SK-4) was isolated from the leaves of a mangrove plant Acanthus ilicifolius. Its crude extract exhibited significant antibacterial activity and was purified to afford two new depsidones, talaromyones A and B (1 and 2), along with five known depsidone analogs (3–7). Their structures, including absolute configuration, were elucidated through extensive spectroscopic data analysis and modified Mosher's method. Compound 2 showed antibacterial activity against Bacillus subtilis with an MIC value of 12.5 μg/mL. In the inhibitory assay against α-glucosidase, compounds 2, 4 and 5 displayed moderate activities with IC₅₀ values ranging from 48.4 to 99.8 μM.     

Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica

Nigrosphaerin A, a new isochromene derivative (1), was isolated from the endophytic fungus Nigrospora sphaerica and chemically identified as 3-(3,4-dihydroxyphenyl)-4,6,8-trihydroxy-1H-isochromen-1-one-6-O-β-d-glucopyranoside. In addition nineteen known compounds (2–20) were isolated from the same fungus and chemically identified. Compounds (1–3, 5, and 7–16) were isolated for the first time from this fungus. In vitro antileukemic, antileishmanial, antifungal, antibacterial and antimalarial activities of (1–20) were examined. Compounds 5, 7, 9 and 10 showed good antileukemic activity against HL60 cells with IC₅₀ values of 0.03, 0.39, 0.2 and 0.4 μg/mL, respectively and against K562 cells with IC₅₀ values of 0.35, 0.35, 0.49 and 0.01 μg/mL, respectively. Compounds 3, 4 and 6 showed moderate antileishmanial activity with IC₅₀ values of 30.2, 26.4 and 36.4 μg/ml, respectively. Compound 7 showed moderate antifungal activity against Cryptococcus neoformans with IC₅₀ value of 14.8 μg/mL.     

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.     

A new bicyclic sesquiterpenoid from Merremia yunnanensis

A new sesquiterpenoid, 1α,4β,8β,9β-eudesmane-tetrol-1-O-β-D-glucopyranoside (1), together with nine known compounds (2–10), were isolated from Merremia yunnanensis. The structures of these compounds were elucidated by spectroscopic methods and compared to data in the literature. All these compounds (1–10) were firstly isolated from this plant, and compounds 3, 5, 7, and 10 were reported from the Merremia genus for the first time. The significance of the chemotaxonomy for these compounds is described herein.     

Acrocalysterols A and B,two new steroids from endophytic fungus Acrocalymma sp

Two new steroids, named acrocalysterols A (1) and B (2), together with five known compounds were isolated and characterized from an endophytic fungus Acrocalymma sp., isolated from the tender stems of Sinomenium acutum. The structures of the isolated metabolites were identified based on UV, IR NMR (1D and 2D), HR-ESI-TOF-MS, single-crystal X-ray diffraction experiment using Cu Kα radiation and CD spectra associated with TD-DFT calculation. The bioassay showed that compound 2 displayed potent cytotoxicity against three cancer cell lines HeLa, HCC-1806, and RKO with IC₅₀ values ranging from 18.37 to 19.64 μM.     

A new meroterpenoid pigment from the basidiomycete Albatrellus confluens

A new farnesyl phenol named (+)-(R)-grifolinone C (1) has been isolated from the fruiting bodies of the basidiomycete Albatrellus confluens. (+)-(R)-Grifolinone C (1), a dimeric meroterpenoid, is accompanied by albatrellin (2), grifolinone B (3), grifolin (4), and grifolinone A (5). Albatrellin (2) exhibited cytotoxic activity against HepG2 human lung carcinoma cells with IC(50) value of 1.55 mug ml(-1). The structures were established on the basis of spectral evidence (IR, 1D- and 2D-NMR, and MS analyses).     

Three new diterpenes and two new sesquiterpenoids from the endophytic fungus Trichoderma koningiopsis A729

Three new diterpenes koninginols A-C (1–3) and two new sesquiterpenoids 11-hydroxy-15-drimeneoic acid (4), koninginol D (5), together with twelve known compounds (6–17) were isolated from the endophytic fungus Trichoderma koningiopsis A729 derived from Morinda officinalis. Their structures were fully assigned with the aid of extensive spectroscopic analysis and reported data from the previous literatures. Koninginols A and B were disclosed as intriguing diterpene alkaloids, whereas the koninginol C was disclosed as one of the two examples of harziandione diterpene. All the isolates were evaluated for their antitumor activity, and compounds 1–2, 4–6, 11–13, 16–17 were evaluated for their antibacterial activity, wherein the new compounds 1 and 2 exhibited significant antibacterial activity against Bacillus subtilis with MIC values of 10 and 2 μg/mL, respectively.     

Three new napthalene derivatives from the endophytic fungus Phomopsis fukushii

An endophytic Phomopsis fukushii was isolated from the rhizome of Paris polyphylla var. yunnanensis, Diaporthaceae family, and three new (1–3) and four known napthalene derivatives (4–7) were isolated from the fermentation products of this fungus. Their structures were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1–3 were evaluated for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity with vancomycin as positive control. The results showed that compounds 1–3 showed good inhibitions with MCI valves of 4, 4 and 6 mg/mL, respectively.     

Induction of funitatin A,a new polyketide from the Yellow River wetland-derived fungus Talaromyces funiculosus

A new, highly modified fatty acid ester, funitatin A (1), was isolated from the Yellow River wetland-derived fungus Talaromyces funiculosus HPU-Y01 cultivated with the histone deacetylase inhibitor suberoylanilide hydroxamic acid (SAHA). The structure of 1 was established by analysis of NMR and HRESIMS data. Compound 1 featured a rare dimeric cyclopaldic acid structure and showed promising antimicrobial activity against both Proteus species and Escherichia coli with MIC values of 3.13 μM.     

A polyphasic approach for the characterization of endophytic Alternaria strains isolated from grapevines

A polyphasic approach was set up and applied to characterize 20 fungal endophytes belonging to the genus Alternaria, recovered from grapevine in different Italian regions.Morphological, microscopical, molecular and chemical investigations were performed and the obtained results were combined in a pooled cluster analysis. Following morphological analyses, all strains were grouped according to their three-dimensional sporulation pattern on PCA and to the colony characteristics on different substrates. After DNA extraction, all strains were analyzed by RAPD-PCR and the resulting profiles were subjected to cluster analysis. The metabolites extracted from the 20 Alternaria endophytes were analyzed by a HPLC and the resulting metabolite profiles were subjected to multivariate statistic analyses. In comparison with reference ‘small-spored’ Alternaria species, the 20 strains were segregated into two morphological groups: one belonging to the A. arborescens species-group and a second to the A. tenuissima species-group. RAPD analysis also showed that grapevine endophytes belonged to either the A. arborescens or the A. tenuissima species-group and that they were molecularly distinct from strains belonging to A. alternata. Chemotaxonomy gave the same grouping: the grapevine endophytic strains belong to A. arborescens or A. tenuissima species-groups producing known metabolites typical of these species-groups. Interestingly, the 20 grapevine endophytes were able to produce also a number of unknown metabolites, whose characterization could be useful for a more precise segregation of the two species-groups.The results show how complementary morphological, molecular and chemical data can clarify relationships among endophyte species-groups of low morphological divergence.     

内生真菌X1-2次级代谢产物研究

在从神农架地区特有植物内生真菌中寻找各种活性次级代谢产物的过程中,从濒危植物珙桐叶片中分离得到一株内生真菌X1-2。经过高效液相色谱(HPLC)和薄板色谱(TLC)分析其固体发酵产物多样性,通过正相硅胶柱层析、重结晶、高效液相色谱制备等手段纯化次级代谢产物,从该真菌中分离获得四个次级代谢产物。经核磁共振波谱(NMR),质谱(MS)等波谱学方法鉴定其结构,四个化合物分别为icosalide A1(1),militarinone A(2),(+)-N-deoxymilitarinone A(3),β-hydroxytetradecanoyl-β-hydroxyl tetraecanoyl-Rha-Rha-C_(14)-C_(14)(4),其中icosalide A1(1),militarinone A(2),(+)-N-deoxymilitarinone A(3)为三个复杂的生物碱类化合物,而化合物4是首次从真菌中获得。     

A new flavonoid from the bark of Ulmus pumila L

A new flavonoid (6), together with eight (1–5 and 7–9) known flavonoids, were isolated from the n-butyl alcohol soluble portion of the EtOH extract of Ulmus pumila L. The chemical structures of the compounds were determined by using spectroscopic methods and further supported by comparison with previously literature values. Among them, flavonoids 4, 6 and 9 were isolated for the first time from the family Ulmaceae. Furthermore, the chemotaxonomic significance of the isolates was also discussed.     

A new meroterpenoid isolated from roots of Ptaeroxylon obliquum Radlk.

The roots of Ptaeroxylon obliquum Radlk. (Rutaceae) afforded a new meroterpenoid, ptaerobliquol, together with chromones, ptaeroxylinol acetate and peucenin, and coumarins, scopoletin and prenyletin. Ptaerobliquol was isolated using centrifugal partition chromatography followed by silica gel column and identified as 7a,8,9,9a,9b,10a-heptahydro-4H-10,10-dimethyl-1,7-dioxa-5-hydroxy-2-hydroxymethylcyclobutyl[1,2,3:3,3a,4]indeno[5,6-a]naphtalen-4-one by extensive NMR and single crystal X-ray analyses. A biosynthetic pathway is proposed for this new compound. Activity of ptaerobliquol toward Toxoplasma gondii was investigated and a moderate activity was found with an IC₅₀ of 5.13 μM.     

一株产石杉碱甲的蛇足石杉内生真菌的分离和鉴定

从药用蕨类植物蛇足石杉叶中分离得到53株内生真菌,在马铃薯葡萄糖液体培养基（PDB）中发酵后对内生真菌发酵提取物液进行TLC、HPLC 和ESI-MS检测,结果表明菌株LF40为产石杉碱甲内生菌株,含量达80.1μg/gdcw,并具有体外乙酰胆碱酯酶抑制活性;运用形态学及ITS-rDNA序列分析方法对菌株LF40进行鉴定,确定为黄曲霉Aspergillus flavus LF40。     

Cycloaspeptide A and pseurotin A from the endophytic fungus Penicillium janczewskii

Penicillium janczewskii K. M. Zalessky was isolated as an endophytic fungus from the phloem of the Chilean gymnosperm Prumnopitys andina. When grown in liquid yeast extract-malt extract-glucose broth, the fungus produced two main secondary metabolites. The compounds were for the first time isolated from this species and identified by spectroscopic methods as pseurotin A and cycloaspeptide A. This is the first report on the production of cyclic peptides by endophytic fungi from Chilean gymnosperms. Pseurotin A and cycloaspeptide A presented low cytotoxicity towards human lung fibroblasts with IC50 > or = 1000 microM. Pseurotin A showed a moderate effect against the phytopathogenic bacteria Erwinia carotovora and Pseudomonas syringae, with IC50 values of 220 and 112 microg ml(-1), respectively.