源于一株青霉菌的4,5-环氧环己烯类次生代谢产物研究

从一株青霉菌Penicillium sp.（XZ075）的发酵粗提物中分离了4个4,5-环氧环己烯类新结构次生代谢产物penoxides A－D（1－4）和同类型的已知化合物eupenoxide（5）,并采用质谱和核磁共振技术确定了新化合物的结构。化合物1的绝对构型是通过与已知化合物5比对核磁数据确定的,而2－4的绝对构型是通过与化合物1比对CD谱图确定的。活性测试结果表明化合物1,2及4对宫颈癌细胞（HeLa）具有中等的细胞毒活性。     

青霉属真菌Penicillium sp. CPCC 400786的抗病毒活性成分

采用抗艾滋病毒抑制剂筛选模型对一株青霉属真菌Penicillium sp. CPCC 400786发酵产物的乙酸乙酯提取物进行活性评价,结果显示,其对艾滋病毒有较强的抑制活性。采用正相硅胶柱、Sephadex LH-20凝胶柱和半制备HPLC等色谱技术对乙酸乙酯提取物进行分离纯化,从中分离得到8个化合物。通过波谱数据分析,分别鉴定为：oxalicine A（1）、oxalicine B（2）、cis-4,6-dihydroxymellein（3）、亚油酸（4）、十八烯酸（5）、肉豆蔻酸（6）、尿嘧啶（7）、胸腺嘧啶（8）。化合物1和2为杂萜类化合物。对化合物1-6进行了抗艾滋病毒（HIV-1）和抗甲型流感病毒（H1N1）的活性评价。结果显示,化合物1具有良好的抗H1N1活性,其IC₅₀值为38.5μmol/L,比阳性对照药利巴韦林稍弱（IC₅₀=20.5μmol/L）;化合物1和2具有抗HIV-1的活性,其IC₅₀值分别为22.4、67.8μmol/L;其他化合物未显示抗病毒活性。本研究为从青霉属中发现更多抗病毒活性杂萜分子提供了依据。     

Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp.

Chromatographic analysis of the ethyl acetate extract of the fungus Penicillium sp., which was isolated from the sediment of the hyper saline lake Wadi El-Natrun in Egypt, afforded two new isochromans (1 and 2) and a new isocoumarin derivative (3), along with six known compounds (4–9). The planar structures of new compounds were unequivocally elucidated on the basis of extensive 1D- and 2D-NMR spectroscopy as well as HRESIMS. The relative configurations of the new compounds were established by analysis of the coupling constants as well as through ROESY experiments, while the absolute configurations were determined by comparison of the [α]_D values and by plausible biosynthetic considerations. Compounds (1–6) were found to share (3S) configuration. All compounds demonstrated a weak to moderate cytotoxic activity against the murine lymphoma L5178Y cell line.     

海洋真菌Penicillium sp. WP-13次级代谢产物研究

本研究分析了海洋真菌Penicillium sp. WP-13的活性次级代谢产物。采用多种柱色谱技术对其发酵液的乙酸乙酯提取物进行分离纯化;根据波谱数据和理化常数分析,并结合文献比对鉴定单体化合物的结构;采用MTT法测定化合物对肿瘤细胞的细胞毒活性。从Penicillium sp. WP-13发酵液的乙酸乙酯提取物中分离鉴定了5个单体化合物,其中2个内酯类化合物为1-hydroxy-3,10-dimethoxy-8-methyl-6,11-dioxo-6,11-dihydrodibenzo[b,e]oxepine-9-carboxylicacid(1)和1,8-dihydroxy-10-methoxy-3-methyl-dibenzo[b,e]oxepine-6,11-dione(2); 3个蒽醌类化合物为endocrocinmethylester(3)、2-chloro-1,3,8-trihydroxy-6-methyl-9,10-anthracenedione (4)和emodin (5)。活性测试结果显示,化合物3和5均对人慢性髓原白血病细胞株K562、人肝癌细胞株BEL-740...     

Diphenyl ether and benzophenone derivatives from the marine mangrove-derived fungus Penicillium sp. MA-37

Further investigation of the marine mangrove-derived fungal strain Penicillium sp. MA-37 led to the isolation of one new benzophenone, iso-monodictyphenone (1), two new diphenyl ether derivatives penikellides A (2) and B (3), and two known analogs monodictyphenone (4) and 6-[2-hydroxy-6-(hydroxymethyl)-4-methylphenoxy]-2-methoxy-3-(1-methoxy-3-methylbutyl)benzoic acid (5). The structures of these compounds were elucidated by spectroscopic analyses including 1D- and 2D-NMR and mass spectrometry. The brine shrimp lethality and antibacterial activity against five aquaculture pathogens were evaluated.     

Antiproliferative metabolites from the endophytic fungus Penicillium sp. FJ-1 isolated from a mangrove Avicennia marina

Two new compounds, named as 4-(2′,3′-dihydroxy-3′-methyl-butanoxy)-phenethanol (1), and 15-hydroxy-6α,12-epoxy-7β,10αH,11βH-spiroax-4-ene-12-one (2), were isolated from the endophytic fungus Penicillium sp.FJ-1 of Avicennia marina. Their structures were elucidated on the basis of spectroscopic analysis. Additionally, compounds 1 and 2 exhibited antiproliferative activities, and compound 2 significantly inhibited the tumor growth of human xenograft osteosarcoma in nude mice.     

NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum

Chemical investigation of the endophytic fungus Penicillium sp. isolated from Limonium tubiflorum growing in Egypt afforded four new compounds of polyketide origin, including two macrolides, penilactone (1) and 10,11-epoxycurvularin (2), a dianthrone, neobulgarone G (7), and a sulfinylcoumarin, sulfimarin (14), along with twelve known metabolites (3-6, 8-13, 15 and 16). The structures of all compounds were assigned by comprehensive spectral analysis (1D and 2D NMR) and mass spectrometry. Compounds 3, 4, 13 and 16 showed pronounced antitrypanosomal activity with mean MIC values ranging from 4.96 to 9.75 ??M. Moreover, when tested against a panel of three human tumor cell lines compounds 3, 4, 6 and 12 showed selective growth inhibition against Jurkat and U937 cell lines with IC₅₀ values ranging from 1.8 to 13.3 ??M. The latter compounds also inhibited TNF??-induced NF-??B activity in K562 cells with IC₅₀ values ranging from 1.6 to 10.1 ??M, respectively.     

An eclectic DNA structure adopted by human telomeric sequence under superhelical stress and low pH.

We have found, with the aid of 2-D gel electrophoresis, that double-stranded human telomeric repeat, (T2AG3)12.(C3TA2)12, being cloned within a plasmid, forms a protonated superhelically-induced structure. Experiments on chemical and enzymatic probing also indicate that the human telomeric repeats adopt an unusual structure. We have proposed an eclectic model for this structure in which four different elements coexist: a non-orthodox intramolecular triplex stabilized by the canonical protonated C.G*C+ base-triads and highly enriched by noncanonical base-triads; the intramolecular quadruplex formed by a portion of the G-rich strand; the single-stranded region encompassing a portion of the G-rich strand and, probably, the (C,A)-hairpin formed by a portion of the C-rich strand.     

Redoxcitrinin, a biogenetic precursor of citrinin from marine isolate of fungus Penicillium sp

A chemical analysis of the fermentation of the marine-derived fungus Penicillium sp. led to the isolation of a biogenetic precursor of citrinin, redoxcitrinin (1), together with polyketide mycotoxins, phenol A (2), citrinin H2 (3), 4-hydroxymellein (4), citrinin (5), and phenol A acid (6). The structures of compounds 1-6 were determined on the basis of physicochemical data analyses. Among them, compounds 1-3 exhibited a potent radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 values of 27.7, 23.4, and 27.2 microM, respectively.     

Metabolites from Penicillium sp., an endophytic fungus from the liverwort Riccardia multifida (L.) S. Gray

Two new metabolites, (3aR,9bR)-6,9b-dihydroxy-8-methoxy-1-methylcyclopentene[c]isochromen-3,5-dione (1) and 6-hydroxyl-deoxyfunicone (2), together with five known compounds (3–7), were obtained from Penicillium sp., an endophytic fungus from the Chinese liverwort Riccardia multifida (L.) S. Gray. Their structures were determined by extensive analysis of their spectroscopic data. Allelopathic test showed that compounds 2 and 4 significantly retarded germination of Arabidopsis thaliana seeds.     

Linking lipid transfer with reduced arbuscule formation in tomato roots colonized by arbuscular mycorrhizal fungus under low pH stress

Arbuscules are the core structures of arbuscular mycorrhizae (AM), and arbuscule development is regulated by environmental stress, e.g., low pH. Recent studies indicate that lipid transfer from plants is essential for AM fungal colonization; however, the role of lipid transfer in arbuscule formation and the dynamics of lipid accumulation in arbuscules under low pH stress are far from well understood. In the symbiosis of tomato and Rhizophagus intraradices under contrasting pH conditions (pH 4.5 vs. pH 6.5), we investigated arbuscule formation, nutrient uptake, alkaline phosphatase activity and lipid accumulation; examined the gene expression involved in phosphate transport, lipid biosynthesis and transfer and sugar metabolism; and visualized the lipid dynamics in arbuscules. Low pH greatly inhibited arbuscule formation, in parallel with reduced phospholipid fatty acids accumulation in AM fungus and decreased P uptake. This reduction was supported by the decreased expression of plant genes encoding lipid biosynthesis and transfer. More degenerating arbuscules were observed under low pH conditions, and neutral lipid fatty acids accumulated only in degenerating arbuscules. These data reveal that, under low pH stress, reduced lipid transfer from hosts to AM fungi is responsible for the inhibited arbuscule formation.     

Polyketides from Penicillium sp. JP-1, an endophytic fungus associated with the mangrove plant Aegiceras corniculatum

Four polyketides, leptosphaerone C (1), penicillenone (2), arugosin I (3) and 9-demethyl FR-901235 (4), as well as five known compounds, bacillosporin A (5), bacillosporin C (6), sequoiamonascin D (7), sequoiatone A (8), and sequoiatone B (9) were isolated from the Penicillium sp. JP-1, an endophytic fungus isolated from Aegiceras corniculatum. Their structures were determined by spectroscopic methods, mainly by 2D NMR spectroscopic analyses. Compound 1 showed cytotoxicity against A-549 cells with an IC50 value of 1.45 microM, while compound 2 showed cytotoxicity against P388 cells with an IC50 value of 1.38 microM.     

Penicillium caerulescens,sp. nov. isolated from soil

One new species of Penicillium Link ex Gray nom. cons. prop. is described and illustrated. This species has been recovered from samples of sandy soil under pine trees. It differs from all species of the Genus described so far and is, therefore, considered and proposed as new taxon: Penicillium caerulescens n. sp.     

红树植物内生真菌Penicillium sp.中新木质素的分离及结构鉴定

应用各种层析手段,从红树植物内生真菌的发酵液中分离纯化了一个新的木质素类化合物,结合多种波谱方法确定其结构为4,4′-二(1-丙烯酸甲酯)-3′-甲氧基-二苯醚(1)。     

Penicillium siamensis sp. nov., from Thailand soil

Fungal flora of 20 samples of lentil seeds collected from Assiut governorate, Egypt, were studied. Seventeen genera and 13 species were isolated on glucose- (15 genera and 27 species), cellulose-(15 genera and 25 species)Czapek's agar media at 28 °C. The most common species were as follows: on glucose-Czapek's agar, Aspergillus fumigatus, A. niger, A. flavus, A. terreus, Penicillium notatum and Rhizopus oryzae and on cellulose agar, A. fumigatus, A. niger, A. flavus and P. notatum. Thin layer chromatographic (TLC) analysis and a biological test (Artemia salina) indicated the presence and the toxicity of aflatoxin in the extract of one sample (aflatoxins B₁, B₂, G₁ and G₂, at 20 mg/kg, total). This is the first report of the natural occurrence of aflatoxins in lentils.     

Calmodulin inhibitors from the fungus Emericella sp.

Two new xanthones identified as 15-chlorotajixanthone hydrate (1) and 14-methoxytajixanthone (2) were isolated from an Emericella sp. strain 25379 along with shamixanthone (3) and tajixanthone hydrate (4). The stereostructures of 1 and 2 were elucidated by spectroscopic and molecular modeling methods. The absolute configuration at the stereogenic centers of 1 was established according to CD measurements. In the case of 2, however, the absolute configuration at C-20 and C-25 was designated as S and R, respectively, by Mosher ester methodology. Thereafter, the configuration at C-14 and C-15 of 2 was established as S and S, respectively by comparing the optical rotation and ¹H–¹H coupling constant experimental values with those obtained through molecular modeling calculations at DFT B3LYP/DGDZVP level of theory for diasteroisomers 2a–2d. The activation of the calmodulin-sensitive cAMP phosphodiesterase (PDE1) was inhibited in the presence of 1–4 in a concentration-dependent manner. The effect of compounds 2 (IC₅₀ = 5.54 μM) and 4 (IC₅₀ = 5.62 μM) was comparable with that of chlorpromazine (CPZ; IC₅₀ = 7.26 μM), a well known CaM inhibitor used as a positive control. The inhibition mechanism of both compounds was competitive with respect to CaM according to a kinetic study. A docking analysis with 2 and 4 using the AutoDock 4.0 program revealed that they interacted with CaM in the same pocket as trifluoropiperazine (TFP).     

红树植物内生真菌Penicillium sp.的化学成分

应用各种层析手段,从红树植物内生真菌GT26158菌丝体的甲醇提取物中分离纯化了7个含氮化合物,结合多种波谱方法(ESI-MS,1D-NMR,2D-NMR),它们被鉴定为2′-deoxyuridine(1)、thymidine(2)、2′-deoxyad-enosine(3)、cyclo(tyrosyl-phenylalanyl,4)、serine(5),cyclo(seryl-tryptophyl,6)、alanine(7)。     

Peniamidienone and penidilamine, plant growth regulators produced by the fungus Penicillium sp. No. 13

Peniamidienone and penidilamine were isolated from cultures of the fungus Penicillium sp. No. 13 as new plant growth regulators and their structures were established by NMR spectroscopic studies. Peniamidienone showed weak inhibition of lettuce seedling growth.