Citrinal A,a novel tricyclic derivative of citrinin,from an algicolous fungus Penicillium sp.i-1-1

Citrinal A(1),a novel tricyclic compound with a rare tetrahydro-2H-benzofuro[7-b][1,4]dioxin-9(3H)-one skeleton,along with two known related compounds,citrinin(2) and 2,3,4-trimethyl-5,7-dihydroxy-2,3-dihydrobenzofuran(3) were isolated from an algicolous fungus Penicillium sp.i-1-1.The structure and stereochemistry of 1 were determined by comprehensive spectral and biogenic analysis.Its cytotoxic effects on the A-549 and HL-60 cell lines were evaluated.     

A novel antifouling alkaloid from halotolerant fungus Penicillium sp. OUCMDZ-776

Penispirolloid A (1), a novel alkaloid possessing a unique spiro imidazolidinyl skeleton, was isolated from a halotolerant fungal strain, Penicillium sp. OUCMDZ-776. Its structure was elucidated on the basis of spectroscopic methods and quantum chemical CD calculation. Compound 1 showed significant antifouling activity toward Bugula neritina larvae with EC₅₀ of 2.40 μg/ml. Plausible biogenesis of compound 1 was also proposed.     

Triterpene glycosides from Cussonia paniculata. III. Structure of glycosides I1, I2, J1a, J1b, J2, K, L1, and L2 from C. paniculata leaves

Structures of eight triterpene glycosides, of which the 28-O-(2-O-acetyl-and 3-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-O-β-D-glucopyranosyl-(1→ 6)-O-β-D-glucopyranosyl esters of hederagenin 3-O-β-D-glucopyranosyl-(1→ 2)-O-α-L-arabinopyranoside (J_1a and J_1b) were new, from Cussonia paniculata (Araliaceae) leaves were established using chemical and NMR spectroscopic methods. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 149–152, March–April, 2006.     

Penicindopene A,a new indole diterpene from the deep-sea fungus Penicillium sp. YPCMAC1

A new indole diterpene, named penicindopene A (1), together with seven known compounds (2?–?8), was isolated from the deep-sea fungus Penicillium sp. YPCMAC1. The structure of penicindopene A was elucidated by extensive spectroscopic analyses (1?D and 2?D NMR, and HRESIMS data), in addition to the ECD calculations for the assignments of its absolute configuration. Penicindopene A represented the first example of indole diterpenes possessing a 3-hydroxyl-2-indolone moiety, and it exhibited moderate cytotoxicities against A549 and HeLa cell lines with IC₅₀ values of 15.2 and 20.5?µM, respectively.     

Synthesis, insecticidal and acaricidal activities of novel 2-arylpyrroles

To search for novel 2-arylpyrroles with unique biological activities,a series of novel 2-arylpyrrole derivatives were designed and synthesized,and their structures were characterized by 1 H and 13 C NMR spectroscopy,MS spectrometry,and elemental analysis.Their insecticidal activities against Lepidopteran pests (e.g.Mythimna separata) and acaricidal activities against mites (e.g.Tetranychus urticae) were evaluated.The results of bioassays indicate that some of these title compounds exhibited excellent insecticidal and acaricidal activities.For example,4-bromo-1-((chloromethoxy)methyl)-2-(4-chloro phenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (6a),4-bromo-2-(4-chlorophenyl)-1-((2-fluoroethoxy)-methyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile (6d) showed insecticidal activity against Mythimna separata and 4-bromo-2-(4-chlorophenyl)1-((isopropoxymethoxy)methyl)-5-(trifluoro methyl)pyrrole-3-carbonitrile (7d) showed acaricidal activity against Tetranychus urticae.They were more effective than Chlorfenapyr,which has been the only commercialized member of a new class of chemicals of 2-arylpyrroles.     

A new polyoxygenated farnesylcyclohexenone from Fungus Penicillium sp.

A new polyoxygenated farnesylcyclohexenone, peniginsengin A (1), was isolated from the fermentation of Penicillium sp. YIM PH30003, an endophytic fungus associated with Panax notoginseng (Burk.) F. H. Chen. The structure was assigned based on a combination of 1 D and 2 D NMR and mass spectral data. The cytotoxicity and antimicrobial activities of compound 1 were investigated.     

Penicillilactone A,a novel antibacterial 7-membered lactone derivative from the sponge-associated fungus Penicillium sp. LS54

One novel 7-membered lactone derivative, penicillilactone A (1), together with two known compounds, rugulosin A (2) and rugulosin (3) were isolated from the sponge-derived fungus Penicillium sp. LS54. Their structures were elucidated on the basis of spectroscopic analysis and comparison with literature data. Remarkably, penicillilactone A (1) is the first natural product containing a 7-membered lactone ring fused with a furan core. Penicillilactone A (1) exhibited moderate antibacterial activity against aquatic pathogen Vibrio harveyi with an MIC value of 8 μg/mL.     

Ukulactones A and B, new NADH-fumarate reductase inhibitors produced by Penicillium sp. FKI-3389

Screening for NADH-fumarate reductase inhibitors led to the isolation of the new polyketide compounds, ukulactones A and B (1 and 2, Fig. 1) from a culture broth of Penicillium sp. FKI-3389. The structure of ukulactone A was elucidated as a methylated derivative of prugosene A1, which was produced by Penicillium rugulosum and NOESY experiment revealed ukulactone B was a stereoisomer of ukulactone A. Ukulactone A showed potent inhibitory activity against NADH-fumarate reductase of the roundworm Ascaris suum in vitro.     

Synthesis of 2′-deoxyribofuranosyl indole nucleosides related to the antibiotics SF-2140 and neosidomycin

The 2′-deoxyribofuranose analog of the naturally occurring antibiotics SF-2140 and neosidomycin were prepared by the direct glycosylation of the sodium salts of the appropriate indole derivatives, with 1-chloro-2- deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose ( 5 ). Thus, treatment of the sodium salt of 4-methoxy-1H- indol-3-ylacetonitrile ( 4a ) with 5 provided the blocked nucleoside, 4-methoxy-1-(2-deoxy-3,5-di-O-p-toluoyl-β- D-erythropentofuranosyl)-1H-indol-3-ylacetonitrile ( 6a ), which was treated with sodium methoxide to yield the SF-2140 analog, 4-methoxy-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indol-3- ylacetonitrile ( 7a ). The neosidomycin analog ( 8 ) was prepared by treatment of the sodium salt of 1H-indol-3-ylacetonitrile ( 4b ) with 5 to obtain the blocked intermediate 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl) ?1H-indol-3-ylace-tonitrile ( 6b ) followed by sodium methoxide treatment to give 1-(2-deoxy-β-D-erythropentofuranosyl)-1H- indol-3-ylacetonitrile ( 7b ) and finally conversion of the nitrile function of 7b to provide 1-(2-deoxy-β-D- erythropentofuranosyl)-1H-indol-3-ylacetamide ( 8 ). In a similar manner, indole ( 9a ) and several other substituted indoles including 1H-indole-4-carbonitrile ( 9b ), 4-nitro-1H-indole ( 9c ), 4-chloro-1H-indole-2-carboxamide ( 9d ) and 4-chloro-1H-indole-2-carbonitrile ( 9e ) were each glycosylated and deprotected to provide 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole ( 11a ), 1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole-4- carbonitrile ( 11b ), 4-nitro-1-(2-deoxy-β-D-erythropentofuranosyl)-1H-indole ( 11c ), 4-chloro-1-(2-deoxy-β-D- erythropentofuranosyl)-1H-indole-2-carboxamide ( 11d ) and 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)- 1H-indole-2-carbonitrile ( 11e ), respectively. The 2′-deoxyadenosine analog in the indole ring system was prepared for the first time by reduction of the nitro group of 11c using palladium on carbon thus providing 4-amino-1-(2-deoxy-β-D-erythropentofuranosyl)- 1H-indole ( 16 , 1,3,7-trideaza-2′-deoxyadenosine).     

Structures of deacetyl glykenins-a,b, and c,glycosidic antibiotics from basidiomycetes sp.

The structures of deacetyl Glykenins (DG)-A, B, and C, basic structures of Glykenins, were elucidated by chemical degradation and interpretation of spectral data.     

A New Polyketide from the Mangrove Endophytic Fungus Penicillium sp. sk14JW2P

Two polyketides were isolated from the mangrove endophytic fungus, Penicillium sp. sk14JW2P, and one derivative with a modified structure. The structures were elucidated by spectroscopic analyses, the structure of the compound 1 was further confirmed by single‐crystal X‐ray diffraction, and its absolute configuration was determined. Compound 1 and 2 showed acetylcholinesterase (AchE) inhibitory activities with IC₅₀ values of 12±0.3 and 79±2 nM , respectively.     

Penicillenols from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum

Six new tetramic acids derivatives, penicillenols A(1), A(2), B(1), B(2), C(1), and C(2) (1-6), together with citrinin, phenol A acid, phenol A, and dihydrocitrinin, were identified from Penicillium sp. GQ-7, an endophytic fungus associated with Aegiceras corniculatum. Their structures were elucidated on the basis of comprehensive spectral analysis. All the new compounds were evaluated for their cytotoxic effects on four cell lines by the MTT method. Penicillenols A(1) and B(1) showed cytotoxicities against HL-60 cell line with IC(50) values of 0.76 microM and 3.20 microM, respectively.     

Antiglioma Natural Products from the Marine-Associated Fungus Penicillium sp. ZZ1750

Marine-derived Penicillium fungi are one of the most important sources for the discovery of new bioactive natural products. This study characterized the isolation, structures, and antiglioma activities of twelve compounds, including three novel ones—penipyridinone B (1), 11S-(−)-penilloid A (2), and 11R,14E-(+)-penilloid A (3)—from the marine fungus Penicillium sp. ZZ1750. The structures of the novel compounds were determined via extensive nuclear magnetic resonance (NMR) spectroscopic analyses, high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, Mosher’s method, optical rotation (OR) calculations, and electronic circular dichroism (ECD) calculations. Penipyridinone B represents the first example of its structural type and showed potent antiglioma activity, with IC₅₀ values of 2.45 μM for U87MG cells and 11.40 μM for U251 cells. The known compounds of questiomycin A (9) and xanthocillin X (10) also showed antiproliferative activity against both U87MG and U251 cells, with IC₅₀ values of 13.65 μM to 22.56 μM. The antiglioma activity of questiomycin A and xanthocillin X may be related to the promotion of reactive oxygen species (ROS) production, the reduction of mitochondrial membrane potential (MMP), and the enhancement of caspase-3 enzyme activity.     

Two new chroman derivations from the endophytic Penicillium sp. DCS523

Strain DCS523 was isolated from the branch tissue of Daphniphyllum longeracemosum and determined to be a Penicillium sp. according to the ITS sequence analysis. The extracts from the PDA solid fermentation media of Penicillium sp. DCS523 were purified to give two new chroman derivatives as well as six known compounds. Based on their spectral data the new compounds were identified as (Z)-6-acetyl- 3-(1,2-dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one and 6-acetyl-2α,5- dihydroxy-2-(2-hydroxypropyl)- 3α,8-dimethylchroman, respectively.     

Three New Xanthones from the Fungus Penicillium sp. NH‐7‐1

Three new xanthones, drimiopsins G–I ( 1 – 3 , resp.), and two known congeners, griseoxanthone C ( 4 ) and norlichexanthone ( 5 ), were isolated from a fungal isolate, Penicillium sp. NH‐7‐1. The structures of all compounds were determined on the basis of extensive spectroscopic analyses, as well as by comparison with literature reports, and the structure of compound 1 was further confirmed by single‐crystal X‐ray diffraction.     

Biverlactones A-D, new circumventors of arbekacin resistance in MRSA, produced by Penicillium sp. FKI-4429

Biverlactones, new circumventors of arbekacin resistance in methicillin-resistant Staphylococcus aureus (MRSA) were isolated from a culture broth of Penicillium sp. FKI-4429. Their structures were elucidated by spectroscopic studies, including various NMR experiments. Biverlactones A-D had novel skeletons, consisting of a lactone ring conjugated with exo- or endo-olefin, a carboxylic group and a characteristic alkyl side chain in common.     

Phormidinines A and B, novel 2-alkylpyridine alkaloids from the cyanobacterium Phormidium sp.

Novel 2-alkylpyridine alkaloids, phormidinines A (1) and B (2), were isolated from cyanobacterium Phormidium sp. Their structures were determined by spectroscopic analysis. The absolute stereochemistry of 1 was established by the modified Mosher’s method.     

Hesseltin A, a novel antiviral metabolite from Penicillium hesseltinei

[structure: see text] Hesseltin A 1, a novel compound of mixed polyketide-terpenoid origins was isolated from the filamentous fungus Penicillium hesseltinei. The structure and stereochemistry were determined from extensive one- and two-dimensional NMR and mass spectral data.