一株红树内生真菌Penicillium sp.(ZZF29#)次级代谢产物分离与鉴定

研究了一株药用红树内生真菌Penicillium sp.(ZZF29#)的次级代谢产物。用硅胶柱层析、制备薄层层析和重结晶等方法,从该菌发酵液的乙酸乙酯相中分离获得8种单体化合物,运用现代波谱技术并与文献数据对照,鉴定其结构分别为:环(苯丙-丙)二肽(1)、环(苯丙-甘)二肽(2)、环(苯丙-苯丙)二肽(3)、环(苯丙-酪)二肽(4)、大黄素(5)、大黄素甲醚(6)、麦角甾醇(7)和过氧化麦角甾醇(8)。     

Palmarumycins from the Endophytic Fungus Lasiodiplodia pseudotheobromae XSZ‐3

One new and three known spiro‐dioxynaphthalene compounds, related to palmarumycins, were isolated from the extracts of fungus Lasiodiplodia pseudotheobromae XSZ‐3. Their structures were established by spectroscopic methods (1D‐ and 2D‐NMR, HR‐ESI‐MS, etc.). The absolute configuration of 1 was determined by comparison of quantum‐chemical TDDFT (time‐dependent density‐functional theory) calculated and experimental ECD (electronic circular dichroism) spectra. The cytotoxic activities of 1 – 4 against HL‐60 cell line were evaluated by trypan blue‐staining assay.     

A new compound: Xyloketal H from mangrove fungus <Emphasis Type="Italic">Xylaria</Emphasis> sp. from the South China Sea coast

A new metabolite xyloketal H (1), was isolated from mangrove fungus Xylaria sp. (No.2508) obtained from the South China Sea. By spectroscopic analyses, primarily 2D NMR methods and X-ray diffraction experiments, its structure was elucidated. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 5–6, January–February, 2008.     

A new biphenyl derivative from an unidentified marine fungus E33

A new biphenyl derivative 3,5′-dihydroxy-4′,5-dimethoxy-2′-methyl-[1,1′-biphenyl]-2-carboxylic acid methyl ester (1), was isolated from the culture broth of a fungus isolated from the rhizosphere soil of mangrove root on the South China Sea. The structure of 1 was determined by comprehensive spectroscopic methods, primarily 2D NMR techniques. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 128–129, March–April, 2008.     

Antiviral peptides from marine gorgonian-derived fungus Aspergillus sp. SCSIO 41501

A new cyclic pentapeptide and three new linear peptides, namely, aspergillipeptides D–G (1–4), were isolated from a culture broth of marine gorgonian-derived fungus Aspergillus sp. SCSIO 41501. Their structures were elucidated by spectroscopic analysis, and their absolute configurations were confirmed by Marfey’s method. Compounds 1 and 2 showed evident antiviral activity against herpes simplex virus type 1 (HSV-1) with IC₅₀ values of 9.5 and 19.8 µM under their non-cytotoxic concentrations against a Vero cell line, respectively, and 1 also had antiviral activity against acyclovir-resistant clinical isolates of HSV-1.     

Furo[3,2-h]isochroman, furo[3,2-h]isoquinoline, isochroman, phenol, pyranone, and pyrone derivatives from the sea fan-derived fungus Penicillium sp. PSU-F40

Nine new fungal metabolites, penicisochromans A-E, penicipyrone, penicipyranone, peniciphenol, and penicisoquinoline, were isolated from the sea fan-derived fungus Penicillium sp. PSU-F40 together with five known compounds. Their structures were determined by spectroscopic analysis. Their antibacterial activity against the standard Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus was evaluated.     

Tetramic acid derivatives and polyphenols from sponge-derived fungus and their biological evaluation

Fifteen compounds, including two tetramic acid derivatives, penicillenol A₁ (1) and penicillenol A₂ (2), six polyphenols containing both phenolic bisabolane sesquiterpenoid and diphenyl ether units, expansols A–F (3–8), together with six phenolic bisabolane sesquiterpenoids (9–14) and diorcinol (15), were isolated from the fermentation broth of the marine-derived fungus ZSDS1-F11 isolated from the sponge Phakellia fusca Thiele collected in the Yongxing island of Xisha. Their structures were elucidated mainly by using extensive NMR spectroscopic and mass spectrometric analyses. Compounds 3–5, 7 and 8 showed potent COX-1 inhibitory activity with IC₅₀ values of 5.3, 16.2, 30.2, 41.0 and 56.8 μM, respectively. Meanwhile, compounds 3–8 showed potent COX-2 inhibitory activity with IC₅₀ values of 3.1, 5.6, 3.0, 5.1, 3.2 and 3.7 μM, respectively. In addition, compound 1 exhibited antituberculosis activity with 96.1% inhibition at concentration of 10 μM.     

A New Cyclic Peptide and a New Steroid from the Fungus Penicillium sp. GD6 Isolated from the Mangrove Bruguiera gymnorrhiza

A rare new cyclic tetrapeptide, 5,5′‐epoxy‐MKN‐349A ( 1 ), featured by a MKN‐349A ( 5 ) skeleton and containing an uncommon ether bridge between C(5) and C(5′), and a new steroid, named 11‐O‐acetyl‐NGA0187 ( 2 ), together with two known steroids, 3 and 4 , were isolated from an endophytic fungus Penicillium sp. GD6 associated with the Chinese mangrove Bruguiera gymnorrhiza. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses and by comparison with the data of related compounds reported in literature. Neither of the compounds 3 and 4 , isolated in this study, showed obvious bioactivities in the antibacterial bioassay experiments.     

DMOA-based meroterpenoids with diverse scaffolds from the sponge-associated fungus Penicillium brasilianum

Bioinformatics analysis of the synthetic gene clusters in association with the qRT-PCR detection led to speculate a marine derived fungus, Penicillium brasilianum WZXY-m122-9, to be potential to produce meroterpenoids. Chromatographic separation of the EtOAc extract of this fungal strain on a large-scale fermentation resulted in the isolation of six new DMOA-related meroterpenoids, namely brasilianoids G?L (1–6), together with nine known meroterpenes. Their structures were determined by extensive analyses of spectroscopic data, including the X-ray diffraction and the ECD data for configurational assignment. Brasilianoid G is characterized by the presence of an unprecedented scaffold bearing a 6/6/5/5/5 pentacyclic nucleus, while brasilianoid K possessing a 7/6/6/6/5 pentacyclic system is uncommonly found from nature. The biogenetic relationship among the isolated compounds was postulated based on the comparative analyses of gene clusters. Brasilianoid L (6), austinol (12), and dehydroaustin (14) exhibited significant inhibition against bacteria invasion into host cells, that was suggested to be mediated by preventing the polymerization of actin in the host cells.     

Pseudapenes A–C,sesquiterpenoids from the marine-derived fungus Pseudallescheria apiosperma F52-1

Three sesquiterpenoids pseudapenes A–C (1–3) were isolated from the marine-derived fungus Pseudallescheria apiosperma F52-1. Pseudapene A (1) has an unprecedented 2-methyl-5-methylene-3-(2-methylbut-2-ene)-dicyclo(3, 3, 0)-octane carbon skeleton and pseudapenes B (2) and C (3) possess an unique 2-methyl-4-methylene-2-(2-methylpent-2-ene)-dicyclo(3, 2, 0)-heptane chemical scaffold. Their structures were determined by use of MS and NMR spectroscopic data, and ECD, optical rotation and ¹³C NMR calculations.