Isoflavones from the mangrove endophytic fungus Fusarium sp. (ZZF41)

A new isoflavone, 5-O-methyl-2'-methoxy-3'-methylalpinumisoflavone (1), together with four known compounds 6-methoxy-5,7,4'-trihydroxyisoflavone (2), 6-methoxy-7,4'-dihydroxyisoflavone (3), (+)-marmesin (4), and 4-methylbenzoic acid carboxymethyl ester (5), were isolated from the mangrove endophytic fungus, Fusarium sp. (ZZF41). Their structures were determined by analysis of spectroscopic data. Compound 1 inhibited HEp-2 and HepG2 cells with IC50 values of 4 and 11 micromol/mL, respectively.     

Two new acids from mangrove endophytic fungus (No. ZZF13)

Two new acids 1 and 2, together with a known compound, purpactin A (3), were isolated from endophytic fungus No. ZZF13. Their structures were elucidated on the basis of 1D, 2D NMR, and HREIMS spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp.336-337, July-August, 2008. Original articlesubmitted April 24, 2007.     

Two new benzaldehyde derivatives from mangrove endophytic fungus (No. ZZF 32)

Two new benzaldehyde derivatives, 6-ethyl-2-hydroxy-4-methoxy-3-methylbenzaldehyde (1), 6-ethyl-2,4-dihydroxy-3-methylbenzaldehyde (2), together with 2, 4-dihydroxy-3,6-dimethylbenzaldehyde (3) were isolated from mangrove fungus (No. ZZF 32#) from the South China Sea. The structures of compounds 1 and 2 were established by comprehensive analysis of the spectral data, especially 2D NMR spectral results.     

A new furanocoumarin from the mangrove endophytic fungus Penicillium sp. (ZH16)

A new furanocoumarin, 5-methyl-8-(3-methylbut-2-enyl) furanocoumarin (1), together with seven known compounds, sterequinone C (2), cyclo(6,7-en-Pro-L-Phe) (3), bergapten, scopoletin, umbelliferone, 1,7-dihydroxyxanthone and 3,5-dimethoxybiphenyl, was isolated from the mangrove endophytic fungus, Penicillium sp. ZH16 obtained from the South China Sea. Their structures were determined by analysis of spectroscopic data. Compound 1 exhibited cytotoxicity against KB and KB(V)200 cells in?vitro with IC(50) values 5 and 10?μg?mL(-1), respectively.     

Two new paeciloxocins from a mangrove endophytic fungus Paecilomyces sp.

Paeciloxocins A and B (2-(1-hydroxy-3-methylbutyl)- and 2-(1-acetoxy-3-methylbutyl)- 11-hydroxy-9-methyl-1-methoxy-5H,7H-dibenzo[b,g]-1,5-dioxocin-5-ones), viz., two new metabolites, were isolated from the mangrove fungus Paecilomyces sp. collected from the Taiwan Strait. Their structures were elucidated by spectral methods. Paeciloxocin A exhibited strong cytotoxicity against the hepG2 cell line.     

南海红树林内生真菌No．ZZF71代谢产物研究

由于海洋环境的特殊性和微生物在生态系统的功能,海洋微生物已经发展出独特的代谢方式,提供了在陆地微生物中未遇到过的代谢产物。研究海洋微生物的活性物质,不但能发现结构新颖的化合物,丰富和发展有机化学理论,而且为寻找新的强效活性药物及其它有用物质提供了一个重要途径[1     

Lasiodiplodins from mangrove endophytic fungus Lasiodiplodia sp. 318#

Four new lasiodiplodins (1–4), together with three known analogues, have been isolated from a mangrove endophytic fungus, Lasiodiplodia sp. 318#. Their structures were elucidated by spectroscopic techniques. Cytotoxic activities of compounds 1–7 were evaluated in vitro against human cancer lines THP1, MDA-MB-435, A549, HepG2 and HCT-116. Compound 4 exhibited moderate cytotoxic activities.     

Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508

(3R*,3aR*,9aR*)-3,9a-Dimethyl-2,3,3a,9a-tetrahydro-4H-furo[2,3-b]chromene-5,7-diol (xyloketal H), a representative of a new family of xyloketals, was isolated from the marine-derived mangrove fungus Xylaria sp. 2508. Its structure was elucidated by spectroscopic data and single-crystal X-ray diffraction analysis. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1051–1052, June, 2006.     

红树林植物角果木内生真菌次级代谢产物的分离鉴定

研究红树林植物角果木根部内生真菌Fusarium sp.JG13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萃取相中分离获得4个单体化合物,以及一对顺反异构体。运用现代波谱技术以及文献数据对照,鉴定其结构分别为physcion(1)、trans physcion bianthrone(2)、cis physcion bianthrone(3)、asperflavin(4)、neoechinulin A(5)和isodihydroauroglaucin(6)。所有化合物均为首次从角果木根内生真菌Fusarium sp.JG13发酵分离得到。     

Adsorption of thorium(IV) from aqueous solution by non-living biomass of mangrove endophytic fungus Fusarium sp. #ZZF51

The adsorption of thorium(IV) from aqueous solution by mangrove endophytic fungus Fusarium sp. #ZZF51 is studied by using a batch experiments. The parameters that affect the thorium(IV) sorption, such as solution pH, initial thorium(IV) concentration, contact time, and biomass dose, are discussed in detail. The maximum biosorption of thorium(IV) and the equilibrium sorption capacity are found to be 91 ± 1 % and 11.35 mg g^?1 respectively at pH 3.0, contact time 20 min, initial thorium(IV) concentration 50 mg L^?1 and non-living biomass dose 4.0 g L^?1. Kinetics data follow the pseudo-second-order model and equilibrium data agree with the Temkin isotherm model very well. FT-IR analysis indicates that hydroxyl and carbonyl groups play an important role in the biosorption process.     

A new antimicrobial sesquiterpene isolated from endophytic fungus Cytospora sp. from the Chinese mangrove plant Ceriops tagal

Abstract

Chemical examination of Chinese mangrove Ceriops tagal endophytic Cytospora sp., yielded a new biscyclic sesquiterpene seiricardine D (1), and eight known metabolites, xylariterpenoid A (2a), xylariterpenoid B (2b) and regiolone (3) 4-hydroxyphenethyl alcohol (4), (22E, 24R)5, 8-epidioxy-5α, 8α-ergosta-6,22E-dien-3ß-ol (5), (22E, 24R)5, 8-epidioxy-5α, 8α-ergosta-6,9(11), 22-trien-3 ß-ol (6), ß-sitosterol (7) and stigmast-4-en-3-one (8). These structures were unambiguously elucidated on the basis of extensive NMR spectroscopic and mass spectrometric analyses. The antimicrobial activities of compounds 1–8 and their effects on a panel of plant and human pathogens were evaluated.     

1H and 13C NMR assignments of two new diaryl ethers phomopsides A and B from the mangrove endophytic fungus (ZZF08)

Two new diaryl ethers, named phomopside A (1) and B (2), together with known excelsione (3) were isolated from the mangrove endophytic fungus Phomopsis sp. (ZZF08) obtained from the South China Sea coast. The structure of 1 was elucidated by NMR spectroscopy and confirmed by X-ray crystallography. Compounds 2 and 3 were identified by NMR spectroscopy and comparing the spectroscopic data with literature values. In addition, the plausible biogenetic path of 1, 2 and 3 is discussed.     

Enhancement of uranium(VI) biosorption by chemically modified marine-derived mangrove endophytic fungus Fusarium sp. #ZZF51

Fusarium sp. #ZZF51, mangrove endophytic fungus originated from South China Sea coast, was chemically modified by formaldehyde, methanol and acetic acid to enhance its affinity of uranium(VI) from waste water. The influencing factors about uranium(VI) adsorption such as contact time, solution pH, the ratio of solid/liquid (S/L) and initial uranium(VI) concentration were investigated, and the suitable adsorption isotherm and kinetic models were determined. In addition, the biosorption mechanism was also discussed by FTIR analysis. Experimental results show that the maximum biosorption capacity of formaldehyde-treated biomass for uranium(VI) at the optimized condition of pH 6.0, S/L 0.6 and equilibrium time 90 min is 318.04 mg g^?1, and those of methanol-treated and HAc-treated biomass are 311.95 and 351.67 mg g^?1 at the same pH and S/L values but different equilibrium time of 60 and 90 min, respectively. Thus the maximum biosorption capacity of the three kind of modified biomass have greatly surpassed that of the raw biomass (21.42 mg g^?1). The study of kinetic exhibits a high level of compliance with the Lagergren’s pseudo-second-order kinetic models. Langumir and Freundlich models have proved to be well able to explain the sorption equilibrium with the satisfactory correlation coefficients higher than 0.96. FTIR analysis reveals that the carboxyl, amino and hydroxyl groups on the cell wall of Fusarium sp. #ZZF51 play an important role in uranium(VI) biosorption process.     

Two new tremulane sesquiterpenes from a mangrove endophytic fungus,Coriolopsis sp. J5

Two new tremulane sesquiterpenes coriolopsin A (1) and coriolopsin B (2), together with two known ones conocenol C (3) and ceriponol E (4), were isolated from the fermentation extract of endophytic fungus Coriolopsis sp. J5 from Ceriops tagal. The structures and absolute configuration of compounds 1 and 2 were determined based on HR-ESI-MS and spectroscopic data (IR, UV, 1D, 2D NMR and X-ray crystallographic analysis).     

A new sesquiterpene from endophytic fungus Aspergillus sp

A fungal strain named YLF-14 was isolated from the leaf of Altingia yunnunensis. Based on the sequence at the internal transcribed spacer (ITS) region, the strain was identified as an Aspergillus sp.. A new sesquiterpene 5β,8aβ-dimethyl-3,4,4aβ,5,6,7,8,8a-octahydronaphthalene-1,2,5α-trimethanol (1) and a known compound 12-N-methylcyclo-(L-tryptophyl-L-phenylalanyl) (2) were isolated from the culture of this strain. Bioassay experiments showed that the two compounds had no obvious effect on the growth of tested bacteria and nematodes.     

1H and 13C NMR assignments of three nitrogen containing compounds from the mangrove endophytic fungus (ZZF08)

A new natural product, named phomopsin A, 1-(meta-hydroxyphenyl)-4-hydroxy-3-isoquinolone (1), together with two known compounds cytochalasin H (2) and glucosylceramide (3), was isolated from the mangrove endophytic fungus Phomopsis sp. (ZZF08) obtained from the South China Sea coast. The structures were elucidated by 1D and 2D NMR experiments including COSY, HMQC, and HMBC. According to NMR and single-crystal X-ray diffraction, it was found that some assignments about (1)H and (13)C NMR data for cytochalasin H (2) were probably uncorrected in the previous reports. In our cytotoxicity assays, compound 1 showed moderate cytotoxicity toward KB cells with IC(50) at 28.0 microg ml(-1) and KBv200 cells with IC(50) at 16.8 microg ml(-1), and compound 2 exhibited strong cytotoxicity toward KB cells and KBv200 cells with IC(50) less than 1.25 microg ml(-1).     

A new xanthone derivative from mangrove endophytic fungus No. ZSU-H16

A new xanthone derivative, 3,5,8-trihydroxy-2,2-dimethyl-3,4,4-trihydro-2H,6H-pyrano[3,2-b]-xanthen-6one (1), together with three known compounds, 5,8-dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen6-one (2), cyclo-(N-O-methyl-L-Trp-L-Ile-D-Pip-L-2-amino-8-oxo-decanoyl) (3), and cyclo-(Phe-Tyr) (4), was isolated from the mangrove endophytic fungus No. ZSU-H16 obtained from the South China Sea coast. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopic techniques. Compound 1 exhibited cytotoxicity against KB and KB_V 200 cells with IC₅₀ values greater than 50 μg/mL, respectively.     

Two new diterpenoids from the endophytic fungus Trichoderma sp. Xy24 isolated from mangrove plant Xylocarpus granatum

Two new harziane diterpenoids, named(9R,10R)-dihydro-harzianone(1) and harzianelactone(2), were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their structures were determined on the basis of extensive spectroscopic(HR-ESI-MS, 1D NMR, 2D NMR and CD) analyses. Among them, 1 was the reductive product of harzianone and 2 was the Baeyer–Villiger monooxygenase catalyzed oxidation product of harzianone. Compound 1 exhibited cytotoxic activity against He La and MCF-7 cell lines with IC_(50) values of 30.1 μmol/L and 30.7 μmol/L,respectively.     

Pestalotiopisorin B,a new isocoumarin derivative from the mangrove endophytic fungus Pestalotiopsis sp. HHL101

Abstract

A new isocoumarin derivative pestalotiopisorin B (1), along with six known compounds, (R)-(-)- mellein methyl ether (2), pestalotiopyrone G (3), (R)-mevalonolactone (4), pestalotiollides A–B (5–6) and pestalotiopsol A(7) were isolated from Pestalotiopsis sp., an endophytic fungus obtained from Chinese mangrove plant Rhizophora stylosa. Their structures were elucidated unambiguously by the comprehensive analysis of extensive spectroscopic data. Compound 1 exhibited modest antibacterial activity against Escherichia coli and Pseudomonas aeruginosa with 12.5?μg/ml, 50?μg/ml, respectively. Compound 4 showed moderate calcineurin inhibitory activity towards p-nitrophenyl phosphate (IC₅₀ =134.29?±?5.377?μM).