Seven polyketides, including an undescribed depsidone () and six previously reported 3,6,8-trihydroxy-1-methylxanthone (), 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (), methyl3-chloro-6-hydroxy-2-(4-hy-droxy-2-methoxy-6-methylphenoxy)-4- methoxybenzoate (), xylarianin A (), 4,5-dihydroxy-6-(6'-methylsalicyloxy)-2-hydro-xymethyl-2-cyclohexen-1-one () and alternariol (), have been isolated from cultures of the mangrove-derived fungus HNNU0006. The structure of compound was elucidated by extensive spectroscopic analysis and X-ray crystallography. Furthermore, all the compounds were evaluated their cytotoxic activities, and compounds and showed weak cytotoxicity against two cell lines Vero and A549 with IC values ranging from 95.
View Article and Find Full Text PDFNine metabolites, including three undescribed alkaloids pyripyropenes VW (1-2), penicioxa A (4), two previously reported pyripyropene A (3), oxaline (5), three grisephenone-type xanthone derivatives (6-8), and a diphenyl ether derivative 4-chloro-7,4'-dihydroxy-5,2'-dimethoxy-2-methylformate-6'-methybenzophone (9), were isolated from cultures of the mangrove-derived fungus Penicillium robsamsonii HNNU0006. Their structures were determined by spectroscopic analysis, ECD calculations, together with DP4+ probability analysis. Furthermore, all the isolated compounds were tested for cytotoxicity and anti-phytopathogenic fungal activities.
View Article and Find Full Text PDFChemical investigation of a culture broth from the marine-derived fungus HNNU0524 yielded two new compounds including a drimane-type sesquiterpenoid named pyrrnoxin A () and a benzoic acid derivative, pyrrnoxin B (), together with three related known analogues (-). The chemical structures of and were determined by detailed analysis of spectroscopic data, single-crystal X-ray crystallography, quantum mechanics-based DP4+ and ECD calculations. Compounds and moderately inhibited NO production of lipopolysaccharide-induced microglia cells BV2 with IC values of 26.
View Article and Find Full Text PDFFour undescribed polyhydroxy cyclohexanes, fissoxhydrylenes A-D (1-4), together with two known biogenetically related polyhydroxy cyclohexanes (5 and 6) were isolated from the stems of Fissistigma tientangense Tsiang et P. T. Li.
View Article and Find Full Text PDFFour prenylated indole alkaloids (-) were targeted isolated from the mangrove rhizosphere soil-derived fungus HK1-6 by using molecular networking strategies. Among them, the planar structure and relative configuration of notoamide X () were elucidated by detailed analysis of the spectroscopic data especially the NOESY spectrum for the first time and its absolute configuration was determined by ECD spectrum. Furthermore, curated molecular networks of MS/MS data were generated with GNPS which allowed highlighting six prenylated indole alkaloids (, , , , , ) that had not previously been identified in this fungus and two (, ) that had never been observed in any fungus.
View Article and Find Full Text PDFA series of secondary metabolites have been isolated from the genus of , most of which show antibacterial and insecticidal activities. In order to find more bioactive secondary metabolites from , one new natural component aminoindole dimer baciindole A (), together with seven known compounds () were isolated from the tomato-derived bacterium Hnu24. The structure of compound was elucidated by its HR-ESI-MS spectral data and 1 D/2D NMR spectroscopic analysis.
View Article and Find Full Text PDFOne new epimer pair of long-chain polyenes penicilqueis E () and F (), and one new long-chain polyene pinophol G (), along with one known compound (), were obtained from EtOAc extract of the mangrove-derived fungus JX4. Their structures were elucidated by detailed analysis of comprehensive spectroscopic data. The inhibitory activities of all compounds against the nitric oxide (NO) production induced by lipopolysaccharide in mouse macrophage RAW 264.
View Article and Find Full Text PDFSix new isocoumarin derivative talaromarins A-F (-), along with 17 known analogues (-), were isolated from the mangrove-derived fungus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and HR-ESI-MS spectra. The absolute configurations of new compounds were determined by the modified Mosher's method and a comparison of their CD spectra with dihydroisocoumarins described in the literature.
View Article and Find Full Text PDFOxalierpenes A and B ( and ), two unusual indole-diterpenoid derivatives, were obtained from the marine-derived fungus . The absolute configurations of and were elucidated by calculated TDDFT ECD and DP4plus methods. Oxalierpene A () represents the first indole-diterpenoid derivative with a five-membered ring of 4-hydroxy-5,5-dimethyldihydrofuran-3-one as a side chain.
View Article and Find Full Text PDFTo enhance the biological activity of the natural product geodin (), isolated from the marine-derived fungus sp., a series of new ether derivatives (-) was designed and semisynthesized using a high-yielding one-step reaction. In addition, the insecticidal and antibacterial activities of all geodin congeners were evaluated systematically.
View Article and Find Full Text PDFFour rare isotachin-derived, isotachins E-H (1-4), together with two known biogenetically related isotachin derivatives (5 and 6) were isolated from the solid rice fermentation of a fungus Penicillium tanzanicum ZY-5 obtained from a medicinal plant Dasymaschalon rostratum collected from the Changjiang County, Hainan Province, China. Their structures were elucidated using comprehensive spectroscopic methods. The single-crystal X-ray diffraction of compound 5 was determined.
View Article and Find Full Text PDFTwo novel aporphine-derived alkaloids, aporaloids A and B (1 and 2), together with eight known biogenetically related alkaloids (3-10), two known isoquinoline alkaloids (3 and 4), and six known aporphinoid alkaloids (5-10) were isolated from the stems of Fissistigma glaucescens. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 1 and 2 represent the rare example of a six-membered lactone ring aporphine-derived alkaloids from natural products.
View Article and Find Full Text PDFJ Asian Nat Prod Res
July 2022
A new isocoumarin, penicimarin N (), along with five known compounds (), were isolated from the mangrove-derived fungus sp. TGM112. The structure of was elucidated on the basis of extensive spectroscopic data analysis, and the absolute configuration of was determined by comparison of their circular dichroism (CD) spectra with the literature.
View Article and Find Full Text PDFThree unusual austins-type meroterpenoids penicianstinoids C-E (-) were obtained from the mangrove-derived fungus sp. TGM112. The structures of - including absolute configurations were determined by detailed NMR, MS spectroscopic data, X-ray diffraction analysis, and calculated electronic circular dichroism data.
View Article and Find Full Text PDFTwo new isocoumarins penicimarins L-M (), along with seven known analogues () were isolated from the mangrove-derived fungus sp. MGP11. Compounds - were established by spectroscopic methods and comparison of their circular dichroism (CD) spectra with the literature.
View Article and Find Full Text PDFFour new cyclohexene derivatives cladoscyclitols A-D (1-4) and one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol (5) were obtained from the EtOAC extract of the mangrove-derived endophytic fungus Cladosporium sp. JJM22. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or comparison of the optical rotations with those of related compounds.
View Article and Find Full Text PDFOne new piperazinedione derivative, nigerpiperazine A (), along with six known compounds () were isolated from the fungus JX-5 from mangrove . Nigerpiperazine A () was elucidated by spectroscopic analyses and C NMR chemical shift calculations, compounds and were determined by X-ray and the CD spectra. The absolute configuration of was identified by X-ray for the first time.
View Article and Find Full Text PDFFungi have been proved as promising and prolific sources of functional secondary metabolites with potent agricultural applications. In this study, 14 xanthone derivatives (-), including six new ones, versicones I-N (, , ), and a biogenetically related derivative (), were isolated from the alga-derived fungus D5. Their structures were elucidated by comprehensive spectroscopic methods.
View Article and Find Full Text PDFA new polyketide derivative, nafuredin C (), a novel heterocyclic dipeptide, trichodermamide G (), together with four known biogenetically related compounds nafuredin A (), trichodermamide A (), aspergillazin A (), and peniisocoumarin H (), were isolated from the mangrove-derived fungus D13. Their structures, including their absolute configurations, were determined by spectroscopic analysis and time-dependent density functional theory-electronic circular dichroism (ECD) calculations. Trichodermamide G was found to be a novel epithiodiketopiperazine derivative with an unprecedented cyclic system containing a sulfur bridge, and nafuredin C represented the third nafuredin derivative of these homologous compounds.
View Article and Find Full Text PDFA new phenol derivative, 3-chloro-5-hydroxy-4-methoxyphenylacetic acid methyl ester (), along with five known compounds methyl 4-hydroxyphenylacetate (), cytosporone B (), ()-striatisporolide A (), ()-butanedioic acid () and ergosterol () were isolated from the mangrove-derived fungus sp. HJ002. Their structures were established by spectroscopic methods, GIAO based C NMR chemical shift calculations and comparison with the data of literature.
View Article and Find Full Text PDFThree new methylated Δ-pregnene steroids, stemphylisteroids A-C (1-3) were isolated from the medicinal plant Polyalthia laui-derived fungus Stemphylium sp. AZGP4-2. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data.
View Article and Find Full Text PDFFour previously unreported chromones, 5-hydroxy-2-(hydroxymethyl)-8-methoxy-4H-chromen-4-one (1), (5R,7S)-5,7-dihydroxy-2-propyl-5,6,7,8-tetrahydro-4H-chromen-4-one (2), (5R,7S)-5,7-dihydroxy-2-methyl-5,6,7,8-tetrahydro-4H-chromen-4-one (3), and (5R,7S)-5,7-dihydroxy-2-[(E)-prop-1-en-1-yl]-5,6,7,8-tetrahydro-4H-chromen-4-one (4), as well as one known analogue 5-hydroxy-2-methyl-4H-chromen-4-one (5) were isolated from the fermentation broth of the endophytic fungus Colletotrichum gloeosporioides derived from the mangrove Ceriops tagal. Their structures were elucidated based on extensive spectroscopic analyses. The absolute configurations of 2-4 were determined by comparison the experimental and calculated electronic circular dichroism (ECD) spectra.
View Article and Find Full Text PDFTwo new polyketides, 8--methylnodulisporin F () and nodulisporin H (), two new naphthoquinones, 5-hydroxy-2-methoxy-6,7-dimethyl-1,4-naphthoquinone () and 5-hydroxy-2-methoxynaphtho[9-]furan-1,4-dione (), and a new naphthofuran 1,3,8-trimethoxynaphtho[9-]furan (), along with five known compounds 4--methyl eleutherol (), 2-acetyl-7-methoxybenzofuran (), (-)-orthosporin (), diaporthin (), and 6-hydroxymellein (), were obtained from the EtOAc extract of the mangrove-derived fungus HJ004. The structures of the isolated compounds were elucidated by extensive NMR and MS analyses, while the absolute configurations of the stereogenic carbons were established based on experimental and calculated electronic circular dichroism spectra. Compounds and displayed a potent inhibitory activity against -glucosidase with the IC values of 5.
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