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1.
Bioorg Chem ; 91: 103167, 2019 10.
Artigo em Inglês | MEDLINE | ID: mdl-31398599

RESUMO

Three new alkaloids, iizukines C-E (1-3), including two aspochalasins (1 and 2), and one brasiliamide derivative (3), along with two known aspochalasins, rosellichalasin (4) and cytochalasin Z17 (5), were isolated from the culture of Aspergillus iizukae. Compound 1 was the first aspochalasin uniquely featuring a 1,2,4-triazole functionality, and 3 showed a pair of NMR signals in CDCl3 with a ratio of about 2:1 due to the existence of conformational isomers. Their structures were determined by extensive spectroscopic analyses and single-crystal X-ray diffractions. In particular, the 1,2,4-triazole moiety in 1 was assigned on the basis of extremely valuable 1H-15N HMBC spectrum. Compound 1 exhibited cytotoxic effect towards HL-60 and A549 cell lines with IC50 values of 3.8 and 7.2 µM, respectively.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Aspergillus/química , Proliferação de Células , Citocalasinas/química , Neoplasias/tratamento farmacológico , Solo/química , Alcaloides/química , Antineoplásicos/química , Humanos , Estrutura Molecular , Neoplasias/patologia , Células Tumorais Cultivadas
2.
Mar Drugs ; 16(6)2018 Jun 18.
Artigo em Inglês | MEDLINE | ID: mdl-29912165

RESUMO

Three new diastereomers of polyketides (PKs), raistrickiones A−C (1⁻3), together with two new analogues, raistrickiones D and E (4 and 5), were isolated from a highly productive strain of Penicillium raistrickii, which was subjected to an experimental thermo-change strategy to tap its potential of producing new secondary metabolites. Metabolites 1 and 2 existed in a diastereomeric mixture in the crystal packing according to the X-ray data, and were laboriously separated by semi-preparative HPLC on a chiral column. The structures of 1⁻5 were determined on the basis of the detailed analyses of the spectroscopic data (UV, IR, HRESIMS, 1D, and 2D NMR), single-crystal X-ray diffractions, and comparison of the experimental and calculated electronic circular dichroism spectra. Compounds 1⁻5 represented the first case of 3,5-dihydroxy-4-methylbenzoyl derivatives of natural products. Compounds 1⁻5 exhibited moderate radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH).


Assuntos
Compostos de Bifenilo/química , Sequestradores de Radicais Livres/química , Penicillium/metabolismo , Picratos/química , Policetídeos/química , Cromatografia Líquida de Alta Pressão , Dicroísmo Circular , Cristalografia por Raios X , Sequestradores de Radicais Livres/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Policetídeos/isolamento & purificação , Estereoisomerismo , Temperatura
3.
Yao Xue Xue Bao ; 38(11): 834-7, 2003 Nov.
Artigo em Chinês | MEDLINE | ID: mdl-14991996

RESUMO

AIM: To study the chemical constituents in the mycelia of Hypomyces sp.. METHODS: Silica gel column chromatography was employed for the isolation and purification. Chemical and spectral methods were used to determine the structures of the isolated compounds. RESULTS: Two compounds were isolated and identified as: hypomycin C (I) and hypomycin D (II). CONCLUSION: Compounds I and II are new compounds.


Assuntos
Hypocreales/química , Perileno/isolamento & purificação , Quinonas/isolamento & purificação , Cromatografia em Gel/métodos , Fermentação , Conformação Molecular , Estrutura Molecular , Micélio/química , Perileno/análogos & derivados , Perileno/química , Quinonas/química
4.
Zhongguo Zhong Yao Za Zhi ; 27(9): 674-6, 2002 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-12776569

RESUMO

OBJECTIVE: To study the chemical constituents of Shiraia bambusicola. METHOD: Column chromatography with silica gel was employed for the isolation and purification of constituents. The structures were elucidated by means of chemical and spectroscopic data. RESULT: Seven compounds were obtained and identified as hypocrellin A (I), hypocrellin B (II), hypocrellin C (III), hypomycin A (IV), ergosterol (V), ergosterol peroxide (VI) and 1,8-dihydroxy anthraquinone (VII). CONCLUSION: Compounds (IV) (VII) were separated from Shiraia bambusicola for the first time.


Assuntos
Antraquinonas/isolamento & purificação , Ergosterol/análogos & derivados , Ergosterol/isolamento & purificação , Hypocreales/química , Antraquinonas/química , Ergosterol/química
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