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1. (Article ID: 9581)
Xu H, Wang L, Zhang L, Liu W, Zhang Q, Zhang H, Zhang C, Zhang W
Configurational Assignment of Malfilamentoside A and a New Furanone Glycoside Malfilamentoside D
Chinese Journal of Organic Chemistry 42(4) (2022)
1229-1234
High performance liquid chromatography-diode array detection (HPLC-DAD)-based chemical analysis of the extract fraction library of the plateau soil-derived fungus Auxarthron umbrinum SCSIO 40432 led to the identification of eight compounds, including a known aromatic furanone glycoside malfilamentoside A (1) whose stereochemistry remained unsolved, and a new malfilamentoside D (2), together with six known compounds (3~8). The planar structures of malfilamentaosides A (1) and D (2) were elucidated by HRESIMS, 1D and 2D NMR spectroscopic analysis. The absolute configuration of malfilamentoside A (1) was unambiguously resolved for the first time by a single crystal X-ray diffraction analysis and the stereochemistry of malfilamentoside D (2) was determined by comparing electronic circular dichroism (ECD) spectra of 1 and 2. Malfilamentoside A (1) exhibited inhibitory activity to xanthine oxidase at the concentration of 20 μmol/L
aromatic furanone glycoside, Auxarthron umbrinum SCSIO 40432, configurational assignment, malfilamentoside
Publication DOI: 10.6023/cjoc202110038Publisher: Beijing: Science China Press
Correspondence: W. Zhang
scsio.ac.cn>
Institutions: Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, University of Chinese Academy of Sciences, Beijing 100049, Sanya Institute of Oceanology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Sanya, Hainan, 572000
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, FTIR, HPLC, UV, extraction, optical rotation measurement, CC, fermentation, HR-ESI-MS, antibacterial assay
The publication contains the following compound(s):
- Compound ID: 23376
|
a-D-GlcpNAc6Me-(1-5)-Subst
Subst = malfilamentoside A aglycon = SMILES O=C1O{5}C(C(CC2=CC=CC=C2)=C1C3=CC=CC=C3)O |
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Structure type: monomer
; 484.1966 [M＋H]＋
C26H30NO8
Trivial name: malfilamentoside A (aromatic furanone glycoside)
- Compound ID: 23377
|
a-D-GlcpNAc-(1-5)-Subst
Subst = malfilamentoside A aglycon = SMILES O=C1O{5}C(C(CC2=CC=CC=C2)=C1C3=CC=CC=C3)O |
Show graphically |
Structure type: monomer
; 470.1809 [M＋H]＋
C25H28NO8
Trivial name: malfilamentoside D (aromatic furanone glycoside)
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