The 2,3-epoxy naphthoquinol produced by endophyte Arthrinium marii M-211

A novel 2,3-epoxy naphthoquinol, named (6R,7R,8R)-theissenone A (1), possessing an oxatricyclo[5.4.0.0 3,5 ]undeca-trien-2-one skeleton, together with two known compounds, (6S,7R,8R)-theissenone (2) and arthrinone (3), were produced by an endophytic fungus, Arthrinium marii M-211, which was isolated...

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Bibliographic Details
Published in:Natural product research 2023-04, Vol.37 (7), p.1060-1066
Main Authors: Sofian, Ferry Ferdiansyah, Suzuki, Takuma, Supratman, Unang, Harneti, Desi, Maharani, Rani, Salam, Supriatno, Abdullah, Fajar Fauzi, Yoshida, Jun, Ito, Yoshiaki, Koseki, Takuya, Shiono, Yoshihito
Format: Article
Language:English
Subjects:
Arthrinium
Ascomycota - chemistry
Circular Dichroism
Cytotoxicity
Data analysis
Density functional theory
Dichroism
Endophytes
Endophytes - chemistry
H4IIE hepatoma cell line
Hepatoma
Magnetic Resonance Spectroscopy - methods
Mass Spectrometry
Mass spectroscopy
Molecular Structure
NMR
Nuclear magnetic resonance
OSMAC
Stereochemistry
Theissenone A
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Summary:A novel 2,3-epoxy naphthoquinol, named (6R,7R,8R)-theissenone A (1), possessing an oxatricyclo[5.4.0.0 3,5 ]undeca-trien-2-one skeleton, together with two known compounds, (6S,7R,8R)-theissenone (2) and arthrinone (3), were produced by an endophytic fungus, Arthrinium marii M-211, which was isolated from mangrove plants. The structure of 1, including the absolute stereochemistry, was elucidated by analysis of nuclear magnetic resonance (NMR) and mass spectrometry (MS) data and time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) spectra. Additionally, the absolute structure of 2 was deduced as a diastereomer of 1 using ECD spectral data analysis. Compounds 1, 2 and 3 exhibited cytotoxic activity against the H4IIE rat hepatoma cells, with IC 50 values of 67.5, 46.6 and 13.4 µM, respectively.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2021.1998899