Alterporriol-type dimers from the mangrove endophytic fungus, Alternaria sp. (SK11), and their MptpB inhibitions.
A new alterporriol-type anthranoid dimer, alterporriol S (1), along with seven known anthraquinone derivatives, (+)-aS-alterporriol C (2), hydroxybostrycin (3), halorosellinia A (4), tetrahydrobostrycin (5), 9α-hydroxydihydrodesoxybostrycin (6), austrocortinin (7) and 6-methylquinizarin (8), were isolated from the culture broth of the mangrove fungus, Alternaria sp. (SK11), from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR spectra. The absolute configurations of 1 and the axial configuration of 2 were defined by experimental and theoretical ECD spectroscopy. 1 was identified as the first member of alterporriols consisting of a unique C-10-C-2' linkage. Atropisomer 2 exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with an IC₅₀ value 8.70 μM.
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. xiagp@mail2.sysu.edu.cn.
Guoping
G
Xia
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. nuekagami@163.com.
Jia
J
Li
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. lihx3@mail.sysu.edu.cn.
Hanxiang
H
Li
School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China. longyh@scnu.edu.cn.
Yuhua
Y
Long
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. linshaoe@mail2.sysu.edu.cn.
Shao'e
S
Lin
School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, China. luyj@mail.sysu.edu.cn.
Yongjun
Y
Lu
School of Life Sciences, Sun Yat-Sen University, Guangzhou 510275, China. helei8688@126.com.
Lei
L
He
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. ceslyc@mail.sysu.edu.cn.
Yongcheng
Y
Lin
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. cesllan@mail.sysu.edu.cn.
Lan
L
Liu
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China. cesshzhg@mail.sysu.edu.cn.
Zhigang
Z
She
D000528:Alternaria / Q000737:chemistry*; D000880:Anthraquinones / Q000737:chemistry* / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000737:chemistry* / Q000494:pharmacology*; D032407:Avicennia / Q000382:microbiology*; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors*; D005285:Fermentation; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D017027:Protein Tyrosine Phosphatases / Q000037:antagonists & inhibitors*
D000880:Anthraquinones; D000995:Antitubercular Agents; D001426:Bacterial Proteins; C414465:MptpA protein, Mycobacterium tuberculosis; D017027:Protein Tyrosine Phosphatases