Steroids and dihydroisocoumarin glycosides from Xylaria sp. by the one strain many compounds strategy and their bioactivities.
10.1016/S1875-5364(23)60394-2
- Author:
Dong GAN
1
;
Chenzhe LI
1
;
Yan SHU
1
;
Jiapeng WANG
1
;
Chengyao WANG
1
;
Li ZHU
1
;
Yujun YANG
1
;
Jiaqi LIU
1
;
Bijian HE
1
;
Le CAI
2
;
Zhongtao DING
3
,
4
Author Information
1. Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
2. Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China. Electronic address: caile@ynu.edu.cn.
3. Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
4. College of Pharmacy, Dali University, Dali 671003, China. Electronic address: ztding@ynu.edu.cn.
- Publication Type:Journal Article
- Keywords:
Bioactivity;
OSMAC strategy;
Secondary metabolite;
Xylaria sp.
- MeSH:
Humans;
Acetylcholinesterase;
Molecular Docking Simulation;
Anti-Bacterial Agents;
Glycosides;
Lactones;
Pain
- From:
Chinese Journal of Natural Medicines (English Ed.)
2023;21(2):154-160
- CountryChina
- Language:English
-
Abstract:
The fungus Xylaria sp. KYJ-15 was isolated from Illigera celebica. Based on the one strain many compounds (OSMAC) strategy, the strain was fermented on potato and rice solid media, respectively. As a result, two novel steroids, xylarsteroids A (1) and B (2), which are the first examples of C28-steroid with an unusual β- and γ-lactone ring, respectively, along with two new dihydroisocoumarin glycosides, xylarglycosides A (3) and B (4), were identified. Their structures were elucidated by spectroscopic methods, X-ray diffraction and electronic circular dichroism (ECD) experiments. All isolated compounds were evaluated for cytotoxicity, DPPH radical scavenging activity, acetylcholinesterase inhibitory and antimicrobial effect. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 2.61 ± 0.05 μmol·L-1. The β-lactone ring unit of 1 is critical for its AChE inhibitory activity. The finding was further confirmed through exploring the interaction of 1 with AChE by molecular docking. In addition, both compounds 1 and 2 exhibited obvious antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) of 2 μg·mL-1. Compounds 3 and 4 exhibited antibacterial activities against Staphylococcus aureus with MICs of 4 and 2 μg·mL-1, respectively, which also exhibited DPPH radical scavenging activity comparable to the positive control with IC50 values of 9.2 ± 0.03 and 13.3 ± 0.01 μmol·L-1, respectively.
