Bioactive cyclohexene derivatives from a mangrove-derived fungus Cladosporium sp. JJM22

Bin Zhang; Jia-Ting Wu; Cai-Juan Zheng; Xue-Ming Zhou; Zhang-Xin Yu; Wan-Shan Li; Guang-Ying Chen; Guo-Yuan Zhu

doi:10.1016/j.fitote.2020.104823

Bioactive cyclohexene derivatives from a mangrove-derived fungus Cladosporium sp. JJM22

Fitoterapia. 2021 Mar:149:104823. doi: 10.1016/j.fitote.2020.104823. Epub 2020 Dec 30.

Authors

Bin Zhang¹, Jia-Ting Wu², Cai-Juan Zheng¹, Xue-Ming Zhou¹, Zhang-Xin Yu¹, Wan-Shan Li¹, Guang-Ying Chen³, Guo-Yuan Zhu⁴

Affiliations

¹ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China; Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China.
² Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China; Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China; Department of Chemistry, Guangdong University of Education, Guangzhou 510800, China.
³ Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, China; Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China. Electronic address: chgying123@163.com.
⁴ State Key Laboratory of Quality Study of Traditional Chinese Medicine, Macau University of Science and Technology, China.

PMID: 33387642
DOI: 10.1016/j.fitote.2020.104823

Abstract

Four new cyclohexene derivatives cladoscyclitols A-D (1-4) and one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol (5) were obtained from the EtOAC extract of the mangrove-derived endophytic fungus Cladosporium sp. JJM22. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or comparison of the optical rotations with those of related compounds. Compounds 2 and 5 displayed potent inhibitory activity against α-glucosidase with the IC₅₀ values of 2.95 and 2.05 μM, respectively.

Keywords: Ceriops tagal; Cladosporium sp.; Cyclohexene derivatives; Ribofuranose phenol.

MeSH terms

China
Cladosporium / chemistry*
Cyclohexenes / isolation & purification
Cyclohexenes / pharmacology*
Endophytes / chemistry
Glycoside Hydrolase Inhibitors / isolation & purification
Glycoside Hydrolase Inhibitors / pharmacology*
Microbial Sensitivity Tests
Molecular Structure
Rhizophoraceae / microbiology*

Substances

Cyclohexenes
Glycoside Hydrolase Inhibitors