The biologically and ecologically important natural products from the Chinese sea hare Bursatella leachii:structures,stereochemistry and beyond
10.1016/S1875-5364(24)60611-4
- Author:
Xinyuan ZHANG
1
;
Mingzhi SU
;
Mingxin ZHU
;
Sha CHEN
;
Zhen GAO
;
Yuewei GUO
;
Xuwen LI
Author Information
1. School of Chinese Materia Medica,Nanjing University of Chinese Medicine,Nanjing 210023,China;State Key Laboratory of Chemical Biology,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China;Shandong Laboratory of Yantai Drug Discovery,Bohai Rim Advanced Research Institute for Drug Discovery,Yantai 264117,China
- Keywords:
Bursatella leachii;
Marine natural product;
Alkaloid;
Sea hare;
Antibacterial activity
- From:
Chinese Journal of Natural Medicines (English Ed.)
2024;22(11):1030-1039
- CountryChina
- Language:Chinese
-
Abstract:
A novel amide alkaloid,bursatamide A(1),featuring an unprecedented propyl-hexahydronaphthalene carbon frame-work,was isolated from the infrequently studied sea hare Bursatella leachi,alongside a new 3-phenoxypropanenitrile alkaloid,bursatellin B(2),and twelve known compounds.The structures of 1 and 2 were elucidated through comprehensive spectroscopic data analyses,while their relative and absolute configurations(ACs)were established through total synthesis and a series of quantum chem-ical calculations,including calculated electronic circular dichroism(ECD)spectra,optical rotatory dispersion(ORD)methods,and DP4+probability analyses.Bursatamide A(1)demonstrated inhibitory effects against the human pathogenic bacteria Listeria monocyt-ogenes and Vibrio cholerae.Erythro-bursatellin B(21),a diastereoisomer of 2,exhibited notable antibacterial activity against the fish pathogenic bacterium Streptococcus parauberis FP KSP28,with an MIC90 value of 0.0472 μg·mL-1.
