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
,
2
,
3
;
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
2. State Key Laboratory of Chemical Biology,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai 201203,China
3. 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.
