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A Series of New Pyrrole Alkaloids with ALR2 Inhibitory Activities from the Sponge Stylissa massa

Authors :
Qi Wang
Chunhua Gao
Zhun Wei
Xiaowen Tang
Lixia Ji
Xiangchao Luo
Xiaoping Peng
Gang Li
Hongxiang Lou
Source :
Marine Drugs, Vol 20, Iss 7, p 454 (2022)
Publication Year :
2022
Publisher :
MDPI AG, 2022.

Abstract

Twelve new and four known alkaloids including five different structural scaffolds were isolated from the sponge Stylissa massa collected in the South China Sea. Compound 1 is the first identified precursor metabolite of the classic 5/7/5 tricyclic skeleton with unesterified guanidine and carboxyl groups, compounds 2–5 and 13–15 belong to the spongiacidin-type pyrrole imidazole alkaloids (PIAs). Z- and E-configurations of the spongiacidin-type PIAs often appeared concomitantly and were distinguished by the chemical shift analysis of 13C NMR spectra. The structures of all twelve new compounds were determined by NMR, MS, and ECD analysis combined with single-crystal data of compounds 1, 5, and 10. In the aldose reductase (ALR2) inhibitory assay, six 5/7/5 tricyclic compounds (2–5, 13–15) displayed significant activities. Compounds 13 and 14, as the representative members of spongiacidin-PIAs, demonstrated their ALR2-targeted activities in SPR experiments with KD values of 12.5 and 6.9 µM, respectively.

Details

Language :
English
ISSN :
20070454 and 16603397
Volume :
20
Issue :
7
Database :
Directory of Open Access Journals
Journal :
Marine Drugs
Publication Type :
Academic Journal
Accession number :
edsdoj.796bce04a56745febbd6bc707a794797
Document Type :
article
Full Text :
https://doi.org/10.3390/md20070454