Kseniya M. Tabakmakher, Tatyana N. Makarieva, Yuri E. Sabutski, Maxim S. Kokoulin, Alexander S. Menshov, Roman S. Popov, Alla G. Guzii, Larisa K. Shubina, Ekaterina A. Chingizova, Artur R. Chingizov, Ekaterina A. Yurchenko, Sergey N. Fedorov, Boris B. Grebnev, Gunhild von Amsberg, Sergey A. Dyshlovoy, Natalia V. Ivanchina, Pavel S. Dmitrenok
{"title":"来自西北太平洋海洋海绵 Lissodendoryx papillosa 的含 L-Idonic Acid 核心的抗菌 4-溴吡咯烷类生物碱 Stonikacidin A","authors":"Kseniya M. Tabakmakher, Tatyana N. Makarieva, Yuri E. Sabutski, Maxim S. Kokoulin, Alexander S. Menshov, Roman S. Popov, Alla G. Guzii, Larisa K. Shubina, Ekaterina A. Chingizova, Artur R. Chingizov, Ekaterina A. Yurchenko, Sergey N. Fedorov, Boris B. Grebnev, Gunhild von Amsberg, Sergey A. Dyshlovoy, Natalia V. Ivanchina, Pavel S. Dmitrenok","doi":"10.3390/md22090396","DOIUrl":null,"url":null,"abstract":"Stonikacidin A (1), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge Lissodendoryx papillosa. The compound is named in honor of Prof. Valentin A. Stonik, who is one of the outstanding investigators in the field of marine natural chemistry. The structure of 1 was determined using NMR, MS analysis, and chemical correlations. The L-idonic acid core was established by the comparison of GC, NMR, MS, and optical rotation data of methyl-pentaacetyl-aldonates obtained from the hydrolysis products of 1 and standard hexoses. The L-form of the idonic acid residue in 1 was confirmed by GC analysis of pentaacetate of (S)-2-butyl ester of the hydrolysis product from 1 and compared with corresponding derivatives of L- and D-idonic acids. The biosynthetic pathway for stonikacidin A (1) was proposed. The alkaloid 1 inhibited the growth of Staphylococcus aureus and Escherichia coli test strains, as well as affected the formation of S. aureus and E. coli biofilms. Compound 1 inhibited the activity of sortase A. Molecular docking data showed that stonikacidin A (1) can bind with sortase A due to the interactions between its bromine atoms and some amino acid residues of the enzyme.","PeriodicalId":18222,"journal":{"name":"Marine Drugs","volume":"13 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-08-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa\",\"authors\":\"Kseniya M. Tabakmakher, Tatyana N. Makarieva, Yuri E. Sabutski, Maxim S. Kokoulin, Alexander S. Menshov, Roman S. Popov, Alla G. Guzii, Larisa K. Shubina, Ekaterina A. Chingizova, Artur R. Chingizov, Ekaterina A. Yurchenko, Sergey N. Fedorov, Boris B. Grebnev, Gunhild von Amsberg, Sergey A. Dyshlovoy, Natalia V. Ivanchina, Pavel S. Dmitrenok\",\"doi\":\"10.3390/md22090396\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Stonikacidin A (1), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge Lissodendoryx papillosa. The compound is named in honor of Prof. Valentin A. Stonik, who is one of the outstanding investigators in the field of marine natural chemistry. The structure of 1 was determined using NMR, MS analysis, and chemical correlations. The L-idonic acid core was established by the comparison of GC, NMR, MS, and optical rotation data of methyl-pentaacetyl-aldonates obtained from the hydrolysis products of 1 and standard hexoses. The L-form of the idonic acid residue in 1 was confirmed by GC analysis of pentaacetate of (S)-2-butyl ester of the hydrolysis product from 1 and compared with corresponding derivatives of L- and D-idonic acids. The biosynthetic pathway for stonikacidin A (1) was proposed. The alkaloid 1 inhibited the growth of Staphylococcus aureus and Escherichia coli test strains, as well as affected the formation of S. aureus and E. coli biofilms. Compound 1 inhibited the activity of sortase A. Molecular docking data showed that stonikacidin A (1) can bind with sortase A due to the interactions between its bromine atoms and some amino acid residues of the enzyme.\",\"PeriodicalId\":18222,\"journal\":{\"name\":\"Marine Drugs\",\"volume\":\"13 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-08-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Marine Drugs\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://doi.org/10.3390/md22090396\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Marine Drugs","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.3390/md22090396","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa
Stonikacidin A (1), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge Lissodendoryx papillosa. The compound is named in honor of Prof. Valentin A. Stonik, who is one of the outstanding investigators in the field of marine natural chemistry. The structure of 1 was determined using NMR, MS analysis, and chemical correlations. The L-idonic acid core was established by the comparison of GC, NMR, MS, and optical rotation data of methyl-pentaacetyl-aldonates obtained from the hydrolysis products of 1 and standard hexoses. The L-form of the idonic acid residue in 1 was confirmed by GC analysis of pentaacetate of (S)-2-butyl ester of the hydrolysis product from 1 and compared with corresponding derivatives of L- and D-idonic acids. The biosynthetic pathway for stonikacidin A (1) was proposed. The alkaloid 1 inhibited the growth of Staphylococcus aureus and Escherichia coli test strains, as well as affected the formation of S. aureus and E. coli biofilms. Compound 1 inhibited the activity of sortase A. Molecular docking data showed that stonikacidin A (1) can bind with sortase A due to the interactions between its bromine atoms and some amino acid residues of the enzyme.
期刊介绍:
Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.