{"title":"Pemuchiamides A 和 B，富含脯氨酸的线性脂肽，从海洋 Hormoscilla sp.","authors":"Kensuke Irie, Ghulam Jeelani, Tomoyoshi Nozaki, Arihiro Iwasaki","doi":"10.1021/acs.jnatprod.4c00733","DOIUrl":null,"url":null,"abstract":"<p><p>Pemuchiamides A and B (<b>1</b> and <b>2</b>) were isolated from a marine <i>Hormoscilla</i> sp. cyanobacterium collected from Pemuchi Beach on Hateruma Island, Japan. Although <b>1</b> and <b>2</b> existed as a complex mixture of rotamers in chloroform-<i>d</i>, detailed analyses of their 2D NMR and tandem mass spectra revealed their planar structures, respectively. The absolute configurations of <b>1</b> and <b>2</b> were established via the degradation and derivatization reactions. Pemuchiamide A (<b>1</b>) exhibited potent growth-inhibitory activity against <i>Trypanosoma brucei rhodesiense</i>, the causative organism of African sleeping sickness, while <b>2</b> showed 10-fold weaker activity than <b>1</b>. This result indicates that the presence of a hydroxy group at the C-3 position of the 4-aminobutanoic acid moiety negatively affects antitrypanosomal activity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2292-2301"},"PeriodicalIF":3.3000,"publicationDate":"2024-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Pemuchiamides A and B, Proline-Rich Linear Lipopeptides, Isolated from a Marine <i>Hormoscilla</i> sp. Cyanobacterium.\",\"authors\":\"Kensuke Irie, Ghulam Jeelani, Tomoyoshi Nozaki, Arihiro Iwasaki\",\"doi\":\"10.1021/acs.jnatprod.4c00733\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Pemuchiamides A and B (<b>1</b> and <b>2</b>) were isolated from a marine <i>Hormoscilla</i> sp. cyanobacterium collected from Pemuchi Beach on Hateruma Island, Japan. Although <b>1</b> and <b>2</b> existed as a complex mixture of rotamers in chloroform-<i>d</i>, detailed analyses of their 2D NMR and tandem mass spectra revealed their planar structures, respectively. The absolute configurations of <b>1</b> and <b>2</b> were established via the degradation and derivatization reactions. Pemuchiamide A (<b>1</b>) exhibited potent growth-inhibitory activity against <i>Trypanosoma brucei rhodesiense</i>, the causative organism of African sleeping sickness, while <b>2</b> showed 10-fold weaker activity than <b>1</b>. This result indicates that the presence of a hydroxy group at the C-3 position of the 4-aminobutanoic acid moiety negatively affects antitrypanosomal activity.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\" \",\"pages\":\"2292-2301\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-09-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Natural Products \",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.jnatprod.4c00733\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/8/15 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c00733","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/8/15 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Pemuchiamides A and B, Proline-Rich Linear Lipopeptides, Isolated from a Marine Hormoscilla sp. Cyanobacterium.
Pemuchiamides A and B (1 and 2) were isolated from a marine Hormoscilla sp. cyanobacterium collected from Pemuchi Beach on Hateruma Island, Japan. Although 1 and 2 existed as a complex mixture of rotamers in chloroform-d, detailed analyses of their 2D NMR and tandem mass spectra revealed their planar structures, respectively. The absolute configurations of 1 and 2 were established via the degradation and derivatization reactions. Pemuchiamide A (1) exhibited potent growth-inhibitory activity against Trypanosoma brucei rhodesiense, the causative organism of African sleeping sickness, while 2 showed 10-fold weaker activity than 1. This result indicates that the presence of a hydroxy group at the C-3 position of the 4-aminobutanoic acid moiety negatively affects antitrypanosomal activity.
期刊介绍：
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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