Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon
{"title":"Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.","authors":"Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon","doi":"10.1021/acs.jnatprod.4c00987","DOIUrl":null,"url":null,"abstract":"<p><p>A bioassay-guided chemical investigation of an Australian pasture-soil-derived <i>Streptomyces</i> sp. yielded the rare carbocyclic <i>ansa</i>-polyketide kendomycin (<b>1</b>) along with a series of new analogues, goondomycins A-H (<b>2</b>-<b>9</b>), featuring unprecedented carbo/heterocyclic scaffolds and chromophores, with structures assigned by detailed spectroscopic analysis, chemical and biochemical transformations, and biosynthetic considerations. Goondomycins B (<b>2</b>) and F (<b>7</b>) are noteworthy in being potent motility inhibitors of heartworm <i>Dirofilaria immitis</i> microfilaria (EC<sub>50</sub> 0.3 and 0.5 μM) and L4 larvae (EC<sub>50</sub> 1.4 and 1.8 μM), while exhibiting no significant antibacterial and antifungal activity or cytotoxicity to mammalian cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3000,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Goondomycins A-H: Carbocyclic <i>ansa</i>-Polyketides from an Australian Pasture <i>Streptomyces</i> with Selective Activity against <i>Dirofilaria immitis</i>.\",\"authors\":\"Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon\",\"doi\":\"10.1021/acs.jnatprod.4c00987\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A bioassay-guided chemical investigation of an Australian pasture-soil-derived <i>Streptomyces</i> sp. yielded the rare carbocyclic <i>ansa</i>-polyketide kendomycin (<b>1</b>) along with a series of new analogues, goondomycins A-H (<b>2</b>-<b>9</b>), featuring unprecedented carbo/heterocyclic scaffolds and chromophores, with structures assigned by detailed spectroscopic analysis, chemical and biochemical transformations, and biosynthetic considerations. Goondomycins B (<b>2</b>) and F (<b>7</b>) are noteworthy in being potent motility inhibitors of heartworm <i>Dirofilaria immitis</i> microfilaria (EC<sub>50</sub> 0.3 and 0.5 μM) and L4 larvae (EC<sub>50</sub> 1.4 and 1.8 μM), while exhibiting no significant antibacterial and antifungal activity or cytotoxicity to mammalian cells.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\" \",\"pages\":\"\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-11-26\",\"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.4c00987\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"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.4c00987","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.
A bioassay-guided chemical investigation of an Australian pasture-soil-derived Streptomyces sp. yielded the rare carbocyclic ansa-polyketide kendomycin (1) along with a series of new analogues, goondomycins A-H (2-9), featuring unprecedented carbo/heterocyclic scaffolds and chromophores, with structures assigned by detailed spectroscopic analysis, chemical and biochemical transformations, and biosynthetic considerations. Goondomycins B (2) and F (7) are noteworthy in being potent motility inhibitors of heartworm Dirofilaria immitis microfilaria (EC50 0.3 and 0.5 μM) and L4 larvae (EC50 1.4 and 1.8 μM), while exhibiting no significant antibacterial and antifungal activity or cytotoxicity to mammalian cells.
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.