Young Eun Du, Jinsheng Cui, Eunji Cho, Sunghoon Hwang, Yong-Joon Jang, Ki-Bong Oh, Sang-Jip Nam and Dong-Chan Oh*,
{"title":"来自沙雷氏菌的抗菌环肽 Serratiomycins D1-D3 和 Serratiomycin 的结构修订","authors":"Young Eun Du, Jinsheng Cui, Eunji Cho, Sunghoon Hwang, Yong-Joon Jang, Ki-Bong Oh, Sang-Jip Nam and Dong-Chan Oh*, ","doi":"10.1021/acs.jnatprod.3c00993","DOIUrl":null,"url":null,"abstract":"<p >Serratiomycin (<b>1</b>) is an antibacterial cyclic depsipeptide, first discovered from a <i>Eubacterium</i> culture in 1998. This compound was initially reported to contain <span>l</span>-Leu, <span>l</span>-Ser, <span>l</span>-<i>allo</i>-Thr, <span>d</span>-Phe, <span>d</span>-Ile, and hydroxydecanoic acid. In the present study, <b>1</b> and three new derivatives, serratiomycin D1–D3 (<b>2</b>–<b>4</b>), were isolated from a <i>Serratia</i> sp. strain isolated from the exoskeleton of a long-horned beetle. The planar structures of <b>1</b>–<b>4</b> were elucidated by using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. Comparison of the NMR chemical shifts and the physicochemical data of <b>1</b> to those of previously reported serratiomycin indeed identified <b>1</b> as serratiomycin. The absolute configurations of the amino units in compounds <b>1</b>–<b>4</b> were determined by the advanced Marfey’s method, 2,3,4,6-tetra-<i>O</i>-acetyl-β-<span>d</span>-glucopyranosyl isothiocyanate derivatization, and liquid chromatography–mass spectrometric (LC–MS) analysis. Additionally, methanolysis and the modified Mosher’s method were used to determine the absolute configuration of (3<i>R</i>)-hydroxydecanoic acid in <b>1</b>. Consequently, the revised structure of <b>1</b> was found to possess <span>d</span>-Leu, <span>l</span>-Ser, <span>l</span>-Thr, <span>d</span>-Phe, <span>l</span>-<i>allo</i>-Ile, and <span>d</span>-hydroxydecanoic acid. In comparison with the previously published structure of serratiomycin, <span>l</span>-Leu, <span>l</span>-<i>allo</i>-Thr, and <span>d</span>-Ile in serratiomycin were revised to <span>d</span>-Leu, <span>l</span>-Thr, and <span>l</span>-<i>allo</i>-Ile. The new members of the serratiomycin family, compounds <b>2</b> and <b>3</b>, showed considerably higher antibacterial activities against <i>Staphylococcus aureus</i> and <i>Salmonella enterica</i> than compound <b>1</b>.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Serratiomycins D1–D3, Antibacterial Cyclic Peptides from a Serratia sp. and Structure Revision of Serratiomycin\",\"authors\":\"Young Eun Du, Jinsheng Cui, Eunji Cho, Sunghoon Hwang, Yong-Joon Jang, Ki-Bong Oh, Sang-Jip Nam and Dong-Chan Oh*, \",\"doi\":\"10.1021/acs.jnatprod.3c00993\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Serratiomycin (<b>1</b>) is an antibacterial cyclic depsipeptide, first discovered from a <i>Eubacterium</i> culture in 1998. This compound was initially reported to contain <span>l</span>-Leu, <span>l</span>-Ser, <span>l</span>-<i>allo</i>-Thr, <span>d</span>-Phe, <span>d</span>-Ile, and hydroxydecanoic acid. In the present study, <b>1</b> and three new derivatives, serratiomycin D1–D3 (<b>2</b>–<b>4</b>), were isolated from a <i>Serratia</i> sp. strain isolated from the exoskeleton of a long-horned beetle. The planar structures of <b>1</b>–<b>4</b> were elucidated by using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. Comparison of the NMR chemical shifts and the physicochemical data of <b>1</b> to those of previously reported serratiomycin indeed identified <b>1</b> as serratiomycin. The absolute configurations of the amino units in compounds <b>1</b>–<b>4</b> were determined by the advanced Marfey’s method, 2,3,4,6-tetra-<i>O</i>-acetyl-β-<span>d</span>-glucopyranosyl isothiocyanate derivatization, and liquid chromatography–mass spectrometric (LC–MS) analysis. Additionally, methanolysis and the modified Mosher’s method were used to determine the absolute configuration of (3<i>R</i>)-hydroxydecanoic acid in <b>1</b>. Consequently, the revised structure of <b>1</b> was found to possess <span>d</span>-Leu, <span>l</span>-Ser, <span>l</span>-Thr, <span>d</span>-Phe, <span>l</span>-<i>allo</i>-Ile, and <span>d</span>-hydroxydecanoic acid. In comparison with the previously published structure of serratiomycin, <span>l</span>-Leu, <span>l</span>-<i>allo</i>-Thr, and <span>d</span>-Ile in serratiomycin were revised to <span>d</span>-Leu, <span>l</span>-Thr, and <span>l</span>-<i>allo</i>-Ile. The new members of the serratiomycin family, compounds <b>2</b> and <b>3</b>, showed considerably higher antibacterial activities against <i>Staphylococcus aureus</i> and <i>Salmonella enterica</i> than compound <b>1</b>.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-04-30\",\"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://pubs.acs.org/doi/10.1021/acs.jnatprod.3c00993\",\"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://pubs.acs.org/doi/10.1021/acs.jnatprod.3c00993","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Serratiomycins D1–D3, Antibacterial Cyclic Peptides from a Serratia sp. and Structure Revision of Serratiomycin
Serratiomycin (1) is an antibacterial cyclic depsipeptide, first discovered from a Eubacterium culture in 1998. This compound was initially reported to contain l-Leu, l-Ser, l-allo-Thr, d-Phe, d-Ile, and hydroxydecanoic acid. In the present study, 1 and three new derivatives, serratiomycin D1–D3 (2–4), were isolated from a Serratia sp. strain isolated from the exoskeleton of a long-horned beetle. The planar structures of 1–4 were elucidated by using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. Comparison of the NMR chemical shifts and the physicochemical data of 1 to those of previously reported serratiomycin indeed identified 1 as serratiomycin. The absolute configurations of the amino units in compounds 1–4 were determined by the advanced Marfey’s method, 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate derivatization, and liquid chromatography–mass spectrometric (LC–MS) analysis. Additionally, methanolysis and the modified Mosher’s method were used to determine the absolute configuration of (3R)-hydroxydecanoic acid in 1. Consequently, the revised structure of 1 was found to possess d-Leu, l-Ser, l-Thr, d-Phe, l-allo-Ile, and d-hydroxydecanoic acid. In comparison with the previously published structure of serratiomycin, l-Leu, l-allo-Thr, and d-Ile in serratiomycin were revised to d-Leu, l-Thr, and l-allo-Ile. The new members of the serratiomycin family, compounds 2 and 3, showed considerably higher antibacterial activities against Staphylococcus aureus and Salmonella enterica than compound 1.
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.