Gina R. De Nicola , Jianzhong Zhu , David I. Pattison , Marcus A. Koch , Dan Staerk , Niels Agerbirk
{"title":"3-Hydroxy-2-methylpropylglucosinolate and other glucosinolates from Reseda luteola (Resedaceae)","authors":"Gina R. De Nicola , Jianzhong Zhu , David I. Pattison , Marcus A. Koch , Dan Staerk , Niels Agerbirk","doi":"10.1016/j.bse.2024.104902","DOIUrl":null,"url":null,"abstract":"<div><p>We identified 3-hydroxy-2-methylpropylglucosinolate in foliage of <em>Reseda luteola</em> L, although the side chain stereochemistry was not resolved. The glucosinolates (GSLs) in <em>R. luteola</em> extracts were bound to an anion exchange column and enzymatically desulfated, followed by isolation by preparative HPLC of the desulfo derivatives, the structures of which were elucidated by NMR and/or MS/MS. Presence of intact 3-hydroxy-2-methylpropylGSL in extracts was supported by direct LC-MS detection and MS2 loss of HSO<sub>4</sub><sup>−</sup>. Prominent GSLs in <em>R. luteola</em> foliage were 3-hydroxy-2-methylpropylGSL as well as the previously known indol-3-ylmethylGSL and the 2<em>R</em> (minor) and 2<em>S</em> (major) isomers of 2-hydroxy-2-phenylethylGSL. Minor GSLs included the expected biosynthetic precursors 2-methylpropylGSL (tentative) and phenethylGSL, as well as 1-methylpropylGSL (tentative) and benzylGSL. The 3-hydroxy-2-methylpropylGSL matched a previously reported but so far unidentified constituent in <em>Limnanthes alba</em> (Limnanthaceae). The identity of investigated <em>R. luteola</em> was confirmed morphologically and from DNA barcoding, and a <em>Reseda</em> phylogeny was constructed. In conclusion, 3-hydroxy-2-methylpropylGSL occurs in at least two basal families of the Brassicales order.</p></div>","PeriodicalId":8799,"journal":{"name":"Biochemical Systematics and Ecology","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.sciencedirect.com/science/article/pii/S0305197824001200/pdfft?md5=6501b2a059cdcd25bb018ae0af9f1681&pid=1-s2.0-S0305197824001200-main.pdf","citationCount":"0","resultStr":"{\"title\":\"3-Hydroxy-2-methylpropylglucosinolate and other glucosinolates from Reseda luteola (Resedaceae)\",\"authors\":\"Gina R. De Nicola , Jianzhong Zhu , David I. Pattison , Marcus A. Koch , Dan Staerk , Niels Agerbirk\",\"doi\":\"10.1016/j.bse.2024.104902\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>We identified 3-hydroxy-2-methylpropylglucosinolate in foliage of <em>Reseda luteola</em> L, although the side chain stereochemistry was not resolved. The glucosinolates (GSLs) in <em>R. luteola</em> extracts were bound to an anion exchange column and enzymatically desulfated, followed by isolation by preparative HPLC of the desulfo derivatives, the structures of which were elucidated by NMR and/or MS/MS. Presence of intact 3-hydroxy-2-methylpropylGSL in extracts was supported by direct LC-MS detection and MS2 loss of HSO<sub>4</sub><sup>−</sup>. Prominent GSLs in <em>R. luteola</em> foliage were 3-hydroxy-2-methylpropylGSL as well as the previously known indol-3-ylmethylGSL and the 2<em>R</em> (minor) and 2<em>S</em> (major) isomers of 2-hydroxy-2-phenylethylGSL. Minor GSLs included the expected biosynthetic precursors 2-methylpropylGSL (tentative) and phenethylGSL, as well as 1-methylpropylGSL (tentative) and benzylGSL. The 3-hydroxy-2-methylpropylGSL matched a previously reported but so far unidentified constituent in <em>Limnanthes alba</em> (Limnanthaceae). The identity of investigated <em>R. luteola</em> was confirmed morphologically and from DNA barcoding, and a <em>Reseda</em> phylogeny was constructed. In conclusion, 3-hydroxy-2-methylpropylGSL occurs in at least two basal families of the Brassicales order.</p></div>\",\"PeriodicalId\":8799,\"journal\":{\"name\":\"Biochemical Systematics and Ecology\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2024-09-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.sciencedirect.com/science/article/pii/S0305197824001200/pdfft?md5=6501b2a059cdcd25bb018ae0af9f1681&pid=1-s2.0-S0305197824001200-main.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Biochemical Systematics and Ecology\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0305197824001200\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Biochemical Systematics and Ecology","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0305197824001200","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
3-Hydroxy-2-methylpropylglucosinolate and other glucosinolates from Reseda luteola (Resedaceae)
We identified 3-hydroxy-2-methylpropylglucosinolate in foliage of Reseda luteola L, although the side chain stereochemistry was not resolved. The glucosinolates (GSLs) in R. luteola extracts were bound to an anion exchange column and enzymatically desulfated, followed by isolation by preparative HPLC of the desulfo derivatives, the structures of which were elucidated by NMR and/or MS/MS. Presence of intact 3-hydroxy-2-methylpropylGSL in extracts was supported by direct LC-MS detection and MS2 loss of HSO4−. Prominent GSLs in R. luteola foliage were 3-hydroxy-2-methylpropylGSL as well as the previously known indol-3-ylmethylGSL and the 2R (minor) and 2S (major) isomers of 2-hydroxy-2-phenylethylGSL. Minor GSLs included the expected biosynthetic precursors 2-methylpropylGSL (tentative) and phenethylGSL, as well as 1-methylpropylGSL (tentative) and benzylGSL. The 3-hydroxy-2-methylpropylGSL matched a previously reported but so far unidentified constituent in Limnanthes alba (Limnanthaceae). The identity of investigated R. luteola was confirmed morphologically and from DNA barcoding, and a Reseda phylogeny was constructed. In conclusion, 3-hydroxy-2-methylpropylGSL occurs in at least two basal families of the Brassicales order.
期刊介绍：
Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology).
In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.
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