Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, Croatia.
Institute de Chimie Organique et Analytique (ICOA), Université d'Orléans, UMR-CNRS 7311, BP 6759, F-45067 Orléans, France.
Molecules. 2023 Feb 12;28(4):1753. doi: 10.3390/molecules28041753.
Glucosinolates (GSLs) are a unique class of thioglucosides that evolved as defense mechanisms in the 16 families of the Brassicales order and present molecular tags which can be placed in a robust phylogenetic framework through investigations into their evolution and diversity. The GSL profiles of three Resedaceae species, , , and , were examined qualitatively and quantitatively with respect to their desulfo-counterparts utilizing UHPLC-DAD-MS/MS. In addition, NMR analysis of isolated 2-hydroxy-2-methylpropyl desulfoGSL () was performed. Three Phe-derived GSLs were found in , including glucotropaeolin () (0.6-106.69 mol g DW), 2-(α-L-ramnopyranosyloxy)benzyl GSL () (8.10-57.89 μmol g DW), glucolepigramin () (8.66 μmol g DW in flower), and Trp-derived glucobrassicin () (0.76-5.92 μmol g DW). The Phe-derived GSLs (50.79-164.37 μmol g DW), gluconasturtiin () (1.97 μmol g DW), and (tr), as well as the Trp-derived GSL glucobrassicin () (3.13-11.26 μmol g DW), were all present in . also contained Phe-derived (0.10-107.77 μmol g DW), followed by Trp-derived (0.85-3.50 μmol g DW) and neoglucobrassicin () (0.23-2.74 μmol g DW). However, regarding the GSLs in , which originated from Leu biosynthesis, was the major GSL (6.48 to 52.72 μmol g DW) and isobutyl GSL () was the minor GSL (0.13 to 1.13 μmol g DW). The discovered profiles, along with new evidence provided by GSL characterizations, were studied in the context of the current knowledge on GLSs in the Resedaceae family. With the exception of , the aliphatic GSLs of which were outliers among the Resedaceae species studied, this family typically contains GSLs derived primarily from Trp and Phe biosynthesis, which modifications resulted in GSLs unique to this family, implying presence of the specific genes. responsible for this diversification.
硫代葡萄糖苷（GSLs）是一类独特的硫代葡萄糖，作为 Brassicales 目中 16 个科的防御机制而进化，通过对其进化和多样性的研究，呈现出可置于稳健系统发育框架中的分子标记。本文利用 UHPLC-DAD-MS/MS 定性和定量研究了瑞香科三种植物， 、 、 ，的脱硫对应物的 GSL 图谱。此外，还对分离得到的 2-羟基-2-甲基丙基脱硫 GSL()进行了 NMR 分析。在 中发现了三种苯丙氨酸衍生的 GSL，包括 （0.6-106.69 mol g DW）、2-（α-L-鼠李吡喃糖基氧基）苄基 GSL()（8.10-57.89 μmol g DW）、 （8.66 μmol g DW，花中）和色氨酸衍生的葡萄糖异硫氰酸酯（）（0.76-5.92 μmol g DW）。 （50.79-164.37 μmol g DW）、葡萄糖野黑樱苷（）（1.97 μmol g DW）和 （tr）以及色氨酸衍生的葡萄糖异硫氰酸酯（）（3.13-11.26 μmol g DW）在 中均有存在。 还含有苯丙氨酸衍生的 （0.10-107.77 μmol g DW），其次是色氨酸衍生的 （0.85-3.50 μmol g DW）和新葡萄糖异硫氰酸酯（）（0.23-2.74 μmol g DW）。然而，对于起源于亮氨酸生物合成的 中 GSL， 是主要的 GSL（6.48 至 52.72 μmol g DW），异丁基 GSL()是次要的 GSL（0.13 至 1.13 μmol g DW）。本文在瑞香科 GLS 现有知识的背景下，研究了所发现的 GSL 图谱以及 GSL 特征提供的新证据。除 外，该科的脂肪族 GSL 是研究的瑞香科物种中的异类，该科通常含有主要来源于色氨酸和苯丙氨酸生物合成的 GSL，这些修饰导致了该科特有的 GSL，这表明存在负责这种多样化的特定基因。
