从大戟乳胶中分离和鉴定 12-脱氧佛波醇酯：通过 UHPLC-HRMSE 进行 12-脱氧佛波醇酯的靶向和有偏非靶向鉴定,Plants

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从大戟乳胶中分离和鉴定 12-脱氧佛波醇酯：通过 UHPLC-HRMSE 进行 12-脱氧佛波醇酯的靶向和有偏非靶向鉴定
Plants ( IF 4.0 ) Pub Date : 2023-11-14 , DOI: 10.3390/plants12223846
Abdellah Ezzanad _{1,

2} , Carolina De Los Reyes _{1,

2} , Antonio J Macías-Sánchez _{1,

2} , Rosario Hernández-Galán _{1,

2}

Affiliation

大戟属的二萜因其调节蛋白激酶 C (PKC) 家族的能力而闻名，该家族介导其促进神经前体细胞 (NPC) 增殖或神经母细胞分化为神经元的能力。在这项工作中，我们描述了从 E.resinifera Berg 乳胶中分离出 15 种 12-脱氧佛波醇酯 (1-15)。本文首次描述了12-脱氧-16-羟基佛波醇(4)的三酯和12-脱氧佛波醇13,20-二酯(13)。此外，还提供了化合物 3、5、6、14 和 15 的详细结构阐明。化合物 3、4、6、13、14 和 15 的绝对构型是通过比较其理论和实验电子圆二色性 (ECD) 建立的。）光谱。获得上述 12-脱氧佛波醇衍生物的集合，具有多种取代模式和连接的酰基部分，允许研究它们在碰撞诱导的多个离子解离中的碎片模式，而无需前体离子分离质谱实验 (HRMSE) ，这反过来又揭示了 HRMSE 谱中特定取代模式与其断裂途径之间的相关性。反过来，这允许对树脂乳胶中的 12-脱氧佛波醇进行靶向 UHPLC-HRMSE 分析和有偏差的非靶向 UHPLC-HRMSE 分析，从而检测和鉴定了先前在初始色谱柱中未分离出的四种额外 12-脱氧佛波醇分馏工作。其中一种被鉴定为 12-脱氧-16-羟基佛波醇 20-乙酸酯 13-苯基乙酸酯 16-丙酸酯 (20)，以前从未被描述过。

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Isolation and Identification of 12-Deoxyphorbol Esters from Euphorbia resinifera Berg Latex: Targeted and Biased Non-Targeted Identification of 12-Deoxyphorbol Esters by UHPLC-HRMSE

Diterpenes from the Euphorbia genus are known for their ability to regulate the protein kinase C (PKC) family, which mediates their ability to promote the proliferation of neural precursor cells (NPCs) or neuroblast differentiation into neurons. In this work, we describe the isolation from E. resinifera Berg latex of fifteen 12-deoxyphorbol esters (1–15). A triester of 12-deoxy-16-hydroxyphorbol (4) and a 12-deoxyphorbol 13,20-diester (13) are described here for the first time. Additionally, detailed structural elucidation is provided for compounds 3, 5, 6, 14 and 15. The absolute configuration for compounds 3, 4, 6, 13, 14 and 15 was established by the comparison of their theoretical and experimental electronic circular dichroism (ECD) spectra. Access to the above-described collection of 12-deoxyphorbol derivatives, with several substitution patterns and attached acyl moieties, allowed for the study of their fragmentation patterns in the collision-induced dissociation of multiple ions, without precursor ion isolation mass spectra experiments (HRMSE), which, in turn, revealed a correlation between specific substitution patterns and the fragmentation pathways in their HRMSE spectra. In turn, this allowed for a targeted UHPLC-HRMSE analysis and a biased non-targeted UHPLC-HRMSE analysis of 12-deoxyphorbols in E. resinifera latex which yielded the detection and identification of four additional 12-deoxyphorbols not previously isolated in the initial column fractionation work. One of them, identified as 12-deoxy-16-hydroxyphorbol 20-acetate 13-phenylacetate 16-propionate (20), has not been described before.

更新日期：2023-11-17

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