High-Resolution LC–MS/MS Characterization of Budmunchiamine-Type Alkaloids in Albizia niopoides

IF 1.8 3区化学 Q4 BIOCHEMICAL RESEARCH METHODS

Rapid Communications in Mass Spectrometry Pub Date : 2026-07-25 DOI:10.1002/rcm.70142

Maria L. A. Majevski, Lienne D'Auria Lima, Adriana C. C. Reis, Leonan I. C. R. Santos, Brenno F. S. Vargas, Markus Kohlhoff, Geraldo Célio Brandão

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Abstract

Rationale

Budmunchiamines are macrocyclic spermine alkaloids that constitute a distinctive class of polyamine natural products predominantly found in species of the genus Albizia. Comprehensive characterization of these compounds remains challenging because of their structural diversity and the limited availability of reference standards. This study aimed to profile the budmunchiamine alkaloids present in the trunk bark of Albizia niopoides using high-resolution tandem mass spectrometry.

Methods

Alkaloids were extracted from the trunk bark of A. niopoides and analyzed by ultrahigh-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC–ESI–QTOF–MS) operated in positive ionization mode. Compound annotation was based on accurate mass measurements (≤ 5 ppm), chromatographic retention behavior, isotopic patterns, and diagnostic MS/MS fragmentation, supported by comparison with published data.

Results

Twenty-six macrocyclic spermine alkaloids were detected and annotated. The MS/MS spectra consistently exhibited characteristic budmunchiamine fragment ions at m/z 214, 171, 169, and 129, together with diagnostic neutral losses, confirming assignment to this structural class. Six compounds were identified as the known budmunchiamines L1, L4, L5, and L6, whereas two corresponded to previously synthesized analogues (Compounds 2 and 21). The remaining 20 compounds displayed distinct precursor ions but closely related fragmentation pathways, indicating previously unreported budmunchiamine-type analogues.

Conclusions

UHPLC–ESI–QTOF–MS/MS proved to be an effective strategy for the dereplication and structural annotation of macrocyclic spermine alkaloids from A. niopoides. The results substantially expand the known chemical diversity of budmunchiamines in this species and demonstrate the value of high-resolution tandem mass spectrometry for the characterization of structurally complex natural products.

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高分辨率LC-MS/MS表征牛角合欢中budmunchamine型生物碱

理由：Budmunchiamines是一种大环精胺生物碱，它是一种独特的多胺类天然产物，主要存在于合欢属的物种中。由于其结构多样性和参考标准的有限性，对这些化合物的综合表征仍然具有挑战性。本研究旨在利用高分辨率串联质谱法分析牛皮合欢主干树皮中存在的budmunchiamine生物碱。方法：采用超高效液相色谱-电喷雾四极杆飞行时间质谱联用（UHPLC-ESI-QTOF-MS），在正离子模式下对牛角参主干树皮中生物碱进行分析。化合物注释基于精确的质量测量（≤5ppm）、色谱保留行为、同位素模式和诊断性MS/MS碎片，并与已发表的数据进行比较。结果：共检出26种大环精胺生物碱。MS/MS光谱一致地在m/z 214、171、169和129处显示出特征的布芒胺片段离子，以及诊断性中性损失，确认了该结构类的归属。6个化合物被鉴定为已知的budmunchiamines L1， L4， L5和L6，而2个化合物对应于先前合成的类似物（化合物2和21）。其余20个化合物显示出不同的前体离子，但密切相关的裂解途径，表明以前未报道的budmunchiamine-type类似物。结论：UHPLC-ESI-QTOF-MS/MS是牛角草大环精胺生物碱分离和结构注释的有效方法。该结果极大地扩展了该物种中已知的budmunchiamines的化学多样性，并证明了高分辨率串联质谱法在结构复杂的天然产物表征中的价值。

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来源期刊

Rapid Communications in Mass Spectrometry 化学-分析化学

CiteScore

4.10

自引率

5.00%

发文量

219

审稿时长

2.6 months

期刊介绍： Rapid Communications in Mass Spectrometry is a journal whose aim is the rapid publication of original research results and ideas on all aspects of the science of gas-phase ions; it covers all the associated scientific disciplines. There is no formal limit on paper length ("rapid" is not synonymous with "brief"), but papers should be of a length that is commensurate with the importance and complexity of the results being reported. Contributions may be theoretical or practical in nature; they may deal with methods, techniques and applications, or with the interpretation of results; they may cover any area in science that depends directly on measurements made upon gaseous ions or that is associated with such measurements.