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分子网络引导的蜂花粉中黄酮糖苷的注释

Molecular Networking-Guided Annotation of Flavonoid Glycosides from Bee Pollen.

作者信息

Joo Yerim, Shin Eunbeen, Kim Hyunwoo, Lee Mi Kyeong, Kim Seon Beom

机构信息

Department of Food Science and Technology, Pusan National University, Miryang 50463, Republic of Korea.

Institute for Future Earth, Pusan National University, Busan 46421, Republic of Korea.

出版信息

Int J Mol Sci. 2025 Aug 17;26(16):7930. doi: 10.3390/ijms26167930.

Abstract

Bee pollen is a primary and secondary metabolite-rich natural product collected by pollinators such as honeybees. Polyphenols, particularly flavonoids, are well known for their potent antioxidant activities. Numerous phytochemical and biological studies have focused on , a member of the Fagaceae family. However, research focusing specifically on pollen is limited. Moreover, bee pollen chemical composition varies significantly depending on its geographical origin and cultivation conditions. In this study, the flavonoid glycosides of pollen were profiled using LC-MS/MS-based molecular networking, which revealed that the largest molecular cluster corresponded to flavonoid glycosides. A total of 69 flavonoid glycosides, primarily comprising 2 kaempferol derivatives, 14 quercetin derivatives, and 46 isorhamnetin derivatives, were annotated based on MS/MS fragmentation patterns, spectral library matches in GNPS (Global Natural Products Social Molecular Networking), and comparison with previously reported data. Two primary compounds, isorhamnetin 3----xylopyranosyl (1→6)---glucopyranoside and isorhamnetin-3--neohesperidoside, were identified by comparison with reference standards. This study offers foundational insights into the flavonoid diversity of pollen, contributing to a broad understanding of its secondary metabolite profile.

摘要

蜂花粉是一种由蜜蜂等传粉者采集的富含初级和次级代谢产物的天然产物。多酚类物质,尤其是黄酮类化合物,以其强大的抗氧化活性而闻名。众多植物化学和生物学研究都集中在壳斗科的一个成员上。然而,专门针对花粉的研究有限。此外,蜂花粉的化学成分因其地理来源和种植条件而有很大差异。在本研究中,利用基于液相色谱-串联质谱的分子网络对花粉中的黄酮苷进行了分析,结果表明最大的分子簇对应于黄酮苷。基于串联质谱碎片模式、全球天然产物社会分子网络(GNPS)中的光谱库匹配以及与先前报道数据的比较,共注释了69种黄酮苷,主要包括2种山奈酚衍生物、14种槲皮素衍生物和46种异鼠李素衍生物。通过与参考标准品比较,鉴定出两种主要化合物,异鼠李素3 - O - 木糖吡喃糖基(1→6) - 葡萄糖吡喃糖苷和异鼠李素 - 3 - 新橙皮糖苷。本研究为花粉的黄酮类化合物多样性提供了基础见解,有助于更全面地了解其次级代谢产物谱。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fb6/12386960/31bb96f936d5/ijms-26-07930-g001.jpg

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