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利用核磁共振计算对高良姜果皮中新的卡瓦内酯二聚体进行结构解析

Structure Elucidation of New Kavalactone Dimers From Alpinia zerumbet Pericarps Using NMR Calculations.

作者信息

Nishidono Yuto, Tanaka Ken

机构信息

College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu, Shiga, Japan.

Research Organization of Science and Technology, Ritsumeikan University, Kusatsu, Shiga, Japan.

出版信息

Magn Reson Chem. 2025 Mar;63(3):180-185. doi: 10.1002/mrc.5501. Epub 2024 Dec 5.

DOI:10.1002/mrc.5501
PMID:39639428
Abstract

Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm, known as shell ginger, is an aromatic plant widely distributed in tropical and subtropical regions. In Guizhou Province of China, its mature fruits have been used by the Miao people for the treatment of cardiovascular diseases. Although the bioactivities of mature fruits of A. zerumbet are derived from phytochemicals in the seeds and pericarps of the plant, there remains a dearth of reports on the isolation of phytochemicals from the pericarp of A. zerumbet. In the present study, the pericarps of mature fruits of A. zerumbet were extracted, and two new kavalactone dimers, alpingsin E (1) and aniba dimer D (2), were isolated. Their structures were determined on the basis of extensive spectroscopic analysis and NMR calculations. Especially, density functional theory-based NMR chemical shift calculations were employed to elucidate and confirm the relative configuration of 1 and 2.

摘要

艳山姜(Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm),又名草扣姜,是一种广泛分布于热带和亚热带地区的芳香植物。在中国贵州省,苗族人一直用其成熟果实治疗心血管疾病。尽管艳山姜成熟果实的生物活性源自该植物种子和果皮中的植物化学物质,但关于从艳山姜果皮中分离植物化学物质的报道仍然很少。在本研究中,对艳山姜成熟果实的果皮进行了提取,分离得到了两种新的卡瓦内酯二聚体,即艳山姜素E(1)和巴西樟二聚体D(2)。通过广泛的光谱分析和核磁共振计算确定了它们的结构。特别是,采用基于密度泛函理论的核磁共振化学位移计算来阐明和确认1和2的相对构型。

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