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戈瓦诺苷 C-F,来自独蒜兰根茎的具有罕见糖的新型甾体皂苷及其对乙酰胆碱酯酶的拮抗作用。

Govanosides C-F, unprecedented steroidal saponins with rare sugars from rhizomes of Trillium govanianum and their antagonistic effects on acetylcholinesterase.

机构信息

C-H Activation & Phytochemistry Lab, Chemical Technology Division CSIR-IHBT, Palampur, Himachal Pradesh 176061, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.

C-H Activation & Phytochemistry Lab, Chemical Technology Division CSIR-IHBT, Palampur, Himachal Pradesh 176061, India.

出版信息

Steroids. 2023 Nov;199:109293. doi: 10.1016/j.steroids.2023.109293. Epub 2023 Aug 6.

DOI:10.1016/j.steroids.2023.109293
PMID:37549778
Abstract

Four previously undescribed steroidal saponins named govanosides C-F (1-4) and nine known compounds (5-13) were isolated from the rhizomes of Trillium govanianum Wall. ex D.Don. Govanosides C-E contained a rare sugar moiety i.e., 6-deoxy allose, while govanoside F has acetylated rhamnose moiety in its glycan part. Also, this is the first report on the isolation of feruloyl sucrose derivatives (11-12) and (E)-4-hydroxy-dodec-2-enedioic acid (13) from the Trillium genus. The structure of isolated compounds was deduced using 1D and 2D NMR, HRESIMS, LC-MS/MS, GC-MS, and saccharide linkage analysis. Steroidal scaffold isolates (1-10) were evaluated for their antagonistic effects on acetylcholinesterase inhibitory activity. Govanoside C (1) significantly inhibited acetylcholinesterase (IC: 2.38 μM). Molecular docking experiments have also been performed to depict the molecule's interaction and binding free energy with acetylcholinesterase.

摘要

从独蒜兰的根茎中分离得到了四个以前未描述的甾体皂甙,分别命名为 govanoside C-F(1-4)和九个已知化合物(5-13)。Govanoside C-E 含有一个罕见的糖部分,即 6-去氧阿洛糖,而 govanoside F 在其糖苷部分则含有乙酰化鼠李糖部分。此外,这是首次从独蒜兰属植物中分离得到阿魏酸蔗糖衍生物(11-12)和(E)-4-羟基-十二-2-烯二酸(13)。通过 1D 和 2D NMR、HRESIMS、LC-MS/MS、GC-MS 和糖链分析推导出了分离化合物的结构。对分离得到的甾体骨架化合物(1-10)进行了乙酰胆碱酯酶抑制活性的拮抗作用评价。Govanoside C(1)对乙酰胆碱酯酶具有显著的抑制作用(IC:2.38 μM)。还进行了分子对接实验,以描绘分子与乙酰胆碱酯酶的相互作用和结合自由能。

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引用本文的文献

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