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来自越南地衣的α-葡萄糖苷酶抑制化合物：及相关方面。

Alpha-glucosidase inhibitory compounds from Vietnamese lichen : and aspects.

作者信息

Do Thanh-Hung, Duong Thuc-Huy, Vu Y-Thien, Tran Huu-Phuoc, Nguyen Thi-Truc-Ngan, Sichaem Jirapast, Nguyen Ngoc-Hong, Nguyen Huy Truong, Pham Duc-Dung

机构信息

Laboratory of Biophysics, Institute for Advanced Study in Technology, Ton Duc Thang University Ho Chi Minh City 700000 Vietnam.

Faculty of Pharmacy, Ton Duc Thang University Ho Chi Minh City 700000 Vietnam

出版信息

RSC Adv. 2024 Oct 15;14(44):32624-32636. doi: 10.1039/d4ra04449e. eCollection 2024 Oct 9.

DOI:10.1039/d4ra04449e
PMID:39411260
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11475664/
Abstract

Using a bio-guided isolation on the Vietnamese lichen based on alpha-glucosidase inhibition, eleven compounds were isolated and structurally elucidated, namely, protocetraric acid (1), 8'-methylstictic acid (2), stictic acid (3), 4,6-diformyl-8-hydroxy-3-methoxy-1,9-dimethyl-11-oxo-11-dibenzo[,][1,4]dioxepine-7-carboxylic acid (4), vicanicin (5), norstictic acid (6), diffractaic acid (7), barbatic acid (8), atranol (9), 5-chlorohaematommic acid (10), and eumitrin A1 (11). Their chemical structures were identified by extensive 1D and 2D NMR analysis and high-resolution mass spectroscopy and compared with those reported in literature. Protocetraric acid (1) and norstictic acid (6) were selected for further modification to derive new compounds, namely, 1a-1e and 6a. Both isolated and synthesized compounds were assessed for their alpha-glucosidase inhibitory activity. Compounds 1-6, 1a-1e, 6a, and 11 showed significant alpha-glucosidase inhibition with IC values ranging from 10.4 to 130 μM. Molecular docking was applied to the most active compounds 1-3, 6, 1a-1e, and 6a to clarify the inhibitory mechanism. Compound 1e was determined to be a mixed inhibitor through a kinetic study.

摘要

基于对越南地衣的α-葡萄糖苷酶抑制作用进行生物导向分离，分离并鉴定了11种化合物的结构，分别为原岛衣酸（1）、8'-甲基扁枝衣酸（2）、扁枝衣酸（3）、4,6-二甲酰基-8-羟基-3-甲氧基-1,9-二甲基-11-氧代-11H-二苯并[，][1,4]二氧杂环庚英-7-羧酸（4）、维卡尼辛（5）、降扁枝衣酸（6）、衍射酸（7）、巴巴地衣酸（8）、阿特拉诺尔（9）、5-氯血石蕊酸（10）和优米曲菌素A1（11）。通过广泛的一维和二维核磁共振分析以及高分辨率质谱对它们的化学结构进行了鉴定，并与文献报道的结构进行了比较。选择原岛衣酸（1）和降扁枝衣酸（6）进行进一步修饰以衍生新化合物，即1a - 1e和6a。对分离得到的化合物和合成化合物均进行了α-葡萄糖苷酶抑制活性评估。化合物1 - 6、1a - 1e、6a和11表现出显著的α-葡萄糖苷酶抑制作用，IC值范围为10.4至130μM。对活性最高的化合物1 - 3、6、1a - 1e和6a进行了分子对接，以阐明抑制机制。通过动力学研究确定化合物1e为混合抑制剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/dc1290a25ce6/d4ra04449e-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/c9724b182c77/d4ra04449e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/90d2f130cb73/d4ra04449e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/be8944c72922/d4ra04449e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/15db48f7d2d8/d4ra04449e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/ab62dea433d2/d4ra04449e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/f9136686efea/d4ra04449e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/1b8b58011032/d4ra04449e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/4b90523537e4/d4ra04449e-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/cac0fc16c0f6/d4ra04449e-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/dc1290a25ce6/d4ra04449e-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/c9724b182c77/d4ra04449e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/90d2f130cb73/d4ra04449e-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/be8944c72922/d4ra04449e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/15db48f7d2d8/d4ra04449e-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/ab62dea433d2/d4ra04449e-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/f9136686efea/d4ra04449e-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/1b8b58011032/d4ra04449e-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/4b90523537e4/d4ra04449e-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/cac0fc16c0f6/d4ra04449e-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2492/11475664/dc1290a25ce6/d4ra04449e-f9.jpg

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