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Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides.

ABSTRACT: Iridoid glycoside, which belongs to the polyhydroxy compound, is a kind of active ingredient of traditional Chinese medicine with a wide range of sources, and has many pharmacological effects such as anti-cancer, anti-inflammatory, anti-virus, hypoglycemic and so on. Its structure contains many hydroxyl groups, including two primary hydroxyl groups. The chemical reactivity of primary hydroxyl groups has very little difference, so it is very important to control the selectivity of hydroxyl groups under certain conditions. In this paper, the difference between the two primary hydroxyl groups in iridoid glycoside was calculated based on computer simulation and verified this result through designed experiments. This study will provide an important way for site-directed modification of hydroxyl in iridoid glycoside in the future.

SUBMITTER: Kong Y

PROVIDER: S-EPMC10637112 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides.

Kong Yuanfang Y Xu Jindan J Zhu Pengbo P Wang Shaopei S Yang Bin B Zhang Jingyu J Dong Chunhong C

RSC advances 20231110 47

Iridoid glycoside, which belongs to the polyhydroxy compound, is a kind of active ingredient of traditional Chinese medicine with a wide range of sources, and has many pharmacological effects such as anti-cancer, anti-inflammatory, anti-virus, hypoglycemic and so on. Its structure contains many hydroxyl groups, including two primary hydroxyl groups. The chemical reactivity of primary hydroxyl groups has very little difference, so it is very important to control the selectivity of hydroxyl groups ...[more]

PMID: 37954426

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Project description:Eucommia ulmoides Oliver is one of the commonly used traditional Chinese medicines for the treatment of osteoporosis, and iridoid glycosides are considered to be its active ingredients against osteoporosis. This study aims to clarify the chemical components and molecular mechanism of iridoid glycosides of Eucommia ulmoides Oliver in the treatment of osteoporosis by integrating network pharmacology and molecular simulations. The active iridoid glycosides and their potential targets were retrieved from text mining as well as Swiss Target Prediction, TargetNet database, and STITCH databases. At the same time, DisGeNET, GeneCards, and Therapeutic Target Database were used to search for the targets associated with osteoporosis. A protein-protein interaction network was built to analyze the interactions between targets. Then, DAVID bioinformatics resources and R 3.6.3 project were used to carry out Gene Ontology enrichment analysis and Kyoto Encyclopedia of Genes and Genomes pathway analysis. Moreover, interactions between active compounds and potential targets were investigated through molecular docking, molecular dynamic simulation, and binding free energy analysis. The results showed that a total of 12 iridoid glycosides were identified as the active iridoid glycosides of Eucommia ulmoides Oliver in the treatment of osteoporosis. Among them, aucubin, reptoside, geniposide and ajugoside were the core compounds. The enrichment analysis suggested iridoid glycosides of Eucommia ulmoides Oliver prevented osteoporosis mainly through PI3K-Akt signaling pathway, MAPK signaling pathway and Estrogen signaling pathway. Molecular docking results indicated that the 12 iridoid glycosides had good binding ability with 25 hub target proteins, which played a critical role in the treatment of osteoporosis. Molecular dynamic and molecular mechanics Poisson-Boltzmann surface area results revealed these compounds showed stable binding to the active sites of the target proteins during the simulations. In conclusion, our research demonstrated that iridoid glycosides of Eucommia ulmoides Oliver in the treatment of osteoporosis involved a multi-component, multi-target and multi-pathway mechanism, which provided new suggestions and theoretical support for treating osteoporosis.

Project description:ObjectiveTo investigate the pharmacological mechanism of the iridoid glycosides from Fructus Gardeniae in Jiangxi province by network pharmacology. To provide a valuable research strategy for the rational use and in-depth research and development of Fructus Gardeniae from Jiangxi.MethodPrevious research results of our group show that the contents of iridoid glycosides in Fructus Gardeniae from Jiangxi province have a significant difference compared with other regions (P < 0.05). Based on our previous experimental results, this study selected six characteristic high-content bioactive iridoid glycosides components of Fructus Gardeniae from Jiangxi province as candidate components. TCMSP database was used to obtain the process parameters of absorption, distribution, metabolism, and excretion (ADME) of candidate components. PubChem and SWISS online database were used to predict the related targets. Cytoscape software was used to the construct compound-target-disease (C-T-D) network of the Fructus Gardeniae iridoid glycosides ingredients. Furthermore, the GO biological process analysis and the pathway enrichment analysis were carried out using the CTD online analysis platform; then, an illustrated network that contains the main "chemicals-targets-pathway (C-T-P)" was constructed to analyze main biological pathways for obtaining the deep mechanism of Fructus Gardeniae in Jiangxi.Results6 iridoid glycosides, namely geniposide, gardenoside, geniposidic acid, genipin 1-gentiobioside, gardoside, and shanzhiside, from Fructus Gardeniae in Jiangxi province were obtained as candidate components through previous work and network pharmacology screening. 36 corresponding targets were acted, such as BCL2, MAPT, F2, BCL2L1, PRKCD, PRKCB, HIF1A, and PRKCA. These targets could joint in pathways, such as signaling by GPCR, neuroactive ligand-receptor interaction, inflammatory mediator regulation of TRP channels, and ion channel transport. Interestingly, these pathways were highly associated with liver diseases, neurological diseases, hypertension, neoplasms, hyperalgesia, and inflammation. Remarkably, we boldly speculate that the Fructus Gardeniae from Jiangxi province can play a pharmacological role in hepatic encephalopathy through regulating multiple signaling pathways in an integrated manner.ConclusionThe method based on system pharmacology could help to find the key targets of characteristic high-content chemical constituents of herb from different producing areas, the signaling pathway and disease network of TCM, and provide useful information and data support for giving a further study on traditional Chinese medicine resources in different regions of China.

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Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides.

Publications

Study on the chemical reactivity difference of primary hydroxyl groups in iridoid glycosides.

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