The chemical constituents of Gentiana macrophylla pall. under acidic condition using gentiopicroside-rich secoiridoids extract

Huang, Rong; Hu, Wenyi; Hou, Shu-Bing; Zhao, Huan; Wang, Xin; Chen, Guang

doi:10.1016/j.phytol.2020.07.004

Cited by 8 publications

(3 citation statements)

References 20 publications

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“…This method is an evolution of traditional phytochemical practices involving the acidic hydrolysis of NPs during extraction, especially aiming to convert glycosides into their aglycone forms, consequently enhancing the proportion of phenolic compounds and impacting the antioxidant potency of the extract. [34][35][36][37][38][39] In addition, it arises from frequent observations of unintended artefactual reactions occurring with extraction solvents, typically alcohols or ethanol-stabilized chloroform. [25,26] Hence, research projects have drawn inspiration from these legacy findings by applying acylation, ethanolysis, oxidation, or reduction conditions to extracts, while others have focused on introducing more heteroatoms into natural chemical structures, as seen in sulfonylation or nitrogen enrichment endeavours.…”

Section: Minor Substitutions or Alterationsmentioning

confidence: 99%

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Beato,

Haudecoeur,

Boucherle

et al. 2024

Chemistry A European J

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The realms of natural products and synthetic compounds exhibit distinct chemical spaces that not only differ but also complement each other. While the convergence of these two domains has been explored through hemisynthesis and conventional pharmacomodulation endeavours applied to natural frameworks, a recent and innovative approach has recently emerged that involves the combinatorial generation of libraries of ‘natural product‐like compounds’ (NPLCs) through the direct synthetic derivatization of natural extracts. This has led to the production of numerous NPLCs that incorporate structural elements from both their natural (multiple saturated rings, oxygen content, chiral centres) and synthetic (aromatic rings, nitrogen and halogen content, drug‐like properties) precursors. Through careful selection of extracts and reagents, specific bioactivities have been achieved, and this strategy has been deployed in various ways, showing great promise without reaching its full potential to date. This review seeks to provide an overview of reported examples involving the chemical engineering of extracts, showcasing a spectrum of natural product alterations spanning from simple substitutions to complete scaffold remodelling. It also includes an analysis of the accomplishments, perspectives and technical challenges within this field.

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Section: Minor Substitutions or Alterationsmentioning

confidence: 99%

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Beato,

Haudecoeur,

Boucherle

et al. 2024

Chemistry A European J

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“…DMY can reduce hepatic steatosis and inflammation response in the pathological process of AFLD in male C57BL/6 mice (Qiu et al, 2017). The Gentianae macrophyllae root extract (GME) was the main source of gentiopicroside and swertiamarin (Huang R. et al, 2020). These two secoiridoid compounds have been shown to prevent and improve cellular inflammatory responses in rats (Saravanan et al, 2014;Zhao et al, 2015).…”

Section: Afld Effectorsmentioning

confidence: 99%

Similarities and Differences: A Comparative Review of the Molecular Mechanisms and Effectors of NAFLD and AFLD

et al. 2021

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Non-alcoholic fatty liver disease (NAFLD) and alcoholic fatty liver disease (AFLD) are the most prevalent metabolic liver diseases globally. Due to the complex pathogenic mechanisms of NAFLD and AFLD, no specific drugs were approved at present. Lipid accumulation, oxidative stress, insulin resistance, inflammation, and dietary habits are all closely related to the pathogenesis of NAFLD and AFLD. However, the mechanism that promotes disease progression has not been fully elucidated. Meanwhile, the gut microbiota and their metabolites also play an important role in the pathogenesis and development of NAFLD and AFLD. This article comparatively reviewed the shared and specific signaling pathways, clinical trials, and potential intervention effectors of NAFLD and AFLD, revealing their similarities and differences. By comparing the shared and specific molecular regulatory mechanisms, this paper provides mutual reference strategies for preventing and treating NAFLD, AFLD, and related metabolic diseases. Furthermore, it provides enlightenment for discovering novel therapies of safe and effective drugs targeting the metabolic liver disease.

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“…Phytochemical studies of G. macrophylla [ 7 ] demonstrated the existence of iridoids [ 8 , 9 , 10 , 11 ], flavonoids [ 12 , 13 ], lignans [ 14 ], triterpenoids [ 15 , 16 ], and other constituents [ 8 , 17 , 18 ]. Among these constituents, the main component iridoid gentiopicroside exhibited anti-rheumatic arthritis effect [ 19 , 20 ] and anti-inflammation in rat articular chondrocyte [ 21 ], as well as protective effects on liver injury [ 22 ], gastric mucosal injury [ 23 ], and neuron injury [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Terpenoid Glucosides from Gentiana macrophylla That Attenuate TNF-α Induced Pulmonary Inflammation in A549 Cells

Huang,

Luo,

Zhang

et al. 2023

Molecules

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Four previously undescribed terpenoid glucosides, including one sesquiterpenoid di-glucoside (1), two new iridoid glucosides (2, 3), and a new triterpenoid tri-glucoside (4), were isolated from a 70% ethanol extract of the root of Gentiana macrophylla (Gentianaceae), along with eight known terpenoids. Their structures were determined by spectroscopic techniques, including 1D, 2D NMR, and HRMS (ESI), as well as chemical methods. The absolute configuration of compound 1 was determined by quantum chemical calculation of its theoretical electronic circular dichroism (ECD) spectrum. The sugar moieties of all the new compounds were confirmed to be D-glucose by GC analysis after acid hydrolysis and acetylation. Anti-pulmonary inflammation activity of the iridoids were evaluated on a TNF-α induced inflammation model in A549 cells. Compound 2 could significantly alleviate the release of proinflammatory cytokines IL-1β and IL-8 and increase the expression of anti-inflammatory cytokine IL-10.

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The chemical constituents of Gentiana macrophylla pall. under acidic condition using gentiopicroside-rich secoiridoids extract

Cited by 8 publications

References 20 publications

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Expanding Chemical Frontiers: Approaches for Generating Diverse and Bioactive Natural Product‐Like Compounds Libraries from Extracts

Similarities and Differences: A Comparative Review of the Molecular Mechanisms and Effectors of NAFLD and AFLD

Terpenoid Glucosides from Gentiana macrophylla That Attenuate TNF-α Induced Pulmonary Inflammation in A549 Cells

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