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The discovery of new phloroglucinol glycosides from Agrimonia pilosa and the mechanism of oxidative dearomatization of the methyl-substituted phloroglucinol derivatives.

ABSTRACT: Six methyl-substituted phloroglucinol glycosides (1-6) were isolated from Agrimonia pilosa, including four new compounds (1-3, 6). The aglycones (1a-4a) of 1-4 and their corresponding oxidized products (1c-4c) were also obtained from A. pilosa. The structures were determined by a series of spectroscopic analyses and chiral separation. Notably, the structures of aglycones 1a-4a were unstable and prone to oxidation spontaneously, to yield the dearomatized structures 1c-4c. The mechanism of oxidative dearomatization was disclosed as a free-radical chain reaction with ³O₂ by the techniques of HPLC-HR-MS², EPR spectra and DFT-calculation, and hydroperoxide was defined as the intermediate.

SUBMITTER: Zhang J

PROVIDER: S-EPMC9034183 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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The discovery of new phloroglucinol glycosides from Agrimonia pilosa and the mechanism of oxidative dearomatization of the methyl-substituted phloroglucinol derivatives.

Zhang Jia J Yang Ya-Nan YN Jiang Jian-Shuang JS Feng Zi-Ming ZM Yuan Xiang X Zhang Xu X Zhang Pei-Cheng PC

RSC advances 20210624 36

Six methyl-substituted phloroglucinol glycosides (1-6) were isolated from Agrimonia pilosa, including four new compounds (1-3, 6). The aglycones (1a-4a) of 1-4 and their corresponding oxidized products (1c-4c) were also obtained from A. pilosa. The structures were determined by a series of spectroscopic analyses and chiral separation. Notably, the structures of aglycones 1a-4a were unstable and prone to oxidation spontaneously, to yield the dearomatized structures 1c-4c. The mechan ...[more]

PMID: 35480819

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Project description:BackgroundResearches and practice of traditional Chinese medicine indicated that Agrimonia pilosa Ledeb could improve insulin resistance (IR) and treat type 2 diabetes (T2DM). To reveal its underling mechanisms, we isolated Flavonoid component (FC) from Agrimonia pilosa Ledeb and elucidated its effects on glucose metabolism to improve IR by suppressing oxidative stress and inflammation.MethodsAdipocytes or mice IR model was established with overdosed glucose and insulin or high-fat diet. The uptake of 2-NBDG and glucose consumption were measured to verify insulin sensitivity in vitro and vivo. Reactive oxidative species (ROS) were detected by flow cytometry, and superoxide dismutase (SOD) activity as well as the malondialdehyde (MDA) content were also measured. Meanwhile, factors associated with insulin signal pathway including PPARγ, insulin receptor substrate-1 (IRS-1), GLUT4, and oxidative stress including NF-E2-related factor 2 (Nrf2), as well as the related inflammatory cytokines such as NF-κB, IL-1β, IL-6 and TNF-α were tested. Furthermore, the JNK/PI3K/Akt signal pathway was also explored.ResultsFC extracted from Agrimonia pilosa Ledeb ameliorated the impaired glucose metabolism significantly. Further study indicated that FC could regulate the insulin signal pathway to improve insulin resistance. Moreover, it could upregulate PPARγ with the similar efficacy as pioglitazone (Piog) straightway. FC also decreased the endogenous ROS and MDA content, increased SOD activity and Nrf2 expression to facilitate oxidative homeostasis. It attenuated expression and secretion of inflammatory cytokines obviously. At last, our results indicated JNK/PI3K/Akt pathway was regulated by FC in adipocytes and adipose tissue.ConclusionFC could ameliorate glucose metabolism and improve IR. It exerted these effects by suppressing oxidative stress and inflammation. FC from Agrimonia pilosa Ledeb has a good prospect to be drugs or functional foods for IR and T2DM.

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The discovery of new phloroglucinol glycosides from Agrimonia pilosa and the mechanism of oxidative dearomatization of the methyl-substituted phloroglucinol derivatives.

Publications

The discovery of new phloroglucinol glycosides from <i>Agrimonia pilosa</i> and the mechanism of oxidative dearomatization of the methyl-substituted phloroglucinol derivatives.

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