New Caffeoylquinic Acid Derivatives and Flavanone Glycoside from the Flowers of Chrysanthemum morifolium and Their Bioactivities

Yang, Pengfei; Yang, Yanan; He, Chao; Chen, Zhifei; Yuan, Qishan; Zhao, Sheng-Chen; Fu, Yufeng; Zhang, Pei‐Cheng; Mao, Duobin

doi:10.3390/molecules24050850

Cited by 16 publications

(17 citation statements)

References 23 publications

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“…The proposed biosynthetic pathway suggested that the unusual compounds ( 55 – 57 ) were formed via the [5 + 2] cycloaddition of 3,4-DCQA ( 69 ) and 4,5-DCQA ( 75 ) with oxypyrylium. In another report, compounds 58 and 59 (Figure ) were isolated and characterized by the same group and were shown to exhibit a moderate neuroprotective effect against hydrogen peroxide (H 2 O 2 )-induced cell injury in SH-SY5Y cells, ranging from 57.19 to 59.57% at 10 μM. Research on the chemical constituents of the flower buds of L.…”

Section: Structural Variety Of Natural Cqasmentioning

confidence: 99%

“…To the best of our knowledge, this report isolated monoterpene-acid-acylated CQAs for the first time. Furthermore, compound 3,5-DCQA (71) showed significant monoamine oxidase B (MAOB) inhibitory activity, with IC 50 values of 20.04 μM.…”

Section: Monocaffeoylquinic Acids (Mcqas)mentioning

confidence: 99%

“…The proposed biosynthetic pathway suggested that the unusual compounds (55−57) were formed via the [5 + 2] cycloaddition of 3,4-DCQA (69) and 4,5-DCQA (75) with oxypyrylium. In another report, 71 compounds 58 and 59 (Figure 6) were isolated and characterized by the same group and were shown to exhibit a moderate neuroprotective effect against hydrogen peroxide 6). Importantly, compound 62 showed significant anti-human hepatitis B virus (HBV) activity, which was better than that of compounds 60 and 61 (clear values not shown).…”

Section: Monocaffeoylquinic Acids (Mcqas)mentioning

confidence: 99%

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Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidence demonstrate that CQAs have a wide range of biological activities, such as antioxidation, antibacterial, antiparasitic, neuroprotective, anti-inflammatory, anticancer, antiviral, and antidiabetic effects. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis, and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis), and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents.

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Section: Structural Variety Of Natural Cqasmentioning

confidence: 99%

Section: Monocaffeoylquinic Acids (Mcqas)mentioning

confidence: 99%

Section: Monocaffeoylquinic Acids (Mcqas)mentioning

confidence: 99%

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Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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“…Flavonoids are the major compounds in chrysanthemum and are responsible for their colorful appearance. Most of them are luteolin, apigenin, acacetin, diosmetin, or their glycosidic derivatives [ 5 , 6 ]. Many analytical technologies have been applied for quality control of Chrysanthemum.…”

Section: Introductionmentioning

confidence: 99%

Hypolipidemic Effects and Preliminary Mechanism of Chrysanthemum Flavonoids, Its Main Components Luteolin and Luteoloside in Hyperlipidemia Rats

et al. 2021

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This study aimed to investigate the key constituents and preliminary mechanism for the hypolipidemic activity of chrysanthemum flavonoids. Hyperlipidemia (HPL) rats were divided into five groups: the model control group (MC); Chrysanthemum flavone intervention group (CF); luteolin intervention group; luteoloside intervention group and simvastatin intervention group. The body weight, organ coefficient, serum lipids, antioxidant activity, and lipid metabolism enzymes were detected. Hematoxylin and eosin (H&E) staining was used to observe the liver and adipose tissue. Chrysanthemum flavonoids, luteolin, and luteoloside can reduce the weight and levels of total cholesterol (TC), triglycerides (TG), and LDL-C, and increase the level of HDL-C in the blood and reduce liver steatosis. Indicators of liver function (AST, ALT, and ALP) improved. The antioxidant activity (GSH-Px, CAT, SOD) and enzymes associated with lipid catabolism (FAβO, CYP7A1, and HL) increased, while lipid peroxidation products (MDA) and enzymes associated with lipid synthesis (FAS, HMG-CoA, and DGAT) decreased. Chrysanthemum flavonoids had a better effect on the antioxidant level and lipid metabolism-related enzyme activity. There was no significant difference in the effects of the chrysanthemum flavonoids, luteolin, and Luteoloside on improving blood lipids and hepatic steatosis—mechanisms that may be related to antioxidant levels and regulating enzymes involved in the metabolism of fatty acids, cholesterol, and triglycerides in the liver. However, chrysanthemum flavonoids had a stronger antioxidant and lipid metabolism regulation ability, and the long-term effects may be better.

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“…Glycosides include some flavonoids and secondary metabolites in plants ( Figure 1 ). The bioactivity of many glycosides has been demonstrated, and traditional use of these compounds has been reported [ 75 , 76 , 77 ]. Additionally, the effect of glycosides against osteoarthritis were reported, with representative glycosides described below.…”

Section: Candidate Therapeutic Agentsmentioning

confidence: 99%

Therapeutic Single Compounds for Osteoarthritis Treatment

et al. 2021

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Osteoarthritis (OA) is an age-related degenerative disease for which an effective disease-modifying therapy is not available. Natural compounds derived from plants have been traditionally used in the clinic to treat OA. Over the years, many studies have explored the treatment of OA using natural extracts. Although various active natural extracts with broad application prospects have been discovered, single compounds are more important for clinical trials than total natural extracts. Moreover, although natural extracts exhibit minimal safety issues, the cytotoxicity and function of all single compounds in a total extract remain unclear. Therefore, understanding single compounds with the ability to inhibit catabolic factor expression is essential for developing therapeutic agents for OA. This review describes effective single compounds recently obtained from natural extracts and the possibility of developing therapeutic agents against OA using these compounds.

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New Caffeoylquinic Acid Derivatives and Flavanone Glycoside from the Flowers of Chrysanthemum morifolium and Their Bioactivities

Cited by 16 publications

References 23 publications

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Hypolipidemic Effects and Preliminary Mechanism of Chrysanthemum Flavonoids, Its Main Components Luteolin and Luteoloside in Hyperlipidemia Rats

Therapeutic Single Compounds for Osteoarthritis Treatment

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