Salicylic Acid Derivatives and Other Components from Gaultheria trichoclada

Xu, Guanling; Liu, Z. Z.; Xie, Meng; Zhang, X.; Yang, Yue; Chen, Yan; Qiao, Wen-Lin; Liu, W. R.; Jiang, Rui; Wang, X. H.; She, Gaimei

doi:10.1007/s10600-016-1621-8

Cited by 9 publications

(9 citation statements)

References 12 publications

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“…Peak 19 with a [M-H] − ion at m / z = 461.07294 was identified as luteolin 7-glucuronide according to characterized fragmentation. From Chinese G. trichocada , one luteolin derivative (luteolin-7- O - β -D-glucoside) was isolated and characterized [ 39 ]. Peak 23 was identified as procyanidin B-type dimer (C 27 H 45 O 13 − ), previously detected on Chilean Gaultheria [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…Peak 5 was identified as the 1- O -protocatechuyl-beta-xylose: uralenneoside (C 12 H 13 O 8 − ) [ 43 ]. Peak 6 (λ max 325 nm) showed a deprotonated molecule at m / z = 353.08804, an adduct ion at m / z = 707.18433 ([2M − H] − ), and daughter ion at m / z = 191.05592 (quinic acid), and thus was tentatively identified as chlorogenic acid (C 16 H 17 O 9 − ), previously isolated from G. trichocada [ 39 ]. Peak 7 showed a [M-H] − ion at m / z = 417.08307 with a daughter ion at m / z = 163.03966 (loss of glucose) and m / z = 119.04950 (decarboxylated coumaric acid), and was identified tentatively as coumaric acid glucoside [ 44 , 45 ].…”

Section: Resultsmentioning

confidence: 99%

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UHPLC-MS Chemical Fingerprinting and Antioxidant, Antiproliferative, and Enzyme Inhibition Potential of Gaultheria pumila Berries

Fernández-Galleguillos

Quesada-Romero

Puerta

et al. 2021

Metabolites

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Gaultheria pumila (Ericaceae) (known as Chaura or Mutilla) is a Chilean native small shrub that produces berry fruits consumed by local Mapuche people. In this study, the chemical fingerprinting and antioxidant, enzyme inhibition, and antiproliferative activities of the berries were investigated for the first time. Thirty-six metabolites were identified in the fruits by ultra-high performance liquid chromatography-photodiode array detection, hyphenated with Orbitrap mass spectrometry analysis (UHPLC-DAD-Orbitrap-MS). Metabolites, included anthocyanins, phenolic acids, flavonoids, iridoids, diterpenes, and fatty acids. Moderate inhibitory activities against acetylcholinesterase (7.7 ± 0.3 µg/mL), butyrylcholinesterase (34.5 ± 0.5 µg/mL), and tyrosinase (3.3 ± 0.2 µg/mL) enzymes were found. Moreover, selected major compounds were subjected to docking assays in light of their experimental inhibition. Results indicated that hydrogen bonding, π–π interaction, and a salt bridge interaction contributed significantly. Gaultheria pumila berries showed a total phenolic content of 189.2 ± 0.2 mg of gallic acid equivalents/g, total flavonoid content of 51.8 ± 0.1 mg quercetin equivalents/g, and total anthocyanin content of 47.3 ± 0.2 mg of cianydin-3-glucoside equivalents/g. Antioxidant activity was assessed using DPPH (92.8 ± 0.1 µg/mL), FRAP (134.1 ± 0.1 μmol Trolox equivalents/g), and ORAC (4251.6 ± 16.9 μmol Trolox equivalents/g) assays. Conversely, Gaultheria pumila showed a scarce antiproliferative potential against several solid human cancer cells. Our findings suggest that Gaultheria pumila berries have several bioactive metabolites with inhibitory effects against acetylcholinesterase, butyrylcholinesterase, and tyrosinase, and have the potential for use in food supplements.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

UHPLC-MS Chemical Fingerprinting and Antioxidant, Antiproliferative, and Enzyme Inhibition Potential of Gaultheria pumila Berries

Fernández-Galleguillos

Quesada-Romero

Puerta

et al. 2021

Metabolites

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“…Other polyphenols such as gallic acid, ellagic acid, and their derivatives were identified mainly in Poincianella pluviosa ( 13 ) extract. These compounds have been described with well‐documented anti‐inflammatory activity with different mechanisms 41–45 . An overview of all phenolic compounds identified in our work shows that there were fewer and lower concentrations in Peltophorum dubium ( 35 ).…”

Section: Resultsmentioning

confidence: 67%

In vivo anti‐inflammatory activity of Fabaceae species extracts screened by a new ex vivo assay using human whole blood

Rosa

Domingos

Salem

et al. 2021

Phytochemical Analysis

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Introduction Plants have been considered a promising source for discovering new compounds with pharmacological activities. The Fabaceae family comprises a large variety of species that produce substances with diverse therapeutic potential, including anti‐inflammatory activity. The limitations of current anti‐inflammatories generate the need to research new anti‐inflammatory structures with higher efficacy as well as develop methods for screening multiple samples, reliably and ethically, to assess such therapeutic properties. Objective Validate and apply a quantification method for prostaglandin E2 (PGE2) production from an ex vivo assay in human blood in order to screen anti‐inflammatory activity present in many Fabaceae species extracts. Methods Human blood was incubated with extracts from 47 Fabaceae species. After lipopolysaccharide (LPS)‐induced inflammation, PGE2 was quantified in the plasma by liquid chromatography with tandem mass spectrometry (LC–MS/MS). The extracts that presented PGE2 production inhibition were further assessed through in vivo assay and then chemically characterised through an analysis of ultra‐performance liquid chromatography electrospray ionisation quadrupole time‐of‐flight tandem mass spectrometry (UPLC‐ESI‐QTOF‐MS2) data. Results The new ex vivo anti‐inflammatory assay showed that five out of the 47 Fabaceae species inhibited PGE2 production. Results from an in vivo assay and the metabolic profile of the active extracts supported the anti‐inflammatory potential of four species. Conclusion The quantification method for PGE2 demonstrated fast, sensitive, precise, and accurate results. The new ex vivo anti‐inflammatory assay comprised a great, reliable, and ethical approach for the screening of a large number of samples before an in vivo bioassay. Additionally, the four active extracts in both ex vivo and in vivo assays may be useful for the development of more efficient anti‐inflammatory drugs.

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“…yunnanensis [13]. Phenolic acids, flavonoids, terpenoids, lignans, methyl salicylate glycosides and other salicylic acid derivatives were also found in G. trichoclada [14]. The salicylic acid derivatives (including methyl salicylate glycosides and methyl salicylate) are widely believed to have a marked anti-inflammatory effect.…”

Section: Different Polarity Fractions Of the G Leucocarpa Var Yunnamentioning

confidence: 99%

“…As mentioned above, chemical constituents and anti-inflammatory activities of Dianbaizhu have been reported [2b, [10][11][12][13][14], but the species and plant parts of Dianbaizhu used in clinical application have no scientific basis. To illuminate its role in folkloric use and to determine the optimal material for clinical use, the current study was performed to investigate the anti-inflammatory effect of the mainstream species, G. leucocarpa var.…”

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confidence: 99%

The Anti-Rheumatoid Arthritis Property of the Folk Medicine Dianbaizhu (Gaultheria leucocarpa var. yunnanensis, Ericaceae)

Xie

Chen

et al. 2014

Natural Product Communications

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The Chinese folk medicine Dianbaizhu, consisting of Gaultheria species, is widely used for the treatment of rheumatoid arthritis by several minority nationalities. The species and plant parts of this genus used as Dianbaizhu in clinical application are confused. In order to elucidate the species and the medicinal parts, as well as to ascertain the effective components and the probable optimal source of Dianbaizhu, the different plant parts and polarity fractions of its mainstream species, G. leucocarpa var. yunnanensis were investigated. The inhibition of nitric oxide and tumor necrosis factor produced in macrophage J774 were used to assess the anti-inflammatory effect of those samples. G. leucocarpa var. yunnanensis may be the preferred species for anti-RA effect. The underground parts of this taxon showed the best anti-inflammatory and anti-RA activities; the n-butanol and water fractions of the underground parts may be the most anti-RA active.

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Salicylic Acid Derivatives and Other Components from Gaultheria trichoclada

Cited by 9 publications

References 12 publications

UHPLC-MS Chemical Fingerprinting and Antioxidant, Antiproliferative, and Enzyme Inhibition Potential of Gaultheria pumila Berries

UHPLC-MS Chemical Fingerprinting and Antioxidant, Antiproliferative, and Enzyme Inhibition Potential of Gaultheria pumila Berries

In vivo anti‐inflammatory activity of Fabaceae species extracts screened by a new ex vivo assay using human whole blood

The Anti-Rheumatoid Arthritis Property of the Folk Medicine Dianbaizhu (Gaultheria leucocarpa var. yunnanensis, Ericaceae)

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