Identification of secondary metabolites in Averrhoa carambola L. bark by high-resolution mass spectrometry and evaluation for α-glucosidase, tyrosinase, elastase, and antioxidant potential

Islam, Syful; Alam, Badrul; Ahmed, Arif; Lee, Seulgidaun; Lee, Sang‐Han; Kim, Sungjune

doi:10.1016/j.foodchem.2020.127377

Cited by 28 publications

(26 citation statements)

References 37 publications

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“…Compounds 33, 35, 36, and 37 with quasi-molecular ions [M-H] − at m/z 129.0916, 143.1061, 195.1384, and 199.1697, were identified as fatty acids including methylcaproic acid, caprylic acid, dodecadienoic acid, and dodecanoic acid, respectively, by comparison with the literature [ 2 , 11 , 12 ].…”

Section: Resultsmentioning

confidence: 99%

“…Compound 40, 41, and 42 with monoisotopic mass ions [M-H] − at m/z 125.0227, 139.0213, and 231.1748 were identified as the flavoring agents, maltol, kahweofuran, and cetone V, respectively, based on the literature [ 2 , 11 , 12 ] and compared with data from the METLIN database ( , accessed date 2 April 2021) and FooDB ( , accessed date 2 April 2021). Compounds 43, 44, and 45 yielded precursor ion peaks [M-H] − at m/z 149.0445, 179.0553, and 341.1087 and were confirmed as the sugar compounds L-arabinofuranose, glucose, and 6- O -β-D-galactopyranosyl-D-galactose, respectively [ 2 , 12 ].…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 43, 44, and 45 yielded precursor ion peaks [M-H] − at m/z 149.0445, 179.0553, and 341.1087 and were confirmed as the sugar compounds L-arabinofuranose, glucose, and 6- O -β-D-galactopyranosyl-D-galactose, respectively [ 2 , 12 ]. Based on the literature [ 2 , 11 , 12 ] and compared with data from the FooDB ( , accessed date 2 April 2021) and METLIN database ( , accessed date 2 April 2021), the precursor ion peaks [M-H] − at m/z 105.0184, 111.0443, 121.0278, 135.0444, 138.0189, 165.0395, 173.0445, 191.0553, and 242.1756, corresponding to compound 46, 47, 48, 49,50, 51, 52, 53, and 54 were identified as glyceric acid, sorbic acid, salicylaldehyde, methyl benzoic acid, hydroxynicotinic acid, ribonic acid, shikimic acid, quinic acid, and N-undecanoylglycine.…”

Section: Resultsmentioning

confidence: 99%

“…For ESI-MS/MS analysis, a stock solution (10 mg/mL) was prepared in 100% HPLC-grade ethanol and then diluted using a 70% ethanolic solution. Homogenization was carried out by vortexing for 1 min, followed by sonication for 5 min in a sonication bath (Powersonic 410, Hwashin Technology Co., Seoul, Korea) [ 11 ].…”

Section: Methodsmentioning

confidence: 99%

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High Resolution Mass Spectroscopy-Based Secondary Metabolite Profiling of Nymphaea nouchali (Burm. f) Stem Attenuates Oxidative Stress via Regulation of MAPK/Nrf2/HO-1/ROS Pathway

et al. 2021

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The secondary metabolites profiling of Nymphaea nouchali stem (NNSE) extract was carried out using a high-resolution mass spectroscopic technique. The antioxidant effects of NNSE, as well as the underlying mechanisms, were also investigated in tert-butyl hydroperoxide (t-BHP)-stimulated oxidative stress in RAW264.7 cells. Tandem mass spectroscopy with (−) negative mode tentatively revealed the presence of 54 secondary metabolites in NNSE. Among them, phenolic acids and flavonoids were predominant. Phenolic acids (brevifolincarboxylic acid, p-coumaroyltartaric acid, niazinin B, lalioside, 3-feruloylquinic acid, and gallic acid-O-rutinoside), flavonoids (elephantorrhizol, apigenin-6-C-galactoside 8-C-arabinoside, and vicenin-2), sialic acid (2-deoxy-2,3-dehydro-N-acetylneuraminic acid), and terpenoid (α-γ-onoceradienedione) were identified in NNSE for the first time. Unbridled reactive oxygen species/nitrogen species (ROS/RNS) and redox imbalances participate in the induction and development of many oxidative stress-linked diseases. The NNSE exhibited significant free radical scavenging capabilities and was also able to reduce t-BHP-induced cellular generation in RAW264.7 cells. The NNSE prevented oxidative stress by inducing the endogenous antioxidant system and the levels of heme oxygenase-1 (HO-1) by upregulating Nrf2 through the modulation of mitogen-activated protein kinases (MAPK), such as phosphorylated p38 and c-Jun N terminal kinase. Collectively, these results indicate that the NNSE exhibits potent effects in preventing oxidative stress-stimulated diseases and disorders through the modulation of the MAPK/Nrf2/HO-1 signaling pathway. Our findings provide new insights into the cytoprotective effects and mechanisms of Nymphaea nouchali stem extract against oxidative stress, which may be a useful remedy for oxidative stress-induced disorders.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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High Resolution Mass Spectroscopy-Based Secondary Metabolite Profiling of Nymphaea nouchali (Burm. f) Stem Attenuates Oxidative Stress via Regulation of MAPK/Nrf2/HO-1/ROS Pathway

et al. 2021

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“…Other phenolic compounds like ferulic acid (IC 50 10.80 ± 0.90 mg/mL) [64] and epicatechin (IC 50 5.86 µg/mL) [65] also possess α-glucosidase inhibition activity. In this study, we identified norathyriol and myricetin from ZLE using negative-mode APCI-MS which possesses a potential α-glucosidase inhibition activity with IC 50 values of 0.81 and 2.09 µg/mL, accordingly [66,67]. Therefore, it was assumed that ZLE showed a significant α-glucosidase inhibition potential due to the combined effect of these compounds.…”

Section: Discussionmentioning

confidence: 98%

Metabolite Profiling of Manilkara zapota L. Leaves by High-Resolution Mass Spectrometry Coupled with ESI and APCI and In Vitro Antioxidant Activity, α-Glucosidase, and Elastase Inhibition Assays

Islam

Alam

Ann

et al. 2020

IJMS

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High-resolution mass spectrometry equipped with electrospray ionization (ESI) and atmospheric pressure chemical ionization (APCI) sources was used to enhance the characterization of phytochemicals of ethanol extracts of Manilkara zapota L. leaves (ZLE). Sugar compounds, dicarboxylic acids, compounds of phenolic acids and flavonoids groups, and other phytochemicals were detected from the leaves. Antioxidant activity and inhibition potentiality of ZLE against α-glucosidase enzyme, and elastase enzyme activities were evaluated in in vitro analysis. ZLE significantly inhibited activities of α-glucosidase enzyme at a lower concentration (IC50 2.51 ± 0.15 µg/mL). Glucose uptake in C2C12 cells was significantly enhanced by 42.13 ± 0.15% following the treatment with ZLE at 30 µg/mL. It also exhibited potential antioxidant activities and elastase enzyme inhibition activity (IC50 27.51 ± 1.70 µg/mL). Atmospheric pressure chemical ionization mass spectrometry (APCI–MS) detected more m/z peaks than electrospray ionization mass spectrometry (ESI–MS), and both ionization techniques illustrated the biological activities of the detected compounds more thoroughly compared to single-mode analysis. Our findings suggest that APCI along with ESI is a potential ionization technique for metabolite profiling, and ZLE has the potential in managing diabetes by inhibiting α-glucosidase activity and enhancing glucose uptake.

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Averrhoa carambola L. fruit polyphenols ameliorate hyperlipidemia, hepatic steatosis, and hyperglycemia by modulating lipid and glucose metabolism in mice with obesity

et al. 2023

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BACKGROUNDHyperlipidemia, hepatic steatosis, and hyperglycemia are common metabolic complications of obesity. The objective of the present study is to investigate the in vivo protective effect of Averrhoa carambola L. fruit polyphenols (ACFP) on hyperlipidemia, hepatic steatosis, and hyperglycemia in mice with high‐fat diet (HFD)‐induced obesity and elucidate the mechanisms of action underlying the beneficial effects of ACFP. Thirty‐six specific pathogen‐free male C57BL/6J mice (4 weeks old, weighing 17.1–19.9 g) were randomly divided into three groups and fed with a low‐fat diet (LFD, 10% fat energy), HFD (45% fat energy), or HFD supplemented with ACFP by intragastric administration for 14 weeks. Obesity‐related biochemical indexes and hepatic gene expression levels were determined. The statistical analyses were conducted using one‐way analysis of variance (ANOVA) followed by Duncan's multiple range test.RESULTSThe results showed that the body weight gain, serum triglycerides, total cholesterol, glucose, insulin resistance index, and steatosis grade in the ACFP group decreased by 29.57%, 26.25%, 27.4%, 19.6%, 40.32%, and 40%, respectively, compared to the HFD group. Gene expression analysis indicated that ACFP treatment improved the gene expression profiles involved in lipid and glucose metabolism compared to the HFD group.CONCLUSIONACFP protected from HFD‐induced obesity and obesity‐associated hyperlipidemia, hepatic steatosis, and hyperglycemia by improving lipid and glucose metabolism in mice. © 2023 Society of Chemical Industry.

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Identification of secondary metabolites in Averrhoa carambola L. bark by high-resolution mass spectrometry and evaluation for α-glucosidase, tyrosinase, elastase, and antioxidant potential

Cited by 28 publications

References 37 publications

High Resolution Mass Spectroscopy-Based Secondary Metabolite Profiling of Nymphaea nouchali (Burm. f) Stem Attenuates Oxidative Stress via Regulation of MAPK/Nrf2/HO-1/ROS Pathway

High Resolution Mass Spectroscopy-Based Secondary Metabolite Profiling of Nymphaea nouchali (Burm. f) Stem Attenuates Oxidative Stress via Regulation of MAPK/Nrf2/HO-1/ROS Pathway

Metabolite Profiling of Manilkara zapota L. Leaves by High-Resolution Mass Spectrometry Coupled with ESI and APCI and In Vitro Antioxidant Activity, α-Glucosidase, and Elastase Inhibition Assays

Averrhoa carambola L. fruit polyphenols ameliorate hyperlipidemia, hepatic steatosis, and hyperglycemia by modulating lipid and glucose metabolism in mice with obesity

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