Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation

Hwang, Joo Tae; Kim, Yesol; Jang, Hyun‐Jae; Oh, Hyun-Mee; Lim, Chi-Hwan; Lee, Seung Woong; Rho, Mun‐Chual

doi:10.3390/molecules21070865

Cited by 29 publications

(19 citation statements)

References 28 publications

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“…Moreover, compound 49 exhibited a similar UV/VIS spectrum (λ max at 220, 280, 323 nm) and fragmentation pattern to compound 47 ( m / z 297, 178, 135) and differed from compound 47 by 30 Da, which could result from methoxylation. Based on the fragmentation ions and reference [17] compound 49 was tentatively assigned as N -feruloylmethoxytyramine, observed in the studied plants for the first time.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

et al. 2019

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The rhizome of Reynoutria japonica is a well-known traditional herb (Hu zhang) used in East Asia to treat various inflammatory diseases, infections, skin diseases, scald, and hyperlipidemia. It is also one of the richest natural sources of resveratrol. Although, it has been recently included in the European Pharmacopoeia, in Europe it is still an untapped resource. Some of the therapeutic effects are likely to be influenced by its antioxidant properties and this in turn is frequently associated with a high stilbene content. However, compounds other than stilbenes may add to the total antioxidant capacity. Hence, the aim of this research was to examine rhizomes of R. japonica and the less studied but morphologically similar species, R. sachalinensis and R. x bohemica for their phytochemical composition and antioxidant activity and to clarify the relationship between the antioxidant activity and the components by statistical methods. HPLC/UV/ESI-MS studies of three Reynoutria species revealed 171 compounds, comprising stilbenes, carbohydrates, procyanidins, flavan-3-ols, anthraquinones, phenylpropanoids, lignin oligomers, hydroxycinnamic acids, naphthalenes and their derivatives. Our studies confirmed the presence of procyanidins with high degree of polymerization, up to decamers, in the rhizomes of R. japonica and provides new data on the presence of these compounds in other Reynoutria species. A procyanidin trimer digallate was described for the first time in, the studied plants. Moreover, we tentatively identified dianthrone glycosides new for these species and previously unrecorded phenylpropanoid disaccharide esters and hydroxycinnamic acid derivatives. Furthermore, compounds tentatively annotated as lignin oligomers were observed for the first time in the studied species. The rhizomes of all Reynoutria species exhibited strong antioxidant activity. Statistical analysis demonstrated that proanthocyanidins should be considered as important contributors to the total antioxidant capacity.

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Section: Resultsmentioning

confidence: 99%

Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

et al. 2019

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“…The structures of the isolated compounds were identified by spectroscopic data acquired using 1 H NMR, 13 C NMR, 1 H- 1 H correlated spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), heteronuclear multiple quantum correlation (HMQC), high resolution electrospray ionization mass spectrometry (HRESIMS), infrared (IR) spectroscopy, and polarimetry techniques. By comparing the NMR data of the isolated compounds with data reported in the literature, the known compounds were identified as trans-N -courmaroyltyramine ( 1 ) [19], trans-N- feruloyloctopamine ( 2 ) [20], trans-N- feruloyltyramine ( 3 ) [19], (7’ S )- trans - N -feruloyloctopamine ( 4 ) [21], ( S )-3-(4-hydroxy-3-methoxyphenyl)- N -(2-(4-hydroxyphenyl)-2-methoxyethyl)-acrylamide ( 5 ) [22], trans - N -feruloyl-3’-methoxytyramine ( 6 ) [21], (7’S)- trans - N -feruloylnormetanephrine ( 7 ) [21], N - trans -hibiscusamide ( 9 ) [21], perillascens ( 10 ) [23], aurantiamide acetate ( 11 ) [24], methyl N -acetylphenylalaninate ( 12 ) [25], N -benzoyl- l -aspartic acid dimethyl ester ( 13 ) [26], N -benzoyl- d -aspartic acid dimethyl ester ( 14 ) [26], scinamide C ( 15 ) [27], oleracein E ( 16 ) [28], methyl hematinate ( 17 ) [29], 3-formylindole ( 18 ) [30], 3-propionylindole ( 19 ) [30], 1-carbomethoxy-beta-carboline ( 20 ) [11], methyl pyroglutamate ( 21 ) [31], and ethyl pyroglutamate ( 22 ) [32].…”

Section: Resultsmentioning

confidence: 99%

1-Carbomethoxy-β-Carboline, Derived from Portulaca oleracea L., Ameliorates LPS-Mediated Inflammatory Response Associated with MAPK Signaling and Nuclear Translocation of NF-κB

Kim¹,

Park

Jang³

et al. 2019

Molecules

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Portulaca oleracea is as a medicinal plant known for its neuroprotective, hepatoprotective, antidiabetic, antioxidant, anticancer, antimicrobial, antiulcerogenic, and anti-inflammatory activities. However, the specific active compounds responsible for the individual pharmacological effects of P. oleracea extract (95% EtOH) remain unknown. Here, we hypothesized that alkaloids, the most abundant constituents in P. oleracea extract, are responsible for its anti-inflammatory activity. We investigated the phytochemical substituents (compounds 1–22) using nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) and screened their effects on NO production in lipopolysaccharide (LPS)-induced macrophages. Compound 20, 1-carbomethoxy-β-carboline, as an alkaloid structure, ameliorated nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), and proinflammatory cytokines associated with the mitogen-activated protein kinase (MAPK) pathways, p38, extracellular signal-regulated kinase (ERK), and c-Jun N-terminal kinase (JNK). Subsequently, we observed that compound 20 suppressed nuclear translocation of nuclear factor κB (NF-κB) using immunocytochemistry. Moreover, we recently reported that compound 8, trans-N-feruloyl-3’, 7’-dimethoxytyramine, was originally purified from P. oleracea extracts. Our results suggest that 1-carbomethoxy-β-carboline, the most effective anti-inflammatory agent among alkaloids in the 95% EtOH extract of P. oleracea, was suppressing the MAPK pathway and nuclear translocation of NF-κB. Therefore, P. oleracea extracts and specifically 1-carbomethoxy-β-carboline may be novel therapeutic candidates for the treatment of inflammatory diseases associated with the activation of MAPKs and NF-κB.

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“…Of these, the chloroform fraction was purified using silica gel and C-18 column chromatographies to yield the two compounds 1 and 2 . The chemical structures of N - trans -coumaroyltyramine ( 1 ) [ 15 ] and N - trans -feruloyltyramine ( 2 ) [ 16 ] were elucidated by analyzing the signals of ESI-Ms and 1 H NMR spectrophotometers and by comparison with reported data.…”

Section: Resultsmentioning

confidence: 99%

In Vitro and In Silico Insights into sEH Inhibitors with Amide-Scaffold from the Leaves of Capsicum chinense Jacq.

Kim

et al. 2018

Computational and Structural Biotechnology Journal

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Two compounds termed 1 and 2 were isolated from the leaves of Capsicum chinense using column chromatography. Their structures were identified as amide scaffolds by analyzing spectroscopic signals. Compounds 1 and 2 have been confirmed to be competitive soluble epoxide hydrolase (sEH) inhibitors that suppress the catalytic reaction of sEH in a dose-dependent manner in vitro. Molecular docking was used for analyzing two binding clusters of ligand and receptor. The results confirmed that the key amino acids interacting with the ligand were Asp335, Tyr383, and Gln384. On the basis of molecular dynamics, inhibitors 1 and 2 were noted to interact at a distance of 3.5 Å from Asp335, Tyr383, Leu408 and Tyr466, and Asp335, Tyr383, and Tyr466, respectively. These results highlight the potential of N-trans-coumaroyltyramine (1) and N-trans-feruloyltyramine (2) as sEH inhibitors.

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Study of the UV Light Conversion of Feruloyl Amides from Portulaca oleracea and Their Inhibitory Effect on IL-6-Induced STAT3 Activation

Cited by 29 publications

References 28 publications

Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

1-Carbomethoxy-β-Carboline, Derived from Portulaca oleracea L., Ameliorates LPS-Mediated Inflammatory Response Associated with MAPK Signaling and Nuclear Translocation of NF-κB

In Vitro and In Silico Insights into sEH Inhibitors with Amide-Scaffold from the Leaves of Capsicum chinense Jacq.

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