N-trans-feruloyltyramine and flavonol glycosides from the leaves of Solanum sordidum

Kanada, Regina Mikie; Simionato, Julliana Izabelle; Arruda, Rafael Ferraz de; Santin, Silvana Maria de Oliveira; Souza, Maria Conceição de; Silva, Cleuza Conceição da

doi:10.1590/s0102-695x2012005000029

Cited by 7 publications

(7 citation statements)

References 15 publications

(15 reference statements)

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“…The six alkaloids (1-6) in Fig. 1 were isolated from methanol extract of C. majus L. by chromatography over silicagel, sephadex LH-20 and octadecyl functionalized silicagel, compounds (1-6) were identified as dihydrosanguinarine (1), (s)-stylopine (2), arnottianamide (3), (+)-chelidonine (4), spallidamine (5), and N-trans-feruloyltyramine (6) by comparing their spectroscopic data of those previously reported (Ma et al, 1999;Kanada et al, 2012 C NMR data enabled carbons corresponding to the 8 C-C double bonds and 1 carbonyl group to be identified and thus accounted for 9 of 15 degrees of unsaturation. The extra six degrees of unsaturation were ascribed to six rings, three of which were aromatics.…”

Section: Resultsmentioning

confidence: 85%

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Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Kim

Lee

Song

et al. 2015

JABC

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Human neutrophil elastase (HNE) represents a good therapeutic target for the treatment of inflammatory diseases as well as invasion of microorganism. The methanol extract of a aerial part of Chelidonium majus L. showed high activity against the neutrophil elastase with an IC 50 value of 100 µg/mL. Due to its potency, subsequent bioactivity-guided fractionation of methanol extract led to six alkaloids (1-6), which were identified as dihydrosanguinarine (1), (s)-stylopine (2), arnottianamide (3), (+)-chelidonine (4), spallidamine (5), and N-transferuloyltyramine (6). Among of them, three alkaloids (2, 5, and 6) inhibited HNE in a dose-dependent manner with IC 50 ranging between 11.6 and 51.0 µM. Lineweaver-Burk and Dixon plots, and their secondary replots showed that alkaloids (2, 5, and 6) were mixed inhibitors of HNE. The analysis of K I and K IS value proved that all inhibitors (2, 5, and 6) had reversible mixed type I mechanism.

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Section: Resultsmentioning

confidence: 85%

“…Fr7 was purified by ODS column chromatography with 80% MeOH as the eluent to give spallidamine (28 mg, 5) and N-trans-feruloyltyramine (56 mg, 6). The chemical structures of these compounds were determined by comparison of their spectroscopic data with those previously reported (Ma et al, 1999;Koul et al, 2002;Kanada et al, 2012 (EC 3. 4.…”

Section: Methodsmentioning

confidence: 99%

Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Kim

Lee

Song

et al. 2015

JABC

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“…L., 43 and in Alchemilla mollis (Buser) Rothm., 44 Elaeagnus angustifolia L., and Potentilla chinensis Ser., Allium cepa L 45 . N ‐ trans ‐feruloyltyramine ( 7 ) is found in plants of genus Hibiscus , such as H. taiwanensis Hu, 46 H. tiliaceus L., 47 H. cannabinus L., 48 and other plants, such as Tinospora tuberculata Beumee, 49 Lycium barbarum L., 50 Solanum sordidum Sendtn., 51 and Portulaca oleracea L 20 . N ‐ trans ‐caffeoyltyramine ( 8 ) has been reported in several species of Annona montana Macfad., 52 Tribulus terrestris L., 21 and Lycium chinense Mill 53 .…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents from Hibiscus hamabo and their antiphotoaging effects on UVA‐induced CCD‐986sk

Park

Jang

Kim

et al. 2022

Bulletin Korean Chem Soc

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To investigate the phytochemical constituents of Hibiscus hamabo, a chromatographic method was used. A new phenolic glucoside, woodorien A (1), along with 10 known compounds, rutin (2), isoquercetin (3), nicotiflorin (4), astragalin (5), trans-tiliroside (6), N-trans-feruloyltyramine (7), N-trans-caffeoyltyramine (8), woodorien (9), quercetin 3 0 -galactopyranoside (10), and cis-tiliroside (11), was isolated. The structure of 1 was identified as ethyl 3-O-β-D -glucopyranosyl-4-hydroxybenzoate. Compounds 8, 9, and 11 were isolated from genus Hibiscus, and 2-7 and 10 were isolated from H. hamabo for the first time. Their chemical structures were determined through the interpretation of spectroscopic data. The properties of the UVA photoaging induction assay of all isolated compounds were measured. Compounds 3, 8, and 10 exhibited recovery from photoaging induced by UVA in CCD-986sk. These results suggest that H. hamabo is a potential source of natural antiphotoaging ingredients and can be used in cosmetic applications. K E Y W O R D S antiphotoaging, ethyl 3-O-β-D -glucopyranosyl-4-hydroxybenzoate, Hibiscus hamabo, phenolic glucoside, woodorien A

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“…N - trans -feruloyltyramine (NTF, Figure 1A) is an alkaloid extracted from several plants, including the stems of Polyalthia suberosa, 6 stems of Tinospora tuberculata, 7 branches of Enicosanthum membranifolium, 8 stems of Polygonum sachalinensis, 9 leaves of Solanum sordidum, 10 aerial parts of Triclisia sacleuxii , 11 seeds of Datura metel , 12 processed bulbs of Allium sativum , 13 and twigs of Celtis occidentalis . 14 Previous studies have reported that NTF is a potent antioxidant 9, 10, 12, 13, 15, 16 and exhibits other pharmacological properties such as α-glucosidase inhibition 9 and anti-tumor activity. 13 In this study, we investigated the protective effects of NTF isolated from the stems of Polyalthia suberosa against H 2 O 2 -mediated cytotoxicity using an in vitro model of human neuroblastoma cell line SK-N-SH.…”

Section: Introductionmentioning

confidence: 99%

N-trans-feruloyltyramine Protects Human Neuroblastoma SK-N-SH Cell Line Against H₂O₂-Induced Cytotoxicity

Soi-ampornkul

Myint

Thangnipon

et al. 2022

Natural Product Communications

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Excessive accumulation of reactive oxygen species (ROS) has been regarded as a major contributor of pathogenesis in neurodegenerative diseases. N- trans-feruloyltyramine (NTF), an alkaloid isolated from several plants, has demonstrated an ability to be a potent antioxidant. In this study, the antioxidative and anti-apoptotic properties of NTF extracted from the stems of Polyalthia suberosa were investigated in the human neuroblastoma cell line SK-N-SH. NTF at concentrations ranging from 10 µM to 500 µM were not toxic to cells and reduced intracellular ROS levels significantly. Furthermore, pre-treatment of NTF significantly decreased H2O2-induced ROS generation and attenuated H2O2-mediated cytotoxicity. An increase in the expression of Bax and activated caspase-3 and reduction of Bcl-2 mediated by H2O2 was reversed by pre-treating the cells with 100 µM NTF. Likewise, NTF suppressed the increase of caspase-3 activity induced by H2O2. In conclusion, the findings reveal that NTF improves H2O2-induced intracellular ROS generation and decreases apoptosis. These protective effects of NTF could be useful for oxidative stress-related neurodegenerative conditions.

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N-trans-feruloyltyramine and flavonol glycosides from the leaves of Solanum sordidum

Cited by 7 publications

References 15 publications

Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Chemical constituents from Hibiscus hamabo and their antiphotoaging effects on UVA‐induced CCD‐986sk

N-trans-feruloyltyramine Protects Human Neuroblastoma SK-N-SH Cell Line Against H₂O₂-Induced Cytotoxicity

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N-trans-feruloyltyramine and flavonol glycosides from the leaves of Solanum sordidum

Cited by 7 publications

References 15 publications

Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Human Neutrophil Elastase Inhibitory Alkaloids from Chelidonium majus L.

Chemical constituents from Hibiscus hamabo and their antiphotoaging effects on UVA‐induced CCD‐986sk

N-trans-feruloyltyramine Protects Human Neuroblastoma SK-N-SH Cell Line Against H2O2-Induced Cytotoxicity

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N-trans-feruloyltyramine Protects Human Neuroblastoma SK-N-SH Cell Line Against H₂O₂-Induced Cytotoxicity