Chemical Constituents of Euscaphis konishii and Their Inhibitory Activities

Ni, Lin; Liang, Wenxian; Huang, Wei; Chen, Jingxin; Zou, Xiong; Li, YanLei; Zou, Shuangquan

doi:10.1007/s10600-019-02825-1

Cited by 5 publications

(3 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…6,7 Significant bioactive constituents of E. konishii, as well as antiinflammatory and fungistatic compounds, have been reported in the previous literature. 8,9 This paper reports continuing research, which resulted in finding a tumor-inhibiting extract, which led to the isolation of 10 constituents described in this study, among them a new ellagic acid with 9 known compounds ( Figure 1). This study describes the isolation, and the identification of the structures and the biological activities of these compounds from the twigs of E. konishi The IR spectrum clearly exhibited the absorption bands of a hydroxy group (3489 cm −1 ), a carbonyl group (1730 cm −1 ), and an aromatic group (1609 cm −1 ).…”

mentioning

confidence: 70%

Chemical Constituents and Their Activities From the Twigs of Euscaphis konishii Hayata

Chen

Zhang

et al. 2020

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

A new ellagic acid derivative 3,3′-di- O-methylellagic acid 4 ′-α-l-arabinopyranoside (1), with 9 known compounds identified as 3,3′-di- O-methylellagic acid (2), 3,3′-di- O-methylellagic acid 4′-α-d-arabinofuranoside (3), 3,3′-di- O-methylellagic acid 4′ -β-d-glucopyranoside (4), 3,3′-di- O-methylellagic acid 4 ′-β-d-xylopyranoglucoside (5), 3,3′,4-tri- O-methylellagic acid 4′-β-d-glucopyranoside (6), tormentic acid (7), ursolic acid (8), euscaphic acid (9), and betulinic acid (10), was isolated from the twigs of Euscaphis konishii Hayata. Compounds 1, 3, and 5 to 7 were isolated from this plant for the first time, and compounds 1 and 5 were obtained from the plant genus for the first time. The structure of the new compound was confirmed by HRESIMS, NMR, and compared with data from the literature . The cytotoxicities of 10 isolated compounds were tested, with compounds 1 to 6 showing moderately inhibited activity against the Human Hepatocarcinoma cell line (HepG2 cells) with an IC50 value ranging from 69.7 to 181.8 μM.

show abstract

mentioning

confidence: 70%

Chemical Constituents and Their Activities From the Twigs of Euscaphis konishii Hayata

Chen

Zhang

et al. 2020

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

show abstract

“…The identification of saccharose and β-fructose was easily confirmed by checking heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond correlation (HMBC), and correlation spectroscopy (COSY) data of fraction EAF 10 and by comparison with literature data. 23 Similarly, clusters 2-11 were identified as ellagic acid and gallic acid 24 (clusters 2, 2′, and 2″; fraction EAF 6 ), a mixture of 6-O-Ecaffeoyl-βdglucopyranoside 25 and malic acid 23 (clusters 3 and 7; fractions EAF 2-8 ), succinic acid 26 (cluster 4; fractions EAF 3-4 ), dotorioside II 27 (cluster 5; fractions EAF 3-4 ), tormentic acid 28 (cluster 6; fraction EAF 1 ), caffeic acid 29 (cluster 7, fraction EAF 7 ), ellagic acid 4-Opentoside (cluster 8; fractions EAF 3-5 ), (+)-catechin (2) 30 (cluster 10; fractions EAF 2-3 ), and 3,3′-di-Omethylellagic acid 31 (cluster 11; fraction EAF 3 ). For the fractions EAF 4-5 , the database proposed a 3-(3,4-dihydroxyphenyl) propyl-glycoside (1), which could not be identified unambiguously (cluster 9).…”

Section: Resultsmentioning

confidence: 99%

Investigation of Antioxidant and Elastase Inhibitory Activities ofGeum urbanumAerial Parts, Chemical Characterization of Extracts Guided by Chemical and Biological Assays

Schmitt

Magid

Hubert

et al. 2020

Natural Product Communications

View full text Add to dashboard Cite

This study presents the bioguided chemical investigation of the 80% aqueous methanol extract of Geum urbanum aerial parts. Liquid–liquid partitioning of this extract in solvents of increasing polarity combined with biological screening showed that the ethyl acetate (EtOAc) soluble fraction was the most active part of the extract. This fraction was chemically profiled by a 13C nuclear magnetic resonance (NMR)-based dereplication method, resulting in the identification of 14 compounds. The dereplication process was followed by the purification of unknown and minor compounds of the EtOAc fraction. A new glycosylated phenol, namely, 3-(3,4-dihydroxyphenyl)propyl-α-l-rhamnopyranoside, together with 6 known compounds were isolated. Their structures were elucidated by spectroscopic methods including NMR and high-resolution electrospray ionization mass spectrometry. The antioxidant activity of fractions and isolated compounds were evaluated by 2,2,1-diphenyl-1-picrylhydrazyl and hydroxyl radical scavenging, and by cupric ion reducing antioxidant capacity assays. In parallel, their enzyme inhibitory property against human neutrophil elastase was assessed. Four subfractions, essentially containing polyphenols and triterpenes, exhibited a significant elastase inhibitory activity and an ellagitannin showed a very high radical scavenging activity.

show abstract

“…Based on the activity results of extract and all fractions, dichloromethane, ethyl acetate, and n -butanol fractions were applied to further isolation and purification by chromotography on Sephadex LH-20 column, silica gel column, ODS, and preparative TLC, as well as semipreparative HPLC, et al Finally, 17 compounds were obtained. Their structures were identified as 1, 2, 3, 4, 6-penta- O -galloyl- β -D-glucoside ( 1 ) [ 14 ], 1, 2, 3, 4, 6-penta- O -galloyl- α -D-glucoside ( 2 ) [ 15 ], 1, 2, 3, 6-tetra- O -galloyl- β -D-glucoside ( 3 ) [ 16 ], 1- O -(3, 4, 5-trihydroxybenzoyl)- β -D-glucoside ( 4 ) [ 17 ], methyl galate ( 5 ) [ 18 ], gallic acid ( 6 ) [ 39 ], 3,4-dihydroxybenzoic acid ( 7 ) [ 19 ], 4-hydroxybenzoic acid ( 8 ) [ 20 ], 1-glycerol gallate ( 9 ) [ 21 ], ethyl gallate ( 10 ) (H. [ 22 ]), ferulic acid ( 11 ) [ 23 ], caffeic acid ( 12 ) [ 24 ], quercetin ( 13 ) [ 25 ], genistein ( 14 ) [ 26 ], gallocatechin ( 15 ) [ 27 ], epicatechin ( 16 ) (M. [ 28 ]), and hexyl- β -D-glucoside ( 17 ) [ 29 ] by comparing their NMR spectroscopic data with data reported in the above references. Compounds 2 , 9 , 15 , and 17 were isolated from the genus Mangifera for the first time.…”

Section: Resultsmentioning

confidence: 99%

Antioxidant and α-Glucosidase Inhibitory Activities Guided Isolation and Identification of Components from Mango Seed Kernel

Yang

Chen

Liu

et al. 2020

Oxidative Medicine and Cellular Longevity

View full text Add to dashboard Cite

In the present study, petroleum ether, dichloromethane, ethyl acetate, and n-butanol fractions of mango seed kernel exhibited different degrees of antioxidant and α-glucosidase inhibitory activity. Thus, quantitative and qualitative analysis of the petroleum ether fraction was conducted by GC-MS. Among identified components, four unsaturated fatty acids had never been reported in natural products before, together with 19 known components. In addition, 17 compounds were isolated and elucidated from other active fractions. Compounds 2, 9, 15, and 17 were isolated for the first time from Mangifera genus. Compounds 1 and 2 exhibited prominent DPPH radical scavenging and α-glucosidase inhibitory effects. In order to further explore their mechanism of α-glucosidase inhibition, their enzyme kinetics and in silico modeling experiments were performed. The results indicated that 1 inhibited α-glucosidase in a noncompetitive manner, whereas 2 acted in a competitive manner. In molecular docking, the stability of binding was enhanced by π-π T-shaped, π-alkyl, π-π stacked, hydrogen bond, and electrostatic interactions. Thus, compounds 1 and 2 were determined to be new potent antioxidant and α-glucosidase inhibitors for preventing food oxidation and enhancing hypoglycemic activity.

show abstract

Chemical Constituents of Euscaphis konishii and Their Inhibitory Activities

Cited by 5 publications

References 9 publications

Chemical Constituents and Their Activities From the Twigs of Euscaphis konishii Hayata

Chemical Constituents and Their Activities From the Twigs of Euscaphis konishii Hayata

Investigation of Antioxidant and Elastase Inhibitory Activities ofGeum urbanumAerial Parts, Chemical Characterization of Extracts Guided by Chemical and Biological Assays

Antioxidant and α-Glucosidase Inhibitory Activities Guided Isolation and Identification of Components from Mango Seed Kernel

Contact Info

Product

Resources

About