Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch

Silchenko, Alexandra S.; Kalinovsky, Anatoly I.; Ponomarenko, L. P.; Avilov, Sergey A.; Andryjaschenko, Pelageya V.; Dmitrenok, Pavel S.; Gorovoy, P. G.; Kim, Natalia Yu.; Stonik, Valentin A.

doi:10.1016/j.phytochem.2014.11.003

Cited by 10 publications

(17 citation statements)

References 18 publications

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“…Nhiem et al [31] isolated this compound from a methanol extract of Acanthopanax koreanum leaves, although it did not possess antioxidant activity. This compound is also found in other plant parts such as apricot fruits [29], sweet potatoes [30], the aerial parts of Ligularia alticola [32], and an ethyl acetate extract of Saccocalyx satureioides [33].…”

Section: Discussionmentioning

confidence: 90%

Characterization of α-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking

et al. 2020

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Psychotria malayana Jack has traditionally been used to treat diabetes. Despite its potential, the scientific proof in relation to this plant is still lacking. Thus, the present study aimed to investigate the α-glucosidase inhibitors in P.malayana leaf extracts using a metabolomics approach and to elucidate the ligand–protein interactions through in silico techniques. The plant leaves were extracted with methanol and water at five various ratios (100, 75, 50, 25 and 0% v/v; water–methanol). Each extract was tested for α-glucosidase inhibition, followed by analysis using liquid chromatography tandem to mass spectrometry. The data were further subjected to multivariate data analysis by means of an orthogonal partial least square in order to correlate the chemical profile and the bioactivity. The loading plots revealed that the m/z signals correspond to the activity of α-glucosidase inhibitors, which led to the identification of three putative bioactive compounds, namely 5′-hydroxymethyl-1′-(1, 2, 3, 9-tetrahydro-pyrrolo (2, 1-b) quinazolin-1-yl)-heptan-1′-one (1), α-terpinyl-β-glucoside (2), and machaeridiol-A (3). Molecular docking of the identified inhibitors was performed using Auto Dock Vina software against the crystal structure of Saccharomyces cerevisiae isomaltase (Protein Data Bank code: 3A4A). Four hydrogen bonds were detected in the docked complex, involving several residues, namely ASP352, ARG213, ARG442, GLU277, GLN279, HIE280, and GLU411. Compound 1, 2, and 3 showed binding affinity values of −8.3, −7.6, and −10.0 kcal/mol, respectively, which indicate the good binding ability of the compounds towards the enzyme when compared to that of quercetin, a known α-glucosidase inhibitor. The three identified compounds that showed potential binding affinity towards the enzymatic protein in molecular docking interactions could be the bioactive compounds associated with the traditional use of this plant.

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Section: Discussionmentioning

confidence: 90%

Characterization of α-Glucosidase Inhibitors from Psychotria malayana Jack Leaves Extract Using LC-MS-Based Multivariate Data Analysis and In-Silico Molecular Docking

et al. 2020

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“…Sesquiterpenoids ( 1 – 116 ) with two six‐membered rings are covered, rich in plant sources such as L. subspicata and L. sagitta . It is interesting to find rare eremophilane‐type sesquiterpene glucosides ( 71 – 77 ) in Ligularia alticola . Compounds ( 78 – 116 ) are noreremophilanes, including liguhodgesonal derivatives ( 78 – 84 ), 11‐noreremophilanes ( 85 – 101 ), dinoreremophilane 101 , 11‐trinoreremophilanes ( 102 – 105 ), and rearranged noreremophilane ( 106 – 116 ).…”

Section: Eremophilanesmentioning

confidence: 99%

Eremophilane Sesquiterpenes from the Genus Ligularia

Liao

Liu³

et al. 2016

Chemistry & Biodiversity

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“…Alticolosides A-I (21-29, Figure 1) were isolated from the aerial parts of this plant [13,14]. It is interesting to note that the main part of glycosides is localized in the leaves of L. alticola, whiles the petioles and inflorescences contain a small quantity of these substances and the stems do not comprise anyone glycoside [13]. The compounds 21, 22 and 24 along with their acetylated analogs 30-32 (Figure 1) were found from the leaves of Ligularia calthifolia Maxim.…”

Section: Occurrence In Naturementioning

confidence: 99%

“…Structures of eremophilane-type glycoside were elucidated by extensive analysis of their 1 H, 13 C NMR, DEPT, 1D NOESY and 2D NMR ( 1 H-1 H COSY, HMBC, H2BC, HSQC, ROESY) and HR ESI mass spectra likewise those of other terpene glycosides. GC analysis of hydrolyzed products and comparison with standards were used for identification of sugar residues.…”

Section: Structural Determination and Diversitymentioning

confidence: 99%

“…Chemical modifications, for example obtaining of silyl esters, were made in this case [4]. A derivatization by R-(-)-or S-(+)-2-octanols with subsequent acetylation was used for determination of absolute configurations of carbohydrate [13]. The treatment of glycosides with cellulase and analysis of the obtained sugar solution by HPLC using an optical rotation detector was used for determination of absolute configuration of carbohydrate residue also [16] 1) [15].…”

Section: Structural Determination and Diversitymentioning

confidence: 99%

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