Benzophenone Glucoside Research Articles

Acylated iridoid glucoside and xanthones from Canscora lucidissima: Their structures and ferroptosis inhibitory activity

Phytochemical study on the whole plants of a Gentianaceous medicinal plant, Canscora lucidissima, gave one new acylated iridoid glucoside, canscorin A (1), and two new xanthone glycosides (2 and 3) together with 17 known compounds including five xanthones, eight xanthone glycosides, two benzophenone glucosides, caffeic acid, and loganic acid. Canscorin A (1) was assigned as a loganic acid derivative having a hydroxyterephthalic acid moiety by spectroscopic analysis together with chemical evidence, while 2 and 3 were elucidated to be a rutinosylxanthone and a glucosylxanthone, respectively. The absolute configurations of the sugar moieties of 2 and 3 were determined by HPLC analysis. The isolated compounds were evaluated for their inhibitory activities against erastin-induced ferroptosis on human hepatoma Hep3B cells and LPS-stimulated IL-1β production from murine microglial cells.

Potential Anti‐hyperuricemic Agents from Proanthocyanidins, Procyanidins, and Benzophenone Glucosides via In Silico Docking Analysis Verified with In Vitro Bioassay

AbstractIn a continuation of searching natural xanthine oxidase inhibitors as anti‐hyperuricemic agent, in silico virtual screening of epicatechin (1) and A‐type proanthocyanidins 2–8, isolated from Machilus philippinensis , by molecular docking was undertaken and subsequent in vitro assay was followed. The bioassay result correlated well with the docking score. Additional A‐type proanthocyanidins 9–16 and procyanidins 17 & 18, present in peanut skin, were isolated and assayed against XO. Although their inhibitory activities were low but correlated well with the docking scores, too. This study indicated in silico virtual docking to be applicable to predict the XO inhibitory activity for proanthocyanidins with the molecular weight ranging from dimers (MW∼550) to hexamers (MW∼1750). For verifying such virtual screening to other phenolics, this approach was extended to benzophenone glucosides 19–22, isolated from Planchonella obovata . Likewise their inhibitory activities against XO correlated well with the docking score. Of these 22 compounds, the tetramer 5, pentamer 7, hexamer 8, and the digalloylated 22, having the docking score around −25.5 Kcal/mol, showed comparable inhibitory activity against xanthine oxidase to allopurinol (IC50∼40.0 vs. 58.5 μM). Further application of such virtual screening on XO template will keep going for searching potential anti‐hyperuricemic drugs.

Benzophenone Glucosides and B-Type Proanthocyanidin Dimers from Zambian Cassia abbreviata and Their Trypanocidal Activities.

Two benzophenone glucosides (1 and 2), five flavan-3-ol dimers (5-9), and 17 known compounds (3, 4, and 10-24) were identified from the bark extract of Cassia abbreviata. The chemical structures display two points of interest. First, as an unusual characteristic feature of the 1H NMR spectra of 1 and 2, the signals for the protons on glucosidic carbons C-2 are shielded as compared to those generally observed for glucosyl moieties. The geometrically optimized 3D structures derived from conformational analysis and density functional theory (DFT) calculations revealed that this shielding effect originates from intramolecular hydrogen bonds in 1 and 2. Additionally, 3-15 were identified as dimeric B-type proanthocyanidins, which have 2R,3S-absolute-configured C-rings and C-4-C-8″ linkages, as evidenced by X-ray crystallography and by NMR and ECD spectroscopy. These results suggest the structure-determining procedures for some reported dimers need to be reconsidered. The trypanocidal activities of the isolated compounds against Trypanosoma brucei brucei, T. b. gambiense, T. b. rhodesiense, T. congolense, and T. evansi were evaluated, and the active compounds were identified.

A new flavanone sulfonate and other phenolic compounds from Fumana montana

The phytochemical study of ethyl acetate and n-butanol extracts of Fumana montana Pomel yielded a new flavanone sulfonate named naringenin-8-sulfonate (1), in addition to nine known compounds including two flavonols; tellimoside (2) and isoquercetrin (3), two flavanols; (−)-gallocatechin (4) and (−)-epigallocatechin (5), one benzophenone glucoside; iriflophenone-2-O-β-glucoside (6), one phenolic glucoside; (−)-rhododendrin (7) and three benzoic acid derivatives; p-hydroxybenzoic acid (8), gallic acid (9) and methyl gallate (10). It should be noted that this is the first report of compounds (2) and (6) in Cistaceae family. The structures of the isolated compounds were determined by comprehensive 1D and 2D NMR analysis, mass spectrometry, IR and by comparison with literature data.

Flavonoids from Cyclopia genistoides and Their Xanthine Oxidase Inhibitory Activity.

The present paper reports the chemical analysis of the methanolic extracts of fermented and non-fermented Cyclopia genistoides herbs and an investigation of the xanthine oxidase inhibitory activity of the isolated constituents. Chemical analysis of the leaves and stems of C. genistoides yielded the isolation and identification of two benzophenone glucosides, iriflophenone 2-O-β-glucopyranoside (1) and iriflophenone 3-C-β-glucopyranoside (2), two pterocarpans, (6aR,11aR)-(-)-2-methoxymaackiain (5) and (6aR,11aR)-(-)-maackiain (6), along with the flavanones liquiritigenin (9) and hesperetin (10), the flavone diosmetin (11), the isoflavones afrormosin (7) and formononetin (8), piceol (3), and 4-hydroxybenzaldehid (4). Among the eleven compounds, nine are reported for the first time from this species, and six from the genus Cyclopia. These compounds, together with previously isolated secondary metabolites of this species, were tested for xanthine oxidase inhibitory activity. The 5,7-dihydroxyflavones luteolin and diosmetin significantly inhibited the enzyme in vitro, while hesperetin (10) and 5,7,3',5'-tetrahydroxyflavone exerted weak activity.

MAO-A Inhibition Profiles of Some Benzophenone Glucosides from Gentiana verna subsp. pontica

Gentiana verna L. subsp. pontica (Soltok.) Hayek, G. pyrenaica L., and G. verna L. subsp. balcanica Pritchard from Turkey were tested for their MAO-A inhibitory effects. A photometric peroxidase linked MAO-A bioassay performed on the H20 extracts prepared from the methanolic extracts of the title plants revealed the potential effect of G. verna subsp. pontica and three benzophenone glucosides; 2,3'-dihydroxy-4-methoxy-benzophenone-6-O-beta-glucopyranoside (1), 2,4,3',4'-tetrahydroxy-benzophenone-6-O-beta-glucopyranoside (maclurin-6-O-f-glucopyranoside) (2) and 2,4,3'-trihydroxy-benzophenone-6-O-beta-glucopyranoside (3) isolated from G. verna subsp. pontica. Among the benzophenone glucosides 1 and 2 exhibited significant inhibition of MAO-A (IC50 = 31.3 +/- 4 microM and 41 +/- 4.7 microM resp.).

MAO-A inhibitory activities of some benzophenones from Gentiana Spec

Inhibition of MAO-A predominantly affects neurotransmitters considered to be important in depression and anxiety disorders. Therefore, MAO inhibitors are expected to be useful in the therapy of psychosis, depression, schizophrenia, and so on (1). To date, MAO inhibitors such as coumarins, xanthones, flavonoids, piperine, and isoquinoline alkaloids have been isolated from natural sources or synthesized for the development of medicine (1–4). In this study MAO-A inhibition of benzophenone glucosides 1, 2 and 3 isolated from G. verna L. subsp. pontica (Soltok.) Hayek. was evaluated. Compounds 1-3 showed significant inhibition on MAO-A with IC50-values 1.2–34µM.

New benzophenone glucosides from the aerial parts of Gentiana verna L. subsp. pontica (Soltok.) Hayek

Three new benzophenone glucosides, 2,3′-dihydroxy-4-methoxy-benzophenone-6- O- β-glucopyranoside ( 1), 2,4,3′,4′-tetrahydroxy-benzophenone-6- O- β-glucopyranoside (maclurin-6- O- β-glucopyranoside) ( 2) and 2,4,3′-trihydroxy-benzophenone-6- O- β-glucopyranoside ( 3) were isolated from the aerial parts of Gentiana verna subsp. pontica. Their structures were determined on the basis of spectroscopic evidence. This is the first report of the isolation of benzophenone glucosides from G. verna subsp. pontica.

BENZOPHENONE GLUCOSIDE ISOLATED FROM THE ETHYL ACETATE EXTRACT OF THE BARK OF MAHKOTA DEWA [Phaleria macrocarpa (Scheff.) Boerl.] AND ITS INHIBITORY ACTIVITY ON LEUKEMIA L1210 CELL LINE

Isolation and elucidation of benzophenone glucoside from ethyl acetate extract of Phaleria macrocarpa bark and its inhibitory activity test against leukemia L1210 cell line have been done. The Phaleria macrocarpa bark were macerated using n-hexane, ethyl acetate, and ethanol, respectively. The ethyl acetate extract was then chromatographed on silica gel column and gradiently eluted by n-hexane - ethyl acetate - ethanol with the composition from 20:1:0 until 0:0:1, gave eight fractions. Separation of fraction 6 using semipreparative HPLC on reverse phase column (Capcell Pak C-18 SG120, 15 mm I.D. x 250 mm) using methanol - water (40:60, 5 mL/min) gave a brown powder, with the melting point of 182.3 ºC. Spectroscopic analysis and comparison of its physico-chemical data, this compound was clarified as 2,4'-dihydroxy-4-methoxy-benzophenone-6-O-b-D-glucopyranoside (3). Inhibitory activity of its compound against leukemia L1210 cell line showed that this compound exhibited inhibitory activity with IC50 was 5.1mg/mL. Keywords: Phaleria macrocarpa, 2,4'-dihydroxy-4-methoxybenzophenone-6-O-b-D-glucopyranoside, cytotoxic activity, leukemia L1210

Three New Benzophenone Glucosides from the Leaves of Planchonella obovata

AbstractChemical investigation of the EtOH extract of the leaves of Planchonella obovata resulted in the isolation of four benzophenone glucosides, 1–4, of which three, 2–4, are new chemical entities together with five known flavonol glycosides. Their structures were elucidated by spectroscopic analysis. Among the isolated compounds, iriflophenone 2‐O‐(2,6‐di‐O‐galloyl)‐β‐D‐glucopyranoside (4) showed some activity (91.4 and 15.0% inhibition at 100 and 10 μg/ml, resp.) against the α‐glucosidase of Bacillus stearothermophilus.

New Benzophenone O-Glucoside from Hypericum Ellipticum

Examination of the acetone extract of the aerial parts of Hypericum ellipticum afforded a new acetylated benzophenone glucoside (3'-O-beta-D-3",4",6"-triacetylglucopyranosyl-2,4,5',6-tetrahydroxybenzophenone) together with catechin and epicatechin. The structure of the benzophenone glucoside was determined by 2D NMR spectroscopic data. The compound inhibited the proliferation of CNS tumor cell line (SF-268) and lipid peroxidation in in vitro assays.

Two new benzophenone glucosides from Cratoxylon cochinchinensis

Two new benzophenone glucosides were isolated from the 60% ethanol extract of the dried stems of Cratoxylum cochinchinense. The structures were elucidated as 3- O- β- d-glucopyranosyl-2′,4,6′-trihydroxy-benzophenone and 3- O- β- d-glucopyranosyl-2′,5,6′-trihydroxybenzophenone on the basis of spectral and chemical methods.

Flavonoid and a Rare Benzophenone Glycoside from the Leaves of Aquilaria sinensis

From the leaves of Aquilaria sinensis (LOUR.) GILG, a novel benzophenone glucoside, designated as aquilarinoside A (1), and a new flavonoid, as 7-beta-D-glucoside of 5-O-methylapigenin (2), along with eight known compounds (3-10) were isolated. The structures of 1 and 2 were fully characterized by spectroscopic methods (1D, 2D NMR and MS) and the relative stereochemistry was assigned based on nuclear Overhauser effect spectroscopy (NOESY) correlations and analyses of coupling constants. The new compounds showed inhibition activity against polymorphonuclear neutrophils (PMNs) respiratory burst stimulated by PMA.

Complete LC/MS analysis of a Tinnevelli senna pod extract and subsequent isolation and identification of two new benzophenone glucosides.

The hydroalcoholic extract of Tinnevelli senna is widely used as a laxative phytomedicine. In order to improve the knowledge of the chemical composition of this extract, LC/MS and LC/MS(n) studies were performed, allowing the on-line identification of most of the known constituents, i. e., flavonoids, anthraquinones and the typical dianthronic sennosides. However, the identity of four compounds could not be ascertained on-line under the given LC/MS conditions. These substances were isolated and their structures elucidated as kaempferol, the naphthalene derivative tinnevellin 8-glucoside and two new carboxylated benzophenone glucosides.

An Iridoid Gentiobioside, a Benzophenone Glucoside and Acylated Flavone C-Glycosides from Tripterospermum japonicum (SIEB. et ZUCC.) MAXIM.

From aerial parts of Tripterospermum japonicum, 6'-O-beta-D-glucopyranosylmorroniside, benzophenone glucoside, named triptephenoside and 2'''- and 4'''-O-acetyl-2''-O-alpha-L-rhamnopyranosylisovitexins were isolated, along with known iridoid and secoiridoid glucosides, and C-glycosyl flavones.

Flavonoid and benzophenone glycosides from Coleogyne ramosissima

A benzophenone glucoside and two flavonol glycosides were isolated together with 27 known polyphenols from the aerial parts of Coleogyne ramosissima, and their structures were elucidated by spectroscopic and chemical methods as iriflophenone 2- O-β-glucopyranoside, isorhamnetin 3- O-2 G-rhamnopyranosylrutinoside-7- O-α-rhamnopyranoside and limocitrin 3- O-rutinoside-7- O-β-glucopyranoside, respectively.