Two acylated flavonoid glycosides from the leaves of Quercus dentata

Two new acylated flavonoid glycosides have been isolated from the leaves of Quercus dentata Thunb. On the basis of chemical and spectral data, the structures of the compounds have been elucidated as kaempferol 3-O-(2", 4"-diacetyl-3"-cis-p-coumaroyl-6"-trans-p-coumaroyl)-beta-D-glucopyranoside (1), and kaempferol 3-O-(2"-trans-p-coumaroyl-3", 4"-diacetyl-6"-cisp-coumaroyl)-beta-D-glucopyranoside (2).     

New flavonoid glycosides and other chemical constituents from Clerodendrum phlomidis leaves: isolation and characterisation

Phytochemical investigation of the plant Clerodendrum phlomidis Linn. F. (Lamiaceae) has now led to the isolation of two new flavonoid glycosides (1, 2) together with six known compounds identified as pectolinaringenin (3), pectolinaringenin-7-O-β-d-glucopyranoside (4), 24β-ethylcholesta-5,22E,25-triene-3β-ol (5), 24β-ethylcholesta-5,22E,25-triene-3β-O-β-D-glucopyranoside (6), (2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (7) and andrographolide (8) mainly by spectroscopic analysis. Compounds 4 and 6–8 are reported for the first time from C. phlomidis.     

New oleanene glycosides from the leaves of Acanthopanax japonicus

The structures of 6 new oleanene glycosides (1--6) isolated from the leaves of Acanthopanax japonicus FRANCH et. SAVART (Araliaceae) were elucidated by mass, 1D, and 2D NMR spectroscopy. The structures of 1--6 were established as 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester of 3beta,23-dihydroxy-olean-12-en-28,29-dioic acid, 3beta,30-dihydroxy-olean-12-en-23,28-dioic acid, 3beta,29-dihydroxy-olean-12-en-23,28-dioic acid (=dianic aicd), 3beta-dihydroxy-olean-12-en-23,28-dioic acid (=gypsogenic acid), 3beta,29-dihydroxy-23-oxo-olean-12-en-28-oic acid, and 3beta-hydroxy-23-oxo-olean-12-en-28,29-dioic acid, designated acanjaposide D (1), E (2), F (3), G (4), H (5), and I (6), respectively.     

New flavonol glycosides from the leaves of Caragana brachyantha

Two new flavonol glycosides, brachysides C and D, together with three known flavonol glycosides, were isolated from the leaves of Caragana brachyantha. The structures of brachysides C and D were elucidated on the basis of detailed spectroscopic analysis as quercetin 5-O-[α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside]-7-O-[α-l-rhamnopyranoside] and quercetin 5-O-[α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside]-7-O-[α-l-rhamnopyranoside]-4′-O-[α-l-rhamnopyranoside], respectively. The presence of flavonol tetra- and triglycosides bearing a sugar moiety at position 5 was the first report from this genus Caragana.     

New cholestane glycosides from the leaves of Cordyline terminalis

Four new cholestane glycosides (1-4) were isolated from the leaves of Cordyline terminalis (Agavaceae). The structures of the new compounds were determined on the basis of spectroscopic analysis and a few chemical transformations followed by chromatographic and spectroscopic analyses.     

New flavonoid and pentacyclic triterpene from Sesamum indicum leaves

Two new and one known compounds were isolated from the methanol extract of Sesamum indicum leaves. By means of spectroscopic methods, their structures were elucidated and identified to be 3-epibartogenic acid (1), kaempferol 3-O-[2-O-(trans-p-coumaroyl)-3-O-α-L-rhamnopyranosyl]-β-d-glucopyranoside (2) and epigallocatechin (3). Compound 1 and 3 strongly inhibited α-amylase with the IC₅₀ values of 146.7 and 303.9 μM, respectively, in comparison with acarbose (IC₅₀ 124.0 μM).     

Acylated flavonoid glycosides from Barringtonia racemosa

Abstract

Using various chromatographic separations, three new acylated flavonoid glycosides, namely barringosides G–I (1–3), were isolated from the water-soluble extract of Barringtonia racemosa branches and leaves. The structure elucidation was performed by extensive analysis of the 1D and 2D NMR and HR-QTOF-MS data. Of the isolated compounds, barringoside I (3) showed moderate inhibitory effects on LPS-induced NO production in RAW264.7 cells with an IC₅₀ of 52.48?±?1.04?µM.     

New phenolic glycosides from the stems and leaves of Casearia multinervosa

Four phenolic glycosides (1-4), including two new ones (3 and 4), have been isolated from the stems of Casearia multinervosa and identified as arbutin (1), 4-O-E-caffeoylarbutin (2), 4-O-E-coumaroylarbutin (3) and 4-O-E-feruloylarbutin (4), respectively. In addition, the two known phenolic glycosides (1 and 2) were also isolated from the leaves. Structures were elucidated on the basis of spectroscopic evidence. Compounds 1-4 were tested for cytotoxicity against the P388 mouse lympholytic cell line by an ATP Lite-M assay method and showed mild to moderate activity.     

Investigation of flavonoid glycosides

Summary 1. The method of differential analysis in the IR region of the spectrum has been used in an investigation of the structure of the carbohydrate part of flavonoid glycosides. This method permits the pyranose and furanose forms of the carbohydrate substituents, the - and -anomers of the pyranosides and other structural features characterizing the nature of the sugars in the glycosides to be determined. The method can also be used to study other glycosides — for example, hydroxyanthraquinone glycosides, furocoumarin glycosides, and cardiac and other glycosides.2. A modified method of comparing molecular rotation has been proposed for determining the configuration of the glycosidic linkages and the size of the oxide rings in the carbohydrate part of the flavonoid glycosides.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 4, pp. 233–241, 1965     

Inhibitory effect of cis-dehydromatricaria ester isolated from Solidago altissima on the growth of mammalian cells

A cell growth inhibitory substance was isolated from Solidago altissima, which is known as a naturalized weed. The data of infrared spectrum, proton and carbon-13 nuclear magnetic resonance spectrum, and mass spectrum were identical with those of cis-dehydromatricaria ester. The compound inhibited both tumor and normal mammalian cells.     

New flavonoid glycosides of phelodendron lavallei and Ph. amurense

Chemistry of Natural Compounds -     

Three new flavonoid glycosides isolated from Elsholtzia bodinieri

Three new flavonoid glycosides, eriodictyol 7-O-(6'-feruloyl)-beta-D-glucopyranoside (1), eriodictyol 7-O-[6'-(3'-hydroxy-4'-methoxy cinnamoyl)]-beta-D-glucopyranoside (2), and luteolin 7-O-[6'-(3'-hydroxy-4'-methoxy cinnamoyl)]-beta-D-glucopyranoside (3), and eight known flavonoids were isolated from the whole plants of Elsholtzia bodinieri. The structures of the 3 new compounds were elucidated on the basis of extensive spectroscopic analysis.     

Phenylpropanoid glycosides from the leaves of Paulownia coreana

Study on the water soluble fraction from the leaves of Paulownia coreana led to the isolation of verbascoside (1), isoverbascoside (2), campneoside II (3), and a new phenylpropanoid glycoside, (R,S)-7-hydroxy-7-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl(1 --> 3)-beta-d-(6-O-caffeoyl)-glucopyranoside (4). The structures of these compounds were established on the basis of spectroscopic evidence.     

Lupane glycosides from the leaves of Acanthopanax koreanum

Three new lupane-type saponins, acankoreosides F--H (1--3) were isolated from the methanol extract of the leaves of Acanthopanax koreanum NAKAI. The structures of these three saponins were established by chemical and spectroscopic analysis as 3alpha,30-dihydroxylup-20(29)-en-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (1), 3alpha,30-dihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (2), and (20S) 3alpha-hydroxylup-23-al-28,29-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (3), respectively. The effects of the isolates (1-3) on the lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 were evaluated in RAW 264.7 macrophages.     

Steroidal glycosides from Digitalis ciliata leaves

Two new steroidal glycosides of the spirostane and furostane classes, derivatives of gitogenin, were found in wastes from producing acetyldigitoxin preparation from Digitalis ciliata Trautv. (Scrophulariaceae). The structures of the glucosides were established using physical constants, chemical transformations, and IR, mass, and NMR spectra. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 452–455, September–October, 2006.     

Lupane-triterpene glycosides from the leaves of Acanthopanax gracilistylus

A novel lupane-triterpene glycoside, called wujiapioside B (1), was isolated from the leaves of Acanthopanax gracilistylus (Araliaceae) together with three known lupane-triterpene glycosides, acankoreoside C (2), acantrifoside A (3) and 3-epibetulinic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (4). Based on spectroscopic data, the chemical structure of 1 was determined as 3alpha,23-dihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester. Compounds 2-3 were obtained for the first time from this plant and compound 4 has not been isolated from Acanthopanax genus yet.     

Flavonoid glycosides from Astragalus galegiformis leaves

New flavonoid oligosides, the structures of which were established by chemical transformations and UV, IR, PMR, and ¹³C NMR spectra, were isolated from Astragalus galegiformis leaves. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 555–558, November–December, 2006.