Acylated flavonol glycosides from Epimedium elatum, a plant endemic to the Western Himalayas

Herba Epimedii is a well-known Botanical preparation used over long time in traditional Chinese medicine. The extracts and chemical constituents from Epimedium species are aphrodisiac as well as to treat many ailments. Chemical investigation of lonely species growing in Kashmir Himalaya Epimedium elatum was undertaken to evaluate its chemical profile. Two unusual substituted acylated flavonol glycosides named Elatoside A (1) and Elatoside B (2) have been isolated from the ethanolic extract of E. elatum along with 23 previously known ones (3-25). All isolates were evaluated for antimicrobial and PPAR-γ ligand binding activity, and some of them appeared to be modestly active.     

A new flavonol glycoside from Millettia speciosa

A new flavonol triglycoside, millettiaspecoside D, was isolated from the caulis of Millettia speciosa Champ. Its structure was elucidated on the basis of spectroscopic analysis.     

Two new glycosidated coumaramides from Clerodendron cyrtophyllum

Two new glycosidated coumaramides clerodendiod A (1) and B (2), together with seven known glycosidic compounds were isolated from the branches of Clerodendron cyrtophyllum Turcz. Clerodendiod A and B were elucidated as β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-[6-O-(E)-p-methoxycinnamoyl]-β-D-glucopyranosyl-(1 → 2)-[4-O-((E)-2-(4-acetamidobutylcarbamoyl)vinyl)-phenyl]-α-L-rhamnopyranoside (1) and 6-O-(E)-p-coumaroyl-β-D-glucopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)-[6-O-(E)-p-methoxycinnamoyl]-β-D-glucopyranosyl-(1 → 2)-[4-O-((E)-2-(4-acetamidobutylcarbamoyl)vinyl)-phenyl]-α-L-rhamnopyranoside (2) on the basis of chemical and spectral evidence. The isolated new compound 2 was assayed for the inhibition of the NF-κB pathway and showed potent activity in inhibiting NF-κB which its IC₅₀ values was found to be 24.9 nM.     

New flavonol glycosides from Aconitum burnatii Gáyer and Aconitum variegatum L.

Six flavonol glycosides, compounds 1-3 from A. burnatii Gáyer and 4-6 from A. variegatum L., were obtained from their methanol extracts of aerial parts. The identified structures were quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-p-coumaroyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (1), quercetin 3-O-β-d-glucopyranoside-7-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (2), quercetin 3-O-β-d-glucopyranoside-7-O-(6-E-caffeoyl)-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside (3), kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-arabinopyranoside (4), quercetin 3-O-β-d-glucopyranoside (5), and kaempferol 3-O-β-d-glucopyranoside (6). Compounds 1, 2 and 4 were isolated for the first time. The antioxidant potential of the methanol extracts and pure compounds was tested with different assays.     

The antifungal constituents from the seeds of Itoa orientalis

Three new phenolic constituents, itolide A (1), itolide B (2), itoside P (3), and 1D-3-deoxy-3-hydroxymethyl-myo-inositol (4), which is described herein for the first time as a natural product, were isolated along with four other known compounds (5 to 8) from the methanol extract of the seeds of Itoa orientalis Hemsl by the activity-guided fractionation. Their structures were determined by spectroscopic means. Compounds 1 to 8 exhibited antifungal activities against Sclerotium rolfsii with IC₅₀ values ranging from 60.12 to 240.00 μM and against Rhizoctonia solani with IC₅₀ values ranging from 45.34 to 233.14 μM, respectively, and compounds 1, 2, 5 exhibited cytotoxic activity against Tn5B1-4 insect cell line with EC₅₀ values of 203.68, 93.41 and 40.37 μM, respectively.     

A new iridoid glycoside from Linaria genestifolia

A new iridoid glycoside named genestifolioside (1) was isolated from the ethanol extract of Linaria genestifolia. Its structure was defined by spectral analysis.     

A new cycloartane glycoside from Camptosorus sibiricus

A new cycloartane glycoside was isolated from the whole herbs of Camptosorus sibiricus. By means of spectroscopic methods its structure was established as 3beta, 7beta, 24beta, 25, 30-pentahydroxycycloartane-24, 30-di-O-beta-D-glucopyranoside (1). proflixian@163.com     

A new naphthalene glycoside from the roots of Smilax bockii

From the roots of Smilax bockii a new compound, 7-hydroxymethyl-1, 4, 5-trihydroxynaphthalene-4-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside, was isolated. The structure of the new compound was elucidated on the basis of spectroscopic methods.     

A new triterpene glycoside from Centella erecta

A new (2α,3β)-23-sulphonyl-2,3-dihydroxyurs-12-en-28-oic acid O-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1) together with eighteen known compounds were isolated from Centella erecta (L.f.) Fern. Their structures were elucidated mainly by NMR and HRESIMS, as well as on comparison with the reported data.     

DPPH radical scavenging activity of two flavonol glycosides from Aconitum napellus sp. lusitanicum

The DPPH radical scavenging activity of two flavonol glycosides obtained from ethanolic extracts of Aconitum napellus sp. lusitanicum was studied. The results showed a high DPPH antiradical activity of compound 1 (quercetin 3-O-(6-trans-caffeoyl)-beta-glucopyranosyl-(1-->2)-beta-glucopyranosyl-7-O-alpha-rhamnopyranoside) when compared with compound 2 (quercetin-3-sophoroside-7-rhamnopyranoside), rutin and ascorbic acid. The relationship between the caffeoyl and rhamnopyranoside groups in the flavonol glycosides structures and the DPPH antiradical activity was also discussed.     

Flavonoids from Acalypha indica

Four known kaempferol glycosides, mauritianin, clitorin, nicotiflorin and biorobin, have been isolated from the flowers and leaves of Acalypha indica. Some formerly published NMR data were corrected.     

A new phenolic glycoside from the aerial parts of Solidago canadensis

A new phenolic glycoside, 2'-hydroxy-4',6'-di-O-beta-D-glucopyranosyl-butyrrophenone (1), was isolated from the aerial parts of Solidago canadensis. The structure was elucidated on the basis of spectroscopic methods.     

Isolation and structural characterization of glycosides from an anti-angiogenic extract of Monnina obtusifolia H.B.K.

Angiogenesis, the growth of new blood vessels from the pre-existing vasculature is of physiological and pathological importance. Substantial data over the last decade has implicated uncontrolled angiogenesis with various pathological states. Vascular endothelial growth factors (VEGFs) play a critical role in its regulation, and have become one of the most interesting anti-angiogenesis targets. We have investigated the anti-angiogenic potential of plant extracts in a preliminary ELISA screening. The n-BuOH extract obtained from the leaves of Monnina obtusifolia (Polygalaceae) demonstrated an inhibition of VEGF-A or Placental Growth Factor interaction with Flt-1 (VEGF receptor 1), with an inhibition over 50% in particular for VEGF-A/Flt-1 interaction at a concentration of 500 μg/mL. Successively fractionation of the bioactive n-BuOH extracts of M. obtusifolia aerial parts led to the isolation of six new compounds, 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (1), 1-O-(isopentenyl)-6-O-β-d-(4-hydroxy-2-methylene-butanoyl)-glucopyranose (2), 1-O-(4-hydroxy-2-methylene-butanoic acid)-6-O-β-d-(isovaleroyl)-glucopyranose (3), 1-O-(3-methylbut-3enyl)-6-O-β-d-(isovaleroyl)-glucopyranose (4), two new sucrose esters, 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(p-coumaroyl)-glucopyranoside (5), and 3,4-O-β-d-di-feruloyl-fructofuranosyl-6-O-α-d-(caffeoyl)-glucopyranoside (6), together with known flavonoids. Their structures were established on the basis of detailed spectral analysis. Since none of the isolated compounds showed a relevant inhibition of VEGFs, the biological activity observed for the butanolic extract might be due to the presence of a combination of compounds acting synergistically.     

New coumarin glycosides from Rhododendron lepidotum

Two new coumarin glycosides, named Rhodonin (1) and Rhodonetin (2) were isolated from the aerial parts of Rhododendron lepidotum.     

Two new cytotoxic isomeric indole alkaloids from the roots of Nauclea orientalis

A pair of new isomeric indole alkaloids, naucleaorals A (1) and B (2) were isolated from the roots of Nauclea orientalis. The structures of compounds 1 and 2 were fully characterized using spectroscopic data, and were tested for their cytotoxicity (HeLa and KB cells) and antimalarial activity. Compound 1 showed significant cytotoxicity to HeLa cells with an IC₅₀ value of 4.0 µg/mL, while compound 2 exhibited very modest cytotoxicity to both cell lines with IC₅₀ values of 7.8 and 9.5 µg/mL, respectively. Both compounds proved to be inactive in antimalarial assays (IC₅₀ > 10.00 µg/mL).     

Humarain: A new dimeric gallic acid glycoside from Punica granatum L. bark

A new dimeric gallic acid glycoside named Humarain (1) was isolated from stem bark of Punica granatum. The structure of the compound was determined by spectroscopic data including 1D and 2D NMR spectral analysis.     

New triterpene saponins from the root of Ilex pubescens

Two new triterpene glycosides named ilexpublesnin A (1) and ilexpublesnin B (2) were isolated from the root of Ilex pubescens. Their structures were determined as 3-O-(β-d-xylopyranosyl)-28-O-(β-d-glucopyranosyl)-3β, 19α-dihydroxyurs-23-oxo-12-en-28-oic acid (1) and 28-O-(β-d-xylopyranosyl-(2 → 1)-β-d-glucopyranosyl)-3β, 19α-dihydroxyurs-23-oxo-12-en-28-oic acid (2) on the basis of chemical and spectroscopic methods.     

A new phenolic glycoside from the aerial parts of Dryopteris fragrans

A new phenolic glycoside, 3,5-dimethyl-6-hydroxy-2-methoxy-4-O-D-glucopyranosyl-oxy-acetophenone (1), was isolated from the aerial parts of Dryopteris fragrans. The structure was elucidated on the basis of spectroscopic methods.     

A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis

A new phenylpropanoid glycosides, 2-feruloyl-O-alpha-D-glucopyranoyl-(1'-->2)-3,6-O-feruloyl-beta-D-fructofuranoside, was isolated from the root of Paris polyphylla var. yunnanensis. The structure of the new glycoside was elucidated by spectroscopic methods. Cytotoxicity test showed that it has cytotoxic effect in a dose-dependent manner against the mice lung adenocarcinoma cell line (LA795).     

New monoterpene glycosides from Paeonia lactiflora

Three new monoterpene glycosides named 4-O-methyl-paeoniflorin (1), isopaeoniflorin (2), and isobenzoylpaeoniflorin (3), together with two known monoterpene glycosides, paeoniflorin (4) and benzoylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora. Their structures were established on the basis of spectral and chemical evidence.