Three new flavonoid glycosides from Smilax glabra and their anti-inflammatory activity

Three new flavonoid glycosides, 2(S)-5-hydroxy-6,8-dimethoxyflavonone-7-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (1), 5-hydroxy-3,8-dimethoxyflavone-7-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (2) and 3,7-dihydroxy-8-methoxyflavone-6-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranoside (3), together with five known flavonoids (4–8) were isolated from the roots of Smilax glabra Roxb. Their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. Three new flavonoids were subjected to evaluate anti-inflammatory activity. Compounds 1–3 inhibited the NF κB induction by 32.2, 55.8 and 61.7%, respectively.     

Three new phenylacetamide glycosides from Dracocephalum tanguticum Maxim and their anti-hyperglycemic activity

Abstract

Three new phenylacetamide glycosides (1–3) together with one known phenylacetamide glycoside (4) and two known flavonoid glycosides (5–6) were isolated from whole plants of Dracocephalum tanguticum. The structure of all compounds were elucidated based on spectroscopic data analysis and comparison with data reported in related literature. Compounds (1–3) were evaluated for their anti-hyperglycemic and anti-fungal (Candida albicans) activities, the results revealed that all of them showed moderate activity with 3T3-L1 adipocytes glucose consumption rate of 20.80?±?1.47%, 21.48?±?2.44%, and 21.57?±?1.35%, respectively at the final concentration of 25?μM. However, none of them showed obvious Candida albicans inhibitory activity.     

Synthesis of Trisaccharide of Incanosides from Caryopteris incana

Recent evidence has accumulated suggesting that free radicals are involved in many deterioration processes. They attack the unsaturated fatty acids in the biomembranes resulting in membrane lipid peroxidation, which is strongly connected with aging, carcinogenesis and atherosclerosis.[1] Free radicals also attack DNA and cause mutation leading to cancer.[2] Thus it is desirable to look for effective radical scavengers. In 1999, Gao et al.[3] isolated incanosides C, D and E from the whole plant of Caryopteris incana (THUNB.). These natural products were proved to exhibit good radical scavenging activities against DPPH radical and inhibitory activities against the oxidation of linoleic acid.[4] Herein, for the first time we report the synthesis of trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamno-pyranosyl-(1→3)-2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (1), which is the common carbohydrate moiety of incanosides C, D and E.     

A new lignan glycoside and phenylethanoid glycosides from Strobilanthes cusia BREMEK

The root of Strobilanthes cusia BREMEK. (Acanthaceae), popularly known as Da-Ching-Yeh, has been commonly used in traditional Chinese medicine. It is used to treat influenza, epidemic cerebrospinal meningitis, encephalitis B, viral pneumonia, mumps, and severe acute respiratory syndrome (SARS). In this study, we found a new lignan glycoside (6) and two new phenylethanoid glycosides (7, 8) together with five known compounds as chemical constituents of Strobilanthes cusia root. Some samples were examined for anti-herpes simplex virus type-1 (HSV-1) activity. Among the tested samples, lupeol showed anti-HSV-1 activity (EC(50): 11.7 microM) and showed 100% inhibition of virus plaque formation at 58.7 microM.     

Two new phenylethanoid glycosides from the roots of Phlomis umbrosa

Two new phenylethanoid glycosides were isolated from the roots of Phlomis umbrosa. Their structures were elucidated by spectroscopic methods.     

Hepatoprotective phenylethanoid glycosides from Cirsium setosum

Two new phenylethanoid glycosides, namely β-D-glucopyranoside, 1″-O-(7S)-7-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-[(8E)-7-(3-methoxyl-4-hydroxyphenyl)-8-propenoate] (1) and β-D-glucopyranoside, 1″-O-(7S)-7-(3-methoxyl-4-hydroxyphenyl)-7-methoxyethyl-3″-α-L-rhamnopyranosyl-4″-[(8E)-7-(4-hydroxyphenyl)-8-propenoate] (2), together with six phenylethanoid glycosides were isolated from Cirsium setosum. Their structures were elucidated by their spectroscopic data and references. Compounds 2, 4, 5, 7 and 8 (10 μM) exhibited moderate hepatoprotective activities. Compounds (3–8) were obtained from this plant for the first time.     

New phenylethanoid glycosides from Bacopa monniera

Three new phenylethanoid glycosides, viz. monnierasides I-III (1-3) along with the known analogue plantainoside B were isolated from the glycosidic fraction of Bacopa monniera. Their structures were elucidated mainly on the basis of two dimensional (2D) NMR spectral analyses.     

Five new phenylethanoid glycosides from the whole plants of Lamium purpureum L

Five new phenylethanoid glycosides, lamiusides A (1), B (2), C (3), D (4) and E (5), were isolated from the whole plants of Lamium purpureum L. (Labiatae) together with seven known compounds (6-12). On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (1), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-feruloyl)-beta-D-glucopyranoside (2), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(6-O-trans-caffeoyl)-beta-D-glucopyranoside (3), 2-(3,4-dihydroxyphenyl)-R,S-methoxy-ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (4) and 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-(4-O-cis-feruloyl)-beta-D-glucopyranoside (5). In addition, the radical-scavenging activities of compounds 1-4 on 1,1-diphenyl-2-picrylhydrazyl radical were examined.     

Two new phenylethanoid glycosides and a new secoiridoid glycoside from the roots of Picrorhiza scrophulariiflora

<正>Two new phenylethanoid glycosides,named scroside H(1),scroside I(2),and a new secoiridoid glycoside,named picrogentioside I(3),have been isolated from the underground parts of Picrorhiza scrophulariiflora.Their structures were elucidated on the basis of spectroscopic evidence.     

Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora

One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora (Scrophulariaceae), together with nine known phenylethanoid and phenolic glycosides: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranoside (3), scroside B (4), hemiphroside A (5), plantainoside D (6), scroside A (7), androsin (8), piceoside (9), and 6-O-feruloyl-beta-D-glucopyranoside (10). The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure-activity relationship is discussed.     

Iridoid,phenylethanoid and flavonoid glycosides from Forsythia suspensa

Abstract

As part of our continuing efforts to explore bioactive compounds from natural resources, a new iridoid glycoside, adoxosidic acid-6′-oleuroperic ester (1), together with one known phenylethanoid glycoside (2) and two known flavonoid glycosides (3–4) were isolated from the fruit of Forsythia suspensa. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data and HR-ESIMS. Interestingly, compound 1 was a monoterpene ester of one iridoid glycoside. Compounds 2–4 were identified as calceolarioside A (2), kaempferol-3-O-rutinoside (3), kampferol-3-O-robinobioside (4) on the basis of NMR spectroscopic data analyses and comparison with the data reported in the literature. The antiviral activity aganisist influenza A (H5N1) virus of compound 1 was studied as well.     

New phenylethanoid glycosides from Veronica pectinata var. glandulosa and their free radical scavenging activities

A known phenylethanoid glycoside, ehrenoside (1), was isolated together with three new phenylethanoid glycosides, verpectoside A (2), B (3) and C (4) from the aerial parts of Veronica pectinata var. glandulosa. On the basis of spectral analysis (UV, FAB-MS, 1H-, 13C- and 2D-NMR), compounds 2-4 were determined to be 2-(3,4-dihydroxyphenyl)ethyl-O-alpha-L-arabinopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-feruloyl)-beta-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-caffeoyl)-beta-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-glucopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-(4-O-trans-feruloyl)-beta-D-glucopyranoside, respectively. Isolated phenylethanoid glycosides exhibited potent radical scavenging activity against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.     

Three new spirostanol glycosides from Helleborus thibetanus

Abstract

An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1?D, 2?D NMR spectra, together with IR and MS methods and acid hydrolysis. This is the first report of the isolation of spirostanol glycoside with xylose at C-24 of the aglycone in Helleborus.     

Free radical scavenging phenylethanoid glycosides from Leucas indica Linn

A new phenylethanoid glycoside, 2-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 6)-4-O-E-feruloyl-beta-D-glucopyranoside (3-O-methyl poliu-moside, 1) along with five known phenylethanoid glycosides (2-6) were isolated from the aerial parts of Leucas indica Linn. The structure of compound 1 has been elucidated on the basis of spectral data. Compounds 1-6 exhibited significant antioxidant activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical assay method. These compounds were also found to be moderate inhibitors of xanthine oxidase (XO) enzyme.     

Iridoid and phenylethanoid glycosides from Phlomis longifolia var. longifolia

From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6), leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, 1D- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.     

Two new xanthone glycosides from Swertia punicea Hemsl. and their anti-inflammatory activity

Abstract

Two new xanthone glycosides (1–2), together with seven known analogues (3–9), were isolated from whole herb of Swertia punicea. The structures of these metabolites were established on the basis of detailed spectroscopic analysis and comparison with data reported in the literature. In an in vitro test, all isolates were evaluated for their anti-inflammatory activity. The results revealed that all of them showed significant anti-inflammatory activity with IC₅₀ values ranging from 1.237 to 3.319?mM. Compounds 3, 4, and 5 (IC₅₀ values in the range 1.237–1.987?mM) displayed more potent anti-inflammatory activity than the positive control, indomethacin (IC₅₀ value of 2.004?mM).     

Three new nortriterpene glycosides and two new triterpene glycosides from the bulbs of Scilla scilloides

Three new norlanostane-type triterpene glycosides, scillanostasides A, B, and C, and two new lanostane-type triterpene glycosides, scillanostasides D and E, were isolated from the bulbs of Scilla scilloides Druce (Liliaceae) along with one known norlanostane-type triterpene heptaglycoside, scillascilloside G-1. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.     

Three new 15,16-seco-cycloartane glycosides from Cimicifuga Rhizome

Three new 15,16-seco-cycloartane glycosides, which were constructed by a C-C bond cleavage in the D ring, have been isolated from Cimicifuga Rhizome for the first time. Their structures were determined by the use of 2D NMR techniques and chemical evidence.     

Three new oleanene glycosides from Sophora flavescens.

Three new oleanene glycosides, sophoraflavosides II-IV (2-4) were isolated together with sophoraflavoside I (1) as the corresponding methyl ester forms from Sophorae Radix, the fresh roots of Sophora flavescens AITON (Leguminosae). Their structures have been elucidated as oxytrogenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D- glucuronopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-alpha-L-arabinopyranoside (3) and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (4), along with unambiguous characterization as 3 beta,22 beta,24-trihydroxyolean-12-en-29-oic acid for their sapogenol, named oxytrogenin (5) on the bases of chemical reactions and spectral analyses.     

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.