A new quinone and a new phenolic glycoside from Thymus quinquecostatus / 中草药

Objective: To study the chemical components of Thymus quinquecostatus in order to find new compounds. Methods: The constituents were separated by column chromatographic methods of silica gel, AB-8 resin, Sephadex LH-20 and ODS column. The structures were elucidated by MS and NMR analyses. Results: Two compounds were isolated and identified as 6-hydroxy-11-methyl-12-hydroxymethyl naphtho [2,3-β] furan-1,4-dione (1) and 2-hydroxy-4-isopropyl-5-methylbenzene-O-β-D- glucopyranoside (2). Conclusion: Compounds 1 and 2 are new compounds, named quinquequinone A and quinqueside A, respectively.

A new phenolic glycoside from stems of Gordonia chrysandra / 中草药

Objective: To study the chemical constituents of the stems of Gordonia chrysandra. Methods: The chemical constituents were isolated and purified by column chromatography on silica gel, MPLC and PHPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis. Results: Five compounds were isolated from the stems of G. chrysandra and elucidated as 3,4-dimethoxyphenol 1-O-β-D-[6-O-(4-hydroxy-3,5-dimethoxylbenzoate)-glucopyranoside (1), 3,4,5- trimethoxyphenyl-6- O-vanilloyl-β-D-glucoside (2), 2α,3β,19α-trihydroxyolean-12-en-23,28-dioic acid (3), betulinic acid (4), 3-O-β-D-galactopyranosyl- (1→2)-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)]-β-D-glucuronopyranosyl-3β,16α,22α,28-tetrahydroxy-22-O-tigloyloxy- olean-12-ene-23-al (5). Conclusion: Compound 1 is a new compound named chrysandroside A, and compounds 3-5 are isolated from this plant for the first time.

Phenolic Glycosides from the Aerial Part of Urena lobata / 中国药学杂志

OBJECTIVE: To study the phenolic glycosides of Urena lobata. METHODS: Compounds were isolated and purified using various column chromatographies such as D101 macroporous adsorption resin, silica gel, Sephadex LH-20, and preparation HPLC. Their structures were established using extensive spectroscopic techniques such as MS and NMR. The anti-inflammatory activities of all compounds were evaluated by using LPS-stimulated RAW264.7 cells. RESULTS: Twelve phenolic glycosides were obtained from the n-BuOH extract of U. lobata including benzyl-7-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (1), phenylethyl-8-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2), phenylethyl-8-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (3), eugenyl-1-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (4), 6-methoxyeugenyl-1-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (5), 3,4,5-trimethoxybenzene-1-O-α-L-rhamnosyl-(1→6)-β-D-glucopyranoside (6), 4-O-(glycer-2-yl)-dihydroconiferylalcohol-1′-O-β-D-mannopyranoside (7), benzyl-7-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (8), 3,5-dimethoxy-4-hydroxyphenylethyl-8-O-β-D-glucopyranoside (9), 3,4,5-trimethoxybenzene-1-O-β-D-glucopyranoside (10), phenylethyl-8-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside(11),and 3,4,5-trimethoxybenzene-1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (12). CONCLUSION: Compounds 2-8 and 10-12 are obtained from the family Malvaceae for the first time, and compounds 3, 8, 9 and 11 show moderate inhibition of nitric oxide production in LPS-stimulated RAW264.7 cells, with IC50values of(40.5±4.9 ), (31.9±4.6),( 37.7±3.3 ), and (36.1±4.6 )μmol•L-1, respectively.

A new phenolic glycoside from honey-fried Eriobotrya japonica / 中国中药杂志

A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-β-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-β-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-β-D-galactopyranoside( 8),quercetin-3-O-β-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.

A new phenolic glycoside from rhizomes of Sinacalia tangutica / 中草药

Objective: To study the chemical constituents from the rhizomes of Sinacalia tangutica. Methods: The compounds were separated and purified by D101 macroporous resin, silica gel, and ODS column chromatography. Their structures were elucidated by extensive spectroscopic methods including 1H-NMR, 13C-NMR, DEPT, HSQC, HMBC, and HR-ESI-MS. Results: One new phenolic glycoside was isolated from S. tangutica, and identified as 5-hydroxyeugenol-4-O-β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranoside (1). Conclusion: Compound 1 is a new compound named singuticoside.

Chemical constituents from a Tibetan herbal medicine Corydalis hendersonii / 中国中药杂志

Nine alkaloids and two phenolic glycosides were isolated from EtOH extract of the whole plants of Corydalis hendersonii by various chromatographic techniques including silica gel, ODS, Sephadex LH-20, and semi-preparative HPLC. Their structures were identified as groenlandicine (1), berberine (2), protopine (3), cryptopine (4), N-trans-feruloyloctopamine(5), 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl] acrylamide (6), N-cis-p-coumaroyloctopamine (7), N-trans-p-coumaroylnoradrenline (8),N-cis-feruloyloctopamine (9), apocynin (10), and glucoacetosyringone (11) by the spectroscopic data analysis and comparison with those in the literature. Among them, compounds 10 and 11 were isolated from this genus for the first time, and 1, 2, and 5-9 were isolated from the species for the first time. All isolates were tested for their protection for in vitro PC12 cell line and antiplatelet aggregation activity. The results showed that compounds 5 and 7 displayed protective effects at a concentration of 10 μmol·L⁻¹, and compound 2 showed antiplatelet aggregation activity induced by THR, ADP, and AA, and compound 3 exhibted inhibitory effect induced by THR.

Phenolic glycosides from root of Oplopanax elatus / 中草药

Objective To investigate the hydrophilic constituents from the anti-colorectal cancer extract of Oplopanax elatus. Methods The compounds were isolated and purified using macroporous resin, silica gel, ODS gel and pre-HPLC, and their chemical structures were identified by spectral data and physicochemical properties. The extracts and compounds from O. elatus were screened for anti-proliferation on HCT-116 and HT-29 cancer cell lines. Results Eleven phenolic compounds had been purified and identified from the n-butanol fraction including six phenylpropanoid glycosides: (E)-sinapic acid-4-O-β-D-glucopyranoside (1), 3- hydroxyphenethyl alcohol-4-O-β-D-glucopyranoside (2), 3-methoxycinnamyl alcohol-4-O-β-D-glucopyranoside (3), homovanillyl alcohol-4-O-β-D-glucopyranoside (4), dihydrosyringin (5), and syringin (6); And five lignan glycosides: 3,3'-dimethoxy-4,9,9'- trihydroxy-4',7-epoxy-5',8-lignan-4,9-bis-O-β-D-glucopyranoside (7), (+)-5,5'-dimethoxylariciresinol 4'-O-β-D-glucopyranoside (8), (+)-isolariciresinol-9'-O-β-D-glucopyranoside (9), (+)-isolariciresinol-4-O-β-D-glucopyranoside (10), and (+)-5,5'-dimethoxylariciresinol- 9'-O-β-D-glucopyranoside (11). All the phenolic glycosides showed no significant effects on the proliferation of HCT-116 and HT-29 cancer cell lines with IC50 > 100 μmol/L. Conclusion Compounds 4, 6, 9, and 11 are isolated and purified from this herb for the first time, while compounds 1, 2, and 10 are firstly obtained from the genus Oplopanax.

Two new phenolic glycosides isolated from the fruits of Citrus aurantium / 中国天然药物

The present study was designed to investigate the chemical constituents of the fruit of Citrus aurantium L.. The compounds were isolated and purified by various chromatographic techniques, and their structures were elucidated on the basis of physicochemical properties and spectral data. Two new phenolic glycosides (compounds 1 and 2) were obtained and identified as 1-O-3, 5-dihydroxyphenyl-(6-O-4-hydroxybenzoyl)-β-D-glucopyranoside (1) and 1-O-3, 5-dihydroxyphenyl-(6-O-3-methoxy-4-hydroxy benzoyl)-β-D-glucopyranoside (2), respectively.

Iridoid and phenylethanoid glycosides from the aerial part of Barleria lupulina

Abstract A new iridoid glycoside, barlupulin C methyl ester (1), together with two known phenylethanoid glycosides (2 and 3) and three known simple phenolic glycosides (4-6) were isolated from the aerial parts of Barleria lupulina Lindl., Acanthaceae. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data, and HR-ESIMS. Interestingly, compound (1) has a formate group attached to the C-6 hydroxy group of the glucose unit. Compounds 2-6 were identified as poliumoside (2), decaffeoylacteoside (3), protocatechuic acid 4-O-β-glucoside (4), vanillic acid 4-O-β-glucoside (5), and leonuriside A (6) on the basis of NMR spectroscopic data analyses and comparison with those reported in the literature. Compounds 3-6 were isolated from B. lupulina for the first time.

Studies on chemical constituents of rhizomes of Smilax trinervula / 中国中药杂志

The chemical constituents were separated and purified from the 70% ethanol extract of Smilax trinervulaby various chromatographic methods including silica gel, Sephadex LH-20, MCI and preparative HPLC. Their structures were obtained and identified by analysis of the spectroscopic data. Compounds 1-11 were separated from this genus for the first time. Compound 12 was obtained from S. trinervula for the first time.

Isolation and identification of anti-inflammatory constituents from Houttuynia cordata / 中国药科大学学报

@#Ten compounds were isolated and purified from the ethyl acetate fraction of Houttuynia cordata by silica gel and ODS column chromatographies. The chemical structures of the compounds were identified on the basis of physicochemical properties as well as spectral data. These isolated compounds were elucidated as sequinoside L(1), a new phenolic glycoside, together with nine known compounds, including sequinoside K(2), methyl chlorogenate(3), chlorogenic acid(4), hydroquinone(5), vanillic acid(6), hyperin(7), isoquercitrin(8), quercetin(9), and quercitrin(10). In addition, the anti-inflammatory activities of compounds 1-10 were evaluated in LPS-induced RAW264. 7 macrophages. Among them, compounds 1, 2, 6 and 9 showed potent anti-inflammatory activity which was similar to that of positive control dexamethasone.

Chemical constituents from the whole plants of Lagopsis supina / 中国药学杂志

OBJECTIVE: To investigate the chemical constituents from the whole plants of Lagopsis supina. METHODS: The compounds were isolated and purified by various column chromatography, and their structures were identified based on their physiochemical properties and spectroscopic data. RESULTS: Thirteen compounds were isolated from the n-hexane, dichloromethane, and water extracts of the whole plants of Lagopsis supina by using various chromatographic methods. Their structures were identified as phytol(1), daucosterol(2), 8-O-acetylharpagide(3), antirrinoside(4), ajugoside(5), ajugol(6), harpagide(7), 1-O-caffeoyl-β-D-glucopyranose(8), 1-O-coumaroyl-β-D-glucopyranose(9), 2-hydroxy-5-(2-hydroxyethyl)phenyl-1-O-β-D-glucopyranoside(10), methyl 2-O-β-D-glucopyranosylbenzoate(11), adenosine(12), and sucrose(13), respectively. CONCLUSION: Compounds 1 and 3-13 are isolated from the plants of Lagopsis genus for the first time.

Inhibitory effects of phenolic glycoside compound xylocontroside D against Aβ1-42 induced neurotoxicity / 中国药学杂志

OBJECTIVE: To investigate the inhibitory effects of phenolic glycoside compound xylocontroside D on neurotoxicity of primary cultured cortical neurons induced by Aβ1-42. METHODS: The primary cortical neurons and microglia cells derived from rat cerebral tissues were used and neurotoxicity were induced by Aβ1-42. Then the thiazolyl blue tetrazolium bromide test (MTT) was applied for detecting cell survivability; cells were incubated with CH3-H2DCF-DA for evaluating cellular endogenous reactive oxygen species (ROS) level by flow cytometry; fluorescent staining of 8-hydroxy-2-deoxyguanosine (8-OH-DG) was applied for identifying the metabolites of ROS based DNA damage; fluorescent imaging was applied for illustrating the activation of microglia cells and the enzyme-linked immunosorbent assay (ELISA) was applied for analysis of pro-inflammatory cytokines, cyclooxygenase-1 (COX-1), cyclooxygen-ase-2(COX-2), interleukin-1beta (IL-1β) and tumor necrosis factor alpha (TNF-α). RESULTS: Xylocontroside D showed significant inhibitory effects on Aβ1-42 induced neurotoxicity, including cell death, cellular endogenous ROS levels and DNA damage caused by ROS reaction. Moreover, this compound could also prevent the activation of microglia, decrease the production or secretion of proinflammatory cytokines that produced by activated microglia, such as COX-1, COX-2, IL-1β and TNF-α. CONCLUSION: Our results indicated that xylocontroside D was able to inhibit the oxidative stress injury and neuroinflammation of primary cultured cortical neurons induced by Aβ1-42.

A new phenolic glycoside from Li medicine Lihua Bidou Yan Prescription / 中草药

Objective: To study the chemical constituents of Li medicine Lihua Bidou Yan prescription. Methods: Chemical constituents were isolated by using various column chromatography. The structures were elucidated on the basis of physicochemical constants and spectral analysis. The anti-inflammatory activities of compound 1 were evaluated using LPS-induced RAW 264.7 cells. Results: Two compounds were obtained from Lihua bidou yan Prescription and identified as rhyncoside A-4-methly ether (1) and rhyncoside C (2), respectively. The NO production in LPS-induced RAW264.7 cells was slightly inhibited by compound 1 at a concentration of 50 μmol/L. Conclusion: Compound 1 is a new phenolic glycoside; Compound 2 is obtained from the prescription for the first time. Rhyncoside A-4-methyl ether has anti-inflammatory activity.

A new steroidal glycoside from Lygodium japonicum / 中国药科大学学报

To investigate the chemical constituents from the aerial parts of Lygodium japonicum. Methods:Various chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by chemical evidence and spectral methods. Results:A new stigmasterol glycoside,(24R)-stigmastan-3β,5α,6β-triol 3-O-β-D-glucopyranoside (1),together with three known phenolic glycosides:6-O-p-coumaroyl-D-glucopyranose (2),6-O-caffeoyl-D-glucopyranose (3),1-O-(E)-caffeoyl-β-D-gentiobiose (4) were obtained and identified by spectroscopic methods. Conclusion:All compounds were isolated from Lygodiaceae for the first time.

Chenoalbuside: an antioxidant phenolic glycoside from the seeds of Chenopodium album L. (Chenopodiaceae)

In addition to three known phytoecdysteroids, a new phenolic glycoside (named, chenoalbuside) was isolated from the methanol extract of the seeds of Chenopodium album. While the structures of all phytoecdysteroids were elucidated by direct comparison of their spectroscopic data with published data, the structure of chenoalbuside was determined unequivocally by a combination of UV, MS and 1D and 2D NMR spectroscopic analyses. The antioxidant potential of the new compound was assessed by the DPPH assay, and the RC50 value was found to be 1.4 x 10-4 mg/mL.

Chemical studies on root bark of Lycium chinense / 中草药

Object To study the chemical constituents of the root bark of Lycium chinense Mill Methods Various chromatographic techniques were used to separate and purify the constituents Their structures were elucidated on the physico chemical properties and spectral data Results Five compounds were isolated from the root bark of L chinense and identified as vanillic acid (Ⅰ), apigenin (Ⅱ), linarin (Ⅲ), glucosyringic acid (Ⅳ) and digupigan A (Ⅴ) Conclusion Digupigan A is a new compound. Except vanillic acid, others were isolated from this plant for the first time

A new phenolic glycoside from fruits of Citrus aurantium / 中草药

Objective To study the bioactive constituents of the immature fruits of Citrus aurantium. Methods Silica gel and Sephadex LH-20 were used to isolate the constituents of this plant. The spectroscopic methods were applied for their structural elucidation. Results Four compounds were isolated from the ethanol extract of the immature fruits of C. aurantium. These compounds were elucidated as 3, 5-dihydroxyphenyl 1-O-(6′-O-trans-feruloyl)-?-D-glucopyranoside (Ⅰ), hesperetin (Ⅱ), 4′, 5, 7, 8-tetra- methoxyflavone (Ⅲ), and limonin (Ⅳ). Conclusion Compound Ⅰ is a new phenolic glycoside.