Phenolic glycosides from the stems and twigs of Strychnos cathayensis and their biological activities / 药学学报

Fourteen compounds were isolated from the n-butanol fraction of the 95% aqueous ethanol extract of the stems and twigs of Strychnos cathayensis by D101 macroporous resin, silica gel, ODS, Sephadex LH-20 column chromatography, and semipreparative RP-HPLC. Their structures were elucidated as ethyl 4-O-β-D-allopyranosyl-vanillate (1), n-butyl 4-O-β-D-allopyranosyl-vanillate (2), n-butyl 4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillate (3), n-butyl 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillate (4), n-butyl 4-O-(6′-O-syringoyl)-β-D-glucopyranosyl-vanillate (5), n-butyl 4-O-α-L-rhamnopyranosyl-syringate (6), methyl 3-methoxy-4-(β-D-allopyranosyloxy) benzoate (7), pseudolaroside B (8), butyl syringate (9), glucosyringic acid (10), methyl syringate (11), methyl 4-hydroxy-3-methoxybenzoate (12), clemochinenoside C (13), and clemoarmanoside A (14), respectively, on the basis of spectroscopic data interpretation and by comparison with literature information. Compounds 1-6 are artificial products of phenolic acid esterified by ethanol or n-butanol. It is noted that the precursors (4-O-(6′-O-syringoyl)-β-D-allopyranosyl-vanillic acid and 4-O-(6′-O-vanilloyl)-β-D-allopyranosyl-vanillic acid) of compounds 3 and 4 are new compounds. The hepatoprotective, anti-inflammatory, antioxidant and cytotoxic activities of compounds 1-13 were evaluated in vitro at a concentration of 10 μmol·L-1. Compounds 1, 2 and 6-10 exhibited potential hepatic protection effects with cell survival rates ranging from 53.6% to 55.5% (acetaminophen, 45.4% at 8 mmol·L-1). Compound 4 demonstrated anti-inflammatory activity with nitric oxide inhibitory rate of 74.6%. Compounds 3 and 5 showed potential antioxidant activities with malondialdehyde inhibitory rates of 53.2% and 56.1%, respectively.

Chemical constituents from leaves of Craibiodendron yunnanense / 中国中药杂志

The present study investigated the chemical constituents from the leaves of Craibiodendron yunnanense. The compounds were isolated and purified from the leaves of C. yunnanense by a combination of various chromatographic techniques including column chromatography over polyamide, silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified by extensive spectroscopic analyses including MS and NMR data. As a result, 10 compounds, including melionoside F(1), meliosmaionol D(2), naringenin(3), quercetin-3-O-α-L-arabinopyranoside(4), epicatechin(5), quercetin-3'-glucoside(6), corbulain Ib(7), loliolide(8), asiatic acid(9), and ursolic acid(10), were isolated. Compounds 1 and 2 were two new compounds, and compound 7 was isolated from this genus for the first time. All compounds showed no significant cytotoxic activity by MTT assay.

A new lignan glucoside from stems and branches of Rhododendron ovatum / 中国中药杂志

Ten lignans were isolated from the ethanol extract of stems and branches of Rhododendron ovatum through column chromatography over silica gel, ODS, Sephadex LH-20, and MCI-gel resin and semi-preparative RP-HPLC. The structures of all compounds were elucidated by extensive spectroscopic data analysis(UV, IR, HR-ESI-MS, ECD and NMR) as(-)-4-epi-lyoniresinol-9'-O-α-L-rhamnopyranoside(1),(+)-lyoniresinol-3α-O-α-L-rhamnopyranoside(2),(+)-5'-methoxyisolariciresinol-9'-O-α-L-rhamnopyranoside(3),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(4),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(5),(-)-4-epi-lyoniresinol-9'-O-β-D-glucopyransoide(6), racemiside(7), neociwujiaphenol(8),(+)-syringaresinol(9), and homohesperitin(10). Among them, compound 1 was a new aryltetralin-type lignan. All the isolated lignans were tested for antioxidant activities in Fe~(2+)-cysteine induced rat liver microsomal lipid peroxidation in vitro, and compounds 8 and 9 showed antioxidant activities on the formation of malondiadehyde(MDA) in rat liver microsomes at 1×10~(-5) mol·L~(-1), with significant inhibitory rates of 75.20% and 91.12%, respectively.

Rhodojaponin VI indirectly targets Cav2.2 channels via N-ethylmaleimide-sensitive fusion protein to alleviate neuropathic pain

Neuropathic pain is a chronic disease that severely afflicts the life and emotional status of patients, but currently available treatments are often ineffective. Novel therapeutic targets for the alleviation of neuropathic pain are urgently needed. Rhodojaponin VI, a grayanotoxin from Rhododendron molle, showed remarkable antinociceptive efficacy in models of neuropathic pain, but its biotargets and mechanisms are unknown. Given the reversible action of rhodojaponin VI and the narrow range over which its structure can be modified, we perforwmed thermal proteome profiling of the rat dorsal root ganglion to determine the protein target of rhodojaponin VI. N-Ethylmaleimide-sensitive fusion (NSF) was confirmed as the key target of rhodojaponin VI through biological and biophysical experiments. Functional validation showed for the first time that NSF facilitated trafficking of the Cav2.2 channel to induce an increase in Ca2+ current intensity, whereas rhodojaponin VI reversed the effects of NSF. In conclusion, rhodojaponin VI represents a unique class of analgesic natural products targeting Cav2.2 channels via NSF.

Research advances in methods of cyclezation mechanism of sesquiterpenes / 中国中药杂志

Terpenes are the largest group of natural products and contain the widest assortment of structural types. Terpene cyclization is also the most complex reaction found in nature. For a long time, terpenoids with diverse structures have attracted natural product chemists to explore their biosynthesis mechanism. Such a large number of terpene skeletons are catalyzed by enzymes called terpene synthase. Sesquiterpene synthase is a kind of terpene synthase, which can catalyze the cyclization of linear precursor farnesyl pyrophosphate(FPP) to sesquiterpene skeletons. Sesquiterpene synthase cyclize a single precursor FPP into many sesquiterpene skeletons. With the continuous discovery of sesquiterpene synthase, the cyclization mechanism of sesquiterpene synthase has been studied deeply. In recent years, with the development and improvement of isotope labeling of substrate FPP and structural analysis of sesquiterpene synthase, the structure and cyclization mechanism of sesquiterpene synthase have been studied more systematically and accurately. In this review, we reviewed the progress of the research methods on the mechanism of sesquiterpene cyclization by substrate isotope labeling and protein structure, as well as the summary and prospect of sesquiterpene synthase research.

Erythrina alkaloids from stems of Erythrina corallodendron / 中国中药杂志

This study aims to investigate Erythrina alkaloids from the stems of Erythrina corallodendron. Eighteen Erythrina alkaloids were isolated from the 95% ethanol extract of the stems of E. corallodendron by silica gel,octadecyl silica( ODS),Sephadex LH-20 column chromatography and preparative HPLC. With nuclear magnetic resonance( NMR) spectroscopy and mass spectrometry( MS),their structures were identified as crstanine A( 1),erytharbine( 2),cristamine C( 3),( +)-erystramindine( 4),10,11-dioxoerythraline( 5),8-oxoerythraline( 6),8-oxo-11β-methoxyerythradine( 7),11-methoxyerythradine( 8),( ±)-11-epi-methoxyerythraline( 9),( +)-erythraline( 10),crystamidine( 11),8-oxoerythrinine( 12),( +)-11α-hydroxyerysotrine( 13),erythrinine( 14),erysodine( 15),erysotrine-N-oxide( 16),( +)-erythratidine( 17),erythratine( 18). Compounds 1-4,7,9,11,13,16 and 17 were isolated from E. corallodendron for the first time. Furthermore,the cytotoxic activities of these Erythrina alkaloids were screened by MTT assay. The results showed that all compounds had no obvious cytotoxic activity. The analgesic activities of compounds1,6 and 8 were evaluated using an acetic acid-induced writhing test in mice. The writhing inhibition rates of compounds 1,6 and 8 at20 mg·kg~(-1)( ip) were 69%,70% and 62%,respectively( P<0. 01),indicating they have significant analgesic activity.

Chemical compositions from roots of Erythrina corallodendron / 中国中药杂志

This project is to investigate chemical compositions from the roots of Erythrina corallodendron. Through the methods of silica gel,ODS,Sephadex LH-20 column chromatography and preparative HPLC,15 compounds were isolated from the 95% ethanol extract of the roots of E. corallodendron. Based on spectroscopic techniques,the structures of these compounds were identified as 10,11-dioxoerythraline( 1),erythrinine( 2),erythraline( 3),11-methoxyerythraline( 4),cristanines B( 5),erythratine( 6),erysotrine( 7),medioresinol( 8),( ±)-ficusesquilignan A( 9),( +)-pinoresinol( 10),nicotinic acid( 11),dibutyl phthalate( 12),vanillic acid( 13),3-hydroxy-1-( 4-hydroxy-3-methoxyphenyl)-1-propanone( 14),and syringic acid( 15). Compounds 8-10 are isolated from genus Erythrina for the first time and all compounds are isolated from E. corallodendron for the first time. Furthermore,this paper screened the antioxidant and cytotoxic activities of the compounds using models of liver microsomal oxidation inhibition and MTT.

Lignans from seed of Hydnocarpus anthelminthica / 中国中药杂志

This project is to investigate lignans from the seed of Hydnocarpus anthelminthica. Thirteen lignans were isolated from the 95% ethanol extract of the seed of H. anthelminthica, by polyamide resin, Sephadex LH-20, ODS column chromatography and preparative HPLC. Their structures were elucidated as(+)-syringaresinol(1), lirioresinol A(2),(+)-medioresinol(3),(7R,8R,8'R)-4'-guaiacylglyceryl-evofolin B(4), leptolepisol C(5),(-)-(7R,7'R,7″R,8S,8'S,8″S)-4',4″-dihydroxy-3,3',3″,5,5',5″-hexamethoxy-7,9':7',9-diepoxy-4,8″-oxy-8,8'-sesquineolignan-7″,9″-diol(6),(-)-(7R,7'R,7″R,8S,8'S,8″S)-4',4″-dihydroxy-3,3',3″,5,5'-pentamethoxy-7,9':7',9-diepoxy-4,8″-oxy-8,8'ses-quineolignan-7″,9″-diol(7), ceplignan(8), hydnocarpusol(9), isohydnocarpin(10),(-)-hydnocarpin(11), hydnocarpin(12), and hydnocarpin-D(13) by spectroscopic data analysis. Compounds 1-8 were obtained from the genus Hydnocarpus for the first time.

A new dimeric xanthanolide from fruits of Xanthium chinense / 中国中药杂志

Through the methods of polyamide resin， Sephadex LH-20， ODS column chromatography and preparative HPLC etc.， 7 compounds were isolated from the 70% ethanol extract of the fruits of Xanthium chinense. Based on ESI-MS and NMR data， the structures of these compounds were identified as pungiolide O(1)， grasshopper ketone(2)， icariside F₂(3)， 7-[(β-D-apiofuranosyl-(1→6)-β-D-glucopyranosyl)oxymethy]-8，8-dimethyl-4，8-dihydrobenzo[1，4]thiazine-3，5-dione(4)，(6R，9S)-3-oxo-α-ionol β-D-glucopyranoside(5)， cryptochlorogenic acid methyl ester(6)， and chlorogenic acid methyl ester(7). Among them， compound 1 is a new compound.

A new indole alkaloid from the stems of Brucea mollis / 药学学报

Eight compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as bruceolline O (1), 1-(1-beta-glucopyranosyl)-1H-indole-3-carbaldehyde (2), canthin-6-one (3), 11-hydroxycanthin-6-one (4), 9-methoxycanthin-6-one (5), 4-methoxycanthin-6-one (6), infractin (7), and beta-carboline-1-propionic acid (8). The cytotoxic activities of compounds 1-8 against HCT-8 and A549 human cell lines were determined, but none of them exhibited significant activity (IC 50 > 10 micromol x L(-1)). Among them, compound 1 is a new indole alkaloid, and compounds 2 and 5-7 were isolated from this plant for the first time.

Chemical constituents from Vaccinium bracteatum / 中国中药杂志

The chemical constituents of Vaccinium bracteatum were studied by means of macroporous resin, ODS column chromatography and preparative HPLC. Eleven compounds were isolated from this plant. By using ESI-MS and NMR, the structures of the eleven compounds were determined as 10-O-trans-p-coumaroyl-6alpha-hydroxyl-dihydromonotropein (1), 10-O-cis-p-coumaroyl -6alpha-hydroxyl-dihydromonotropein (2), vaccinoside (3), 10-O-cis-p-coumaroyl monotropein (4), isolariciresinol-9-O-beta-D-xyloside (5), tectoridin (6), vicenin-3 (7), quercetin-3-O-alpha-L-rhamnoside (8), quercetin-3-O-alpha-L-arabinopyranoside (9), quercetin-3-O-beta-D-galactopyranoside (10), and quercetin-3-O-beta-D-glucuronide (11), respectively. Compounds 1 and 2 are new, and compounds 4, 6 and 7 are isolated from the genus Vaccinium for the first time.

Study on secondary metabolites of endophytic fungi Penicillium polonicum / 中国中药杂志

The PDB culture medium was selected to ferment the endophyte strain, and the secondary metabolites of endophytic fungi Penicillium polonicum were studied. Combined application of Sephadex LH-20, ODS and HPLC chromatographies over the ethyl acetate extract of the fermented culture led to the isolation of 6 compounds. By spectral methods, the structures were elucidated as [3, 5-dihydroxy-2-(7-hydroxy-octanoyl)]-ethylphenylacetate (1), (3, 5-dihydroxy-2- octanoyl)-ethyl phenylacetate (2), (5, 7-di- hydroxy-9-heptyl)-isobenzo pyran-3-one (3), 3-(hydroxymethyl) 4-(1E)-1- propen-1-yl-(1R, 2S, 5R, 6S)-7-oxabicyclo [4.1.0] hept-3-ene-2, 5-diol (4), (E)-2-methoxy-3-(prop-1-enyl) phenol (5) and p-hydroxylphenylethanol (6).

Chemical constituents from roots of Illicium majus / 中国中药杂志

Ten compounds, including seven sesquiterpenes, two phenols and one phenylpropanoid, were isolated from the roots of Illicium majus by means of silica gel, ODS, Sephadex LH-20, and preparative HPLC. On analysis of MS and NMR spectroscopic data , their structures were established as cycloparviflorolide (1), cycloparvifloralone (2), tashironin (3), tashironin A (4), anislactone A(5), anislactone B (6), pseudomajucin (7), syringaldehyde (8), methyl-4-hydroxy-3, 5-dimethoxybenzoate (9), and (E)-3-methoxy-4,5-methylenedioxycinnamic alchol (10), respectively. Compounds 1-4 and 8-10 were first isolated from this plant. In the in vitro assays, at a concentration of 1.0 x 10(-5) mol x L(-1), compounds 5 and 6 were active against LPS induced NO production in microglia with a inhibition rate of 75.31% and 53.7%, respectively.

Chemical constituents of Periploca forrestii / 中国中药杂志

The chemical constituents of Periploca forrestii were studied by means of macroporous resin, silica gel, ODS column chromatography and PHPLC. Nine compounds were isolated from this plant. By using ESI-MS and NMR, the structures of the nine compounds were determined as scopoletin (1), trans-3, 4-methylenedioxycinnamyl alcohol (2), syringaresinol (3), syringaresinol 4-0-beta-D-glucopyranoside (4), 6'-0-(E)-feruloylsucrose (5), loliolide (6), 4-hydroxy-3-methoxyl-benzaidehyde (7), delta5-pregnene-3beta, 17alpha, 20alpha-triol (8) and delta5-pregnene-3 beta, 17alpha, 20 alpha-triol-20-0-beta-D-canaropyranoside (9), respectively. Compounds 1, 2 and 5-7 are isolated from Periplocagenus for the first time.

Flavonoid glycosides from leaves of Turpinia arguta and their anti-inflammatory activity / 中国中药杂志

Eight compounds were isolated from the leaves of Turpinia arguta by various chromatograhic techniques such as D101 macroporous resin, polyamide, Sephadex LH-20,and HPLC chromatography, and their structures were elucidated as rhoifolin (1), apigenin-7-O- [2"-O-alpha-L-rhamnopyranosyl-6"-O-alpha-L-rhamnopyranosyl] -beta-D-glucopyranoside (2), acacetin-7-O- [2"-O-alpha-L-rhamnopyranosyl-6"-O-beta-D-glucopyranosyl] -beta-D-glucopyranoside (3), acacetin-7-O- [2"-O-alpha-L-rhamnopyranosyl-6"-O-alpha-L-rhamnopyranosyl] -beta-D-glucopyranoside(neobudofficide, 4), luteolin-7-O-[2"-O-beta-D-glucopyranosyl] -beta-D-glucopyranoside (5), chrysoeiml-7-O-[2"-O-beta-D-glucopyranosyl] -beta-D-glucopyranoside (6), acacetin-7-O-alpha-L-rhamnopyranosyl-(1 --> 6) -O-beta-D-glucopyranoside (buddleoside, linarin, 7), and apigenin 6, 8-di-C-beta-D-glucopyranoside (8) on the basis of spectral data analysis. Compounds 3-8 were isolated from T. arguta for the first time. Compounds 2, 3 showed weak anti-inflammatory effect on LPS-stimulated RAW264.7 cell.

Chemical constituents from stems of Brucea mollis and their cytotoxic activity / 中国中药杂志

Ten compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as deacetylated isobrucein B (1), indaquassin X (2), cleomiscosin A (3), cleomiscosin B (4), (+)-lyoniresinol (5), (+)-epipinoresinol(6), (+)-pinoresinol (7), (+)-syringaresinol (8), 4,5-dihydroblumenol A (9) and adenosine (10) on the basis of spectroscopic data analysiS. All compounds were obtained from this plant for the first time, moreover, compound 1 was a new natural product. Compound 2 showed significant cytotoxic activities against the human cell lines HT-29, HepG2, BGC-823 and SKOV3 with IC50 values of 0.84-3.97 micromol x L(-1).

Metabolites of Aspergillus fumigatus / 中国中药杂志

Aspergillus fumigatus, a type of endophytic fungi from Erthrophleum fordii, was fermented with GPY culture medium. Fermented liquid and mycelium were extracted from fermented products after freezing and thawing treatment. After alcohol extraction, mycelium was extracted with ethyl acetate and n-butyl alcohol, respectively. According to the results of cytotoxity of tumor cells, ethyl acetate extracts were studied for their chemical constituents. Five diketopiperazine compounds were separated and purified with silica gel, MCI and Sephadex LH-20 column chromatography, reversed-phase chromatographic column and preparative HPLC, their structures were identified as cyclo- (R-Pro-R-Phe) (1), cyclo- (trans-4-OH-D-Pro-D-Phe) (2), cyclo- (R-Tyr-S-Ile) (3), cyclo-(R-Phe-S-Ile) (4), and cyclo-(R-Val-S-Tyr) (5) by using spectral methods.

Blocking extracellular HMGB1 activity protects against doxorubicin induced cardiac injury in mice / 药学学报

This study aims to investigate the preventive role and potential mechanisms of blocking extracellular HMGB1 function on doxorubicin induced cardiac injury. Mice were treated with HMGB1 blocker glycyrrhizin 1 h before and one time every day (intraperitoneal, 10 mg per mouse) after doxorubicin injection, and sacrificed on the day 14 after doxorubicin challenge. Cardiac function was evaluated by echocardiography and hemodynamic measurement. Myocardial inflammation and collagen deposition were analyzed by immunohistochemistry and picrosirius red staining. The interaction of HMGB1 and TLR2 was assessed by co-immunoprecipitation and confocal microscopy. The protein contents of HMGB1, MyD88, p65NF-kappaB and phospho-p65NF-kappaB were measured by Immunoblot. Compared with mice treated with saline, doxorubicin treatment led to an upregulation in HMGB1 expression. Blocking HMGB1 activity with glycyrrhizin protected mice against cardiac dysfunction, inflammatory response, and cardiac fibrosis induced by doxorubicin challenge. Glycyrrhizin inhibited the interaction of HMGB1 and TLR2, and blocked the downstream signaling of TLR2. In conclusion, blocking HMGB1 protected against doxorubicin induced cardiac injury by inhibiting TLR2 signaling pathway.

Studies on chemical constituents from leaves of Lysidice brevicalyx / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Lysidice brevicalyx.</p><p><b>METHOD</b>Various chromatographic techniques were used to isolate and purify the constituents such as column chromatography on silica gel, Rp-silica gel, Sephadex LH-20 and HPLC. The structures were elucidated by chemical evidence and spectroscopic methods.</p><p><b>RESULT</b>Seven compounds were isolated from the 95% ethanol extract of the leaves of L. brevicalyx and these compounds were elucidated as 2-0-[1-(3-methylbutyryl)phloroglucin-ol]-beta-D-glucopynanoside (1), 3-beta-D-glucopyranosyloxy-4, 5-dimethoxy-benzoic acid (2), benzyl alcohol O-beta-D-glucopyra noside (3), polydatin (4), quercetin-3-alpha-L-rhamnopyranoside (5), ethyl gallate (6), benzyl 6-O-alpha-L-arabinofurano syl-beta-D-glucopynanoside (7).</p><p><b>CONCLUSION</b>All Compounds were isolated from this plant for the first time. Compounds 2, 3, 5-7 were obtained from this genus for the first time.</p>

Study on phenylpropanoids from Dregea sinensis var. corrugata / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Dregea sinensis var. corrugata.</p><p><b>METHOD</b>The chemical constituents were isolated by various column chromatographic techniques. Structures were elucidated on the basis of NMR data.</p><p><b>RESULT</b>Eight compounds were isolated and their structures were elucidated as syringaresinol (1), syringaresinol-O-3-D-glycopyranoside (2), 3, 4'-dimethoxyl-4, 9, 9'-trihydroxyl-benzofuranneolignan-7'-ene (3), 3, 4'-di- methoxyl-4, 9-dihydroxyl-9'-hydroethyl-benzofuranneolignan-7'-ene (4), conifer-aldehyde (5), sinapic aldehyde (6), 3-hydoxy-1-(4-hydroxy-3-methoxy-phenyl)-propan-1-one (7), 3-hydroxy-1-(3-methoxy-4-hydroxyphenyl)-propan-1-one (8).</p><p><b>CONCLUSION</b>Compounds 1-8 were isolated from Dregea sinensis var. corrugata for the first time.</p>