Dichapetalin-type triterpenoids from Dichapetalum longipetalum and their anti-inflammatory activity.

A phytochemical research on the twigs of Dichapetalum longipetalum (Turcz.) Engl. Resulted in five undescribed dichapetalin-type triterpenoids 1-5. Their chemical structures were determined by spectroscopic analysis of HR-ESIMS and NMR spectra and the absolute configuration of compound 1 was completely elucidated by single crystal X-ray crystallography. Through preliminary anti-inflammatory activity assessment, compound 1 exhibited inhibitory effect on LPS-induced NO production in RAW264.7 murine macrophages with an IC50 value of 2.09 µM.

Nine new dichapetalin-type triterpenoids from the twigs of Dichapetalum gelonioides (Roxb.) Engl.

Nine previously undescribed dichapetalin-type triterpenoids (1-9), along with 12 reported compounds (10-21), were isolated from the twigs of Dichapetalum gelonioides. Their chemical structures were mainly elucidated by comprehensive analysis of HRMS, 1D and 2D NMR spectroscopic data. The absolute configuration of compound 1 was further determined based on single-crystal X-ray diffraction. In addition, a part of compounds were evaluated the effects of inhibitory NO production in LPS-induced RAW264.7 macrophages.

[Anti-tumor metastatic constituents from Rhodiola wallichiana].

To study the anti-tumor metastatic constituents in Rhodiola wallichiana (HK) S H Fu var Cholaensis (Praeg) S H Fu, chemical constituents were isolated and purified by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). Their structures were elucidated on the basis of spectral data analysis. The anti-tumor metastasis assay was applied to evaluate the activities of the isolated compounds. Ten compounds (1-10) were isolated and their structures were identified by comparison of their spectral data with literature as follows: syringic acid (1), salidroside (2), tyrosol (3), scaphopetalone (4), berchemol (5), 2,6-dimethoxyacetophenone (6), rhobupcyanoside A (7), miyaginin (8), chavicol-4-O-ß-D-apiofuranosyl-(1 --> 6)-O-ß-D-glucopyranoside (9), eugenyol-O-ß-D-apiofuranosyl-(1 --> 6)-O-ß-D-glucopyranoside (10). Compounds 4-6 and 8-10, were isolated from this genus for the first time, while compound 7 was isolated from this plant for the first time. Compounds 2, 6-8 showed positive anti-tumor metastatic activities, and compounds 2 and 8 showed significant anti-tumor metastatic activities.

Inhibitory Effects of JEUD-38, a New Sesquiterpene Lactone from Inula japonica Thunb, on LPS-Induced iNOS Expression in RAW264.7 Cells.

We isolated JEUD-38, a new sesquiterpene lactone from Inula japonica Thunb. JEUD-38 dramatically attenuated lipopolysaccharide (LPS)-induced nitric oxide (NO) production. Consistent with this finding, the protein expression of inducible nitric oxide synthase (iNOS) was blocked by JEUD-38 in a concentration-dependent manner. To elucidate the mechanism, we examined the effect of JEUD-38 on LPS-stimulated nuclear factor-κB (NF-κB) nuclear translocation, inhibitory factor-κB (IκB) phosphorylation, and degradation. JEUD-38 reduced the translocation of p65, via abrogating IκB-α phosphorylation and degradation. In addition, JEUD-38 inhibited LPS-stimulated phosphorylation of mitogen-activated protein kinases (MAPKs) including extracellular signal-regulated kinase 1/2 (ERK1/2), c-Jun N-terminal kinase (JNK), and p38. Since iNOS as well as the upstream NF-κB and MAPKs are known to be closely involved in inflammation, these results suggest that JEUD-38 is a promising candidate for prevention and therapy of inflammatory diseases.

[Anti-inflammatory constituents from Inula japonica].

Chemical constituents of Inula japonica were isolated and purified by repeated column chromatographies, over silica gel, and Toyopearl HW-40, and preparative HPLC. On the basis of spectral data analysis, including NMR and MS data, the structures of the isolates were elucidated and their anti-inflammatory activities were assayed. Fifteen compounds were isolated from the ethyl acetate extract of I. japonica, and their structures were elucidated as dihydrosyringenin (1), (3S, 5R, 6S, 7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (2), (6R, 7E) -9-hydroxy-4,7-megastigmadien-3-one (3), arnidiol (4), taraxasterol acetate (5), 8,9,10-trihydroxythymol (6), taxifolin (7), luteolin (8), napetin (9), eupatin (10), spinacetin (11), quercetin (12), p-hydroxycinnamic acid (13), caffeic acid (14), and caffeoyl acetate (15). Compounds 1, 2, 7, 13 and 15 were isolated from the genus Inula for the first time, and compounds 3, 4, 9-11 and 14 were isolated from this plant for the first time. The anti-inflammatory activity result showed that compounds 3, 6-12 and 14 exhibited inhibition effect against leukotriene C4 (LTC4) synthesis and degranulation definitely in c-Kit Ligand (KL) induced mast cells, and compound 8 and 12 also had the suppression effect against lipopolysacharide(LPS) induced nitric oxide (NO) activity in RAW264.7 macrophages. It is firstly reported that compounds 7 and 9-11 possessed potent inhibition activities against LTC4 generation and degranulation in mast cells.

Anti-inflammatory terpenes from flowers of Inula japonica.

Five new terpenes (1-5) and ten known compounds (6-15) were isolated from Inula japonica, and their structures were identified by spectroscopic analysis. Compounds 3 and 14 showed positive inhibitory effects on nitric oxide production. Furthermore, compound 14 suppressed both leukotriene C4 synthesis and degranulation in c-kit ligand-induced bone marrow-derived mast cells.

Flavonoids from Tetrastigma obtectum enhancing glucose consumption in insulin-resistance HepG2 cells via activating AMPK.

Four new flavonoids including three C-glycosidic flavonoids, named tetrastigma A-D (1-4) and five known flavones (5-9) were isolated from the herbs of Tetrastigma obtectum (Wall.) Planch. The structures of 1-4 were elucidated by 1D- and 2D-NMR and HR mass spectrometric methods. Compound 1 caused significant enhancement in glucose consumption by insulin-resistant HepG2 cells compared with control cells. In addition, compound 1 stimulated phosphorylation of AMPK, which plays an important role in glycometabolism.

[Chemical constituents from Pachysandra terminalis].

To study chemical constituents from Pachysandra terminalis. By repeated column chromatography, including silica gel, Toyopearl HW-40, and preparative HPLC, four new (14) and one known (5) compounds were isolated and purified. On the basis of spectral data analysis, the structure of isolated compounds were elucidated as follow: 2-methyl-3-methylenepentane-1, 2, 5-triol (1), 4-methyl-3-methylenepentane-1, 2, 5-triol (2), 4-methyl-3-methylenepentane-1, 2, 5-triol-5-O-beta-D-glucopyranoside (3), 4-methyl-3-methylenep- entane-1, 2, 5-triol-1-O-beta-D-glucopyranoside (4), (7S, 8R, 8' R)-(+)-lariciresinol-9-O-beta-D-glucopyrano-side (5). Compound 5 was isolated from this genus for the first time.

[Chemical constituents contained in Tetraena mongolica].

To study chemical constituents contained in Tetraena mongolica. Chemical constituents were separated and purified by using such methods as silica gel, Toyopearl HW-40C and HPLC preparative chromatography. Their structures were identified by organic spectral method. One new compound was separated from T. mongolica and identified olean-11-oxo-12-en-28-ol-3beta-yl-caffeate.

Four new triterpenes from the endemic relict shrub Tetraena mongolica.

A chemical investigation of the endemic relict shrub Tetraena mongolica led to the isolation of four new triterpenes: 11α,12α:13ß,28-diepoxyoleanane-3ß-yl trans-caffeate (1), 3ß-hydroxy-11α,12α-epoxyoleanane-28-al (2), olean-11-en-28-al-3ß-yl trans-caffeate (3), and 28-acetoxy-olean-12-en-3ß-yl trans-caffeate (4). Their structures were elucidated by extensive spectroscopic methods.

[Chemical constituents of Phymatopteris hastate and their antioxidant activity].

OBJECTIVE: To study chemical constituents contained in Phymatopteris hastate and their antioxidant activity. METHOD: Chemical constituents were separated and purified from P. hastate by using such methods as silica gel, Toyopearl HW-40C and HPLC preparative chromatography. Their structures were identified by spectroscopic methods such as NMR. Furthermore, 1, 1-diphenyl-2-picryl-hydrazyl(DPPH) method was used to assess the antioxidant activity of each compound. RESULT: Fourteen compounds were separated and identified as 4-O-beta-D-glucopyranosyl-ethyl-trans-caffeicate (1), kaempferlo-7-O-alpha-L-rhamnopyranside (2), kaempferol-3, 7-di-O-alpha-L-rhamnopyranoside (3), kaempferol-3-O-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (4), juglanin (5), naringin (6), naringenin-7-O-beta-D-glucopyranoside (7), trans-caffeic acid (8), trans-caffeic acid-3-O-beta-D-glucopyranoside (9), trans-cinnamic acid-4-O-beta-D- glucopyranoside (10), trans-melilotoside (11), cis-melilotoside (12), ethyl chlorogenate (13), protocatechuic acid (14). The antioxidation experiment showed an obvious antioxidant activity in compounds 1-9, 13-14. CONCLUSION: All of the compounds were separated from this genus for the first time. Among them, compound 1 was not seen in literature reports and assumed to be a new artifact derived from compound 9 and ethanol. Compounds 1-9, 13-14 showed a remarkable antioxidant activity.

Alkaloids from Pachysandra terminalis inhibit breast cancer invasion and have potential for development as antimetastasis therapeutic agents.

The aim of the present study was to identify potentially useful natural compounds for the development of novel therapeutic agents to inhibit metastasis. A phytochemical investigation of Pachysandra terminalis resulted in the isolation of seven new pregnane alkaloids, terminamines A-G (1-7), and seven known alkaloids (8-14). The structures of 1-7 were elucidated by 1D- and 2D-NMR spectroscopic and mass spectrometric methods. Compounds 1-5 and 8-14 inhibited the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor. In addition, compound 1 inhibited phosphorylation of integrin ß(1), which plays an important role in MB-MDA-231 cell adhesion and metastasis.

[Antioxidant constituents from Smilax riparia].

By repeated column chromatography, including silica gel, toyopearl HW-40 and preparative HPLC, thirteen compounds (1-13) were isolated and purified from Smilax riparia. On the basis of spectral data analysis, the structures of isolated compounds were elucidated as 5-methoxy-[6]-gingerol (1), dehydroabietic acid (2), pteryxin (3), 2-methylphenyl-1-O-beta-D-glucopyranoside (4), 3,5-dimethoxy-4-hydroxybenzonic acid (5), isovanillin (6), vanillic acid (7), p-hydroxycinnamic acid (8), p-hydroxycinnamic methyl ester (9), p-hydroxybenzaldehyde (10), ferulic acid methyl ester (11), benzoic acid (12) and 5-hydroxy-methyl-2-furalclehyde (13). Compounds 1-4 and 8-12 were isolated from this genus for the first time. All compounds were isolated from this plant for the first time. Compounds 1 and 5-11 showed antioxidant activities on DPPH method.

[Phenol constituents of Pachysandra terminalis and their antioxidant activity].

OBJECTIVE: To study the phenol constituents from Pachysandra terminalis and their antioxidant activities. METHOD: Constituent isolation and purification was carried by repeated column chromatography (silica gel, Toyopearl HW-40 and preparative HPLC), and their structures were elucidated on the basis of spectral data analysis. DPPH method was used to evaluate the free radical scavenging activity of the isolated compounds. RESULT: Nine phenol compounds (1-9) were isolated and their structures were identified as follow: p-hydroxybenzaldehyde (1), vanillin (2), 1-(4-hydroxy-3-methoxyphenyl) -ethanone (3), syringaldehyde (4), salicylic acid (5), p-hydroxybenzoic acid (6), ferulic acid (7), 2,3,4-trihydroxybenzoic acid (8), 3,4-dihydroxybenzoic acid (9). The isolated compounds showed obviously antioxidant activity. At the concentration of 50 micromol x L(-1), compounds 7-9 revealed DPPH free radical scavenging rates were 87.8%, 97.8% and 92%, respectively. CONCLUSION: Compounds 1-9 were isolated from this genus for the first time. They showed the significant antioxidant activity.

[Studies on the chemical constituents of Pachysandra terminalis and their antioxidant activity].

OBJECTIVE: To study the chemical constituents from Pachysandra terminalis and their antioxidant activity. METHODS: Chemical constituents were isolated by repeated column chromatography (silica gel, Toyopearl HW-40C and preparative HPLC). The structures of isolated compounds were elucidated on the basis of spectral data analysis. DPPH method was used to evaluate the free radical scavenging activity of the isolated compounds. RESULTS: Six compounds were isolated and their structures were identified as follow: 2-Phenylethyl-beta-D-glucopyranoside (1), (+)Pinoresinol-4'-O-beta-D-glucopyranoside (2), Pinoresinol (3), cis-Syringin (4), 4-hydroxy-4-(3-oxo-l-butenyl)-3,5,5-trimethylcyclohex-2-en-l-one (5), 3alpha-hydroxy-5,6-epoxy-7-megastigmen-9-one (6). Compounds 2, 4, 5 showed obviously antioxidant activity, their DPPH free radical scavenging rates were 82.50%, 87.36%, and 84.56% on the concentration of 50 micromol/L, respectively. CONCLUSION: Compounds 1-6 are isolated from this genus for the first time. Compounds 2, 4, and 5 showed significant antioxidant activities.

[Study on extraction of anti-diabetes active constituents from Potentilla chinesis].

OBJECTIVE: To study the extraction technology of anti-diabetes active constituents from Potentilla chinesis. METHODS: Through single factor test, the effects of factors such as concentration of ethanol, temperature, ratio of liquid-solid, extraction time and times of extraction were investigated. Through orthogonal experiment, the optimal conditions of extraction were obtained on the basis of single factor test. RESULTS: The optimum extraction conditions of Potentilla flavone from P. chinesis were determined as follows: refluxing for 3 times, 1.5 hours each time, and 8-6-6 for the multiple of 60% EtOH and material. CONCLUSION: The extraction process is stable and suitable for industry.

[Studies on chemical constituents of rhizome of Buddleia davidii].

OBJECTIVE: To study the chemical constituents of Rhizome of Buddleia davidii. METHODS: The chemical constituents were isolated by repeated column chromatography (Toyopearl HW-40C and HPLC) and their structures were elucidated on the basis of physico-chemical properties and spectroscopic features. RESULTS: From the petroleum ether extract of the material, eight compounds were isolated. Their structures were identified as: Buddlindeterpene B(1), Buddledin B(2), Buddledin C(3), deacetyldihydrobuddledin A(4), dihydrobuddledin C(5), Suberosol B(6), Gadain (7) and Hinokinin (8). CONCLUSION: Compounds 1,4 - 8 are isolated from B. davidii for the first time.