Chemical constituents from leaves of Jatropha curcas

Objective: To investigate the chemical constituents from the leaves of Jatropha curcas and evaluate their inhibition on lipopolysaccharide (LPS)-activated BV-2 microglia cells. Methods: The n-BuOH extract of the leaves of J. curcas was isolated by macroporous adsorption resin, silica gel, ODS, column chromatography and semi-preparative HPLC. The structures of the compounds were identified by MS, NMR, ECD, and other spectroscopic methods. In addition, anti-neuroinflammatory effects of isolated compounds were evaluated by measuring the production of nitric oxide (NO) in over-activated BV-2 cells. Results: Seventeen compounds, including (7R,8S)-crataegifin A-4-O-β-D-glucopyranoside (1), (8R,8''R)-arctigenin (2), arctigenin-4''-O-β-D-glucopyranoside (3), (-)-syringaresinol (4), syringaresinol-4''-O-β-D-glucopyranoside (5), (-)-pinoresinol (6), pinoresinol-4''-O-β-D-glucopyranoside (7), buddlenol D (8), (2R,3R)-dihydroquercetin (9), (2S,3S)-epicatechin (10), (2R,3S)-catechin (11), isovitexin (12), naringenin-7-O-β-D-glucopyranoside (13), chamaejasmin (14), neochamaejasmin B (15), isoneochamaejasmin A (16), and tomentin-5-O-β-D-glucopyranoside (17) were isolated and identified. Compounds 2, 4 and 8 significantly inhibited the release of NO in BV-2 microglia activated by LPS, with IC50 values of 18.34, 29.33 and 26.30 μmol/L, respectively. Conclusion: Compound 1 is an undescribed compound, and compounds 2, 3, 8, 14–17 are isolated from Jatropha genus for the first time. In addition, lignans exhibited significantly inhibit NO release and the inhibitory activity was decreased after glycosylation.     

Chemical Constituents with Antihyperlipidemic Activities from Desmodium triquetrum

Objective To study the chemical constituents from Desmodium triquetrum and their antihyperlipidemic activities. Methods The constituents of D. triquetrum were isolated and purified using various column chromatographies. Their chemical structures were elucidated using extensive spectroscopic methods. The lipid-lowering effects of the isolates were evaluated in HepG2 cells. Results Nine compounds were obtained from the ethanol extract of D. triquetrum and determined to be 6′-O-cis-p-coumaroyl-3,5-dihydroxyphenyl-β-D-glucopyranoside(1), tadehaginoside(2), rutin(3), quercetin-3-O-β-D-glucopyranoside(4), quercetin-3-O-β-D-galactopyranoside(5), 6-O-(E)-p-hydroxy-cinnamoyl-β-glucose(6), 6-O-(E)-p-hydroxy-cinnamoyl-α-glucose(7), kaempferol-3-O-β-D-rutinoside(8), and 3-O-β-D-galacopyranosyl(6-1)-α-L-rhamnosyl quercetin(9). Compounds 1 and 2 significantly reduced the intracellular content of total cholesterols and triglycerides. Conclusion Compound 1 is a new phenolic compound and exhibits potent anti-hyperlipidemic activity. Additionally, compounds 6 and 7 are isolated from D. triquetrum for the first time.     

Chemical Constituents from Dried Aerial Parts of Eclipta prostrata

Objective To study the constituents in the dried aerial parts of Eclipta prostrata.Methods The constituents were isolated and purified by column chromatography and their structures were elucidated by spectroscopic methods(1D,2D NMR,UV,IR,and HRESI-TOF-MS)and chemical analyses.Results Eight compounds were isolated and identified as 7-O-methylorobol-4′-O-β-D-glucopyranoside(1),3′-hydroxybiochanin A(2),echinocystic acid28-O-β-D-glucopyranoside(3),ecliptasaponin A(4),eclalbasaponin I(5),eclalbasaponin IV(6),echinocystic acid(7),and 3-oxo-16α-hydroxy-olean-12-en-28-oic acid(8).Conclusion Compound 1 is a new compound and compound 3 is obtained from this genus for the first time.     

Chemical constituents from acid hydrolyzates of Panax quinquefolius total saponins and their inhibition activity to α-glycosidase and protein tyrosine phosphatase 1B

Objective: To investigate the hypoglycemic components from the acid hydrolyzates of Panax quinquefolius total saponins, and screen the active compounds by in vitro inhibitory activities to α-glycosidase enzymes and protein tyrosine phosphatase-1 B(PTP1 B).Methods: The hydrolyzates were chromatographed repeatedly over silica gel column, and the structures of the compounds were determined by means of NMR. The in vitro bioassay was performed through the inhibitory effects on α-glucosidase or/and PTP1 B.Results: Eight compounds were isolated, which identified as 20(S)-panaxadiol(1),(20 S,24 R)-dammarane-20,24-epoxy-3β,6α,12β,25-tetraol(2), 20(R)-dammarane-3β,12β,20,25-tetraol(3), 20(S)-dammarane-3β,6α,12β,20,25-pentol(4), 20(R)-dammarane-3β,12β,20,25-tetrahydroxy-3β-O-β-D-glucopyranoside(5),β-sitosterol(6), oleanolic acid(7) and 20(S)-protopanaxadiol(8). Compound 5 was ginseng triterpenoid isolated from the acid hydrolysates of total saponins from P. quinquefolius for the first time. In this paper,the possible in vitro inhibitory activities were investigated. Compound 5 exhibited significantly inhibitory activity against α-glucosidase, and the IC50 value [(0.22 ± 0.21) μmol/L] was about 43-fold lower than positive control. For the PTP1 B inhibition assay, compound 5 indicated the strongest inhibitory effect with IC50 of(5.91 ± 0.38) μmol/L, followed by compound 4 with IC50 of(6.21 ± 0.21) μmol/L, which were all showed competitive inhibitory pattern by using a Lineweaver-Burk plot.Conclusion: These results supported the potential application of dammaranes from acid hydrolyzates of P. quinquefolius total saponins can be used as ingredients of ancillary anti-diabetic agent or functional factor.     

A New Phenylpropanol Glycoside and Its Five Known Analogues from Boschniakia rossica

Objective To study the constituents in the whole plant of Boschniakia rossica. Methods The constituents were separated and purified with chromatographic methods. Their structures were elucidated by spectroscopic methods (1D, 2D NMR, UV, IR, and HRESI-TOF-MS) and chemical analyses. Results One new phenylpropanol glycoside (1) and its five known analogues were obtained from B. rossica. They were identified as trans-p-coumaryl- (2′-O-β-D-glucopyranosyl)-β-D-glucopyranoside (1), salidroside I (2), rossicasin A (3), trans-p-coumaryl alcohol 1-O-β-glucopyranosyl(1→4)-α-rhamnopyranosyl(1→3)-β-glucopyranoside (4), salidroside (5), and acetoside (6). Conclusion Among the known compounds, compound 2 is firstly isolated from the plants in genus Boschniakia C. A. Mey. ex Bongard. Meanwhile, the 13 C-NMR data of 9 and 4′ positions in compound 4 are corrected.     

Saponins from Roots of Panax notoginseng

Objective To study the chemical constituents in the dried roots of Panax notoginseng.Methods The constituents were isolated and purified with chromatographic methods.Their structures were elucidated by spectroscopic methods(1D,2D NMR,UV,IR,[α]D,and HRESI-TOF-MS)and chemical analyses.Results Twenty saponins including 20(S)-ginsenoside Rh1(1),6-O-β-D-(6′-acetyl)-glucopyranosyl-24-ene-dammar-3β,6α,12β,20S-tetraol(2),ginseno-side Rf(3),notoginsenoside R2(4),ginsenoside Rg2(5),ginsenoside Rg1(6),notoginsenoside Rt(7),koryoginsenoside R1(8),6-O-(β-D-glucopyranosyl)-20-O-(β-D-xylopyranosyl)-3β,6α,12β,20(S)-tetrahydroxy-dammar-24-ene(9),pseudoginsenoside Rt3(10),notoginsenoside R1(11),ginsenoside Re(12),notoginsenoside N(13),ginsenoside F1(14),ginsenoside U(15),ginsenoside Rk3(16),3β,12β-dihydroxydammar-(E)-20(22),24-diene-6-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside(17),ginsenoside Rh4(18),pseudoginsenoside Rt5(19),and vinaginsenoside R22(20)were obtained.Conclusion Compounds 2,19,and 20 are isolated from this species for the first time.The 1H-NMR data of compound 19 and1H-NMR and 13C-NMR data of compound 20 are first reported.Meanwhile,the NMR data ofβ-D-xylopyranosyl group in compound 9 is corrected.     

Cathayanalactone G and other constituents from leaves and twigs of Callicarpa cathayana

Objective: To study the chemical constituents from the leaves and twigs of Callicarpa cathayana. Methods: The chemical constituents were isolated and purified by column chromatography on silica gel, MCI gel CHP 20P/P120, Sephadex LH-20, and HPLC. The structures of the compounds were determined by HR-ESI-MS, 1D and 2D NMR data. Results: A total of 24 compounds were isolated from the 85% methanol extract of leaves and twigs of C. cathayana. They were identified as cathayanalactone G (1), a new diterpene, and 23 known compounds as patagonic acid (2), (-)-16-hydroxycledroda-3,13-dien-16,15-olide-18-oic acid (3), 15-methoxypatagonic acid (4), oleanolic acid (5), ursolic acid (6), siaresinolic acid (7), pomolic acid (8), α-amyrin (9), tormentic acid (10), lupeol (11), 5,7-dihydroxy-3,4''-dimethoxyflavone (12), 5,4''-dihydroxy-3,7,3''-dimethoxyfla-vone (13), 5-hydroxy-3,6,7,4''- tetramethoxyflavone (14), salvigenin (15), kaemferol (16), astragalin (17), pinoresinol 4-O-β-D-glucopyranoside (18), paulownin (19), β-sitosterol (20), β-sitosterol β-D-glucopyranoside (21), 5-hydroxy-coumarin (22), isocopoletin (23), and 4-hydroxycinnamic acid (24). Conclusion: Compound 1 is a new labdane diterpene. Compounds 10, 13, 16 and 17 are isolated from the genus Callicarpa for the first time. Compounds 7, 8, 9, 12, 14, 23 and 24 are reported from C. cathayana for the first time.     

Chemical Constituents from Leaves of Oplopanax horridus

Objective To study the chemical constituents from the leaves of Oplopanax horridus. Methods The chemical constituents were isolated and purified by column chromatography on silica gel and Sephadex LH-20 gel columns, 1H-NMR and 13C-NMR were applied for the identification of chemical structure. Results Ten compounds were isolated and identified as dammara-20,24-dien-3β-ol acetate(1), phytol(2), 16 Z,19Z-pentacosadienoic acid(3), β-sitosterol(4),(3S,8S)-falcarindiol(5), maltol(6), acankoreagenin(7), daucosterol(8), stigmasterol-3-O-β-D-glucopyranoside(9), and acankoreoside A(10). Conclusion Compounds 1-3, 6, and 10 are isolated from this plant for the first time. Compounds 1-3 and 6 are isolated from the plants in genus Oplopanax Miq. for the first time. Moreover, Compounds 1, 3, and 6 are isolated from the plants in the family of Araliaceae for the first time.     

Phenolic Compounds from Roots of Imperata cylindrica var. major

Objective To study the chemical constituents from the roots of Imperata cylindrica var.major.Methods The chemical constituents were isolated and purified by combination of silica gel,Sephadex LH-20,polyamide,and ODS column chromatography.The structures of the isolated compounds were identified by means of spectral data and physicochemical property.Results Twelve phenolic compounds were isolated from I.cylindrica var.major and identified as 4,7-dimethoxy-5-methylcoumarin(1),7-hydroxy-4-methoxy-5-methylcoumarin(2),7-O-β-D-glucopyranosyl-4-methoxy-5-methylcoumarin(3),6-hydroxy-5-methoxyflavone(4),5-methoxyflavone(5),5,7-dihydroxy-8-methoxyflavone(6),4-hydroxybenzaldehyde(7),4-hydroxy-cinnamic acid(8),4-hydroxy-3-methoxybenzoic acid(9),3,4-dimethoxyphenyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(10),impecyloside(11),and graminone A(12).Conclusion Compounds 2—4,6,and 10 are obtained from this plant for the first time.     

Chemical Constituents from Barks of Lannea coromandelica

Objective To study the chemical constituents from the barks of Lannea coromandelica.Methods The chemical constituents were isolated and purified by column chromatography on silica gel column.NMR spectra were used for structural identification.Results Thirteen compounds were isolated and identified as quercetin(1),(2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoyl amino]-10-octadecene-1,3,4-triol(2),aralia cerebroside(3),5,5′-dibuthoxy-2,2′-bifuran(4),β-sitosteryl-3β-glucopyranoside-6′-O-palmitate(5),β-sitosterol palmitate(6),myricadiol(7),protocatechuic acid(8),p-hydroxybenzoic acidethyl ester(9),isovanillin(10),transcinnamic acid(11),palmitic acid(12),and stearic acid(13).Conclusion Compounds2-13 are isolated from this plant for the first time.     

A phytochemical study on Dichocarpum auriculatum???an endangered medicinal plant peculiar to China

Objective: Dichocarpum auriculatum, an endangered perennial herb, is endemic to China and has been used as folk medicines for the treatment of cough, hepatitis, scrofula, and epilepsy. However, there is no phytochemical report on this herbal so far. For the resource development and protective importance of this endangered medicinal plant, a phytochemical study was undertaken.Methods: The chemical constituents were purified by silica gel column, Sephadex LH-20 column, and semi-preparative reversed phase HPLC. NMR and MS spectra were used for structural identification.Results: Thirteen compounds were isolated from D. auriculatum. Their structures were characterized as jatrorrhizine(1), berberine(2), steponine(3), magnoflorine(4), coclauril(5), menisdaurin(6), menisdaurilide(7), aquilegiolide(8),(6 R, 9 S)-3-oxo-α-ionol-β-D-glucopyranoside(9), blumenol C glucoside(10),palmitic acid(11), dibutylphthalate(12), and auriculatum A(13).Conclusion: Compound 13 is a new diester terephthalate derivative. All the compounds are obtained from the genus Dichocarpum for the first time, and compounds 9 and 10 have potential chemotaxonomic significance to the genus Dichocarpum.     

Chemical constituents of Lomatogonium carinthiacum and Halenia corniculata

Objective: To study the chemical constituents from traditional characteristic Lomatogonium carinthiacum and Halenia corniculate. Methods: The chemical constituents were isolated and purified by silicagel column, Sephadex LH-20, ODS and high performance liquid chromategramphy. The structures were identified by NMR and MS analysis technics. Results: Twelve compounds were isolated and identified as isovitexin (1), Luteolin-5-O-β-D-glucoside (2), Isosaponarin (3), Luteolin-7-O-β-D-glucoside (4,7), 1,4,8-Trimethoxy-xanthone-6-O-β-D-glucoronyl-(1→6)O-β-Dglucoside (5), friginosideD (6), 1-hydroxy-2,3,5-trimethoxyxanthone (8), 1-hydroxy-2,3,4,5-tetramethoxyxanthone (9), 1-hydroxy-2,3,4,7-tetramethoxyxanthone(10), 1-hydroxy-2,3,4,5,7-pentamethoxyxanthone (11) and usnic acid (12). Conclusion: Compounds 6 and 12 are obtained from this medicine for the first time.     

Three new triterpenoid saponins from Aralia echinocaulis

Objective: To study the active ingredients in the root bark of Aralia echinocaulis. Methods: Three triterpenoid saponins were separated from the 70% ethanol extracts and purified by column chromatography and their structures were determined by spectroscopic analysis. Compound 1 and 3 were evaluated for antioxidant activity by the in vitro DPPH free radical scavenging ability and the protective effect of OH- induced DNA oxidative damage. Results: Compound 1 was a new type of triterpenoid saponin, named as echinocaulisaglycone 3-O-β-D-glucopyranoside (echinocaulisaponin A), and it had good antioxidant activity. Compound 2 was similar to compound 1, named as 1-hydroxyl-echinocaulisaglycone 3-O-β-D-glucopyranoside (echinocaulisaponin B). Compound 3 was also a new type of triterpenoid saponin, named as echinocaulisaglycone II 3-O-α-L-arabinopyranosyl-(1”→4’)-β-D-glucopyranosiduronic acid (echinocaulisaponin C), and its antioxidant activity was weaker than compound 1. Conclusion: In this study, three new compounds were discovered and two of them were carried out in vitro anti-oxidation studies, laying the foundation for further research on the treatment of related diseases (cardiovascular disease, arthritis, age-related macular degeneration, etc.) through anti-oxidation or quenching free radical function.     

New coumarin glucopyranosides from roots of Angelica dahurica

Objective: To investigate the chemical constituents from the roots of Angelica dahurica.Methods: The chemical constituents were isolated and purified by AB-8 macroporous adsorption resin and Sephadex LH-20 column as well as semi-preparative reversed phase HPLC.The chemical structures were identified by spectral data.Results: Ten compounds were isolated and identified as xanthoarnol-3-O-β-d-glucopyranoside(1),angedahuricoside A(2),angedahuricoside B(3),isofraxidin-7-O-β-d-glucopyranoside(4),fraxidin-8-O-β-d-glucopyranoside(5),(-)-marmesinin(6),(2 S,3 R)-3-hydroxymarmesinin(7),hyuganoside V(8),daucosterol(9),and sucrose(10).Conclusion: Compounds 1 –3 are new ones and compounds 4 –6 and 8 are obtained from title plant for the first time.     

Bioactive polyphenols in Ximenia americana and the traditional use among Malian healers

Ethnopharmacological relevance

Ximenia americana is a medicinal bushy, spiny shrub or small tree used in Mali in West Africa for treatment of various diseases, most common are infectious and inflammatory ailments.

Aims of the study

(1) To perform an ethnopharmacological survey on the traditional use of Ximenia americana among healers in Mali. (2) To isolate and identify chemical constituents from the ethanol extract of Ximenia americana leaves and to study their radical scavenging and enzyme inhibitory effects.

Materials and methods

In five different districts in Mali, 38 healers were interviewed about their medicinal use of Ximenia americana. An aqueous ethanol extract of the leaves of this tree was prepared and further fractionated with liquid-liquid extraction, VersaFlash and Sephadex LH-20 column chromatography, and preparative HPLC. Isolated compounds were identified by 1D and 2D NMR spectroscopy. Extracts, subfractions and isolated compounds were investigated as DPPH radical scavengers and as inhibitors of xanthine oxidase and 15-lipoxygenase.

Results

Major areas of use by Malian healers were against throat infection, amenorrhea and as tonic. Fractionation of the ethanol extract led to the isolation and identification of the cyanogenic glycoside sambunigrin (1), which is previously known from the plant. Additionally, gallic acid (2) and the gallotannins β-glucogalline (3) and 1,6-digalloyl-β-glucopyranose (4) were found. The following flavonoids were isolated: quercetin (5), quercitrin (quercetin-3-O-α-rhamnopyranoside) (6), avicularin (quercetin-3-O-α-arabinofuranoside) (7), quercetin-3-O-β-xylopyranoside (8), quercetin-3-O-(6″-galloyl)-β-glucopyranoside (9) and kaempferol-3-O-(6″-galloyl)-β-glucopyranoside (10). The flavonoids were active both as enzyme inhibitors and DPPH radical scavengers.

Conclusion

Sambunigrin (1) was the main compound in the EtOAc soluble fraction of the alcoholic extract of Ximenia americana leaves. Gallic acid (2), gallotannins (3-4) and flavonoids (5-10) were identified for the first time in the genus Ximenia. The identified compounds may give a rationale for the traditional use of Ximenia americana in Mali. Healers interviewed reported the use against throat infections, amenorrhea, as tonic, for wound healing and against pain.     

铁皮石斛中一个新化合物

 目的 研究铁皮石斛的化学成分。方法 采用硅胶色谱法、HP₂MGL型大孔树脂色谱法、Sephadex LH-20、Sephadex G-25凝胶色谱法、RP-HPLC制备柱色谱法进行分离纯化,通过现代波谱技术进行结构鉴定。结果 鉴定了10个化合物,分别为2-甲氧基苯基-1-O-β-D-芹糖-(1→2)-β-D-葡萄糖苷(1), 3,4,5-三甲氧基苯基-1-O-β-D-芹糖-（1→2）-β-D-葡萄糖苷(2), leonuriside A（3）,(1′R)-1′-(4-羟基-3,5-二甲氧基苯基)-1-丙醇-4-O-β-D-葡萄糖苷（4）,左旋丁香脂素（5）,丁香脂素-4,4′-O-双-β-D-葡萄糖苷（6）,(+)-丁香脂素-4-O-β-D-吡喃葡萄糖苷（7）,icariol A₂-4-O-β-D-glucopyranoside（8）,(+)-lyoniresinol-3a-O-β-D-glucopyranoside（9）,裂异落叶松脂醇（10）。结论 1为新化合物,2～4,6～10为首次从本属植物中发现,5为首次从本植物中发现。
     

冰糖草总黄酮含量测定及显色方法优化

目的:建立用紫外-可见分光光度法测定冰糖草总黄酮含量的方法.方法:对显色剂的种类、浓度与用量进行考察,采用NaNO2-Al(NO3)3-NaOH显色反应体系,测定冰糖草中总黄酮含量.结果:以芦丁为对照品,测定波长为506 nm,在4.8～96.2 mg·L-1线性关系良好(r =0.999 3),平均回收率为103.71％ (RSD 2.68％,n=6).结论:该方法简便、快捷、准确,可作为冰糖草总黄酮含量测定的方法.     

文冠果种仁粕中的一个新香豆素

Objective: To study the coumarin from the seeds oil leavings of Xanthoceras sorbifolia.Methods: The chemical constituents were isolated and purified by combination of silica gel, macroporous resin, Sephadex LH-20, and ODS column chromatography. Their structures were elucidated by spectral and chemical methods. The cytotoxicity of the new compound against 10 selected human cancer cell lines was assayed.Results: Five comarins were isolated and identified as fraxetin-7-O-β-D-[6'-(3"–hydroxyl–3"-methylglutaryl)] glucopyranoside(1), fraxoside(2), fraxetin(3), scopoline(4), and esculetin(5), respectively.Conclusion: Compound 1 is a new compound. Unfortunately, this compound exhibited no cytotoxicity with tested cell lines.     

麻栗坡红丝线中的酚类和酰胺类成分

目的:研究茄科红丝线属植物麻栗坡红丝线Lycianthes marlipoensis根部化学成分.方法:应用柱色谱分离技术分离纯化,并通过波谱分析确定化合物结构.结果:从麻栗坡红丝线根部的乙醇提取物中,分离得到了10个酚类化合物和7个酰胺化合物,分别鉴定为[4] -gingerol(1),[6]-gingerol(2),[10]-gingerol (3),(3S,5S)-3,5-dihydroxy-1-(4-hydroxy-3-methoxyphen7yl) decane(4),(3R,5S)-3,5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)decane(5),[6]-shogaol(6),[10] -shogaol (7),gingerenoneA(8),hexahydrocurcumin(9),(3R,5R)-3,5-dihydroxy-1,7-bis (4-hydroxy-3-methoxyphenyl)heptane( 10),piperine(11),isochavicine( 12),isopiperine( 13),N-trans-p-coumaroyl tyramine( 14),N-trans-feruloyl tyramine(15),N-trans-p-coumaroyl octopamine(16),N-trans-feruloyl octopamine(17).结论:化合物1～13和17为首次从该属植物中分得.     

黑刺菝葜茎的化学成分研究

 目的研究黑刺菝葜茎的化学成分,为充分利用黑刺菝葜药用植物资源鉴定基础。方法利用大孔树脂、硅胶和Sephadex LH-20等色谱分离手段进行分离纯化,通过理化性质和光谱分析鉴定结构。结果从黑刺菝葜茎乙醇提取物的乙酸乙酯、正丁醇萃取物分离鉴定了5个化合物,分别为反式白藜芦醇(1)、槲皮素-3-O-β-D-葡萄糖苷(2)、木犀草素-7-O-β-D-葡萄糖苷(3)、拉克索皂苷元-3-O-[α-L-吡喃阿拉伯糖基-(1→6)]-β-D-吡喃葡萄糖苷(4)、拉克索皂苷元-3-O-[β-D-吡喃葡萄糖基-(1→4)][α-L-吡喃阿拉伯糖基-(1→6)]-β-D-吡喃葡萄糖苷(5)。结论化合物1～3首次从本植物中分离得到。