Flavonoid glycosides from Rhazya orientalis

Six new flavonoid glycosides, quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (1), quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (2), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (3), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (4), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-cis-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (5), and isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-feruloyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (6), were isolated from the dried aerial parts of Rhazya orientalis. The structures of 1-6 were determined by spectroscopic and chemical means.     

Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata

Two new myricetin glycosides, myricetin 7-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1) and myricetin 7-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (2), together with the known compounds quercetin 3-O-beta-D-glucopyranoside (3), quercetin 3-O-alpha-L-rhamnopyranoside (4), quercetin 3-O-beta-D-galactopyranoside (5), methyl gallate (6), isovanillin (7), 4-hydroxymethylbenzoate (8), 3,4-dihydroxymethylbenzoate (9), and caffeoyl aldehyde (10) were isolated from the leaves of Tachigalia paniculata. The structures of these compounds were determined by spectroscopic methods. Their antioxidant activity was determined by measuring free-radical scavenging effects using three different assays, namely, the Trolox Equivalent Antioxidant Capacity (TEAC) assay, the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay), and the inhibition of xanthine oxidase activity. Compounds 1, 2, and 6 showed activity in the TEAC test, compounds 5-7 and 10 were moderately active in the autoxidation assay, while compounds 1 and 2 were the most potent of the isolates in the xanthine oxidase test.     

Isoflavone diglycosides from Glycosmis pentaphylla

Six new apiosyl-(1-->6)-glucosyl isoflavones (1-6) and four known ones were isolated from the stems of Glycosmis pentaphylla. The structures of the new glycosides are 3',7-dihydroxy-4',5,6-trimethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), 2',7-dihydroxy-4',5',5,6-tetramethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), 7-hydroxy-4',8-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (4), 7-hydroxy-4',6-dimethoxyisoflavone 7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (5), and 4',5-dihydroxy-3',7-dimethoxyisoflavone 4'-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (6). Their structures were established primarily by NMR experiments and chemical methods.     

New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume

The methanolic extract from the fresh flowers of Prunus mume exhibited inhibitory effects against aldose reductase and platelet aggregation. From the methanolic extract, two new flavonol oligoglycosides, 2' '-O-acetylrutin and 2' '-O-acetyl-3'-O-methylrutin, and two new polyacylated sucroses, prunoses I and II, were isolated together with 11 known constituents. The structures of 2' '-O-acetylrutin, 2' '-O-acetyl-3'-O-methylrutin, and prunoses I and II were determined on the basis of chemical and physicochemical evidence as quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-2' '-O-acetyl-beta-D-glucopyranoside, 3'-O-methylquercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-2' '-O-acetyl-beta-D-glucopyranoside, 1,4,3',4',6'-penta-O-acetyl-6-O-p-coumaroylsucrose, and 1,3',4',6'-tetra-O-acetyl-6-O-p-coumaroylsucrose, respectively. The flavonol glycosides and prunose I were found to inhibit aldose reductase, while prunoses I and II inhibited platelet aggregation induced by thrombin.     

Megastigmane glycosides and an acylated triterpenoid from Eriobotrya japonica.

Two new megastigmane glycosides, eriojaposides A (1) and B (2), and a new acylated triterpenoid (3) were isolated along with nine known compounds from a leaf extract of Eriobotrya japonica. The structures of 1--3 were characterized as (6R,9R)-3-oxo-alpha-ionyl-9-O-beta-xylopyranosyl-(1' '-->6')-beta-glucopyranoside, (6R,9R)-3-oxo-alpha-ionyl-9-O-alpha-rhamnopyranosyl-(1' '-->6')-beta-glucopyranoside, and 3 alpha-trans-feruloyloxy-2 alpha-hydroxyurs-12-en-28-oic acid, respectively, on the basis of spectral and chemical evidence.     

藏药五脉绿绒蒿中非生物碱成分

目的:研究藏药五脉绿绒蒿Meconopsis quintuplinervia的化学成分。方法:应用色谱技术分离纯化,用波谱学方法确定化合物结构。结果:从乙醇提取物中分离得到12个化合物,分别鉴定为:槲皮素-3-O-β-D-葡萄糖苷(Ⅰ),槲皮素-3-O-[β-D-半乳糖(1→6)]-β-D-葡萄糖苷(Ⅱ),山柰素-3-O-[β-D-葡萄糖(1→2)]-β-D-葡萄糖苷(Ⅲ),异鼠李黄素-3-O-[β-D-半乳糖苷(1→6)]-β-D-葡萄糖(Ⅳ),咖啡酸(Ⅴ),原儿茶酸(Ⅵ),对羟基肉桂酸(Ⅶ),2-(3,4-二羟苯基)-乙醇β-D-吡喃葡萄糖苷(Ⅷ),对羟基苯甲酸β-D-吡喃葡萄糖酯苷(Ⅸ),肉桂酸4-O-β-D-吡喃葡萄糖苷(Ⅹ),5,7-二羟基色原酮(Ⅺ),胡萝卜苷(Ⅻ)。结论:除Ⅵ和Ⅻ外,其余10个化合物均为首次从该属植物中发现。     

Antiprotozoal activity of the constituents of Conyza filaginoides

Bioassay-guided fractionation of the antiprotozoal extract of Conyza filaginoides led to the isolation of three new flavonol caffeoyl glycosides, namely, kaempferol 3-O-(6' '-O-E-caffeoyl)-beta-D-galactopyranoside (1), isorhamnetin 3-O-(6' '-O-E-caffeoyl)-beta-D-galactopyranoside (2), and quercetin 3-O-(6' '-O-E-caffeoyl)-beta-D-glucopyranoside (3). In addition, seven known compounds, erythrodiol (4), beta-caryophyllene-4,5-alpha-oxide (5), astragalin (6), isoquercitrin (7), nicotiflorin (8), narcissin (9), and rutin (10), were obtained. The structures of the new isolates were elucidated by spectroscopic and chemical methods. Compounds were also assessed for antiamoebic and antigiardial activities, but none was significantly active compared to the standard drugs evaluated.     

Phenolic glycosides from Viscum angulatum

Three new glycosides, pinocembrin 7-O-apiosyl(1-->5)apiosyl(1-->2)-beta-D-glucopyranoside (1), 2',3',4',3' '-tetramethoxy-1,3-diphenylpropane 5',4' '-di-O-beta-D-glucopyranoside (2), and rhamnocitrin 3-O-apiosyl(1-->5)apiosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->6)]-beta-D-glucopyranoside (3), were isolated from Viscum angulatumalong with viscumneoside V, naringenin, and homoeriodictyol. Their structures were established by spectral and chemical methods.     

Antioxidant flavan-3-ols and flavonol glycosides from Maytenus aquifolium

TLC autographic assay revealed, in the EtOAc extract obtained from leaves and root bark of Maytenus aquifolium (Celastraceae), the presence of fi ve compounds exhibiting antioxidant properties towards beta-carotene. They were isolated and identified as epigallocatechin (1), (+) ouratea-catechin (2), proanthocyanidin (3), kaempferol 3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[beta-D-glucopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)]-O-beta-D-glucopyranosyl (4) and quercetin 3-O-alpha-L-rhamnopyranosyl (1-->6)-O-[beta-D-glucopyranosyl (1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)]-O-beta-D-glucopyranosyl (5). The isolates were investigated for their redox properties using cyclic voltammetry and for their radical scavenging abilities through spectrophotometric assay on the reduction of 2,2-diphenyl-pycryl hydrazyl (DPPH). These results were correlated to the inhibition of beta-carotene bleaching on TLC autographic assay and to structural features of the flavonoids.     

Five phenolic glycosides from Alangium chinense

From the dried leaves of Alangium chinense, five novel phenolic glycosides, 6'-O-galloylsalicin (1); 4',6'-di-O-galloylsalicin (2); 4',6'-O-(S)-hexahydroxydiphenoylsalicin (3); 4', 6'-O-(R)-hexahydroxydiphenoylsalicin (4); and pyrocatechol 1-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (5) were isolated. The structures of these new compounds were determined by spectroscopic methods.     

Triterpene saponins from the leaves of Ilex kudingcha

Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.     

Phenolic glycosides from berries of Pimenta dioica

Four new phenolic glycosides, (2-hydroxy-3-methoxy-5-allyl)phenyl beta- d-(6-O-E-sinapoyl)glucopyranoside (1), (1' R,5' R)-5-(5-carboxymethyl-2-oxocyclopentyl)-3 Z-pentenyl beta-D-(6-O-galloyl)glucopyranoside (2), (S)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (3), and (R)-alpha-terpinyl [alpha-L-(2-O-galloyl)arabinofuranosyl]-(1-->6)-beta-D-glucopyranoside (4), were isolated from the berries of Pimenta dioica together with eight known flavonoids. The structures of 1-4 were elucidated on the basis of MS and NMR data and enzymatic hydrolysis. All four glycosides showed radical-scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals.     

Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation.

We have undertaken a systematic survey of the genus Buddleja used in traditional Chinese medicine for antiinflammatory and other indications by testing extracts and isolated natural products for their activity against the enzymes of the arachidonate cascade. This was done by using elicited rat peritoneal leukocytes, a physiologically relevant established whole cell system that expresses both cyclo-oxygenase (COX) and 5-lipoxygenase (5-LOX) activity. Lipophilic extracts of B. globosa roots and B. myriantha stem exhibited inhibitory activities in the 5-LOX and COX enzyme assays, whereas those of B. officinalis flowers, B. yunanesis stems, and B. asiatica stems showed inhibitory activities only against COX. The phytochemical investigation of these extracts, and consequent structure elucidation of isolated compounds using spectroscopic data, led to the isolation from B. globosa of three new terpenoid compounds named dihydrobuddledin A, buddledone A, and buddledone B and four known compounds-buddledins A, B, and C and zerumbone; 12 known compounds from B. officinalis-calceolarioside, campneoside, verbascoside, echinacoside, forsythoside B, angoroside A, crocetin monogentibiosyl ester, acacetin, acacetin-7-O-alpha-L-rhamnopyranosyl (1-6)-beta-D-glucopyranoside, acacetin-7-O-alpha-L-rhamnopyranosyl (1-6)[alpha-L-rhamnopyranosyl (1-2)]-beta-D-glucopyranoside, songarosaponin A, delta-amyrone; and eight known compounds fromB. yunanesis-11,14-dihydroxy-8,11, 13-abietatrien-7-one, beta-sitosterol, verbascoside, echinacoside, forsythoside B, angoroside A, methylcatapol, and sucrose. Tests on the isolated compounds for inhibition of eicosanoid synthesis showed that buddledin A, crocetin monogentibiosyl ester, and acacetin exhibited an inhibitory effect on COX with IC(50) values of 13.7 microM, 28.2 microM, and 77.5 microM, respectively, whereas buddledin A exhibited inhibitory effect on 5-LOX with an IC(50) value of 50.4 microM.     

Four new isoflavone triglycosides from Sophora japonica

Four new isoflavone triglycosides, genistein 7-O-beta-D-glucopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (1), genistein 7-O-beta-D-glucopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (2), genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(alpha-L-rhamnopyranosyl)-(1-->2)-beta-D-glucopyranoside] (3), and genistein 7-O-alpha-L-rhamnopyranoside-4'-O-[(beta-D-glucopyranosyl)-(1-->2)-beta-D-glucopyranoside] (4), together with nine known compounds, namely, genistein 7-O-beta-D-glucopyranoside-4'-O-beta-D-glucopyranoside, sophorabioside, prunetin 4'-O-beta-D-glucopyranoside, sophororicoside, genistin, rutin, kaempferol 3-O-beta-rutinoside, quercetin 3-O-beta-D-glucopyranoside, and kaempferol 3-O-beta-D-glucopyranoside, were isolated from the pericarps of Sophora japonica. The structures of 1-4 were determined by spectroscopic methods.     

Bioactive constituents from Boswellia papyrifera

Phytochemical investigation of the stem bark extract of Boswellia papyrifera afforded two new stilbene glycosides, trans-4',5-dihydroxy-3-methoxystilbene-5-O-{alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (1), trans-4',5-dihydroxy-3-methoxystilbene-5-O-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), and a new triterpene, 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oic acid (3), along with five known compounds, 11-keto-beta-boswellic acid (4), beta-elemonic acid (7), 3alpha-acetoxy-11-keto-beta-boswellic acid (8), beta-boswellic acid (9), and beta-sitosterol (10). The stilbene glycosides exhibited significant inhibition of phosphodiesterase I and xanthine oxidase. The triterpenes (3-9) exhibited prolyl endopeptidase inhibitory activities.     

轮叶棘豆的化学成分研究

目的：研究轮叶棘豆的化学成分。方法：90%乙醇冷浸提取,所得浸膏经硅胶,聚酰胺,C-18,Sephadex LH-20等多种材料进行柱色谱分离,通过波谱学方法鉴定化合物的结构。结果：分离鉴定了8个化合物,分别鉴定为azukisapogenol(1),(22E,24R)-24-甲基-5α-胆甾-7,22-二烯-3β,5α,6β-三醇(2),芹菜素(3),3′,4′-二甲氧基-槲皮素-3-O-β-D-半乳糖吡喃苷 (4),7,4′- 二甲氧基-槲皮素-3-O-α-L-鼠李糖吡喃基(1→2)-β-D-葡萄糖吡喃苷(5),(2S,3S,4R)-N-［(R)-2′-羟基二十四烷醇基］-1,3,4-三羟基-2-氨基-十八-6-烯(6),β-谷甾醇(7),胡萝卜苷(8)。结论：所有化合物均为首次从该植物中分得。     

鲜鱼腥草的黄酮类化合物研究

目的：研究三白草科Saururaceae蕺菜属植物蕺菜Houttuynia cordata的黄酮类化学成分。方法：利用Diaion HP-20,Sephadex LH-20,ODS和硅胶柱色谱进行分离纯化,根据化合物的理化性质和光谱数据鉴定结构。结果：分离得到5个化合物,分别鉴定为槲皮素-3-O-β-D-半乳糖-7-O-β-D-葡萄糖苷(1),山柰酚-3-O-β-D-［α-L-吡喃鼠李糖(1→6)］吡喃葡萄糖苷(2),槲皮苷(3),金丝桃苷(4),槲皮素-3-O-α-D-鼠李糖-7-O-β-D-葡萄糖苷(5)。结论：化合物1,2,5为首次从该属及本植物中分离得到。     

地乌中的三萜皂苷类成分

目的：研究地乌Anemone flaccida中的化学成分。方法：采用硅胶柱色谱、凝胶柱色谱、反相HPLC制备色谱等多种方法分离化合物，采用波谱方法鉴定化合物的结构。结果：从地乌根茎中分离得到12个三萜类化合物，分别为齐墩果酸(1)，齐墩果酸3-O-β-D-吡喃葡萄糖-(1→2)-β-D-吡喃木糖苷(2)，五加苷K(3)，齐墩果酸3-O-α-L-吡喃鼠李糖-(1→2)-β-D-吡喃木糖苷(4)，齐墩果酸3-O-β-D-吡喃葡萄糖-(1→2)-α-L-吡喃阿拉伯糖苷(5)，齐墩果酸3-O-βD--吡喃葡萄糖醛酸(6)，齐墩果酸3-O-β-D-吡喃葡萄糖醛酸甲酯(7)，齐墩果酸28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(8)，齐墩果酸3-O-β-D-吡喃葡萄糖醛酸28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(9)，齐墩果酸3-O-β-D-吡喃葡萄糖醛酸甲酯28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(10)，齐墩果酸3-O-β-D-吡喃葡萄糖-(1→2)-β-D-吡喃木糖28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(11)，齐墩果酸3-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖苷(12)。结论：化合物5～8，10,12为首次从该植物中分离得到；化合物2,5,11对Hela,BEL-7402和HL-60细胞具有细胞毒性。     

罗布麻叶黄酮类成分的研究

目的：对罗布麻叶黄酮类成分进行研究。方法：利用反复的聚酰胺柱色谱分离和Sephadex LH-20柱色谱纯化,通过波谱分析鉴定化合物的结构。结果：分离并鉴定6个化合物,分别是：槲皮素(1),山柰酚(2),山柰酚-3-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷(3),槲皮素-3-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷(4),槲皮素-3-O-(6″-O-乙酰基)-β-D-吡喃半乳糖苷(5),山柰酚-7-O-α-L-吡喃鼠李糖苷(6)。结论：化合物5,6为首次从该属中分离得到。     

滇重楼的抗肿瘤活性成分研究

目的：研究滇重楼Paris polyphylla Smith var. yunnanensis根茎中具有抗肿瘤作用的活性成分。方法：利用硅胶柱色谱,Sephadex LH-20,反相制备HPLC等手段进行分离纯化,并通过波谱技术进行结构鉴定。采用MTT法对分离到的化合物进行抗肿瘤活性筛选。结果：从醋酸乙酯和正丁醇层中分离得到了6个化合物,鉴定为薯蓣皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(1)、偏诺皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(2)、异鼠李素-3-O-β-D-葡萄糖苷(3)、乙基-α-D-呋喃果糖苷(4)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(5)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(6)。结论：化合物1～4为首次从滇重楼中分离得到,化合物3和4为首次从重楼属植物中分离得到,化合物5为首次从滇重楼的根茎中分离得到。药理实验表明,化合物1～3,5和6对小鼠肺腺癌细胞LA795都显示出一定的抑制作用,其中化合物5和6最显著。