Phytochemical investigation of Anaphalis lactea

Four new compounds, 2',6'-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-4'-methoxychalcone ( 1), 4,6-dihydroxy-7-isobutyryl-5-prenyl-2(3 H)-benzofuranone ( 4), 7- O-(beta- D-glucopyranosyloxy)-5-hydroxy-1(3 H)-isobenzofuranone ( 6) and (2 R,3 S)-3-methyl-2-(5-oxo-2-isopropenylhexyl)-cyclopentanone ( 7), along with thirteen known compounds were isolated from the whole plant of Anaphalis lactea. Their structures were established based on spectroscopic methods including IR, UV, MS, CD, 1 D NMR and 2 D NMR techniques. Compounds 2, 4 - 6 and 8 - 16 were tested for free-radical scavenging properties in the DPPH assays.     

猫眼草的抗氧化活性成分的分离鉴定与活性测定

目的研究猫眼草(Euphorbia lunulataBge.)全草抗氧化活性成分。方法以抗氧化活性为指标,运用多种柱色谱等现代分离手段对体积分数60%乙醇提取物进行活性追踪分离;根据理化性质和谱学技术分析确定化合物的化学结构;采用DPPH自由基清除法对提取物、各流份及分离得到的化合物进行体外抗氧化活性评价。结果从猫眼草体积分数60%乙醇提取物的乙酸乙酯萃取层(活性部位)中分离得到8个化合物。分别鉴定为东莨菪素(scopoletin,1)、异嗪皮啶(isofraxi-din,2)、金丝桃苷(hyperin,3)、柚皮素-7-O-β-D-葡萄糖苷(naringenin-7-O-β-D-glucopyranoside,4)、quercetin-3-O-(6″-galloyl)-β-D-galactopyranoside(5)、quercetin-3-O-(2″-galloyl)-β-D-galactopyrano-side(6)、槲皮素(quercetin,7)、芹菜素-7-O-β-D-葡萄糖苷(apigenin-7-O-β-D-glucopyranoside,8)。结论化合物1~5首次从猫眼草中分离得到;化合物8首次从大戟属植物中分离得到。化合物3、5、6、7具有较强的抗氧化活性。     

黄芩化学成分研究

目的 研究唇形科植物黄芩（Scutellaria baicalensis Georgi）根的化学成分。方法 利用各种色谱技术进行分离,根据波谱数据鉴定结构。结果 从黄芩根中分离得到9个已知成分,分别鉴定为汉黄芩素(1)、千层纸素-A(2)、苯乙酸(3)、对羟基苯乙醇葡萄糖苷(4)、4-O-β-D-吡喃葡萄糖基反式苯丙烯酸(5)、4-O-β-D-吡喃葡萄糖基顺式苯丙烯酸(6)、黄芩苷(7)、黄芩素-7-O-β-D-吡喃葡萄苷(8)、黄芩素-7-O-β-D-吡喃葡萄糖醛酸甲酯(9)。结论 化合物3、5、6为首次从该属植物中分离得到。     

巴戟天根皮中的醌类成分的分离与鉴定

目的研究巴戟天(Morinda officinalisHow.)化学成分。方法运用多种色谱学方法对巴戟天根皮体积分数70%乙醇提取物的化学成分进行分离,并根据光谱数据鉴定化合物的结构。结果从该植物中分离得到17个化合物,分别鉴定为rubiasin A(1)、rubiasin B(2)、2-羟基-1-甲氧基蒽醌(2-hydroxy-1-methoxy-anthraquinone,3)、3-羟基-1-甲氧基-2-甲基蒽醌(3-hydroxy-1-methoxy-2-methyl-anthraquinone,4)、1,3-二羟基-2-甲氧基蒽醌(1,3-dihydroxy-2-methoxy-anthraquinone,5)、2-甲基蒽醌(2-methyl-anthraquinone,6)、1,3-二羟基-2-甲基蒽醌(1,3-dihydroxy-2-methyl-anthraqui-none,7)、2-羟甲基蒽醌(2-hydroxymethyl-anthraquinone,8)、3-羟基-1,2-二甲氧基蒽醌(3-hydroxy-1,2-dimethoxy-anthraquinone,9)、1,8-二羟基-3-甲氧基-6-甲基蒽醌(1,8-dihydroxy-3-methoxy-6-methyl-anthraquinone,10)、苯乙醇-O-β-D-吡喃葡萄糖苷(2-phenylethyl-O-β-D-glucopyranoside,11)、2-丁醇-O-β-D-吡喃葡萄糖苷(sec-butyl-O-β-D-glucopyranoside,12)、3,4-二羟基苯乙醇(3,4-di-hydroxyphenylethanol,13)、3-(4-羟基-苯基)-1,2-丙二醇(3-(4-hydroxyphenyl)-1,2-propandiol,14)、阿魏酸(ferulic acid,15)、熊果酸(ursolic acid,16)、β-谷甾醇(β-sitosterol,17)。结论化合物1,2,11~14为首次从巴戟天属植物中分离得到。     

寄生藤水溶性成分的分离与鉴定

目的研究寄生藤的水溶性成分。方法利用反相色谱的方法对寄生藤水溶性成分进行分离纯化,根据化合物的化学性质与波谱数据鉴定结构。结果从寄生藤的水提取物中分得9个化合物,确定其结构分别为thero-1-C-syringylglycerol(1)、erythro-1-C-syringylglycerol(2)、erythro-guaia-cylglycerol(3)、tachioside(methoxyhydroquinone-4-β-D-glucopyranoside,4)、isotachioside(methoxy-hydroquinone-1-β-D-glucopyranoside,5)、3,5-二甲氧基-4-羟基-苯酚-1-O-β-D-吡喃葡萄糖苷(3,5-di-methoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside,6)、2,6-二甲氧基-4-羟基-苯酚-1-O-β-D-吡喃葡萄糖苷(2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside,7)、1,2,3-三羟基苯(benzene-1,2,3-triol,8)、异鸟嘌呤核苷(isoguanosine,9)。结论化合物1~9为首次从寄生藤属植物中分离得到。     

Cycloartane and oleanane saponins from egyptian astragalus spp. as modulators of lymphocyte proliferation

From the roots of Astragalus kahiricus DC., three known saponins, namely, astraversianin VI, astraversianin X, astragaloside VIII, and a new saponin were isolated and identified by spectral data. The structure of the latter was elucidated by spectral means and assigned as cycloastragenol 3- O-[ beta- D-(2',3'-diacetyl, 4'- trans-2-butenoyl)-xylopyranosyl], 6- O- beta- D-xylopyranoside (kahiricoside I). From the aerial parts of A. hamosus L., the known compounds azukisaponin V and peregrinoside I were isolated. As judged by in vitro tests, the saponins isolated from Astragalus spp. endemic to Egypt were not cytotoxic against a variety of human cancer cells. However, dose-related modulation of lymphocyte proliferation was observed, and structure-activity relationships are described.     

Isolation and Structure Elucidation of Two Highly Acylated Iridoid Diglycosides from Scrophularia scopolii

Two new triacyl iridoid diglycosides, named scropolioside A and B ( 1 and 2), have been isolated from the roots of SCROPHULARIA SCOPOLII var. SCOPOLII. Their structures were elucidated on the basis of chemical and spectral data as 6- O-(2', 4'-di- O-acetyl-3'- O- P-methoxy- TRANS-cinnamoyl)-alpha- L-rhamnopyranosylcatalpol ( 1) and 6- O-(2'- O-acetyl-3', 4'- O-di- TRANS-cinnamoyl)-alpha- L-rhamnopyranosylcatalpol ( 2).     

Flavonoids from Pterocaulon alopecuroides with antibacterial activity

Three flavonoids, (2 R,3 R)-5,4'-dihydroxy-3'- O-methyl-7-(gamma,gamma-dimethylallyloxy)dihydroflavonol 1, (2 R,3 R)-5,7,4'-trihydroxy-3'- O-methyl-6-(alpha,alpha-dimethylallyl)dihydroflavonol 2, and (2 R,3 R)-5,7,4'-trihydroxy-6-(alpha,alpha-dimethylallyl)dihydroflavonol 3, together with three known flavonoids ( 4 - 6), were isolated from the aerial parts of PTEROCAULON ALOPECUROIDES. The structures of the compounds were determined by mass and by 1 D and 2 D NMR spectroscopy. Screening of the antibacterial activity of all six compounds was conducted by a disc diffusion test against BACILLUS CEREUS, BACILLUS SUBTILIS, SALMONELLA TYPHIMURIUM and PROTEUS MIRABILIS. The minimum inhibitory concentration (MIC) of the active compounds ( 2, 3, 4, 6) was determined by a microdilution assay. These compounds were active only against both Gram+ bacteria with MIC values < or = 200 microg/mL.     

Constituents with DNA topoisomerases I and II inhibitory activity and cytotoxicity from the roots of Rubia cordifolia

Activity-directed isolation of the ethyl acetate fraction from the roots of Rubia cordifolia resulted in the identification of a new anthraquinone, 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone-3- O- α- L-rhamnopyranosyl-(1?→?2)- β-D-(6'-O-acetyl)-glucopyranoside (1), two new dihydronaphtoquinones, 1,4-dihydroxy-2-carbomethoxy-3-prenylnaphthalene-1-O- β-D-glucopyranoside (2) and mollugin-1-O- β- D-glucopyranoside (3), and a new monoterpenoid, 3 R,3a S,4 R,6a R-3,4,6-tris(hydroxymethyl)-3,3a,4,6a-tetrahydro-2 H-cyclopenta[ B]furan-2-one (4), together with nine known compounds (5-13). The structures of these compounds were elucidated on the basis of spectroscopic evidence. In addition, their DNA topoisomerases I and II inhibitory activity and cytotoxicity were measured.     

黄牛木的化学成分

目的研究黄牛木的化学成分,为开发利用黄牛木植物资源提供依据。方法运用大孔吸附树脂、硅胶柱色谱、LH-20葡聚糖凝胶柱色谱、ODS柱色谱及制备液相等方法进行分离,根据化合物的理化性质及光谱数据鉴定化合物的结构。结果从黄牛木体积分数为65%乙醇提取物的正丁醇部分分离得到8个化合物,分别鉴定为(-)-南烛木树脂酚-3α-O-β-D-葡萄糖苷(-)-lyo-niresinol-3α-O-β-D-glucopyranoside(1)、(-)-5′-甲氧基异落叶松脂醇-9-O-β-D-葡萄糖苷((-)-5′-methoxyisolariciresinol-3α-O-β-D-glucopyranoside,2)、(+)-异落叶松脂醇-9-O-β-D-葡萄糖苷(isolariciresinol-9-O-β-D-glucopyranoside,3)、2,6-二甲氧基-4-羟基苯酚-1-短线问题-O-β-D-吡喃葡萄糖(2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside,4)、儿茶素(catechin,5)、表儿茶素(epicatechin,6)、原矢车菊素B-2(procyanidinB-2,7)、2a,3a-环氧-5,7,3′,4′-四羟基黄烷-(4b→8)-表儿茶素(2a,3a-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4b→8)-epicatechin,8)。结论化合物1-4、8为首次从该属植物中分离得到。     

首乌藤的化学成分

目的分离和鉴定首乌藤中的化学成分。方法利用硅胶柱色谱、Sephadex LH-20柱色谱法等进行分离纯化,并通过理化常数测定和光谱分析鉴定了其化学结构。结果分离得到9个化合物,分别鉴定为:大黄素甲醚(physcion,1)、大黄素-8-甲醚(questin,2)、2,5-二甲基-7-羟基色原酮(2,5-dimethyl-7-hydroxychromone,3)、大黄素(emodin,4)、儿茶素(catechin,5)、大黄素甲醚-8-O-β-D-葡萄糖苷(physcion-8-O-β-D-glucopyranoside,6)、决明蒽酮-8-O-β-D-葡糖苷(torachrysone-8-O-β-D-glucopyranoside,7)、大黄素甲醚-8-O-β-D-葡萄糖苷(emodin-8-O-β-D-glucopyranoside,8)、2,3,5,4′-四羟基二苯乙烯-2-O-β-D-葡萄糖苷(2,3,5,4′-tetrahydroxystil-bene-2-O-β-D-glucopyranoside,9)。结论化合物3、7为该种植物中首次分离得到的化合物。     

Triterpenoid Saponins from Anemone flaccida

From the rhizome of ANEMONE FLACCIDA Fr. Schmidt, used in Chinese folk medicine, four saponins of oleanolic acid-A,B,C,D were isolated. By means of spectroscopy and chemical transformation, saponins A, B, and D were identified as 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-alpha- L-arabinopyrasyl]-oleanolic acid, 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-xylopyranosyl]-oleanolic acid, and 3- O-[alpha- L-rhamnopyranosyl-(1-->2)-beta- D-glucopyranosyl]-oleanolic acid. These three saponins are known compounds but isolated from ANEMONE plants for the first time. Saponin C was elucidated as 3- O-[beta- D-glucopyranosyl-(1-->2)-beta- D-xylopyranosy1]-oleanolic acid, which has not been reported in the literature before, and is named as flaccidoside I.     

松花粉化学成分的分离与鉴定

目的对松花粉的化学成分进行研究。方法采用反复硅胶、聚酰胺、Sephadex LH-20和ODS柱色谱等方法进行分离纯化,根据理化性质和1H-NMR、13C-NMR等谱学数据对分离得到的化合物进行结构鉴定。结果从松花粉中分离得到9个化合物,分别鉴定为柚皮素(naringenin,1)、花旗松素(taxifolin,2)、双氢山柰酚(dihydrokaempferol,3)、山柰酚(kaempferol,4)、柑橘查耳酮(chal-conaringenin,5)、异鼠李素-3-O-β-D-吡喃葡萄糖苷(isorhamnetin-3-O-β-D-glucopyranoside,6)、山柰酚-3-O-β-D-吡喃葡萄糖苷(kaempferol-3-O-β-D-glucopyranoside,7)、酪醇(tyrosol,8)、杜鹃醇(rhododendrol,9)。结论化合物1、2、5～9为首次从松花粉中分离得到。     

Speciosaperoxide, a new triterpene acid, and other terpenoids from Chaenomeles speciosa

Investigation on the EtOH extract of the fruits of Chaenomeles speciosa led to the isolation of a new triterpene acid bearing an unusual hydroperoxyl substitute group at C-11, speciosaperoxide (1), along with six known triterpenoids, 3beta-acetoxyurs-11-en-13beta,28-olide (2), 3-O-acetyl ursolic acid (3), oleanolic acid (4), ursolic acid (5), masilinic acid (6), and tormentic acid (7), and three known norsesquiterpenoids, roseoside (8), vomifoliol (9) and (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-[beta-d-xylopyranosyl (1 --> 6)-glucopyranoside] (10). Their structures were elucidated on the basis of spectroscopic data and comparison with reference data. Besides compound 1, compounds 2, 8-10 were obtained from this genus for the first time. None of these compounds exhibited inhibitory activity against T-and B-lymphocyte proliferation.     

Triterpenoid saponins from Androsace umbellata and their anti-proliferative activities in human hepatoma cells

Two new triterpenoid saponins, along with five known ones, were isolated from the EtOH extract of the whole plants of Androsace umbellata. The structures of the new triterpenoid saponins were identified as 3- O-[ beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)-[ beta- D-glucopyranosyl-(1-->2)]- alpha- L-arabinopyranosyl]-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 1) and 3- O- beta- D-xylopyranosyl-(1-->2)- beta- D-glucopyranosyl-(1-->4)- alpha- L-arabinopyranosyl-3 beta-hydroxy-13 beta,28-epoxy-16-oxo-oleanan-30-al ( 2) on the basis of their spectral and chemical properties. All these compounds showed significant cytotoxic activities in human hepatoma cells.     

Flavan-3-ols from Ulmus davidiana var. japonica with inhibitory activity on protein glycation

Four flavan-3-ols, (+)-catechin ( 1), (+)-catechin 7- O- beta- D-apiofuranoside ( 2), (+)-catechin 7- O- beta- D-xylopyranoside ( 3), (+)-catechin 7- O- beta- D-glucopyranoside ( 4), and proanthocyanidin A-1 ( 5) as well as three other constituents, isolated from an EtOAc-soluble extract of the stem barks of Ulmus davidiana var. japonica, were evaluated for inhibitory activity against the formation of AGEs. Compounds 1 - 5 exhibited a significant inhibitory activity on the formation of AGEs in an AGEs-BSA assay by specific fluorescence and this was confirmed by an indirect AGEs-ELISA. Moreover, compounds 1 and 5 markedly reduced AGEs-BSA cross-linking to collagen in a dose-dependent manner. AGEs:advanced glycation end products BSA:bovine serum albumin CC:column chromatography CD:circular dichroism.     

刺五加的化学成分

目的研究五加科五加属植物刺五加[Acanthopanax senticosus(Rupr.et Maxim.)Harms]的化学成分。方法利用各种色谱技术进行分离,根据化合物的理化性质和光谱数据鉴定结构。结果从刺五加中分离得到7个已知成分,分别鉴定为香草醛(vanillin,1)、香草酸(vanillic acid,2)、丁香苷(syringin,3)、β-谷甾醇(β-sitosterol,4)、胡萝卜苷(daucosterol,5)、2,6-二甲氧基-4-羟基-苯酚-1-O-β-D-吡喃葡萄糖苷(2,6-dimethoxy-4-hydroxyphenyl-1-O-β-D-glucopyranoside,6),3,5-二甲氧基-4-羟基-苯酚-1-O-β-D-吡喃葡萄糖苷(3,5-dimethoxy-4-hydroxyphenyl-1-O-β-D-glucopyranoside,7)。结论化合物6、7为首次从该植物中分离得到。     

Two acylated flavonoid glycosides from Stachys bombycina, and their free radical scavenging activity

Preparative reversed-phase HPLC analysis of the methanol extract of the aerial parts of Stachys bombycina (Lamiaceae) afforded two acylated flavonoids glycosides, chrysoeriol 7-O-[6-O-acetyl-beta-D-allopyranosyl]-(1 --> 2)-beta-D-glucopyranoside (1) and apigenin 7-O-beta-D-(6-p-coumaroyl)-glucopyranoside (2), the former being a new natural product. The structures of these compounds were elucidated unambiguously by UV spectroscopic analyses using shift reagents, ESIMS, and 1D and 2D NMR spectroscopic techniques. The free radical scavenging activity of 1 and 2 compounds were assessed by DPPH assay, and the RC50 values were 1.25 x 10(-2) and 7.69 x 10(-4) mg/mL, respectively.     

Constituents of the flowers of Erigeron annuus with inhibitory activity on the formation of advanced glycation end products (AGEs) and aldose reductase

Seven phenolic compounds, caffeic acid (1), 4-hydroxybenzoic acid (2), 4-methoxybenzoic acid (3), protocatechuic acid (4), eugenol O-beta-D: -glucopyranoside (5), 3,6-di-O-feruloylsucrose (6), and 3,5-di-O-caffeoylquinic acid methyl ester (7), were isolated from an EtOAc-soluble partition of the flowers of Erigeron annuus. The structures of 1-7 were determined by spectroscopic data interpretation, particularly 1D and 2D NMR studies, and by comparison of their data with those published in the literature. All the isolates were subjected to in vitro bioassays to evaluate their inhibitory activities against the formation of advanced glycation end products (AGEs) and rat lens aldose reductase (RLAR). Of the compounds, 1, 6, and 7 exhibited potent inhibitory activities against the formation of AGEs. In the RLAR assay, compound 7 showed the most potent inhibitory activity.