Phenolic compounds from the roots of Lindera fruticosa

The phenolic compounds isolated from the roots of Lindera fruticosa included four new compounds, 2-methoxy-3,4-methylenedioxybenzophenone (1), (S)-2-methoxy-3,4-methylenedioxybenzhydryl alcohol (2), 3-hydroxy-5-methoxybiphenyl (3), and 1-methoxy-2,5,7-trihydroxyxanthone (4). Three previously identified phenolics were also identified, namely, 3,5-dimethoxybiphenyl (5), benzyl 2-hydroxy-6-methoxybenzoate (6), and 1,7-dihydroxyxanthone (7). These compounds were evaluated for their inhibitory effects on human acyl-CoA:cholesterol acyltransferase activity and on the in vitro oxidation of low-density lipoprotein.     

Six new diarylheptanoids from the seeds of Alpinia blepharocalyx

Chromatographic separation of part of an EtOH extract of the seeds of Alpinia blepharocalyx resulted in the isolation of six new (1-6) and two known (7, 8) diarylheptanoids together with 12 known compounds. The structures of the new compounds, including their absolute stereochemistry, were elucidated by spectroscopic and chemical methods as (3S,5S)- (1) and (3S,5R)-3-hydroxy-5-methoxy-1-(4-hydroxyphenyl)-7-phenyl-6E-heptene (2), (3S,5S)- (3) and (3S,5R)-3-hydroxy-5-ethoxy-1-(4-hydroxyphenyl)-7-phenyl-6E-heptene (4), (3S)-methoxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one (5), and 1,7-bis(4-hydroxyphenyl)hepta-4E,6E-dien-3-one (6). Among the isolated compounds, 5, (3S,5S)-3,5-dihydroxy-1,7-bis(4-hydroxyphenyl)heptane (8), 4'-hydroxy-5,6-dehydrokawain (14), and/or phloroglucinol (20) showed significant antiproliferative activity against murine colon 26-L5 carcinoma (ED(50): 5, 5.2 microM; 8, 12.8 microM; 14, 20.7 microM; 20, 26.4 microM) and human HT-1080 fibrosarcoma (ED(50): 5, 10.1 microM; 14, 20.1 microM; 20, 20.9 microM) cells.     

Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease

From Curcuma longa, two novel compounds, 4' '-(3' "-methoxy-4' "-hydroxyphenyl)-2' '-oxo-3' '-enebutanyl 3-(3'-methoxy-4'hydroxyphenyl)propenoate (calebin-A, 1) and 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one (2), and seven known compounds, 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (curcumin, 3), 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (demethoxycurcumin, 4), 1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (bisdemethoxycurcumin, 5), 1-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-6-heptene-3,5-dione (6), 1,7-bis(4-hydroxyphenyl)-1-heptene-3,5-dione (7), 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (8), and 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one (9), were isolated following a bioassay-guided fractionation scheme utilizing an assay to detect protection of PC12 cells from beta-amyloid insult. Compounds 1, 3-5, and 7 were found to more effectively protect PC12 cells from betaA insult (ED(50) = 0.5-10 microg/mL) than Congo red (10) (ED(50) = 37-39 microg/mL).     

Bromophenols coupled with nucleoside bases and brominated tetrahydroisoquinolines from the red alga Rhodomela confervoides

Three new bromophenols C-N coupled with nucleoside base derivatives (1-3) and three new brominated 1,2,3,4-tetrahydroisoquinolines (5-7), together with a new brominated tyrosine derivative (4), have been isolated from polar fractions of an ethanolic extract of the red alga Rhodomela confervoides. By spectroscopic and chemical methods including HRMS and 2D NMR data, their structures were determined as 7-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-3,7-dihydro-1H-purine-2,6-dione (1), 7-(2,3-dibromo-4,5-dihydroxybenzyl)-3,7-dihydro-1H-purine-2,6-dione (2), 9-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]adenine (3), (-)-8S-(3-bromo-5-hydroxy-4-methoxy)phenylalanine (4), (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5), methyl (-)-3S-8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (6), and methyl (-)-3S-6-bromo-8-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (7). Compounds 5-7 were semisynthesized by using 4 as the starting material.     

Trypanocidal diarylheptanoids from Aframomum letestuianum

Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids were tested for growth inhibitory activity in vitro versus bloodstream forms of African trypanosomes. IC(50) values in the range of 1-3 microg/mL were found for compounds 3 and 5.     

Mycophenolic derivatives from Eupenicillium parvum

A new compound, euparvic acid (1, C(14)H(16)O(6)), and the known compounds 5,7-dihydroxy-4-methylphthalide (2), 6-(3-carboxybutyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (3), 6-(5-carboxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (4), and 6-(5-carboxy-4-hydroxy-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one (5) were isolated from the EtOAc extract of Eupenicillium parvum. The structure of 1 was determined by interpretation of MS and homo- and heteronuclear 2D NMR spectroscopic data and confirmed by X-ray crystallography. The absolute configuration of 5 was determined via MPA ester derivatization.     

Constituents of Eremurus chinensis

A novel bianthraquinone glycoside, 8-O-beta-D-glucopyranosyl-1,1', 8'-trihydroxy-3,3'-dimethyl-2,7'-bianthraquinone (1); two naphthalene derivatives, 2-acetyl-1-hydroxy-8-methoxy-3-methylnaphthalene (2) and 2-acetyl-1, 8-dimethoxy-3-methylnaphthalene (3); and a novel pre-anthraquinone, 1-oxo-4(S),9-dihydroxy-8-methoxy-6-hydroxymethyl-1,2,3, 4-tetrahydroanthracene (4), were isolated from Eremurus chinensis. Their structures were established by spectroscopic and chemical methods. In addition, the known compounds chrysophanol, chrysophanol 8-methyl ether, aloesaponol III 8-methyl ether (5), and 10-(chrysophanol-7'-yl)-10-hydroxychrysophanol-9-anthrone were also isolated and identified from this plant.     

Mixed lignan-neolignans from Tarenna attenuata

Six new mixed lignan-neolignans and 20 known compounds were isolated from the whole plant of Tarenna attenuata. By analysis of physical and spectroscopic data, the structures of the new compounds were elucidated as (1R,5R,6R)-6-{4-O-[2-(1-(4-hydroxy-3-methoxyphenyl))glycerol]-3,5-dimethoxyphenyl}-3,7-dioxabicyclo[3.3.0]octan-2-one (1), 5' '-methoxyhedyotisol A (2), 4' '-O-(8-guaiacylglycerol)buddlenol A (3), 5' '-methoxy-4' '-O-(8-guaiacylglycerol)buddlenol A (4), 4,6-dimethoxy-5-hydroxy-3-hydroxymethyl-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrobenzofuran (5), and 7-O-ethylguaiacylglycerol (6). Compounds 1, 5, 6, and 8 showed potent antioxidant activities against H2O2-induced impairment in PC12 cells, and compounds 1, 2, 5, and 7 scavenged DPPH radical strongly with IC50 values of 72, 87, 45, and 55 microM, respectively.     

瑞香狼毒细胞培养物的化学成分研究

采用常压与减压硅胶柱色谱、半制备HPLC、Sephadex LH-20等方法,从瑞香狼毒Stellera chamaejasme细胞培养物85％乙醇提取物的乙酸乙酯部分分离纯化得到了17个化合物,依据理化性质和各种波谱技术分别鉴定为:丁香脂素(1),杜仲树脂酚(2),松脂素(3),(1R,2S,5R,6S) -2-(4-hydroxyphenyl) -6-( 3-methoxy-4- hydroxyphenyl)-3,7-dioxabicyclo[3,3,0]octane(4),表松脂酚(5),caruilignan D(6),3-羰基愈创木烷-4-烯-11,12-二醇(7),落叶松脂素(8),tetrahydro-2-( 4-hydroxy-3-methoxyphenyl) -4-[ (4-hydroxyphenyl) methyl] -3-furanmethanol(9),5′-甲氧基落叶松脂醇(10),vladinol D( 11),环(L-脯氨酸-L-缬氨酸)(12),7′-羰基马台树脂醇(13),(+) -guayarol( 14),acutissimalignanB(15),异落叶松脂素(16)以及β-谷甾醇(17).其中化合物12为环二肽类化合物,7为倍半萜类化合物.除化合物7,12与17外,其余均为木脂素类化合物.17个化合物均首次从该植物组织培养物中获得.     

New dihydrophenanthrene and phenyldihydroisocoumarin constituents of Trema orientalis.

In the course of the chemical investigation of extracts of the trunk bark and root bark of Trema orientalis, three new compounds were isolated, namely, (9S*,10S*)-3-[7-(3,10-dihydroxy-9-hydroxymethyl-2,5-dimethoxy)-9,10-dihydrophenanthrenyl]propenal (1), (9S*,10S*)-3-[7-(5-O-beta-glucopyranosyl-10-hydroxy-9-hydroxymethyl-2,6-dimethoxy)-9,10-dihydrophenanthrenyl]propenal (2), and (3R*,3aR*,4R*,5S*)-6-O-alpha-arabinopyranosyl-8-hydroxy-3-(4-hydroxyphenyl)-4-(4-hydroxyphenyl)-5-(3,5-dihydroxyphenyl)-3,3a-dihydrocyclopenta[1,2,3-de]isobenzopyran-1-one (3, orientoside A). The structures of 1-3 were determined by spectral methods.     

雀鹿蕊化学成分研究

目的 研究产自内蒙古自治区的雀鹿蕊的化学成分.方法 雀鹿蕊乙醇提取液依次用石油醚、乙酸乙酯和正丁醇萃取,萃取物经色谱柱重结晶HPLC纯化,数据分析鉴定结构.结果 分离鉴定了13个化合物,(+)-松萝酸(1),2,4-二羟基-6-戊基苯甲酸-3-羟基-4-甲氧羰基-5-戊基苯基酯(2),黑茶渍素(3),2,4-二羟基-3,6-二甲基苯甲酸-3-羟基-4-甲氧羰基-2,5-二甲基苯基酯(4),赤星衣酸乙酯(5),丁二酸(6),十四酸乙酯(7),α-香树脂醇乙酸酯(8),2,4-二羟基-3,6-二甲基苯甲酸甲酯(9),2,4-二羟基-3-醛基-6-甲基苯甲酸甲酯(10),2-羟基-4-甲氧基-6-正戊基苯甲酸(11),2-羟基-4-甲氧基-6-正戊基苯甲酸甲酯(12),2-羟基-4-甲氧基-6-正戊基苯甲酸乙酯(13).结论 化合物2、4、6、7、8、10、12、13为首次从该植物中分离得到.     

Terpenoids and a diarylheptanoid from Zingiber ottensii

Four new terpenoids and a diarylheptanoid were isolated together with 16 known compounds from rhizomes of Zingiber ottensii. The structures of the new compounds were determined to be 1,10,10-trimethylbicyclo[7,4,0]tridecane-3,6-dione (1), (E)-14-hydroxy-15-norlabda-8(17),12-dien-16-al (2), (E)-labda-8(17),12,14-trien-15(16)-olide (3), (E)-14,15,16-trinorlabda-8(17),11-dien-13-oic acid (4), and rel-(3R,5S)-3,5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(3, 4-dihydroxyphenyl)heptane (5) by spectroscopic evidence.     

Five new phenolics from the roots of Ficus beecheyana

From the ethanolic extract of the roots of Ficus beecheyana, threo-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (1), erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (2), trans-4,5-bis(4-hydroxy-3-methoxyphenyl)-1,3-dioxacyclohexane (3), threo-3-(4-hydroxy-3,5-dimethoxyphenyl)-3-ethoxypropane-1,2-diol (4), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (5), and 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (6) were isolated. The structures of the new compounds 1-5 were elucidated by the analysis of their spectroscopic data.     

��ͩ����ѧ�ɷ��о�

??OBJECTIVE To investigate the chemical constituents in flowers of Paulownia fortunei (Seem.) Hemsl. METHODS The flowers of Paulownia fortunei (Seem.) Hemsl. were extracted with 50% aqueous acetone by tissue disruption extraction. The compounds were isolated and purified by Diaion HP-20, Toyopearl HW-40, Sephadex LH-20, MCI Gel CHP-20, silica gel column chromatography and preparative HPLC, and their structures were elucidated on the basis of spectral data and physiochemical properties. RESULTS Nineteen compounds were elucidated as 2-(3-methoxy-4-hydroxyphenyl)-propane-1,3-diol(1), 1-phenylpropane-1,2,3-triol(2), 3,4-dihydroxy-β-methoxyphenethy alcohol(3), chryseriol(4), phenylpropanoid(5), apigenin(6), luteolin(7), 4-hydroxy-3-methoxybenzoic acid(8), 2-(4-hydroxyphenyl) ethanol(9), 3,4-dihydroxyphenylethyl alcohol(10), vanillic acid(11), 3-(4-hydroxy-3,5-dimethoxyphenyl) propane-1,2-diol(12), p-hydroxybenzoic acid(13), astragalin(14), nicotinic acid(15), thymidine(16), thymine(17), 5-(4′-hydroxybenzyl) hydantoin(18) and 1-(3-indolyl)-2,3-dihydroxypropan-1-one(19). CONCLUSION Compounds 1-3, 5, 8-10, 12, 14-19 are isolated from this plant for the first time.     

白花蛇舌草化学成分的研究

目的：对白花蛇舌草的化学成分进行研究。方法：采用聚酰胺,Sephadex LH-20,硅胶和HPLC等多种色谱方法进行分离,理化性质,光谱数据鉴定结构。结果：分离鉴定9个化合物：2,6-二羟基-1-甲氧基-3-甲基蒽醌(1),2-羟基-1-甲氧基-3-甲基蒽醌(2),2-羟基-3-甲基蒽醌(3),quercetin-3-O-［2-O-(6-O-E-sinapoyl)-β-D-glucopyranos-yl］-β-glucopyranoside(4),quercetin-3-O-［2-O-(6-O-E-feruloyl)-β-D-glucopyranosyl］-β-glucop-yranoside(5),kaempferol-3-O-［2-O-(6-O-E-feruloyl)-β-D-glucopyranosyl］-β-galactopyranoside(6),quercetin-3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranoside(7),芦丁(8),槲皮素(9)。结论：化合物1和8为首次从该种植物中得到,其中化合物1为新化合物。     

刺异叶花椒根中香豆素类成分

目的:对刺异叶花椒Zanthoxylum dimorphophyllum var. spinifolum根的化学成分进行研究.方法:采用现代色谱分离技术进行化学成分的分离,运用波谱方法确定结构.结果:从中分离得到5个化合物,分别鉴定为5-甲氧基-7-羟基-6-(3'-甲基-2',3'-二羟基丁基)-香豆素(Ⅰ),6-(3'-甲基-2',3'-二羟基丁基)-7-甲氧基-8-(3″-甲基-丁-2″-烯基)-香豆素(Ⅱ),6-(3'-甲基-2',3'-二羟基丁基)-7-羟基-8-(3″-甲基-丁-2″-烯基)-香豆素(Ⅲ),6-(3'-甲基-2',3'-环氧丁基)-7-甲氧基-8-(3″-甲基-丁-2″-烯基)-香豆素(Ⅳ),7-甲氧基-8-(3'-甲基-丁-2'-烯基)-香豆素(Ⅴ).结论:以上化合物均为首次从该植物中分得.     

Isolation, structure elucidation, and cytotoxic evaluation of furanonaphthoquinones from in vitro plantlets and cultures of Streptocarpus dunnii

Two new furanonaphthoquinones, (3R)-7-methoxy-α-dunnione (5) and (3R)-6-hydroxy-7-methoxy-α-dunnione (6), along with the known (3R)-dunnione (1), (3R)-α-dunnione (2), (3R)-7-hydroxy-α-dunnione (3), and 1-hydroxy-2-methylanthraquinone (4), were isolated from in vitro cultures of Streptocarpus dunnii. The structures of compounds 5 and 6 were established by spectroscopic means. This is the first report of hydroxylated furanonaphthoquinones in a Streptocarpus species. Compounds 1-3 demonstrated cytotoxic activity against a range of breast cancer and pancreatic tumor cell lines.     

Aromatase inhibitors from Broussonetia papyrifera.

Bioassay-guided fractionation of an ethyl acetate-soluble extract from the whole plants of Broussonetia papyrifera, using an in vitro aromatase inhibition assay, led to the isolation of five new active compounds, 5,7,2',4'-tetrahydroxy-3-geranylflavone (1), isogemichalcone C (8), 3'-[gamma-hydroxymethyl-(E)-gamma-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate (9), demethylmoracin I (10), and (2S)-2',4'-dihydroxy-2' '-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone (11), and 10 known (12-21) compounds which were also found to be active. Of these compounds, the most potent were 9 (IC(50) 0.5 microM), 11 (IC(50) 0.1 microM), isolicoflavonol (12, IC(50) 0.1 microM), and (2S)-abyssinone II (13, IC(50) 0.4 microM). Additionally, six new compounds, 5,7,3',4'-tetrahydroxy-6-geranylflavonol (2), 5,7,3',4'-tetrahydroxy-3-methoxy-6-geranylflavone (3), (2S)-7,4'-dihydroxy-3'-prenylflavan (4), 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane (5), 1-(2,4-dihydroxy-3-prenylphenyl)-3-(4-hydroxyphenyl)propane (6), and 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxy-3-prenylphenyl)propane (7), were isolated and characterized, but proved to be inactive as aromatase inhibitors, as were an additional 21 known compounds. The structures of the new compounds (1-11) were elucidated by spectroscopic methods. Structure-activity relationships in the aromatase assay were determined for the benzofurans, biphenylpropanoids, coumarins, and various types of flavonoids (chalcones, flavans, flavanones, and flavones) obtained among a total of 42 constituents of B. papyrifera.     

Three new arylobenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor

Three new 2-phenyl-benzofurans, ebenfuran I, ebenfuran II, and ebenfuran III, were isolated from Onobrychis ebenoides. Their structures were elucidated on the basis of chemical and spectral data as 2-(2,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-benzofuran (1), 2-(2,4-dihydroxyphenyl)-3-formyl-4-hydroxy-6-methoxy-benzofuran (2), and 2-(2, 4-dihydroxyphenyl)-3-formyl-4-hydroxy-6-methoxy-5-(3-methyl-buten- 2-y l)-benzofuran (3). The affinity of these compounds for the estrogen receptor was studied using a receptor-binding assay.     

海南黄檀化学成分研究

目的 :研究海南黄檀叶Dalbergiahainanensis的化学成分。 方法 :用硅胶和聚酰胺柱层析进行分离纯化 ,根据理化性质和光谱数据进行结构鉴定。结果 :得到 13个化合物 ,分别为 8-C-葡萄糖基-7-甲氧基-4′,5-二羟基异黄酮 (1) ,8-C-葡萄糖基-7,4′ ,5-三羟基异黄酮 (2 ) ,2-hydroxy-5-methoxybiochaninA (3) ,formononetin (4) ,3,5 二甲氧基 4 羟基苯甲醛 (5 ) ,1-O-β-D-吡喃葡萄糖基 (2S,3S,4R ,8Z) 2 [(2R)-2-羟基二十二碳酰胺基 ]-8-十八烯-1,3,4-三醇 (6 ) ,木栓酮 (7) ,taraxerol (8) ,3β-hydroxy glutin-5-ene (9) ,熊果酸 (10 ) ,β-谷甾醇 (11) ,胡萝卜苷 (12 ) ,羽扇豆醇 (13)。结论 :所有化合物均首次从该植物中获得。