Absolute configuration of lippifoliane and africanane derivatives

The absolute configuration of naturally occurring lippifoliane derivatives isolated from the widely used plant Lippia integrifolia was assigned by analysis of the circular dichroism data in combination with density functional theory minimum energy molecular models of (1S,4R,6S,9S,10R)-lippifolian-1-ol-5-one (1), (4R,9S,10R)-lippifoli-1(6)-en-5-one (2), and (4S,9S,10R)-lippifoli-1(6)-en-4-ol-5-one (3) and application of the octant rule for saturated ketone 1 and the helicity rules for alpha,beta-unsaturated ketones 2 and 3. The results were reinforced by the anomalous dispersion effect observed in the X-ray diffraction analysis of (4S,9S,10R)-4,10,11-tribromo-10,11-seco-lippifoli-1(6)-en-5-one (4) prepared from 2. The biogenetic relationships between lippifolianes 1-3 and africanane derivatives 7-9 and 13 isolated from the same species, together with chiroptical data for africananes isolated from the Hepaticae family, complete a stereochemical scenario in relation to the absolute configuration of africananes from L. integrifolia.     

三角叶凤毛菊中类异戊二烯和苯丙素类化学成分

目的:研究菊科药用植物三角叶凤毛菊Saussurea deltoidea的化学成分.方法:利用正/反相硅胶柱层析色谱、凝胶分子筛色谱、HPLC等色谱方法进行化合物的分离,利用波谱学方法鉴定化合物结构.结果:从三角叶凤毛菊中分离出10个化合物,其结构分别鉴定为(3R,6R,7E)-3-hydroxy-4,7 -megastigmadien-9 -one(1),(3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (2),3 -h ydroxy-β-damascone(3),S-(+)-dehydrovomifoliol(4),megastigman-5 -ene-3β,9R-diol(5),coniferaldehyde(6),β-hydroxypropiovanillone (7),3-hydroxy-1- (4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (8),dihydrosyringenin(9),4-[(1S)-3-hydroxy-1-methoxypropyl]-2,6-dimenthoxyphenol( 10).结论:化合物1～10均是首次从该植物中分离得到.     

大黄橐吾的化学成分研究Ⅱ

目的:从菊科橐吾属植物大黄橐吾的根及根茎中提取分离活性成分,为其资源开发提供科学依据。方法:以90%乙醇提取,采用硅胶柱色谱、凝胶柱色谱、重结晶等方法分离纯化化合物,根据理化常数及波谱数据进行结构鉴定。结果:共分离鉴定了9个化合物,分别为Δ^12,13-羽扇豆醇(1),异莨菪亭(2),isoline(3),duciformine(4),(2S,3S,4R)-鞘氨醇-(2′R)-Δ^5′,6′(E)-2′-羟基正二十四碳酰胺(5),正二十四碳酸(6),正二十四酸单甘油酯(7),反式-阿魏酸正二十二酯(8),反式-咖啡酸正二十二酯(9)。结论:化合物1,2,5~7为首次自该植物中分离得到,其中化合物2,5~7为首次自橐吾属中分得。     

桫椤化学成分研究

目的:研究桫椤Cyathea spinulosa Wall.的化学成分。方法:采用各种柱色谱进行分离纯化,根据理化性质和光谱数据进行结构鉴定。结果:从桫椤的乙醇提取物中共分离鉴定了8个化合物,分别为:豆甾-4-烯-3,6-二酮(1)、豆甾-3,6-二酮(2)、麦角甾醇(3)、原儿茶醛(4)、1-O-β-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctade-canoyl)amido]-4,8-octadecadiene-1,3-diol(5)、(2S,3S,4R)-2-[(2'R)-2'-hydroxytetracosanoylamino]-1,3,4-octade-canetriol(6)、β-谷甾醇(7)、胡萝卜苷(8)。结论:其中,化合物1～6为首次从该植物中分离得到。     

多穗金粟兰中1对倍半萜对映异构体的研究

目的对多穗金粟兰Chloranthus multistachys中倍半萜类化学成分进行研究。方法利用多种色谱方法进行分离纯化,然后利用1D-NMR、2D-NMR、单晶X射线衍射等方法进行结构鉴定。结果从多穗金粟兰二氯甲烷部位中分离得到10个倍半萜类化合物,分别鉴定为(1R,4R,5R,8S,10R)-1-羟基-4-乙氧基桉叶-7(11)-烯-12,8-内酯(1a)、(1S,4S,5S,8R,10S)-1-羟基-4-乙氧基桉叶-7(11)-烯-12,8-内酯(1b)、(9S,10S)-(-)-9β-hydroxycyclocolorenon(2)、myrrhterpenoidN(3)、1α,8α,9α-三羟基桉叶-3(4),7(11)-二烯-8β,12-内酯(4)、dihydrocurcolone(5)、curvularin(6)、neolitacumone A(7)、银线草内酯F(8)和苍术内酯Ⅲ(9)。结论其中化合物1a和1b为1对新的倍半萜对映异构体,分别命名为(+)-多穗金粟兰内酯M和(-)-多穗金粟兰内酯M;化合物2为1个新的天然产物,化合物3~6为首次从该属植物中分离得到,其余化合物均为首次从该植物中分离得到。     

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。     

信前胡化学成分的研究

目的研究信前胡Peucedanum praeruptorum Dunn的化学成分。方法信前胡乙醇提取物的正丁醇部位采用D101、TLC、HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到9个化合物,分别鉴定为(3′S,4′S)-3′-acetoxy-4′-angeloyloxy-3′,4′-dihydroseselin(1)、trans-3′,4′-diacetylkhellacton(2)、praerosideⅥ(3)、scopoletin(4)、umbelliferone(5)、rutarin(6)、isorutarin(7)、rutaretin(8)、dibutyl phthalate(9)。结论化合物1~2、9为首次从该植物中分离得到。     

绵头雪莲花的化学成分研究

目的:对西藏产绵头雪莲花Saussurea laniceps全草进行化学成分研究。方法:采用硅胶柱色谱法进行分离纯化,通过波谱解析进行结构鉴定。结果:从该藏药材乙醇提取物中分离得到15个化合物,分别鉴定为β-谷甾醇(1),伞形花内酯(2),对羟基苯乙酮(3),东莨菪素(4),异东莨菪素(5),雪莲内酯(6),3-(2′,4′-二羟基苯基)丙酸甲酯(7),芹菜素(8),neoechinulin A(9),胡萝卜苷(10),东莨菪素苷(11),雪莲内酯8-O-β-D-吡喃葡萄糖苷(12),芹菜素-7-O-β-D-葡萄糖苷(13),芹菜素-7-O-β-D-芦丁糖苷(14)和紫丁香苷(15)。结论:化合物5~15系首次从该植物中分离得到,其中化合物7,9系首次从该属植物中首次发现。     

南刘寄奴中的一个新1,10-裂环愈创木烷型倍半萜(英文)

目的:研究南刘寄奴中化学成分。方法:采用硅胶和 ODS 等柱层析分离手段以及半制备高效液相, 运用 NMR、MS 以及理化性质鉴定化合物的结构。结果:从南刘寄奴中分离得到 8 个化合物, 其结构鉴定为 3β-ethoxytanapartholide (1), ((4S*,5S*)-dihydro-5-[(1R*, 2S*)-2-hydroxy-2-methyl-5-oxo-3-cyclopenten-1-yl]-3-methylene-4-(3-oxobutyl)-2(3H)-furanone) (2), ligucy-peronol (3), cyperusol C (4), santamarin (5), 1α, 2α, 3α, 4α, 10α-pentahydroxyguaia-11(13)-ene-12, 6α-olide (6), balanophonin (7),methyl 3-(2’-hydroxy-4’-methoxyphenyl) propanoate (8)。结论:化合物 1 是新人工产物, 化合物 4 和 8 为首次从蒿属中分离得到, 化合物 2–3, 5–7 为首次从该植物中分离得到。     

桑椹醇提物的化学成分研究

目的研究桑椹Mori Fructus醇提物的化学成分。方法采用硅胶、Sephadex LH-20和ODS柱色谱法及半制备型高效液相色谱进行分离纯化,通过其理化性质和波谱数据对化合物结构进行鉴定。结果从桑椹醇提物中分离得到12个化合物,分别鉴定为桑脂素苷(1)、(7R,8S)-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside(2)、2-苯乙基-β-D-吡喃葡萄糖苷(3)、1′-O-苯乙基-β-D-呋喃芹菜糖基-(1→2)-β-D-吡喃葡萄糖苷(4)、苯甲醇-O-β-D-吡喃葡萄糖苷(5)、过氧麦角甾醇(6)、(24R)-6β-hydroxy-24-ethyl-cholest-4-en-3-one(7)、(22E)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol(8)、trans-(S)-(+)-脱落酸(9)、cis-(S)-(+)-脱落酸(10)、(S)-(+)-1-甲基-脱落-6-酸(11)、菜豆酸(12)。结论化合物1为未见文献报道的新化合物,化合物2、7~12为首次从该植物中分离得到。     

小花清风藤中黄酮类成分的研究

目的研究小花清风藤中黄酮类成分。方法小花清风藤甲醇提取物采用D101、硅胶、制备HPLC进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到7个黄酮类化合物,分别鉴定为槲皮素-3-O-龙胆双糖苷(1)、camellianoside(2)、芦丁(3)、tsubakioside A(4)、山柰酚-3-O-芸香糖苷(5)、异鼠李素-3-O-芸香糖苷(6)、山柰酚(7)。结论化合物1~2、4~6为首次从清风藤属中分离得到,且为首次从该植物中分离得到。     

构树的化学成分研究

目的：对构树枝条的化学成分进行分离和鉴定。方法：使用硅胶、Sephadex LH-20反复柱色谱分离、纯化,利用ESI-MS和NMR技术确定结构。结果：分离鉴定了6个化合物,分别为(2S)-7,3′-dihydroxy-4′-methoxyflavan(1),过氧化麦角甾醇(ergosterol peroxide,2),D-半乳糖醇(D-galacitol,3),sulfuretin (4),黑立脂素苷(liriodendrin,5),graveolone (6)。结论：化合物1～6均为首次从构树中分离得到。     

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。     

贯叶金丝桃化学成分研究

目的:研究贯叶金丝桃Hypericum perforatum的化学成分。方法:通过各种柱色谱进行分离纯化,根据理化性质和波谱数据对所得化合物进行结构鉴定;测定化合物对基因重组人PTP1B的抑制率。结果:从中分离并鉴定了10个化合物:D-甘露醇(1),邻苯二甲酸二异丁酯(2),(7E,6R,9S)-9-hydroxy-4,7-megastigmadien-3-one(3),(6S,9R)-roseoside(4),2,6-dim-ethoxy-4-hydroquinone-1-O-β-D-glucopyranoside(5),2,6-dimethoxy-4-hydroxybenzyl alcohol 1-O-β-D-glucopyranoside(6),syringate4-O-β-glucopyranoside(7),金丝桃素(8),skyrin-6-O-β-D-glucopyranoside(9),(R)-3,4-二羟基-苯甲酸-1’-丙三醇酯(10)。在2μmol.L-1时,化合物9对基因重组人PTP1B的抑制率为96.4%,IC50为2.5μmol.L-1。结论:化合物10为新化合物,化合物2～4,7为首次从该属中分离得到,化合物5,6从该植物中首次得到。体外活性筛选表明化合物8具有显著的PTP1B抑制作用。     

Steroidal saponins from the rhizomes of Polygonatum sibiricum

Four new steroidal saponins, named neosibiricosides A-D (1-4), were isolated from the rhizomes of Polygonatum sibiricum, along with two known spirostanol glycosides. The structures of the new glycosides were elucidated by spectroscopic methods and acid hydrolysis as (23S,24R,25R)-1-O-acetylspirost-5-ene-1beta,3beta,23,24-tetrol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranoside (1), (25S)-1-O-acetylspirost-5-ene-1beta,3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (2), (25S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-2-O-acetyl-beta-D-galactopyranoside (3), and (25R,S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated with human MCF-7 breast cancer cells.     

Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides

Four monoterpene hydroperoxides were isolated from aerial parts of Chenopodium ambrosioides along with ascaridole (1), the anthelmintic principle of this plant, as anti-trypanosomal compounds. The structures of these monoterpenes were determined to be (-)-(2S,4S)- and (-)-(2R,4S)-p-mentha-1(7),8-dien-2-hydroperoxide (2a and 3a) and (-)-(1R,4S)- and (-)-(1S,4S)-p-mentha-2,8-dien-1-hydroperoxide (4a and 5a) on the basis of spectroscopic methods and chemical correlations. In vitro trypanocidal activities of ascaridole (1) and these hydroperoxides (2a-5a) against epimastigotes of Trypanosoma cruzi were 23, 1.2, 1.6, 3.1, and 0.8 microM, respectively. Fresh leaves of C. ambrosioides also contained isomeric hydroperoxides 6a and 7a, and the content ratio of 2a-7a suggested that these hydroperoxides were formed through the singlet-oxygen oxidation of limonene.     

Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and -2

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.     

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.     

Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production

A new prenylated chalcone, 3' ',3' '-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (1), was isolated from the heartwood of Artocarpus communis. Two flavonoid derivatives, (-)-cycloartocarpin (9) and (-)-cudraflavone A (10), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (2), morachalcone A (3), gemichalcones B (4) and C (5), artocarpin (6), cudraflavone C (7), licoflavone C (8), and (2S)-euchrenone a(7) (11), were isolated and identified from this plant for the first time. Compounds 1-4, 6, and 11 exhibited potent inhibitory activity on nitric oxide production in RAW264.7 LPS-activated mouse macrophage cells with IC(50) values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3 microM, respectively. The structure of compound 1 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments.     

红藻扇形叉枝藻中的降碳倍半萜及其衍生物

目的：对红藻扇形叉枝藻Gymnogongrus flabelliformis进行化学成分研究。方法：利用正相和反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱和反相HPLC等手段进行分离纯化,借助MS,1D和2D NMR等波谱方法鉴定化合物结构；通过MTT法对分离鉴定的单体化合物在人肺癌细胞株(A549)、人肝癌细胞株(Bel 7402)、人胃癌细胞株(BGC 823)、人结肠癌细胞株(HCT-8)和人卵巢癌细胞株(A2780)上进行肿瘤细胞毒活性筛选。结果：从红藻扇形叉枝藻中分离得到5个降碳倍半萜类化合物,分别鉴定为(3S,6R,7E)-(+)-3-hydroxyl-4,7-megastigmadien-9-one(1),(3S,5R,6S,7E)-(-)-3-hydroxy-5,6-epoxy-7-megastig-mene-9-one(2),(3S,5S,6R,7E)-(+)3-hydroxy-5,6-epoxy-7-megastigmene-9-one(3),dehydrovomifoliol(4)和(3R)-(-)-4-［(2R,4S)-4-acetoxy-2-hydroxy-2,6,6-trimethylcyclohexylidene］-3-buten-2-one(5)。结论：以上化合物均为首次从该属海藻中分离得到,其中化合物1为新天然产物。细胞毒活性试验结果显示所有化合物在10 μg·mL^-1均无明显细胞毒活性。