鹿蹄草化学成分研究

从鹿蹄草(Pyrola callianthaH.Andres)中分离得到11个化合物,经光谱分析确定其结构为(4R)-1-四氢萘酮(1),(4S)-1-四氢萘酮(2),夹竹桃麻素(3),没食子酸(4),3,4-二羟基苯甲酸(5),鹿蹄草素(6),5-羟甲基糠醛(7),金丝桃苷(8),2″-O-没食子酰基金丝桃苷(9),鹿蹄草苷B(10),4-羟基-2,7-二甲基萘基-1-O-β-D-吡喃葡萄糖苷(11)。其中化合物1,2,3,5,6,11为首次从该植物中分离得到,化合物7为首次从该属中分离得到。     

黄海棠化学成分的研究

从黄海棠植物中共分离得到15个化合物,并运用质谱、1H NMR和13C NMR等波谱方法将他们的结构鉴定为9,9'-O-di-(E)-feruloyl-(-)-secoisolariciresinol(1),山奈酚(2),槲皮素(3),金丝桃苷(4),槲皮素-3-O-β-D-吡喃葡萄糖苷(5),山奈酚-3-O-β-D-吡喃半乳糖苷(6),山奈酚-3-O-β-D-吡喃葡萄糖苷(7),原儿茶酸(8),1,7-二羟基-9-氧杂蒽酮(9),对香豆酸(10),对羟基苯甲酸(11),山奈素-3-O-(6"-O-巴豆酰)-β-D-葡萄糖苷(12),1,3,6,7-四羟基-9-氧杂蒽酮(13),没食子酸(14)和β-谷甾醇(15)。其中化合物1、4和6~14为首次从该植物中分离得到。     

核桃青皮化学成分及其抗肿瘤活性研究北大核心CSCD

采用柱色谱、重结晶等方法从核桃青皮Walnut green husk进行分离得到13个化合物,利用现代波谱学方法鉴定了它们的结构,分别鉴定为3,5-二甲氧基-4-羟基-苯甲酸-7-O-β-D-葡萄糖苷(1)、myricananin F(2)、β-谷甾醇(3)、齐墩果酸(4)、核桃酮(5)、积雪草酸(6)、常春藤皂苷元(7)、β-胡萝卜苷(8)、(4R)-4,8-二羟基-α-四氢萘酮-4-O-β-D-吡喃葡萄糖苷(9)、3β,23-二羟基-12-烯-28-乌苏酸(10)、熊果酸(11)、丁香酸(12)、Juglanoside B(13)。其中,化合物1、2、6、7、9、10均为首次从该属植物中分离得到。经体外抗肿瘤活性筛选,发现化合物4对人肝癌细胞(Hep G-2)的增殖显示了较强的生长抑制活性,化合物9对人乳腺癌细胞(MCF-7)的增殖具有一定的生长抑制活性。     

核桃青皮化学成分及其抗肿瘤活性研究

采用柱色谱、重结晶等方法从核桃青皮Walnut green husk进行分离得到13个化合物,利用现代波谱学方法鉴定了它们的结构,分别鉴定为3,5-二甲氧基-4-羟基-苯甲酸-7-O-β-D-葡萄糖苷(1)、myricananin F(2)、β-谷甾醇(3)、齐墩果酸(4)、核桃酮(5)、积雪草酸(6)、常春藤皂苷元(7)、β-胡萝卜苷(8)、(4R)-4,8-二羟基-α-四氢萘酮-4-O-β-D-吡喃葡萄糖苷(9)、3β,23-二羟基-12-烯-28-乌苏酸(10)、熊果酸(11)、丁香酸(12)、Juglanoside B(13)。其中,化合物1、2、6、7、9、10均为首次从该属植物中分离得到。经体外抗肿瘤活性筛选,发现化合物4对人肝癌细胞(Hep G-2)的增殖显示了较强的生长抑制活性,化合物9对人乳腺癌细胞(MCF-7)的增殖具有一定的生长抑制活性。     

天山棱子芹化学成分的研究

从天山棱子芹中首次分离得到15个已知化合物,通过NMR、MS及IR等波谱数据,分别鉴定为6,7-二羟基香豆素(1),( )-marmesin(2),marmesinin(3),5,7,4'-三羟基黄酮(4),莰非醇3-O-α-L-吡喃鼠李糖甙(5),藤黄菌素3'-O-β-D-吡喃葡萄糖甙(6),(R)-6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methylcyclohex-2-enone(7),4-羟基苯甲酸(8),3-甲氧基4羟基苯甲酸(9),3-甲氧基-4,5-亚甲二氧基苯甲酸(10),丁香酸甲酯(11),丁香酸甲酯4-O-β-D-吡喃葡萄糖甙(12),姜油酮4’-O-β-D-吡喃葡萄糖甙(13),2-(4-羟基苯基)-乙醇(14)和正二十八醇(15)。其中化合物7为一新的天然产物。     

扁桃叶的化学成分研究

从芒果属植物扁桃(Mangifera persiciformis C.Y.Wu et T.L.Ming)叶乙醇提取物乙酸乙酯萃取部位中分离得到7个化合物,经波谱鉴定为没食子酸甲酯(1),没食子酸(2),3,4-二羟基苯甲酸(3),槲皮素(4),山奈酚-3-O-β-D-葡萄糖苷(5),槲皮素-3-O-β-D-葡萄糖苷(6)和芒果苷(7).其中化合物1、3、5、6为首次从该植物中分离得到.     

鸦胆子果实的化学成分研究

为了解鸦胆子(Brucea javanica)的化学成分,从鸦胆子果实中分离得到13个已知化合物,经波谱学分析鉴定为：对羟基苯甲醛(1),对羟基苯甲酸(2),3,4-二羟基苯甲酸(3),3,4-二羟基苯甲酸甲酯(4),没食子酸(5),丁香酸(6),二氢阿魏酸(7),毛地黄黄酮(8),angophorol (9),2β,6β,9β-trihydroxyclovane (10),硬脂酸(11),β-谷甾醇(12)和β-胡萝卜苷(13)。化合物2,4,6~10均系从鸦胆子果实中首次分离得到。     

油榄仁果实化学成分的研究

为了解油榄仁(Terminalia bellirica Roxb.)的化学成分,从油榄仁果实的乙酸乙酯提取物中分离得到11个化合物,通过波谱分析,分别鉴定为:表松脂酚(1)、(–)-芝麻素(2)、麻醉椒苦素(3)、二氢醉椒素(4)、异香兰素(5)、3,4-二羟基苯甲酸(6)、没食子酸(7)、没食子酸甲酯(8)、没食子酸乙酯(9)、3,4,8,9,10-五羟基二苯骈[b,d]吡喃-6-酮(10)、polystachyol(11),其中化合物1~6、10和11为首次从油榄仁果实中分离得到。     

钟花报春花的化学成分研究(Ⅱ)

从钟花报春花Primula sikkmensis Hook.中分离得到5个化合物,通过波谱分析其结构分别鉴定为5-羟基黄酮(1),2-苯基色原酮(2),5,8-二羟基黄酮(3),2’-羟基黄酮(4),3’-羟基-黄酮-4’-O-β-D-吡喃葡萄糖苷(5)。其中化合物1～4首次从该属植物中分离得到,化合物5首次从该植物中分离得到,并首次对3的NMR数据进行了归属。     

秃叶黄皮树叶子的化学成分研究(英文)

从秃叶黄皮树叶子(Phellodendron chinensevar.glabriusculumSchneid)分离到7个化合物,经波谱解析鉴定为6-O-乙酰基黄柏苷(1),6-O-乙酰基二氢黄柏苷(2),(2R)-4′,5-二羟基-7-O-β-D-吡喃葡萄糖基-8-异戊烯基-二氢黄酮(3),黄柏苷(4),2-O-β-D-吡喃葡萄糖基-6-羟基-苯甲酸苄酯(5),柑橘素C(6),3-羰基齐墩果烷(7),其中化合物1～3,5～7为首次从秃叶黄皮树叶子中分离得到。     

Sulphated flavonoid glycosides from leaves of Atriplex hortensis

Two flavonoid sulphates, i.e. quercetin 3-O-sulphate-7-O-α-arabinopyranoside and kaempferol 3-O-sulphate-7-O-α-arabinopyranoside, were isolated from leaves of Atriplex hortensis L. The structures of these compounds were established by UV, ¹H and ¹³C NMR, 2D NMR and MS spectra. The compounds were isolated for the first time from plant material.     

Bioguided Fractionation and Isolation of an Antiplasmodial Saponin from the Roots of Nauclea xanthoxylon (A.Chev.) Aubrév. (Rubiaceae)

The root extract of Nauclea xanthoxylon (A.Chev.) Aubrév. displayed significant 50 % inhibition concentration (IC₅₀s) of 0.57 and 1.26 μg/mL against chloroquine resistant and sensitive Plasmodium falciparum (Pf) Dd2 and 3D7 strains, respectively. Bio-guided fractionation led to an ethyl acetate fraction with IC₅₀s of 2.68 and 1.85 μg/mL and subsequently, to the new quinovic acid saponin named xanthoxyloside ( 1 ) with IC₅₀s of 0.33 and 1.30 μM, respectively against the tested strains. Further compounds obtained from ethyl acetate and hexane fractions were the known clethric acid ( 2 ), ursolic acid ( 3 ), quafrinoic acid ( 4 ), quinovic acid ( 5 ), quinovic acid 3-O-β-D-fucopyranoside ( 6 ), oleanolic acid ( 7 ), oleanolic acid 3-acetate ( 8 ), friedelin ( 9 ), β-sitosterol ( 10a ), stigmasterol ( 10b ) and stigmasterol 3-O-β-D-glucopyranoside ( 11 ). Their structures were characterised with the aid of comprehensive spectroscopic methods (1 and 2D NMR, Mass). Bio-assays were performed using nucleic acid gel stain (SYBR green I)-based fluorescence assay with chloroquine as reference. Extracts and compounds exhibited good selectivity indices (SIs) of >10. Significant antiplasmodial activities measured for the crude extract, the ethyl acetate fraction and xanthoxyloside ( 1 ) from that fraction can justify the use of the root of N. xanthoxylon in ethnomedicine to treat malaria.     

Flavonol glycosides from Chenopodium foliosum Asch

Three new flavonol glycosides, namely 6-methoxykaempferol-3-O-β-gentiobioside, gomphrenol-3-O-β-gentiobioside and gomphrenol-3-O-α-l-rhamnopyranosyl-(1 → 2)[β-d-glucopyranosyl-(1 → 6)]-β-d-glucopyranoside as well as the known patuletin-3-O-β-gentiobioside and spinacetin-3-O-β-gentiobioside were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR, and HRMS). DPPH free radical scavenging activity of the new compounds was low or lacking.     

Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae)

Three new triterpenoid saponins, elucidated as 3-O-β-d-glucopyranosyloleanolic acid 28-O-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranoside (parkioside A, 1), 3-O-[β-d-apifuranosyl-(1→3)-β-d-glucopyranosyl]oleanolic acid 28-O-[β-d-apifuranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)β-d-xylopyranoside (parkioside B, 2) and 3-O-β-d-glucuronopyranosyl-16α-hydroxyprotobassic acid 28-O-α-l-rhamnopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranoside (parkioside C, 3), were isolated from the n-BuOH extract of the root bark of Butyrospermum parkii, along with the known 3-O-β-d-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities. Compound 2 showed cytotoxic activity against A375 and T98G cell lines, with IC₅₀ values of 2.74 and 2.93 μM, respectively. Furthermore, it showed an antioxidant activity comparable to that of Trolox or butylated hydroxytoluene (BHT), used as controls, against 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), oxygen and nitric oxide radicals.     

Flavonoid C- and O-glycosides from the Mongolian medicinal plant Dianthus versicolor Fisch

Eighteen flavonoids were identified from an aqueous extract of the aerial parts of Dianthus versicolor, a plant used in traditional Mongolian medicine against liver diseases. The flavonoid C- and O-glycosides isoorientin-7-O-rutinoside, isoorientin-7-O-rhamnosyl-galactoside, isovitexin-7-O-rutinoside, isovitexin-7-O-rhamnosyl-galactoside, isoscoparin-7-O-rutinoside, isoscoparin-7-O-rhamnosyl-galactoside, isoscoparin-7-O-galactoside, and isoorientin-7-O-galactoside were isolated and structurally elucidated. Their structures were established on the basis of extensive spectroscopic techniques including LC–UV–DAD, LC–MSⁿ, LC–HRMS, 1D and 2D NMR spectroscopy, and by GC–MS analysis after hydrolysis. Flavonoids with such a high glycosylation pattern are rare within the genus Dianthus. Furthermore, isovitexin-7-O-glucoside (saponarin), isovitexin-2″-O-rhamnoside, apigenin-6-glucoside (isovitexin), luteolin-7-O-glucoside, apigenin-7-O-glucoside, as well as the aglycons luteolin, apigenin, chrysoeriol, diosmetin, and acacetin were identified by TLC and LC–DAD–MSⁿ in comparison to reference substances or literature data. The NMR data of seven structures have not been reported in the literature to date.     

Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury

Seven new triterpenoids (1–7), together with two known ones (8–9), were isolated from the aerial parts ofIlex cornuta. The leaves of I. cornuta are the major source of “Kudingcha”, a popular herbal tea consumed in China and other countries. The structures of compounds 1–7 were determined as 20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (1), 20-epi-urs-12,18-dien-28-oic acid 2′-O-acetyl-3β-O-α-l-arabinopyranoside (2), 20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (3), 3β,23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (4), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (5), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronic acid (6), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (7), on the basis of spectroscopic analyses (IR, ESI–MS, HR-ESI–MS, 1D and 2D NMR) and chemical reactions. Protective effects against H₂O₂-induced H9c2 cardiomyocyte injury were tested in vitro for compounds 1–9, and the data showed that compound 4 had significant cell-protective effect. Compounds 1-9 did not show significant DPPH radical scavenging activity.     

Phytochemical,Antiplasmodial, Cytotoxic and Antimicrobial Evaluation of a Southeast Brazilian Brown Propolis Produced by Apis mellifera Bees

Seven phenolic compounds (ferulic acid, caffeic acid, 4-methoxycinnamic acid, 3,4-dimethoxycinnamic acid, 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-β-D-glucopyranoside), a flavanonol (7-O-methylaromadendrin), two lignans (pinoresinol and matairesinol) and six diterpenic acids/alcohol (19-acetoxy-13-hydroxyabda-8(17),14-diene, totarol, 7-oxodehydroabietic acid, dehydroabietic acid, communic acid and isopimaric acid) were isolated from the hydroalcoholic extract of a Brazilian Brown Propolis and characterized by NMR spectral data analysis. The volatile fraction of brown propolis was characterized by CG-MS, composed mainly of monoterpenes and sesquiterpenes, being the major α-pinene (18.4 %) and β-pinene (10.3 %). This propolis chemical profile indicates that Pinus spp., Eucalyptus spp. and Araucaria angustifolia might be its primary plants source. The brown propolis displayed significant activity against Plasmodium falciparum D6 and W2 strains with IC₅₀ of 5.3 and 9.7 μg/mL, respectively. The volatile fraction was also active with IC₅₀ of 22.5 and 41.8 μg/mL, respectively. Among the compounds, 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-β-D-glucopyranoside showed IC₅₀ of 3.1 and 1.0 μg/mL against D6 and W2 strains, respectively, while communic acid showed an IC₅₀ of 4.0 μg/mL against W2 strain. Cytotoxicity was determined on four tumor cell lines (SK-MEL, KB, BT-549, and SK-OV-3) and two normal renal cell lines (LLC-PK1 and VERO). Matairesinol, 7-O-methylaromadendrin, and isopimaric acid showed an IC₅₀ range of 1.8–0.78 μg/mL, 7.3–100 μg/mL, and 17–18 μg/mL, respectively, against the tumor cell lines but they were not cytotoxic against normal cell lines. The crude extract of brown propolis displayed antimicrobial activity against C. neoformans, methicillin-resistant Staphylococcus aureus, and P. aeruginosa at 29.9 μg/mL, 178.9 μg/mL, and 160.7 μg/mL, respectively. The volatile fraction inhibited the growth of C. neoformans at 53.0 μg/mL. The compounds 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 7-oxodehydroabietic acid were active against C. neoformans, and caffeic and communic acids were active against methicillin-resistant Staphylococcus aureus.     

Regioselective acylation of several polyhydroxylated natural compounds by Candida antarctica lipase B

Regioselective acylation of four polyhydroxylated natural compounds, deacetyl asperulosidic acid (1), asperulosidic acid (2), puerarin (3) and resveratrol (4) by Candida antarctica Lipase B in the presence of various acyl donors (vinyl acetate, vinyl decanoate or vinyl cinnamoate) was studied. Compounds 1, 2 and 4 were regioselectively acetylated with vinyl acetate to afford products, 3′-O-acetyl-10-O-deacetylasperulosidic acid (1a), 3′,6′-O-diacetyl-10-O-deacetylasperulosidic acid (1b), 3′-O-acetylasperulosidic acid (2a), 3′,6′-O-diacetylasperulosidic acid (2b), 4′-O-acetylresveratrol (4a), respectively, with yields of 22 to 50%, while reactions with vinyl decanoate and vinyl cinnamoate were slow with lower yields. Compound 3 was readily acylated with all three acyl donors and quantitatively converted to products 6″-O-acetylpuerarin (3a), 6″-O-decanoylpuerarin (3b), 6″-O-cinnamoylpuerarin (3c), respectively. The structures of these acylated products were determined by spectroscopic methods (MS and NMR).     

Metabolomics-oriented isolation and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana

In order to conduct metabolomic studies in a model plant for genome research, such as Arabidopsis thaliana (Arabidopsis), it is a prerequisite to obtain structural information for the isolated metabolites from the plant of interest. In this study, we isolated metabolites of Arabidopsis in a relatively non-targeted way, aiming at the construction of metabolite standards and chemotaxonomic comparison. Anthocyanins (5 and 7) called A8 and A10 were isolated and their structures were elucidated as cyanidin 3-O-[2-O-(β-d-xylopyranosyl)-6-O-(4-O-(β-d-glucopyranosyl)-E-p-coumaroyl)-β-d-glucopyranoside]-5-O-[6-O-(malonyl)-β-d-glucopyranoside] and cyanidin 3-O-[2-O-(2-O-(E-sinapoyl)-β-d-xylopyranosyl)-6-O-(4-O-(β-d-glucopyranosyl)-E-p-coumaroyl)-β-d-glucopyranoside]-5-O-[β-d-glucopyranoside] from analyses of 1D NMR, 2D NMR (¹H NMR, NOE, ¹³C NMR, HMBC and HMQC), HRFABMS, FT-ESI-MS and GC-TOF-MS data. In addition, 35 known compounds, including six anthocyanins, eight flavonols, one nucleoside, one indole glucosinolate, four phenylpropanoids and a derivative, together with three indoles, one carotenoid, one apocarotenoid, three galactolipids, two chlorophyll derivatives, one steroid, one hydrocarbon, and two dicarboxylic acids, were also isolated and identified from their spectroscopic data.     

Structures of the novel diterpene glycosides from Stevia rebaudiana

From the commercial extract of the leaves of Stevia rebaudiana, two new diterpenoid glycosides were isolated besides the known steviol glycosides including stevioside, rebaudiosides A–F, rubusoside, and dulcoside A. The structures of the two new compounds were identified as 13-[(2-O-6-deoxy-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (1), and 13-[(2-O-6-deoxy-β-d-glucopyranosyl-3-O-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-d-glucopyranosyl ester (2), on the basis of extensive NMR and MS spectral data as well as chemical studies.