Isolation and antiproliferative activity of chemical constituents from Asystasia buettneri Lindau

N-hexane and methanol extracts of Asystasia buettneri Lindau aerial parts exhibited antiproliferative activity on leukaemia blood carcinoma, K-562. Hexadecane (1), 1,3-propan-2-ol (9Z,12′Z,15″Z)-bis(doeicos-9,12,15-trienoate) (2), hydrocarbon, 2,3,3,10,23-pentamethyl tetraeicos-10,13,16-trien-1-ol (3), hexadecanoic acid (4) and taraxerol (5) were isolated from n-hexane extract; stigmasterol (6) and (Z)-9-octadecenoic acid (7) were isolated from ethyl acetate extract; while unsaturated hydrocarbons, octadecene (8), 8-methyl tetradec-6-ene (9) and 19-methyl eicos-1-ene (10), fatty acids, (Z)-5-hexadecenoic acid (11), 11,22-dimethyl ethyltrieicos-11-enoate (12) and taraxasterol (13) were isolated from methanol extract of the plant. Compounds 4, 5, 7, 11, 12 and 13 exhibited antiproliferative activity against K-562, while compounds 5, 6, 7 and 9 revealed antiproliferative activity by inhibiting hepatic liver (WRL68) cell lines.     

海洋软珊瑚群柱虫化学成分的分离与鉴定

海洋软珊瑚中已发现了许多具有强烈生理活性和化学结构特殊的化合物.本文报道软珊瑚群柱虫(clavularia sp~≠)的化学成分研究.采得之样品,一部分浸泡于95％乙醇中(以下称湿品),一部分晒干(以下称干品).各按实验部分所述的方法提取分离,可得到化合物1和6及一些酯类混合物,兹分述于下:(一)化合物1为无色透明液体,分子式 C_(20)H_(32),[α]_D~(12) 20.4°(c0.225,CHCl_3).UV210nm 以上无吸收,表明无共轭双键.v_(max):3050,1640,885cm~(-1);δ_H:5.19(1H,t,J=7Hz),5.07(1H,t,J=7Hz),4.99(1H,t,J=7Hz)ppm,分别为三个三取代双键的氢.4.72(1H,s),4.66(1H,s)ppm为 C(?)CH_2的两个氢.1.66(3H,s),1.59(3H,s),1.57(6H,s)ppm 为四个连接在双键上的甲基.1以 PtO_2-H_2常压氢化,吸收四摩尔当最的 H_2生成饱和化合物2,分子式 C_(20)H_(40),[α]_D~(12) 0.6°(c1.71,CHOl_3),含有一个碳环.1经臭氧化、铬酸     

New chemical constituents from the Piper betle Linn. (Piperaceae)

The phytochemical investigation of chloroform extract from Piper betle var. haldia, Piperaceae, leaves has resulted in the isolation of two new chemical constituents which were identified as 1-n-dodecanyloxy resorcinol (H1) and desmethylenesqualenyl deoxy-cepharadione-A (H4), on the basis of spectroscopic data 1D NMR (¹H and ¹³C) and 2D NMR (¹H-¹H COSY and HMBC) as well as ESI-MS, FT-IR and HR-ESI-MS analyses. Compounds H1 and H4 showed excellent antioxidant DPPH free radical scavenging activity with IC₅₀ values of 7.14 μg/mL and 8.08 μg/mL compared to ascorbic acid as a standard antioxidant drug with IC₅₀ value of 2.52 μg/mL, respectively. Evaluation of cytotoxic activity against human hepatoma cell line (PLC-PRF-5) showed moderate effect with the GI₅₀ values of 35.12 μg/mL for H1, 31.01 μg/mL for H4, compared to Doxorubicin^® as a standard cytotoxic drug with GI₅₀ value of 18.80 μg/mL.     

短萼海桐化学成分研究

从云南昆明地区采集的短萼海桐树皮中分离得到五个齐墩果烷型三萜皂苷元,其中5为一新化合物,命名短萼海桐皂苷元,其余四个分别为已知的齐墩果酸,常春藤皂苷元,茶皂苷元D,和R~1-barrigenol.     

峨嵋葛花异黄酮类化合物的研究(Ⅰ)

对峨嵋葛花(Flos Pueraria omeiensis)的化学成分进行研究,从乙醇浸提液的乙酸乙酯提取部位首次分离得到了三个异黄酮类化合物,根据理化和光谱分析鉴定为:鸢尾甙元(1),二甲基鸢尾甙元(2),大豆甙(3).     

循环制备液相色谱分离芳香新塔花中的化学成分

建立了交替循环和直接循环液相色谱相结合的方法用于制备芳香新塔花中的化学成分.芳香新塔花样品经溶剂提取、柱色谱和中压制备色谱初步分离后得到芳香新塔花的不同馏分.以甲醇-水为流动相,利用双柱交替循环法对组分进行分离,同时,流动相经恒流泵循环输入色谱柱.以馏分Ⅰ和馏分Ⅱ为例,在混合循环模式下分离得到5个化合物.通过核磁共振对其进行鉴定,确定分别为乔松素-7-O-芸香糖苷、白杨素-7-O-芸香糖苷、金合欢素-7-O-芸香糖苷、云杉素和原儿茶酸.实验结果表明,该制备方法分离效率高,节省流动相,是分离天然产物的有效手段.     

西沙仙掌藻Halimeda xishensis的化学成分研究(Ⅰ)

对西沙仙掌藻Halimeda xishaensis样品进行化学成分研究,从中分离得到了三个化合物,其结构通过MS、NMR及X射线单晶衍射等波谱方法进行鉴定,确定结构为:1-正二十三碳酸甘油酯(Ⅰ),豆甾-4-烯-3β,6β-二醇(Ⅱ),丁四醇(Ⅲ);对此样品的进一步研究正在进行中.     

Bioactive chemical constituents from Hyptis suaveolens stem

Our previous studies have found that the aerial part of Hyptis rhomboides and the seed of Hyptis suaveolens contain xanthine oxidase (XO) inhibitors, inspiring us to investigate the chemical constituents of H. suaveolens stem. The EtOH extract of H. suaveolens stem was fractionated by liquid-liquid partitioning, followed by separation over Sephadex LH-20, silica gel, and reverse-phase column chromatography, centrifugal partition chromatography, and semi-preparative RP-HPLC, to give 17 bioactive isolates. Of these, dimethyl melitrate A ( 9 ) is a new natural product, 10 is likely (7″ E)-9′-methyl melitrate A, only caffeic acid ( 2 ) is the same as those isolated from the seed of the same plant, and only nepetoidins A ( 14 ) and B ( 11 ) are the same as those from H. rhomboides stem. Nepetoidin B ( 11 ) showed the best anti-XO activity. Rosmarinic acid ( 3 ) is the most abundant (>661 ppm; w/w, dried stem), while melitric acid ( 12 ) (>277 ppm), caffeic acid ( 2 ; >125 ppm), and methyl rosmarinate ( 4 ; >81 ppm) are the major ones. This outcome could serve as a good basis for chemotaxonomy of the Hyptis plants and is beneficial for developing H. suaveolens stem as anti-hyperuricemic nutraceutical.     

阿尔泰狗娃花化学成分研究

本文从阿尔泰狗娃花Heteropappus altaicus的乙醇提取物中分离出12个已知化合物,经过红外光谱(IR),质谱(MS),核磁共振谱(NMR)等分析方法及与标准品对照,鉴定了它们的结构。分别为:木栓酮(1),表木栓醇(2),达玛烷-20,24-二烯-3β-醇(3),达玛烷-20,24-二烯-3β-乙酰基(4),α-波甾醇(5),槲皮素(6),3'-甲氧基槲皮素(7),槲皮素-3-O-β-D-葡萄糖苷(8),阿魏酸(9),β-谷甾醇(10),β-胡萝卜苷(11),没食子酸乙酯(12)。其中化合物9和12为首次从该属植物中分离得到,化合物5,6,9和12为首次从该植物中分离得到。     

大叶桉化学成分的研究 - 大叶桉酚乙和其它成分的分离和鉴定

从大叶桉叶的乙醇提取物中分离并鉴定出九种已知成分:5-羟基-4',7-二甲氧基6,8-二甲基黄酮,4',5-二羟基-7-甲氧基6,8-二甲基黄酮,3β-羟基-乌索-11-烯-28,13β-内酯,13β-乙酰氧基-乌索-11-烯-28,13β-内酯;3β,28-二羟基-乌索-12-烯,β-谷甾醇,2-甲基5,7-二羟基-苯骈吡喃酮-7β-葡萄糖苷,正卅烷醇和正卅烷酸,另外,分得一种新的酰基间苯三酚类成分,命名为大叶桉酚乙,其结构为2-甲氧基-4,6-二羟基异丁酰基苯,并进行化学合成确证,大叶桉酚乙在管碟法中对金黄色葡萄球菌和枯草杆菌有抑菌作用。     

The chemical constituents from Schisandra propinqua var intermedia

A new cirmamic acid monoterpenoid ester, intermedin C (1), was isolated from the aerial parts of Schisandra propinqua vat. intermedia. The structure of 1 was elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques.     

Bioactive constituents from Rollinia emarginata (Annonaceae)

From an Argentine collection of the tropical tree Rollinia emarginata (Annonaceae), vomifoliol, dehydrovomifoliol, blumenol C, loliolide, 7-epiloliolide, vanillin, dihydroactinolide, as well as other common plant constituents were obtained, and identified by their NMR and MS features compared with authentic samples. Antifeedant and toxic actions were exerted to the polyphagous moth Spodoptera frugiperda by the ethanol extract of the plant, at 250 ppm in the larval diet. Additionally, in greenhouse studies, a 200 ppm aqueous solution of the extract produced a post-emergency herbicidal effect on the annual weed common lambsquarter (Chenopodium album).     

Structural studies of the chemical constituents of Tithonia tagetiflora Desv. (Asteraceae)

Tithonia tagetiflora Desv. (Asteraceae) is a widespread plant in Vietnam, and the species of Tithonia are known as plants containing many biologically active compounds. However, T. tagetiflora's chemical composition remains mostly unknown. Therefore, we now report the structural elucidation of two new sesquiterpene lactones, 8‐angeloyloxy‐2,14‐epoxygermacra‐4,10(1),11(13)‐trien‐6,12‐olide (1) and 6‐angeloyloxy‐1‐hydroxy‐3,4‐epoxygermacra‐9,11(13)‐dien‐8,12‐olide (2), together with three known compounds, including two norisoprenoids, (6S,9S)‐vomifoliol or (6R,9R)‐vomifoliol (3) and (6S,9S)‐roseoside (4), and one glutinane type triterpene, epi‐glutinol (5), from the leaves of T. tagetiflora. Their structures are established by 1D and 2D NMR spectroscopy, as well as ESI‐MS analysis and comparison with literature data. Copyright © 2013 John Wiley & Sons, Ltd.     

Studies on the chemical constituents of Eucalyptus robusta Sm.: Isolation and identification of robustaol B and other constituents

Nine known compounds, 5-hydroxy-4′,7-dimethoxy-6,8-dimethylflavone, 4′,5-dihydroxy-7-methoxy-6,8-dimethylflavone, 3β-hydroxy-urs-11-ene-28-oic-13(28)-lactone, 3β-acetoxy-urs-11-ene-28-oic-13(28)-lactone, uvaol, β-sitosterol, 7β-O-glucoside of 5,7-dihydroxy-2-methylchromone, 1-triacontanol and 1-triacontanoic acid, and a new acylphloroglucinol named robustaol B 6 were isolated from the leaves of Eucalyptus robusta Sm. 6 was shown to be 4,6-dihydroxy-2-methoxy isobutyrophenone by spectral analyses and was confirmed by synthesis. 6 showed inhibition against Staphylococcus aureus 209P and Bacillus subtilis 6633 in vitro.     

Comparative study of chemical constituents of rhubarb from different origins

A comparative study of the pharmacologically active constituents of 24 rhubarb samples, which were identified genetically as Rheum tanguticum, 3 intraspecies groups of R. palmatum and R. officinale, was conducted using reversed-phase high performance liquid chromatography (HPLC) methods. Thirty compounds belonging to anthraquinones, anthraquinone glucosides, dianthrones, phenylbutanones, stilbenes, flavan-3-ols, procyanidins, galloylglucoses, acylglucoses, gallic acid, and polymeric procyanidins were analyzed quantitatively. The drug samples derived from the same botanical source showed similar chromatographic profiles, and the comparable specific shape that appeared in the 10-directed radar graphs constructed on the basis of the results of quantitative analysis indicated the relationship between chemical constituent patterns and genetic varieties of rhubarb samples.     

Isolation,structural elucidation and cytotoxicity evaluation of a new pentahydroxy-pimarane diterpenoid along with other chemical constituents from Aerva lanata

Aervalanata possesses various useful medicinal and pharmaceutical activities. Phytochemical investigation of the plant has now led to the isolation of a new 2α,3α,15,16,19-pentahydroxy pimar-8(14)-ene diterpenoid (1) together with 12 other known compounds identified as β-sitosterol (2), β-sitosterol-3-O-β-D-glucoside (3), canthin-6-one (4), 10-hydroxycanthin-6-one (aervine, 5), 10-methoxycanthin-6-one (methylaervine, 6), β-carboline-1-propionic acid (7), 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2′R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol (8), 1-O-(β-D-glucopyranosyl)-(2S,3S,4R,8Z)-2-[(2′R)-2′-hydroxytetracosanoylamino]-8(Z)-octadene-1,3,4-triol (9), (2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (10), 6′-O-(4″-hydroxy-trans-cinnamoyl)-kaempferol-3-O-β-D-glucopyranoside (tribuloside, 11), 3-cinnamoyltribuloside (12) and sulfonoquinovosyldiacylglyceride (13). Among these, six compounds (8–13) are reported for the first time from this plant. Cytotoxicity evaluation of the compounds against five cancer cell lines (CHO, HepG2, HeLa, A-431 and MCF-7) shows promising IC₅₀ values for compounds 4, 6 and 12.     

Anti-inflammatory activities of the chemical constituents isolated from Trametes versicolor

Twenty-seven compounds including nine triterpenoids (1–9), eight sterols (10–17), two ribonucleotides (18, 19), four phenols (20–23), three glycosides (24–26), and one furan (27) were isolated from the fruiting bodies of Trametes versicolor (L.) Lloyd. This study is the first confirmation of the presence of the 11 compounds (3, 5, 6, 8, 18, 20, 21, 23–25, and 27) isolated from the Polyporaceae family, with six of these (2 and 12–16) from the genus Trametes. Compounds 3, 4, 10, 11, 16 and 17 were found to significantly inhibit the production of NO, TNF-α and IL-6 in a dose-dependent manner.     

南海柳珊瑚Menella Spinifera Kukenthal化学成分的研究(二)

从中国南海针小月柳珊瑚（MenellaSpiniferaKukenthal）中分离到一种内盐，其结构经UV、IR、MS、1HNMR和13CNMR分析确定为：N-甲基吡啶羧酸内按盐。本文是首次报导这个化合物的波谱数据。     

Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea

Exhaustive hydro-distillation of the leaves of Piper aduncum and fruits of Piper gibbilimbum (Piperaceae) afforded colorless and pale orange colored oils in 0.35 and 0.30 % yields, respectively. Detailed chemical analysis by GC/MS indicated the volatile constituents of Piper aduncum to be composed of dill apiole (43.3%), beta-caryophyllene (8.2%), piperitione (6.7%) and alpha-humulene (5.1%), whilst the oil of P. gibbilimbum is dominated by the gibbilimbols A-D (74.2%), with the remaining major constituents being the terpenes camphene (13.6%) and alpha-pinene (6.5%).     

罗汉松科植物中化学成分的研究:I.竹柏中的抗肿瘤成分

从罗汉松科植物竹柏(Podocarpus nagi(thunb.)Zoll.ct Mor.ex Zoll.)种子中分得七种成分。根据理化性质、波谱数据及化学反应鉴定为竹柏内酯A(1)、1-去氧-2α-羟基竹柏内酯A(3)、竹柏内酯苷A(4)、柳杉酚(5)、β-谷甾醇及蔗糖, 其中4是新化合物, 5是首次从该植物中分得。生物试验表明, 二萜双内酯化合物1-3具有较强的细胞毒作用, 4 无效。对2及3进行了结构改造, 提示了它们的构效关系。