猪殃殃酚性成分研究

目的:对猪殃殃Galium aparine var.tenerum全草中酚性成分进行研究.方法:采用各种色谱法分离,运用多种波谱技术鉴定化合物结构.结果:从猪殃殃乙醇提取物的醋酸乙酯萃取部位分离鉴定了6个化合物,分别鉴定为对羟基苯乙酮(1),香草酸(2),3,4-二羟基苯甲酸(3),对羟基桂皮酸(4),没食子酸(5),4-羟基古柯间二酸(6).结论:化合物6为首次从天然产物中得到,并运用二维核磁共振波谱技术(~1H-~1H COSY,HMQC和HMBC)首次对其碳谱和氢谱数据进行了全归属,化合物1-5均为首次从该属植物中得到.     

Extract of gravel root (rhizome of Eupatorium purpureum) inhibits integrin-dependent U937 cell adhesion

The effect of the antirheumatic herbal drug, gravel root (rhizome of Eupatorium purpureum), was investigated on integrin-dependent U937 cell adhesion to endothelial cells and extracellular matrix protein, fibronectin. In the presence of gravel root extract (6.3–200 μg/mL), U937 cells lowered their capacity for phorbol myristate acetate (PMA)-mediated adhesion to tumour necrosis factor-α (TNF)-activated endothelial cells or ICAM-1 coated plates. Similarly, the PMA mediated, LFA-1-dependent, homotypic cell aggregation in U937 cells was potently inhibited by gravel root extract. The α₄β₁ and α₅β₁-mediated adhesion of unstimulated U937 cells to fibronectin coated plates was also inhibited by gravel root extract. Neither the TNF-induced enhancement of expression of ICAM-1 on endothelial cell surface nor the TNF-induced endothelial adhesiveness to U937 cells was, however, inhibited by gravel root extract. Since all concentrations of gravel root extract tested failed to alter the proliferation of U937 cells, the observed activity was unlikely to be due to nonspecific suppression of cells. © 1998 John Wiley & Sons, Ltd.     

Andrographolide inhibits the tumour necrosis factor-α-induced upregulation of ICAM-1 expression and endothelial-monocyte adhesion

Andrographolide, a diterpene isolated from Andrographis paniculata, has been shown to have several biological activities including analgesic, antipyretic and antiinflammatory effects. Since the upregulation of adhesion molecules expression and endothelial-leucocytes adhesion are key steps in the development of inflammation, the present study examines whether andrographolide modulates these biological processes in vitro. Incubation of endothelial cells with non-toxic concentrations (0.16–16.7 υg/mL) of andrographolide attenuated the tumour necrosis factor-α (TNF)-induced intercellular adhesion molecule-1 (ICAM-1) expression. Similar concentration ranges of andrographolide also inhibited the TNF-induced endothelial-monocyte adhesion in a concentration-dependent manner. These effects of andrographolide may account for its reported in vivoantiinflammatory activity. © 1998 John Wiley & Sons, Ltd.     

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??OBJECTIVE To study the polar chemical constituents from Prunella vulgaris L.. METHODS Silica gel, reverse-phase octadecylsilyl (ODS), Sephadex LH-20 chromatographic methods, MCI and HPLC were applied to isolate and purify compounds. MS and NMR methods were used to determine the structures of the compounds. Furthermore, the cytotoxicity of these chemical components for MCF-7, MDA-MB-231 and MCF-10A cell lines was measured by MTT method. RESULTS A total of 12 compounds were isolated from the fruits of P. vulgaris and their structures were identified as methyl 3,4,??-trihydroxypropionate(1), danshensu (2), methyl rosmarinate (3), 3,4-dihydroxybenzoic acid (4), quercetin-3-O-glycopyranoside (5), hyperoside (6), 2??,3??,19??,24-tetrahydroxylurs-12-en-28-oic acid (7), 2??,3??,24-trihydroxyolean-12-en-28-oic acid (8), cytidine (9), daucosterol (10), (3S,5R,10S)-7-oxo-12-methoxyabieta-8,11,13-triene-3,11,14-triol (11), and 2??,3??,24-trihydroxyolean-12,20(30)-dien-28-oic acid (12). The results of antitumor assay indicated that compound 2, 3, 5 and 6 significantly inhibited the activity of MCF-7, compound 3 could inhibit the activity of MDA-MB-231, but all of them also significantly inhibited the activity of normal cell lines MCF-10A. CONCLUSION Compounds 9 and 11 are isolated from the genus of Prunella L. for the first time. Some chemical constituents form Prunella L. show certain anti-breast cancer activity.     

水栀子中酚性成分研究

目的研究水栀子Gardenia jasminosides var.radicans的酚性成分。方法采用硅胶、Toyopearl HW-40、Sephadex LH-20、MCI gel CHP-20、ODS柱色谱法及制备液相进行分离纯化,根据理化性质和波谱数据鉴定化合物结构。结果从水栀子醋酸乙酯部位分离得到17个酚性化合物,分别鉴定为3,3′,5-trimethoxy-9,9′-epoxylignane-4,4′-diol(1)、3,4-二香草酰基四氢呋喃(2)、marphenol C(3)、芥子醛(4)、对羟基肉桂酸(5)、异阿魏酸(6)、咖啡酸(7)、异秦皮啶(8)、异莨菪内酯(9)、6-甲氧基-7-羟基香豆素(10)、6,7-二羟基香豆素(11)、丁香酸(12)、3-羟基-4-甲氧基苯甲酸(13)、3,4-二羟基苯甲酸(14)、对羟基苯甲酸(15)、没食子酸-3-甲基醚(16)、没食子酸(17)。结论以上化合物均为首次从水栀子中分离得到。     

A New Phenolic Component from Triticum aestivum Sprouts and its Effects on LPS‐Stimulated Production of Nitric oxide and TNF‐α in RAW 264.7 Cells

An unusual new phenolic component, triticumoside (1), and eight known compounds, isoorientin (2), isoscoparin (3), (2R)‐2‐O‐β‐D‐glucopyranosyloxy‐4,7‐dimethoxy‐2H‐1,4‐benzoxazin‐3(4H)‐one (4), adenosine (5), β‐sitosterol (6), daucosterol (7), 6′‐O‐linolenoyl daucosterol (8), α‐tocopherol (9), were isolated from Triticum aestivum sprouts. The hybrid structure of 1, which is a hybrid between a flavone and a polyoxygenated benzene, is rarely found in natural sources. In addition, the effects of these compounds on LPS‐induced NO and TNF‐α production in RAW 264.7 cells were evaluated. At a concentration of 2.0 μM, compounds 2–4 significantly inhibited the production of both NO and TNF‐α. Compound 1 exhibited inhibitory activity on the secretion of TNF‐α at concentrations as low as 2.0 μM, but it did not reduce NO levels at any of the tested concentrations. Copyright © 2013 John Wiley & Sons, Ltd.     

Inhibition of tumor-promoting effects by poricoic acids G and H and other lanostane-type triterpenes and cytotoxic activity of poricoic acids A and G from Poria cocos

The structures of two novel 3,4-seco-lanostane-type triterpenes isolated from the sclerotium of Poria cocos were established to be 16alpha-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (1; poricoic acid G) and 16alpha-hydroxy-3,4-seco-24-methyllanosta-4(28),8,24(24(1))-triene-3,21-dioic acid (2; poricoic acid H) on the basis of spectroscopic methods. These two, and eight other known compounds isolated from the sclerotium, poricoic acid B (3), poricoic acid A (4), tumulosic acid (5), dehydrotumulosic acid (6), 3-epidehydrotumulosic acid (7), polyporenic acid C (8), 25-hydroxy-3-epidehydrotumulosic acid (9), and dehydroabietic acid methyl ester (10), showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). Evaluation of the cytotoxicity of compounds 1 and 4 against human cancer cell lines revealed that 1 was significantly cytotoxic to leukemia HL-60 cells [GI(50) (concentration that yields 50% growth) value 39.3 nM], although it showed only moderate cytotoxicity to the other cells. Compound 4 exhibited moderate cytotoxicity to all of the cancer cell lines tested.     

桂野桐化学成分的研究

目的研究桂野桐Mallotus conspurcatus中的化学成分。方法采用各种色谱分离手段对桂野桐75%乙醇粗提物的醋酸乙酯萃取部分进行分离纯化。运用1H-NMR、13C-NMR、ESI-MS等波谱方法以及与文献数据对比,鉴定化合物结构。结果从桂野桐根中分离得到18个化合物,分别鉴定为1,5-二羟基-3-甲氧基-7-甲基蒽醌(1)、(-)-丁香脂素(2)、2,3-二羟基-5,7-二-甲氧基-2,8-二甲基-6-(3-甲基-2-丁基)-吡喃-4-酮(3)、2,3-二氢-5,7-二羟基-2,6,8-三甲基-吡喃-4-酮(4)、paeoveitol B(5)、pinellic acid(6)、反式对羟基肉桂酸(7)、反式对甲氧基肉桂酸(8)、反式对羟基肉桂酸乙酯(9)、对羟基苯甲酸(10)、3-甲氧基-4-羟基苯甲酸(11)、3,4-二羟基苯甲酸(12)、阿魏酸(13)、丁香酸(14)、丁香酸乙酯(15)、1-正十六酸甘油酯(16)、没食子酸(17)和没食子酸乙酯(18)。结论除化合物3、4和13外,其余均为首次从野桐属植物中分离得到。     

猫爪草化学成分的研究(Ⅱ)

 目的研究猫爪草的化学成分。方法经柱色谱分离,理化常数和光谱分析鉴定化合物结构。结果从氯仿部分得到8个化合物,分别为邻苯二甲酸正丁酯(Ⅰ),β-单棕榈酸甘油酯(Ⅱ),β-单硬脂酸甘油酯(Ⅲ),2-氨基-3-(3,4-二羟基-苯基)-丙酸甲酯(Ⅳ),2-氨基-3-(3,4-二羟基-苯基)-丙酸乙酯(Ⅴ),5-羟甲基糠醛(Ⅵ),5-羟甲基糠酸(Ⅶ),维太菊苷(Ⅷ)。结论Ⅰ, Ⅱ,Ⅲ,Ⅵ,Ⅶ系首次从毛茛属中得到,Ⅳ,Ⅴ为提取分离过程中人工产物。     

Growth inhibitory activity of biflavonoids and diterpenoids from the leaves of the Libyan Juniperus phoenicea against human cancer cells

Three biflavonoids [cupressuflavone ( 1 ), amentoflavone ( 2 ), and sumaflavone ( 3 )], four diterpenoids [13‐epi‐cupressic acid ( 4 ), imbricatholic acid ( 5 ), 3‐hydroxy‐sandaracopimaric acid ( 6 ), and dehydroabietic acid ( 7 )], and one lignan [β‐peltatin methyl ether ( 8 )] were isolated from the cytotoxic fractions of the extracts of the leaves of the Libyan Juniperus phoenicea L. The structures of these compounds were elucidated by spectroscopic means. Cytotoxicity of compounds 1 – 6 were assessed against the human lung cancer cell line A549 using the MTT assay. Compounds 1 and 3 showed cytotoxicity against the A549 cells (IC₅₀ = 65 and 77 μM, respectively), whereas compound 2 did not show any activity. Diterpenes 4 – 6 exhibited weak cytotoxicity against the A549 cells with the IC₅₀ values of 159, 263, and 223 μM, respectively. The cytotoxicity of each compound was compared with the anticancer drug, etoposide (IC₅₀ = 61 μM). Cupressuflavone ( 1 ) was evaluated also for cytotoxicity against both the human PC3 cancer cell line and the normal prostate cell line (PNT2), and this compound revealed a high degree of cytotoxic selectivity towards the prostate cancer cells (PC3), with IC₅₀ value of 19.9 μM, without any evidence of cytotoxicity towards the normal prostate cell line (PNT2).     

Inhibition of UVB‐induced pro‐inflammatory cytokines and MMP expression by Zanthoxylum rhetsa bark extract and its active constituent hesperidin

The antiphoto aging property of Zanthoxylum rhetsa obtained from Pangkor Island, Malaysia, was evaluated. Solvent fractions of different polarity obtained from the methanolic extract of the bark material were initially tested for anticollagenase and antielastase activities. The ethyl acetate fraction showed bioactivity against the protease enzymes. Hence, it was subjected to further purification via column chromatography, to yield a major constituent, hesperidin. Subsequently, the ethyl acetate fraction and hesperidin were tested for their effects against UVB‐induced cytotoxicity and expressions of inflammatory cytokines (IL‐6, IL‐1β, and TNF‐α), NF‐κB, and MMPs (MMP1, 3, and 9) in human dermal fibroblasts (HDF). Both fraction and pure compound prevented UVB‐induced cytotoxicity in HDF cells, in a dose dependent manner. Moreover, the ethyl acetate fraction inhibited the increase of pro‐inflammatory cytokines induced by UVB to a level similar to the control (without UV treatment). Additionally, the fraction significantly inhibited the expressions of NF‐κB, MMP 1, MMP 3, and MMP 9 in HDF cells treated with UVB. Similar effects were observed with hesperidin. The results obtained suggested that the ethyl acetate fraction of Z. rhetsa and its bioactive constituent, hesperidin, have the potential to be used as active ingredients in sunscreen and antiphoto aging formulations.     

贵州獐牙菜的化学成分研究

对龙胆科 Gentianaceae 獐牙菜属植物贵州獐牙菜Swertia kouitchensis 90%乙醇提取物乙酸乙酯萃取部分的化学成分进行研究。利用各种柱色谱方法对其进行分离纯化,通过波谱数据分析(¹H-NMR,¹³C-NMR,MS) 进行结构鉴定。从中分离鉴定了28个化合物,包括6个裂环烯醚萜、2个 NFDE8 酮及其苷、3个少见的内酯烯胺酮、 2个三萜、1个木质素和14个其他类化合物,分别为红白金花内酯(erythrocentaurin, 1)、erythrocentaurin dimethylacetal(2)、獐牙菜苦苷(swertiamarin, 3)、vogeloside(4)、2'-O-actylswertiamarin(5)、狭叶獐牙菜苷 D(swertianoside D, 6)、獐牙菜烯胺酮 A~B(gentiocrucines A~B, 7~8)、gentiocrucine(9)、1-羟基-3,7,8-三甲氧基 NFDE8 酮(1-hydroxy-3,7,8-trimethoxyxanthone, 10)、1-羟基-3,5,6-三甲氧基 NFDE8 酮(1-hydroxy-3,5,6-trimethoxyxanthone, 11)、3-表-蒲公英赛醇(3-epitaraxerol, 12)、erythrodiol 3-O-palmitate(13)、(+)-丁香脂素((+)-syringaresinol, 14)、咖啡酸(caffeic acid, 15)、松柏醛(trans-coniferyl aldehyde, 16)、松柏醇(trans-coniferyl alcohol, 17)、3,4-二羟基苯甲酸(3,4-dihydroxybenzoic acid, 18)、4-羟基-3-甲氧基苯甲酸(4-hydroxy-3-methoxybenzoic acid, 19)、3,4-二羟基苯甲醛(3,4-dihydroxybenzoic aldehyde,20)、2,3-二羟基苯甲酸(2,3-dihydroxybenzoic acid, 21)、对羟基苯甲酸(4-hydroxybenzoic acid,22)、3-乙酰氧基苯甲酸(3-acetoxybenzoic acid, 23)、间羟基苯甲酸(3-hydroxybenzoic acid, 24)、间羟基苯甲醇(3-hydroxybenzoic alcohol, 25)、烟酸(nicotinic acid, 26)、2-糠酸(2-furoic acid, 27)、尿嘧啶(uracil, 28)。其中化合物 1~4,6~28 为首次从贵州獐牙菜中分离得到。     

白茅根的化学成分研究

应用色谱法对白茅根的化学成分进行研究,应用波谱法结合文献报道的波谱数据鉴定化合物结构.结果分离鉴定了13个化合物,其中3个苯丙素类成分,1-(3,4,5-三甲氧基苯基)-1,2,3-丙三醇(1),1-O-对香豆酰基甘油酯(2),4-甲氧基-5-甲基香豆素-7-O-β-D-吡喃葡萄糖苷(3);4个有机酸类成分,对羟基苯甲酸(4),3,4-二羟基苯甲酸(5),香草酸(6),3,4-二羟基丁酸(7);1个酚类成分,水杨苷(8);以及5个三萜类成分,芦竹素(9),白茅素(10),羊齿烯醇(11),西米杜鹃醇(12),粘霉酮(13).其中1～8为首次从白茅属植物中分离得到.     

Antiinflammatory and lipoxygenase inhibitory compounds from vitex agnus‐castus

Several secondary metabolites, artemetin (1), casticin (2), 3,3′‐dihydroxy‐5,6,7,4′‐tetramethoxy flavon (3), penduletin (4), methyl 4‐hydroxybenzoate (5), p‐hydroxybenzoic acid (6), methyl 3,4‐dihydroxybenzoate (7), 5‐hydroxy‐2‐methoxybenzoic acid (8), vanillic acid (9) and 3,4‐dihydroxybenzoic acid (10) were isolated from a folkloric medicinal plant, Vitex agnus‐castus. The structures of compounds 1–10 were identified with the help of spectroscopic techniques. Compounds 3–10 were isolated for the first time from this plant. These compounds were screened for their antiinflammatory and lipoxygenase inhibitory activities. Compounds 6, 7 and 10 were found to have significant antiinflammatory activity in a cell‐based contemporary assay, whereas compounds 1 and 2 exhibited a potent lipoxygenase inhibition. Copyright © 2009 John Wiley & Sons, Ltd.     

Resveratrol derivatives from Commiphora africana (A. Rich.) Endl. display cytotoxicity and selectivity against several human cancer cell lines

Commiphora africana (A. Rich.) Endl. (Burseraceae) is a medicinal plant widely used in Nigerian ethnomedicine. The in vitro cytotoxicity of the stem bark extract of C. africana and isolated cytotoxic compounds was investigated. Three resveratrol derivatives: (E)‐resveratrol 3‐O‐rutinoside ( 1 ), 5‐methoxy‐(E)‐resveratrol 3‐O‐rutinoside ( 2 ), and pinostilbene ( 3 ), together with 3‐hydroxy‐5‐methoxybenzoic acid ( 4 ) were isolated from the methanol fraction of C. africana. Their structures were determined by extensive analysis of their HREIMS and NMR spectra. The cytotoxicity of the isolated compounds against four human carcinoma cells was determined using the MTT assay. Compound 1 displayed the highest antiproliferative effect on the cell lines, with IC₅₀ values of 16.80, 21.74, 17.89, and 17.44 μM, against MCF7, A549, PC3, and HepG2 human cancer cell lines, respectively. In addition, compounds 1 – 3 showed low toxicity against normal human prostate cell line, with selectivity indices greater than five across the carcinoma cells, indicating that the compounds possess potential in the development of low‐toxicity chemotherapeutic agents. These results support the traditional use of this plant in the treatment of cancer.     

无柄新乌檀化学成分研究

从无柄新乌檀(Neonauclea sessilifolia)的枝干乙酸乙酯部位分离到7个化合物,经波谱分析鉴定其分别为丹皮酚、3,4-二羟基苯甲酸、东莨菪内酯、葸醌大黄酚、5,7-二羟基2-甲基吡喃酮、β-谷甾醇,Δ5,22豆甾醇-β-D-葡萄糖甙,这7个化合物均为首次从该属、该种中分离得到。     

皱盖假芝子实体中1个新的降木脂素类化合物

目的对皱盖假芝Amaurodermarude子实体的化学成分进行研究,以期发现新的活性化合物。方法运用硅胶、凝胶、MCI-gel树脂及RP-HPLC等多种色谱技术进行分离纯化,并根据理化性质和波谱数据鉴定化合物的结构。结果从皱盖假芝子实体中分离得到了3个化合物,分别鉴定为4-乙氧基-E-3-(3,4-二羟基苯亚甲基)-5-(3,4-二羟基苯基)呋喃-2-酮(1)、七叶内酯(2)、咖啡酸(3)。结论化合物1为新化合物,命名为皱盖假芝素A。