嗜碱放线菌YIM-80147次生代谢产物的化学成分研究

对嗜碱放线菌YIM-80147的发酵产物进行化学成分的研究,从中分离得到6个化合物。根据光谱数据的分析,鉴定其结构分别为P371A2(1),4-hydroxymethyl-3-(i-hydroxy-6-methyl-heptyl)-dihydro-furan-2-one(2),nonactic acid(3),homononactinic acid(4),对羟基肉桂酸(5),阿魏酸(6)。     

嗜碱放线菌生理学特性的初步研究*

对从新疆、青海采集的盐碱土样中分离获得的29株嗜碱放线菌(AlkAlipbilic actinomyeetes)及1株模式菌株Nocardiopsis prasina的pH实验,不同碱性物质KOH、K2CO3、NaOH、Na2CO3对生长的影响,及对NaCl、KCl耐受性进行了研究。结果发现,少数嗜碱放线菌对Na^ 有一定的依赖性,对K^ 碱性物质敏感;一些嗜碱放线菌对CO3^2-敏感,NaCl、KCl对一些嗜碱放线菌的生长有抑制作用;4种碱性物质对Nocardiopsis菌株生长无影响,且它们可耐受高浓度NaCl、KCl。因此提出高碱性环境中是否存在K^ 、CO3^2-专一性依赖的嗜碱放线菌的推测。     

中度嗜盐或耐盐放线菌生长对阴离子选择性研究*

长期以来Cl^-被作为主要阴离子来分离和培养中度嗜盐放线菌,但是盐湖中还含有NO3^-、SO4^2-、CO3^2-和HCO3^-等阴离子。培养基中只加入含有Cl^-的盐,不能完全模拟出自然界的环境,因此对中度嗜盐或耐盐放线菌的研究会有一定的限制。实验通过研究部分中度嗜盐或耐盐放线菌菌株生长对阴离子的选择影响,结果发现中度嗜盐或耐盐放线菌对部分阴离子如NO3^-和SO4^2-没有太大的选择性,Cl^-可以被NO3^-和SO4^2-所代替;但有些阴离子如CO3^2-和HCO3^-仅对拟诺卡氏菌属(Nocardiopsis)影响较小,对盐碱环境中的其他属的放线菌,如普氏菌属(Prauserella)、链单孢菌属(Streptomonospora)、糖单孢菌属(Saccharomonospora)等影响较大。     

地果根茎化学成分研究

采用柱色谱法从地果Ficus tikoua根茎的90%甲醇粗提物中分离得到7个化合物。通过理化性质和波谱数据分析分别鉴定为hydroxyalpinum isoflavone(1),佛手柑内酯(2),β-豆甾醇(3),齐墩果酸(4),β-谷甾醇(5),香草酸(6)和2,6-二甲氧基-1,4-苯醌(7)。其中,化合物1、3、6和7为首次从该植物中分离得到。     

土壤放线菌Streptomyces sp．2215代谢物的分离鉴定及抗肿瘤活性研究

土壤来源的放线菌Streptomyces sp.2215 经发酵罐发酵,培养液经乙酸乙酯提取,硅胶柱层析、C18反相色谱、Sephadex LH-20、及TLC 和HPLC分离纯化得到四个化合物,并通过理化性质,IR,FAB-MS,1H,13C NMR,1H-1HCOSY,HSQC,HMBC等鉴定为单亚砜棘霉素(monosulfoxide quinomycine,1)、棘霉素(echinomycin,2)、喹喔啉-2-羧酸(3)、十六烷酸(4).其中化合物1、2经MTT法测定体外对K562细胞具有抑制活性,其IC50值分别为34.0、1.5 ng/mL.     

粗糙肉齿菌子实体化学成分研究

利用硅胶柱层析、RP-8层析及Sephadex LH-20分离的方法,从高等真菌粗糙肉齿菌(Sarcodon scabrosus)干燥子实体的甲醇提取物中分离并鉴定了8个化合物,经现代光谱技术鉴定分别为苯甲酸(1)、麦角甾-5,7,22-三烯-3β-醇(2)、2',3'-二乙酰基-3,4,5',6',4″-五羟基-对联三苯(3)和1-乙基-β-D-吡喃葡萄糖苷(4)、对羟基苯甲酸(5)、丁二酸(6)、腺嘌呤(7)、腺嘌呤核苷(8).以上化合物均为首次从粗糙肉齿菌中获得.     

肾茶化学成分研究

采用色谱法从肾茶中分离得到18个化合物,利用波谱学方法鉴定了它们的结构,分别命名为(7'S,8'S)-8-epiblechnic acid diacetate(1)、threo-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol(2)、9-hydroxy-4,7-megastigmadien-3-one(3),dehydrololiolide(4),3-hydroxy-4-oxo-7,8-dihydro-β-ionone(5)、3-hydroxy-7,8-dehydro-β-ionol(6)、3-hydroxy-5,6-epoxy-β-ionone(7)、loliolide(8)、threo-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxy-propan-1-ol(9)、erythro-2,3-bis-(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol(10)、松脂醇(11)、(+)-丁香脂素(12)、(+)-(7R,7'R,7'R,7''R,8S,8'S,8'S,8''S)-4',4''-dihydroxy-3,3',3',3'',5,5'-hexame-thoxy-7,9':7',9-diepoxy-4,8':4',8''-bisoxy-8,8'-dineolignan-7',7'',9',9''-tetraol(13)、fragransin B1(14)、fragransin B2(15)、fragransin B3(16)、sacidumol A(17)和5,6,7,3',4'-五甲氧基黄烷酮(18)。其中化合物1和2为新化合物,除了化合物12和18外,其余化合物均为首次从肾茶属中被分离得到。化合物1由于含有二个乙氧基,因此其可能产生于分离过程,我们采用ECD计算确定了其绝对构型。     

微波处理对嗜碱和嗜盐海洋放线菌分离效果的影响

【目的】研究微波处理对于分离嗜碱和嗜盐海洋放线菌的效果。【方法】用微波处理7份海泥样品,梯度稀释后涂布于3种分离培养基,分离具有嗜碱和嗜盐特性的海洋放线菌。【结果】微波处理后的7份样品中,4份样品中嗜碱海洋稀有放线菌和3份样品的嗜盐海洋稀有放线菌数量极显著提高;7份样品中的嗜碱、嗜盐海洋小单孢菌属、游动放线菌属、诺卡氏菌属等稀有放线菌数量均有显著增加,不同样品中新分离到链孢菌属、小双孢菌属、链孢囊菌属及其他未鉴定的海洋稀有放线菌,分离到属的数量提高了1-4个。【结论】微波处理不仅显著提高嗜碱和嗜盐海洋放线菌的分离数量,而且明显增加了海洋稀有放线菌的分离种类。     

云南油杉的化学成分研究

从云南油杉(Keteteeria evelyniana)枝条中首次分离得到19个化合物,通过MS与NMR等方法将它们分别鉴定为(-)-epinortrachelogenin(1),(-)-α-conidendrin(2),cedrusin(3),( )-dihydrodehydrodiconiferyl alcohol (4),oxomatairesinol(5),(-)-7'(S)-5-hydroxymatairesinol(6),vladinol D(7),(E)-3-hydroxy-5-methoxy-stilbene (8),resveratrol-3-O-β-D-glucopyranoside(9),pinocembrin(10),(2S,3R)-3,5,7,3',4'-pentahydroxyflavan(11),kaempferd(12),kaempferol-3-O-β-D-glucopyranoside(13),(E)-ferulic acid tetracosyl ester(14),ω-hydroxypropioquaiacone(15),vanillin(16),hemisceramide(17),β-sitosterol(18)和β-daucosterol(19).     

高效启动子在微生物生产4-羟基丁酸中的应用

4-羟基丁酸(4HB)是一种精神类药物,还可用于合成聚-4-羟基丁酸酯(P4HB)、聚(3-羟基丁酸酯-co-4-羟基丁酸酯)(P3HB4HB)等聚合物。在醇脱氢酶(DhaT)和醛脱氢酶(AldD)的共同作用下,1,4-丁二醇(BD)可转化为4-羟基丁酸。通过引入T7和PRe两种高效启动子,加强了dhaT和aldD基因的表达,促进合成4-羟基丁酸的反应进行。同时还研究了底物1,4-丁二醇的浓度对4HB生产的影响。结果表明:提供10 g/L的1,4-丁二醇,受PRe启动子调控的重组菌A.hydrophila 4AK4(pZQ01)可生产6.00 g/L的4-羟基丁酸,比对照组提高43.20%;而受T7启动子调控的重组菌A.hydrophila 4AK4(pZQ04)可生产4.87 g/L 4-羟基丁酸,比对照组提高16.23%。意味着T7和PRe这两种启动子确实发挥了提高基因表达水平的作用,加速了4-羟基丁酸的生物合成。     

Prenylated flavonoids from Moghania philippinensis

Five prenylated flavonoids, 8-(1,1-dimethylallyl)genistein (1), 5,7,3',4'-tetrahydroxy-2',5'-di(3-methylbut-2-enyl)isoflavone (2), 5,7,3'-trihydroxy-2'-(3-methylbut-2-enyl)-4',5'-(3,3-dimethylpyrano)isoflavone (3), (2R)-5,2',4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4a) and (2S)-5, 2', 4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4b), were isolated from the roots of Moghania philippinensis. The structures of these compounds were determined on the basis of spectroscopic and chemical means.     

Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa

Chemical investigation of the methanol extract of the viscous secretion on the surface of immature fruits of Paulownia tomentosa furnished nine geranylated flavanones, 6-geranyl-5,7-dihydroxy-3',4'-dimethoxyflavanone (1), 6-geranyl-3',5,7-trihydroxy-4'-methoxyflavanone (2), 6-geranyl-4',5,7-trihydroxy-3',5'-dimethoxyflavanone (3), 6-geranyl-4',5,5',7-tetrahydroxy-3'-methoxyflavanone (4), 6-geranyl-3,3',5,7-tetrahydroxy-4'-methoxyflavanone (5), 4',5,5',7-tetrahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]-3'-methoxyflavanone (6), 3,3',4',5,7-pentahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]flavanone (7), 3,3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone (8), and 3,4',5,5',7-pentahydroxy-3'-methoxy-6-(3-methyl-2-butenyl)flavanone (9), along with six known geranylated flavanones. Among these, compounds 4, 6-9 and the known 6-geranyl-3',4',5,7-tetraahydroxyflavanone (diplacone), 6-geranyl-3,3',4',5,7-pentahydroxyflavanone (diplacol) and 3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone showed potent radical scavenging effects towards DPPH radicals.     

Benzofurans and another constituent from seeds of Styrax officinalis

The benzofuran constituents of the seeds of Styrax officinalis were investigated. From the hexane extract, two new constituents named 5-(3"benzoyloxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl)-benzofuran (5) and 4-[3"-(1c-methylbutanoyloxy)propyl]-2-methoxy-(3',4'-methylenedioxyphenyl)-1a, 5b-dihydrobenzo-[3,4]-cyclobutaoxirene (6) were isolated together with four known compounds, 5-[3"-(1c-methylbutanoyloxy)propyl]-7-methoxy-2-(3',4'-dimethoxyphenyl)-benzofuran (4), 5-[3"-(1c-methylbutanoyloxy)propyl]-7- methoxy-2-(3',4'-methylenedioxyphenyl)-benzofuran (3), 5-(3"-acetoxypropyl)-7-methoxy2-(3',4'-methylenedioxphenyl)-benzofuran (2) and 5-(3"-hydroxypropyl)-7-methoxy-2-(3',4'-met hylenedioxyphenyl)-benzofuran (1). Although the compounds 1, 2, and 3 have been isolated previously from the seeds of Styrax obassia, this is the first record of their isolation from seeds of Styrax officinalis. The structures of the isolated compounds were established by 1D- and 2D-NMR (HMBC, HMQC, COSY), FABMS and high-resolution ESI FTMS.     

Methoxy-phenyl substituted ansa-titanocenes as potential anti-cancer drugs derived from fulvenes and titanium dichloride

Starting from 6-(4'-methoxyphenyl)fulvene (1a), 6-(2',4',6'-trimethoxyphenyl)fulvene (1b), or 6-(3',5'-dimethoxyphenyl)fulvene (1c), [1,2-di(cyclopentadienyl)-1,2-di(4'-methoxyphenyl)-ethanediyl] titanium dichloride (2a), [1,2-di(cyclopentadienyl)-1,2-bis(2',4',6'-trimethoxyphenyl)-ethanediyl] titanium dichloride (2b), and [1,2-di(cyclopentadienyl)-1,2-bis(3',5'-dimethoxyphenyl)-ethanediyl] titanium dichloride (2c) were synthesised. When titanocenes 2a-c were tested against pig kidney carcinoma cells (LLC-PK) inhibitory concentrations (IC50) of 2.8 x 10(-4), 3.6 x 10(-4) and 2.1 x 10(-4) M, respectively, were observed.     

Natural PTP1B inhibitors from Broussonetia papyrifera

Two new compounds, 8-(1,1-dimethylallyl)-5'-(3-methylbut-2-enyl)-3',4',5,7-tetrahydroxyflanvonol (1), 3'-(3-methylbut-2-enyl)-3',4',7-trihydroxyflavane (2) and three known compounds 3,3',4',5,7-pentahydroxyflavone (3), uralenol (4), broussochalcone A (5) were isolated from the roots of Broussonetia papyrifera, and their structures determined by spectroscopic methods. Compounds 1, 3, 4 and 5 significantly show the inhibitory activities against the PTP1B enzyme.     

The induction of hepatic microsomal UDP-glucuronosyltransferase by the methylsulfonyl metabolites of polychlorinated biphenyl congeners in rats

The effects of nine methylsulfonyl (MeSO(2)) metabolites of tetra-, penta- and hexachlorinated biphenyls (tetra-, penta- and hexaCBs; 20 micromol/kg once daily for 4 days) on the hepatic microsomal UDP-glucuronosyltransferase (UDP-GT) were investigated in male Sprague-Dawley rats. Each of the seven 3-MeSO(2)-PCBs, 3-MeSO(2)-2, 2',4',5-tetraCB (3-MeSO(2)-CB49), 3-MeSO(2)-2,3',4',5-tetraCB (3-MeSO(2)-CB70), 3-MeSO(2)-2,2',3',4',5-pentaCB (3-MeSO(2)-CB87), 3-MeSO(2)-2,2',4',5,5'-pentaCB (3-MeSO(2)-CB101), 3-MeSO(2)-2,2',3', 4',5,6-hexaCB (3-MeSO(2)-CB132), 3-MeSO(2)-2,2',3',4',5,5'-hexaCB (3-MeSO(2)-CB141), 3-MeSO(2)-2,2',4',5,5',6-hexaCB (3-MeSO(2)-CB149) and 4-MeSO(2)-2,2',4',5,5'-pentaCB (4-MeSO(2)-CB101) increased the activities of UDP-GT toward chloramphenicol, 4-nitrophenol and 4-methylumbelliferone. 4-MeSO(2)-2,2',4',5,5',6-hexaCB (4-MeSO(2)-CB149) increased the activity of UDP-GT toward chloramphenicol (UGT2B1) but not toward 4-nitrophenol (UGT1A6) and 4-methylumbelliferone (UGT1A6). The activity of UDP-GT toward thyroxine (T(4)) significantly increased after the administration of each of the seven 3-MeSO(2)-PCBs and 4-MeSO(2)-CB101. Significant correlation was found between the activity of UDP-GT toward T(4) and serum total T(4) concentration after the administration of each of the MeSO(2) derivatives except 4-MeSO(2)-CB149. In conclusion, seven 3-MeSO(2)-PCBs and 4-MeSO(2)-CB101 induce both UGT2B1 and UGT1A6, and 4-MeSO(2)-CB149 induces UGT 2B1. The results from the present study indicate that increase in the hepatic T(4) glucuronidation after the administration of the seven 3-MeSO(2)-PCBs and 4-MeSO(2)-CB101 possibly because of the induction of both UGT1A1 and UGT1A6 caused the reduction of serum T(4) levels.     

Interaction of muscle glycogen phosphorylase b with riboflavin, its tetraacetyl derivative and their analogs

The interaction of rabbit skeletal muscle glycogen phosphorylase b with riboflavin, 2',3',4',5'-tetraacetylriboflavin and their analogues, containing different substituents in the positions 6, 8 and 8 alpha, has been studied. Dissociation constant for the complex of the enzyme and riboflavin was determined to be 12.5 microM (pH 6.8; 20 degrees C) by sedimentation velocity method. Riboflavin and its analogues have been found to inhibit glycogen phosphorylase b. The inhibitor half-saturation concentration values increase in the following order: riboflavin (18 microM), 8-methoxy(nor)rifoblavin (23 microM), 8 alpha-bromo-2',3',4',5'-tetraacetylriboflavin (40 microM), 6-bromoriboflavin (40 microM), 8 alpha-hydroxyriboflavin (60 microM), 8-hydroxy(nor)riboflavin (90 microM), 8 alpha-(gamma-carboxypropylamino-2',3',4',5'-tetraacetylriboflav in (90 microM), 8 alpha-[p-(5-ethyl-1,3,4-thiodiazol-2-ylsulfamido)phenylamino ]- 2',3',4',5'-tetraacetylriboflavin (100 microM), 8 alpha-(L-methionyno)-2',3',4',5'-tetraacetylriboflavin (120 microM), 8 alpha-[p-(thiazol-2-ylsulfamido)phenylamino]- 2',3',4',5'-tetraacetylriboflavin (140 microM), 8 alpha-(p-sulfamidophenylamino)-2',3',4',5'-tetraacetylriboflavi n (180 microM), 8 alpha-(p-carboxyphenylamino)-2',3',4',5'-tetraacetylriboflavin+ ++ (210 microM), 2',3',4',5'-tetraacetylriboflavin (250 microM), 8 alpha-(L-homoserino)-2',3',4',5'-tetraacetylriboflavin (340 microM), 8 alpha-(L-glutamo)-2',3',4',5'-tetraacetylriboflavin (360 microM). The existence of glycogen phosphorylase b complexes with riboflavin and its analogues has been proved by methods of absolute and difference spectrophotometry.     

Iridoid glucosides and flavones from the aerial parts of Avicennia marina

Two new iridoid glucosides, namely, 2'-O-[(2E,4E)-5-phenylpenta-2,4-dienoyl]mussaenosidic acid (1; mussaenosidic acid = [1S-(1alpha,4aalpha,7alpha,7aalpha)]-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid) and 2'-O-(4-methoxycinnamoyl)mussaenosidic acid (2), were isolated from the aerial parts of the mangrove plant Avicennia marina. Beside that, one known iridoid glucoside, 2'-O-coumaroylmussaenosidic acid (3) and four known flavones (flavone = 2-phenyl-4H-1-benzopyran-4-one) including 4',5-dihydroxy-3',7-dimethoxyflavone (4), 4',5-dihydroxy-3',5',7-trimethoxyflavone (5), 4',5,7-trihydroxyflavone (6), and 3',4',5-trihydroxy-7-methoxyflavone (7) were also isolated and identified. The structures of these compounds were elucidated by NMR spectroscopy and by low- and high-resolution mass spectrometry. The chemotaxonomic significance of these findings was discussed. In addition, each isolated compound was evaluated for the ability of alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity.     

Metabolism of Lignin Model Compounds of the Arylglycerol-beta-Aryl Ether Type by Pseudomonas acidovorans D(3)

A natural bacterial isolate that we have classified as Pseudomonas acidovorans grows on the lignin model compounds 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (compound 1) and 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (compound 1'), as well as on the corresponding 1-oxo compounds (2 and 2') as sole sources of carbon and energy. Metabolic intermediates present in cultures growing on compound 1 included compound 2, 2-methoxyphenol (guaiacol [compound 3]), beta-hydroxypro-pioveratrone (compound 4), acetoveratrone (compound 5), and veratric acid (compound 6). Also identified were compounds 1', 2', beta-hydroxypropiovanillone (compound 4'), and acetovanillone (compound 5'), indicating that 4-O demethylation also occurs. The phenolic intermediates were the same as those found in cultures growing on compound 1'. Compounds 2 and 2' were in part also reduced to compounds 1 and 1', respectively. Compound 3 was shown to be derived from the 2-methoxyphenoxy moiety. A suggested degradation scheme is as follows: compound 1-->2-->(3 + 4)-->5-->6 (and similarly for 1'). In this scheme, the key reaction is cleavage of the ether linkage between C-2 (C(beta)) of the phenylpropane moiety and the 2-methoxyphenoxy moiety in compounds 2 and 2' (i.e., beta-aryl ether cleavage). On the basis of compounds identified, viz., 3 and 4 (4'), cleavage appears formally to be reductive. Because this is unlikely, the initial cleavage products probably were not detected. The implications of these results for the enzyme(s) responsible are discussed.     

Isolation of novel phenolic compounds with multidrug resistance (MDR) reversal properties from Onychium japonicum

We isolated seven novel compounds, namely, 3',4',6-trihydroxy-2,4-dimethoxy-3-(3″,4″-dihydroxybenzyl)chalcone (1), 3',6-dihydroxy-2,4,4'-trimethoxy-3-(3″,4″-dihydroxybenzyl)chalcone (2), α,β-dihydro-3',6-dihydroxy-2,4,6'-trimethoxy-3-(3″,4″-dihydroxybenzyl)chalcone (3), 3',4,4'-trihydroxy-2,6-dimethoxychalcone (4), 4',5,7-trihydroxy-6-(3″,4″-dihydroxybenzyl)flavone (5), 3-(3',4'-dihydroxybenzyl)-6,7-dihydroxycoumarin (6), 3-(3',4'-dihydroxyphenyl)-3,4-dihydroisocoumarin (7), as well as a known compound, 3',4',7-trihydroxy-5-methoxyflavanone (8) from the whole grass of Onychium japonicum, and elucidated their structures by spectroscopic methods. Compounds 1-3 exhibited significant multidrug resistance (MDR) reversal effects on MCF-7/ADR and Bel-7402/5-Fu cell lines.