Diglucosylation of salicyl alcohol by cell suspension cultures of Solanum laciniatum

A new biotransformation product, salicyl alcohol-7-O-β-D-(β-1,6-D-glucopyranosyl)-gluco-pyranoside was isolated from cell suspension cultures of Solanum laciniatum, following administration of salicyl alcohol, and its structure was elucidated using a combination of one-and two-dimensional ¹H and ¹³C-NMR data, and positive and negative ion ESMS data.     

N-acetylation and N-formylation of m-aminobenzoic acid by cell suspension cultures of Solanum laciniatum

Two new biotransformation products, N-acetyl-m-aminobenzoic acid and N-formyl-m-aminobenzoic acid were isolated from cell suspension cultures of Solanum laciniatum following administration of m-aminobenzoic acid, and their structures were elucidated using one- and two-dimensional ¹H- and ¹³C-NMR data.     

Diglucosylation of Salicyl Alcohol by Cell Suspension Cultures of Solanum Laciniatum

Abstract

A new biotransformation product, salicyl alcohol-7-O-β-D-(β-1,6-D-glucopyranosyl)-gluco-pyranoside was isolated from cell suspension cultures of Solanum laciniatum, following administration of salicyl alcohol, and its structure was elucidated using a combination of one-and two-dimensional ¹H and ¹³C-NMR data, and positive and negative ion ESMS data.     

N-Acetylation and N-Formylation of m-Aminobenzoic acid by Cell Suspension Cultures of Solanum Laciniatum

Abstract

Two new biotransformation products, N-acetyl-m-aminobenzoic acid and N-formyl-m-aminobenzoic acid were isolated from cell suspension cultures of Solanum laciniatum following administration of m-aminobenzoic acid, and their structures were elucidated using one- and two-dimensional ¹H- and ¹³C-NMR data.     

Biotransformation of 4(20),11-taxadienes by cell suspension cultures of Platycodon grandiflorum

Platycodon grandiflorum cell suspension cultures were employed to biotransform the taxane diterpenoids 2 f ,5 f , 10 g ,14 g -tetraacetoxy-4(20),11-taxadiene ( 1 ) and 9 f -hydroxy-2 f , 5 f ,10 g ,14 g -tetraacetoxy-4(20),11-taxadiene ( 2 ). One product, 10 g -hydroxy-2 f ,5 f ,14 g -triacetoxy-4(20),11-taxadiene ( 3 ) was obtained from 1 and two products, 9 f ,10 g -dihydroxy-2 f ,5 f ,14 g -triacetoxy-4(20),11-taxadiene ( 4 ) and 10 g -hydroxy-2 f ,5 f ,9 f ,14 g -tetraacetoxy-4(20),11-taxadiene ( 5 ) were obtained from 2 incubated with Platycodon cultured cells respectively, among which 5 is characterized as a new taxoid compound. The effects of the addition stage for 1 and 2 on the biotransformation were investigated and the results revealed that: (1) the optimal addition stage for 1 was in the early logarithmic phase (6th day) of the cell growth period, in which 78% of 1 was converted and the yield for 3 reached 75%; (2) the optimal addition stage for 2 was on the mid-logarithmic phase (12th day) of the cell growth period, in which 25.3% of 2 was converted and the yields for 4 and 5 reached 18.9 and 14.5%, respectively.     

C-27 and C-3 Glucosylation of Diosgenin by Cell Suspension Cultures of Costus Speciosus

Abstract

3-O-[β-D-glucopyranosyl-(1″ → 2′)-β-D-glucopyranosyl], 27-O-β-D-glucopyranosyl-(25R)-spirost-5-ene-3β,27-diol was isolated from cell suspension cultures of Costus speciosus, following incubation with diosgenin, and its structure was elucidated using a combination of one- and two-dimensional ¹H and ¹³C NMR spectral data, and positive and negative ion ESMS spectral data.     

High yield formation of o -aminobenzoic acid-7- O -β- d -(β-1,6- O - d -glucopyranosyl)-glucopyranosyl ester in cell suspension cultures of Solanum mammosum

Cell suspension cultures of Solanum mammosum cultivated in modified Murashige & Skoog media could synthesize o -aminobenzoic acid-7- O - β- d -( β-1,6- O - d -glucopyranosyl)-glucopyranosyl ester from o -amino benzoic acid with a yield of about 20% dry weight in 7 days. The maximum production of o -aminobenzoic acid-7- O - β- d -( β-1,6- O - d -glucopyranosyl)-glucopyranosyl ester was 31.8% on dry weight basis.     

C-27 and C-3 Glucosylation of Diosgenin by Cell Suspension Cultures of Costus Speciosus

3-O-[β-D-glucopyranosyl-(1' → 2')-β-D-glucopyranosyl], 27-O-β-D-glucopyranosyl-(25R)-spirost-5-ene-3β,27-diol was isolated from cell suspension cultures of Costus speciosus, following incubation with diosgenin, and its structure was elucidated using a combination of one- and two-dimensional ¹H and ¹³C NMR spectral data, and positive and negative ion ESMS spectral data.     

商陆培养细胞对6β-santonin的生物转化

目的利用商陆培养细胞对6β-santonin (1)进行生物转化，以获得多种利于进一步进行结构改造的衍生物。方法将底物1与商陆培养细胞共孵化，采用色谱分离技术得到产物，通过理化性质和光谱数据对产物进行结构鉴定。结果与商陆培养细胞共孵化7 d后，底物1转化为5个产物(2～6)，其中3为新化合物。结论利用商陆培养细胞可对6β-santonin进行选择性还原及羟基化反应，可为其进一步化学结构改造提供有价值的中间体。     

Growth and production of camptothecin by cell suspension cultures of Nothapodytes foetida

Callus cultures were initiated from stem parts of Nothapodytes foetida on Murashige and Skoog's medium supplemented with different growth regulators. Suspension cultures were established and the cell biomass was higher in the presence of NAA in comparison with 2,4-D. Culture medium supplemented with NAA (10.74 microM) and BA (2.22 microM) attained 31.3 g/l DW during 20 days of cultivation in shake flasks. In the presence of NAA, maximum concentrations of camptothecin (0.035 mg/ml) and 9-methoxycamptothecin (0.026 mg/ml) were found in the medium. Alkaloid production was reduced in presence of 2,4-D in the culture medium. Cells contained trace amount of alkaloids. Alkaloids were detected and identified by means of TLC and HPLC.     

Biotransformation of triptolide and triptonide by cell suspension cultures of Catharanthus roseus

Catharanthus roseus cell suspension cultures were used to bioconvert both triptolide (1) and triptonide (2). The same reaction path was followed in both biotransformations. Two biotransformed products were obtained and their structures identified as triptriolide (3) and 12beta,13alpha-dihydroxytriptonide (4), respectively, from 1 and 2. Product 4 is a new compound.     

刺囊毛霉对天麻素的生物转化研究

利用刺囊毛霉(Mucor spinosus)3．3450的培养液对天麻素进行生物转化,得到其酶水解产物甙元对羟基苯甲醇,转化率接近100％。通过无细胞抽提液对底物转化的研究,证明催化该反应的酶为组成酶、胞外酶。     

Perceptions of alcohol by student drinkers at university

To provide a framework in which to design alcohol interventions for university students that would take account of their subjective experiences and perspective, student drinkers were surveyed about selected alcohol-related behaviours and attitudes and asked to nominate what they considered to be the primary negative and positive aspects of alcohol use. The results revealed a concentration on short-term negative outcomes and an emphasis on sociability as the major benefit of consumption. Drinking specifically for intoxication was also a positive outcome for males in particular. The implications of these results for the preparation of meaningful interventions are discussed.     

High yield formation of o-aminobenzoic acid-7-O-beta-D-(beta-1,6-O-d-glucopyranosyl)-glucopyranosyl ester in cell suspension cultures of Solanum mammosum

Cell suspension cultures of Solanum mammosum cultivated in modified Murashige & Skoog media could synthesize o-aminobenzoic acid-7-O-beta-D-(beta-1,6-O-D-glucopyranosyl)-glucopyranosyl ester from o-amino benzoic acid with a yield of about 20% dry weight in 7 days. The maximum production of o-aminobenzoic acid-7-O-beta-D-(beta-1,6-O-D-glucopyranosyl)-glucopyranosyl ester was 31.8% on dry weight basis.     

Regio-selective deglycosylation of icariin by cell suspension cultures of Glycyrrhiza uralensis and Morus alba

Biotransformations of icariin (1) by cell suspension cultures of Glycyrrhiza uralensis and Morus alba yielded two new metabolites, icaruralins A and B (2 and 3), and one known metabolite, baohuoside I (4). Their structures were determined on the basis of extensive spectroscopic analysis. This is the first report that the cell suspension cultures of G. uralensis and M. alba possess deglycosylation functionality.     

Production of paclitaxel and the related taxanes by cell suspension cultures of Taxus species

Medicinal plants are the most promising source for the development of drugs, and many types of active ingredients from the plant resources have been studied in order to clarify the relationship between the chemical structure and the activity. However, it is not easy to develop drugs from those active compounds, and in many cases, the supply of active compounds can have some problems: 1) limited quantity of active compounds in plant; 2) low plant growth rate; 3) the limited localization of active ingredients in the specific organs; and 4) from the perspective of the conservation of natural resources. Therefore, the stable supply of the compounds commercially is very difficult and contains risk hedge. Plant cell culture is an attractive technology to solve these problems by securing the stable supply of the active compounds without damage to the natural plant resources. Recently, an efficient production process of anticancer drug paclitaxel by Taxus cell suspension cultures was constructed. The established Taxus cell lines produced paclitaxel and related taxanes by specific external stimuli, such as methyl jasmonate. The time-course analysis revealed that there are two regulatory steps existing in the paclitaxel biosynthesis: the taxane-ring formation step that is up-regulated by MeJA, and the acylation step at the C-13 position. By applying the data from the two-stage culture and the high-density culture, a large-scale culture process was developed with a stable paclitaxel production in the range of 140-295 mg L(-1), reaching 295 mg L(-1) at maximum.     

HPLC法测定中药白英中16-妊娠双烯醇酮的含量

目的用HPLC法测定不同来源白英中16-妊娠双烯醇酮含量。方法选用Apollo C18(4.6 mm×250 mm,5μm)色谱柱,流动相为乙腈-水(体积比为60∶40),检测波长为236 nm,柱温为室温。结果16-妊娠双烯醇酮在5.06~45.54 mg.L-1内呈良好线性关系,平均回收率为98.8(RSD=1.7%,n=9);不同来源的白英药材中16-妊娠双烯醇酮的含量有较大差异,购于上海徐汇、上海蔡同德和上海虹桥中药饮片有限公司的白英中的含量质量分数分别为0.16%、0.16%、0.33%。结论该方法可为白英药材质量控制提供定量依据。     

Enhanced production of silymarin by Ag+ elicitor in cell suspension cultures of Silybum marianum

Cell suspension cultures of Silybum marianum L. Gaertn (Compositae) produce silymarin, a mixture of flavonolignans. In an attempt to increase cell growth and silymarin production, we exposed cell cultures to various levels of Ag⁺ (0.2, 0.4, 0.8, 1, and 2?mM) for different exposure times (12, 24, 48, 72, 144, and 216?h). A dramatic increase in cell growth was observed after 12?h in media supplemented with 0.2, 0.4, 0.8, and 1?mM Ag⁺, and the value in medium treated by 1?mM Ag⁺ after 72?h was 7.21?g, which was about two-fold that of the control (3.32?g). The highest silymarin production reached about 56 μg g^?1 DW, 24?h after treatment with Ag⁺ (0.8?mM), which was 30-fold that of the control. Silybin, isosilybin, silychristin, silydianin, and taxifolin were abundant flavonolignans. Ag⁺ in low concentrations is a positive elicitor for cell growth and silymarin production in cell suspension cultures of Silybum marianum.     

Biotransformation of 4(20),11-taxadienes by cell suspension cultures of Platycodon grandiflorum

Platycodon grandiflorum cell suspension cultures were employed to biotransform the taxane diterpenoids 2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (1) and 9alpha-hydroxy-2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (2). One product, 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (3) was obtained from 1 and two products, 9alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (4) and 10beta-hydroxy-2alpha,5alpha,9alpha,14beta-tetraacetoxy-4(20),11-taxadiene (5) were obtained from 2 incubated with Platycodon cultured cells respectively, among which 5 is characterized as a new taxoid compound. The effects of the addition stage for 1 and 2 on the biotransformation were investigated and the results revealed that: (1) the optimal addition stage for 1 was in the early logarithmic phase (6th day) of the cell growth period, in which 78% of 1 was converted and the yield for 3 reached 75%; (2) the optimal addition stage for 2 was on the mid-logarithmic phase (12th day) of the cell growth period, in which 25.3% of 2 was converted and the yields for 4 and 5 reached 18.9 and 14.5%, respectively.     

HPLC-ELSD法测定白英中碱苷A的含量

目的研究白英化学成分,建立HPLC-ELSD法测定白英中碱苷A[3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside-(25ξ)-solanidan-3β,23β-diol]的含量的方法。方法采用硅胶、ODS柱色谱进行分离纯化。运用NMR数据及理化性质鉴定单体化合物的结构。色谱柱为Elite-ODS C18(200 mm×4.6 mm,5μm),流动相为乙腈-体积分数为0.02%三乙胺水溶液(体积比为56∶44),检测器漂移管温度为95℃,氮气流速2.3 L.min-1。结果从白英提取物中分离得到碱苷A。碱苷A在0.4～4.0μg线性关系良好(r=0.999 6),平均回收率为99.6%(RSD=2.0%)。结论HPLC-ELSD法可用于白英中碱苷A的测定。