超高效液相色谱-串联质谱法鉴别十字花科植物中硫代葡萄糖苷

建立超高效液相色谱–串联质谱法鉴别十字花科植物中硫代葡萄糖苷的分析方法。采用70%甲醇水溶液提取白芥种子中的硫代葡萄糖苷,通过反相C18柱分离,电喷雾–离子阱–飞行时间质谱测定。利用硫代葡萄糖苷二级质谱裂解产生的m/z 195,241,259,275,291特征离子和伴随产生的80,162,163,196,242 Da中性分子丢失规律,共鉴别出5种硫代葡萄糖苷。     

Lepidium graminifolium L.: Glucosinolate Profile and Antiproliferative Potential of Volatile Isolates

Glucosinolates (GSLs) from Lepidium graminifolium L. were analyzed qualitatively and quantitatively by their desulfo-counterparts using UHPLC-DAD-MS/MS technique and by their volatile breakdown products-isothiocyanates (ITCs) using GC-MS analysis. Thirteen GSLs were identified with arylaliphatic as the major ones in the following order: 3-hydroxybenzyl GSL (glucolepigramin, 7), benzyl GSL (glucotropaeolin, 9), 3,4,5-trimethoxybenzyl GSL (11), 3-methoxybenzyl GSL (glucolimnanthin, 12), 4-hydroxy-3,5-dimethoxybenzyl GSL (3,5-dimethoxysinalbin, 8), 4-hydroxybenzyl GSL (glucosinalbin, 6), 3,4-dimethoxybenzyl GSL (10) and 2-phenylethyl GSL (gluconasturtiin, 13). GSL breakdown products obtained by hydrodistillation (HD) and CH₂Cl₂ extraction after hydrolysis by myrosinase for 24 h (EXT) as well as benzyl ITC were tested for their cytotoxic activity using MTT assay. Generally, EXT showed noticeable antiproliferative activity against human bladder cancer cell line UM-UC-3 and human glioblastoma cell line LN229, and can be considered as moderately active, while IC₅₀ of benzyl ITC was 12.3 μg/mL, which can be considered as highly active.     

Glucosinolates in wild and cultivated Brassica montana Pourret (Brassicaceae) from southern France

Abstract

The glucosinolate (GL) profiles of wild and cultivated Brassica montana Pourret (seed, stem, leaf, root) from southern France were established using LC-MS analysis. In this investigation we have confirmed the presence of 9 known GLs: but-3-enyl- (1), prop-2-enyl- (2), pent-4-enyl- (3), (2R)-2-hydroxybut-3-enyl- (4), 4-hydroxyindol-3-ylmethyl- (5), 4-(methylsulfinyl)butyl- (6), 4-(methylsulfanyl)butyl- (7), 1-methoxyindol-3-ylmethyl- (8), and indol-3-ylmethyl (9) GL. In addition, we tentatively identified for the first time the presence in the plant of 1-methylpropyl GL (10) in all plant parts. In addition, we have pointed out differences in GL profiles between plant organs and between wild and cultivated B. montana.     

油菜籽中主要硫甙的分离提纯

用柱色谱方法从甘蓝型油菜籽中分离提纯了1-硫［(1Z)-3-羟基-1-［(磺酸基)亚氨基］-4-戊烯基］-1-硫代-β-D-葡萄糖钾盐(progoitrin)。用甲醇溶液提取菜籽中的硫甙,得到粗提物;粗提物经酸性氧化铝色谱柱与反相C18硅胶柱进一步分离提纯,得到纯品。对纯品进行紫外光谱、红外光谱、核磁共振氢谱、质谱和元素分析,测得的数据与文献值相符。用高效液相色谱测得硫甙提取物的纯度为99%。该方法操作简便,得到的硫甙样品纯度高,是一种有价值的硫甙提取方法,具有良好的应用前景。     

红外光声光谱技术结合稳健回归用于油菜籽定量分析

将稳健偏最小二乘回归和偏稳健M回归应用于油菜籽红外光声光谱分析中含氮量、含油量与硫苷含量的测定。结果表明,利用红外光声光谱技术可以实现油菜籽品质的快速测定。同时,稳健回归模型较经典偏最小二乘回归模型可以更好地规避异常值影响,进而优化定量分析结果;其中,稳健偏M回归稍优于稳健偏最小二乘回归。     

Contactless conductivity detection for screening myrosinase substrates by capillary electrophoresis

Myrosinase is a unique enzyme that catalyzes the hydrolysis of glucosinolates (GLS) to isothiocyanate (ITC), glucose and sulfate. Isothiocyanates display a diversified very interesting biological activity. In this study, capillary electrophoresis (CE) was used for the first time for evaluating myrosinase kinetics (maximum velocity V_max and Michaelis–Menten constant K_m) and to assess the affinity of a variety of substrates toward this enzyme.     

油菜籽中4-戊烯基硫代葡萄糖苷的提取、分离及结构鉴定

报道了一个分离鉴定油菜籽中硫苷组分的有效方法。利用溶剂萃取法去除大部分杂质。经弱阴离子交换剂吸附法制得硫代葡萄糖苷粗品。然后利用液相制备色谱进一步分离纯化。制得一系列硫代葡萄糖苷纯品。对其中分离较好的一个组分经液-质联用、核磁共振、红外及紫外等方法确定其结构为4-戊烯基硫苷。此方法可以作为进一步提取特种硫苷的有效手段。     

Glucosinolates of the only three Brassicales indigenous to French Polynesia

Abstract

The glucosinolate (GL) profiles in leaf and stem of Rorippa sarmentosa (G.Forst. ex DC.) J.F.Macbr., Lepidium bidentatum Montin var. bidentatum, and Capparis spinosa subsp. cordifolia (Lam.) Fici indigenous to French Polynesia were investigated for the first time using LC-MS analysis. In the present study, we have established the presence of 8 known GLs in R. sarmentosa: 4-(methylsulfinyl)butyl- (1), but-3-enyl- (2), 5-(methylsulfinyl)pentyl- (3), 6-(methylsulfinyl)hexyl- (4), indol-3-ylmethyl- (6), 2-phenylethyl- (7), 8-(methylsulfinyl)octyl- (8), and 9-(methylsulfinyl)nonyl- (9) GLs. We have also tentatively identified for the first time the presence in R. sarmentosa of 7-(methylsulfinyl)heptyl GL (5). In addition, we have identified two known GLs in L. bidentatum var. bidentatum: benzyl- (10) and 4-methoxybenzyl- (11) GLs. Finally, the known methyl GL (12) was shown to be largely predominant in C. spinosa subsp. cordifolia.     

Chemical Analysis of Eruca sativa Ethanolic Extract and Its Effects on Hyperuricaemia

In vivo assays and chemical analyses were performed on the ethanolic extract from leaves of Eruca sativa. UHPLC-ESI-QTOF analysis confirmed the presence of glucosinolates and flavonol glucosides. The major flavonoid of the ethanolic extract, kaempferol-3,4′-di-O-β-glucoside, was isolated, a HPLC-DAD method developed and validated to quantify its content in the extract. In vivo experiments were carried out on Wistar rats with hyperuricaemia induced by potassium oxonate and uric acid. A hypouricaemic effect was observed in hyperuricaemic Wistar rats treated with ethanolic extract at dose of 125 mg/kg and kaempferol-3,4′-di-O-β-glucoside at dose of 10 mg/kg. The main anti-hyperuricaemic mechanism observed in the extract was uricosuric. Kaempferol-3,4′-di-O-β-glucoside was identified as an important component responsible for the total activity of the ethanolic extract and was considered as a good chemical and biological marker of the ethanolic extract of E. sativa. The obtained results indicated the potential of E. sativa in the treatment of hyperuricaemia and its comorbidities.     

油菜籽中主要硫甙的提纯与抗肿瘤活性

油菜籽中主要硫甙的提纯与抗肿瘤活性;硫代葡萄糖苷;分离提纯;S180;抗肿瘤作用