Immunosuppressive terpenoids from Tripterygium wilfordii

Two new terpenes,triptobenzene P（1）and wilforone（2）were isolated from Tripterygium wilfordii,as well as 10 known terpenes.Their structures were elucidated by spectroscopic methods.Compounds 2-4,8,10,and 11 showed significant immunosuppressive activities.     

Simultaneous determination of triptolide, tripdiolide and tripterine in human urine by high-performance liquid chromatography coupled with ion trap atmospheric-pressure chemical ionization mass spectrometry

An accurate and selective method for the simultaneous determination of triptolide, tripdiolide and tripterine in human urine using hydrocortisone as an internal standard (IS) by high-performance liquid chromatography coupled with atmospheric-pressure chemical ionization mass spectrometry in negative ion mode has been developed. After triptolide, tripdiolide and tripterine in human urine were extracted with ethyl acetate and cleaned by solid-phase extraction with C(18) cartridges, a satisfactory separation was achieved on an XDB C(18) short column (30 x 2.1 mm i.d., 3 microm) using the mobile phase of acetic acid-ammonium acetate (5 mmol/L, pH = 4.5)-acetonitrile-methanol in gradient elution. Detection was operated by APCI in selected ion monitoring mode. The target ions m/z 359, m/z 375, m/z 449 and m/z 419 were selected for the quantification of triptolide, tripdiolide, tripterine and IS, respectively. The linear range was 1.0-100.0 ng mL(-1), and the limits of quantification in human urine were found to be 0.1-0.5 ng mL(-1) for the three compounds. The precisions (CV%) and accuracies were 6.6-12.9 and 85.1-97.0%, respectively. The developed method could be applied to the determination of triptolide, tripdiolide and tripterine in human urine for diagnosis of the intoxication and for forensic purposes.     

Immunosuppressive Sesquiterpene Pyridine Alkaloids from Tripterygium wilfordii Hook. f.

Tripterygium wilfordii Hook. f. is a well-known traditional Chinese medicine used to treat autoimmune diseases. Sesquiterpene pyridine alkaloids (SPAs) are a major class of components found in this herb that have piqued the interest of researchers due to their complex and diverse structures as well as significant biological activities. In this study, ten new SPAs, wilfordatine A–J (1–10), were isolated from the roots of T. wilfordii, along with ten known analogues (11–20). Their structures were primarily elucidated by extensive 1D and 2D NMR spectroscopic analysis. To search for more immunosuppressive ingredients related to the clinical efficacy of T. wilfordii, the total alkaloids (TA) and compounds 4, 5, and 9–16 were tested for their inhibitory effects on nuclear factor-kappa B (NF-κB) pathway in Lipopolysaccharide (LPS) induced HEK293/NF-κB-Luc cells. Among them, TA, compounds 5, 11, and 16 showed potent immunosuppressive activity, with IC₅₀ values of 7.25 μg/mL, 8.75 μM, 0.74 μM, and 15.66 μM, respectively, and no influence on the cell viability at a concentration of 100 μg/mL (TA) or 100 μM (5, 11, and 16). Accordingly, TA, 5, 11, and 16, especially 11, were identified as promising candidates for further investigation into their potential use as immunosuppressive agents.     

Fingerprint chromatogram analysis of extracts from the leaves of Tripterygium wilfordii Hook. F. by high performance liquid chromatography

A simple and reliable high performance liquid chromatographic (HPLC) method has been developed and validated for the study of fingerprint chromatograms of extracts from the leaves of Tripterygium wilfordii Hook. F. (TWHF) and for controlling the quality of the herb. HPLC separation of the extracts was performed on a Lichrospher RP-18 column and detected by ultraviolet absorbance at 210 nm. The column temperature was maintained at 35 degrees C. A mobile phase composed of acetonitrile:H2O in the ratio of 39:61 (v/v) was found to be most suitable for this separation at a flow rate of 0.8 mL/min with isocratic elution. Under the chromatographic conditions described, the peak profile of the 10 components collected within 35 min made up the fingerprint of the extracts from leaves of TWHF with universal features. The fingerprint chromatograms had a good stability, precision, and reproducibility. The similarity of the extracts from leaves of TWHF collected in summer and winter was studied with triptolide as a reference peak. The method is suitable for differentiation of extracts from the leaves of TWHF, and can be used as a quality control method for this herb.     

First total synthesis of tripdiolide

The first total synthesis of tripdiolide 1 from the readily available abietic acid 3 in 22 steps is described and this synthesis furnishes a 5.8% overall yield of 1 with an average yield of 87%.     

Application of a sensitive and specific LC‐MS/MS method for determination of wilforine from Tripterygium wilfordii Hook. F. in rat plasma for a bioavailability study

A highly selective and specific LC‐MS/MS method was developed and validated for the determination of wilforine in rat plasma. The analyte was separated from plasma matrix by using methyl tertiary butyl ether liquid–liquid extraction with bulleyacinitine A as internal standard (IS). The analysis was carried out on a Sepax GP‐Phenyl column using a mixture of methanol and 10 mmol/L ammonium formate buffer solution containing 0.1% formic acid (75:25, v/v) as the mobile phase pumped at a flow rate of 1.0 mL/min. The detection was operated using a triple‐quadrupole mass spectrometer in multiple selected reaction monitoring with the parent‐to‐product quantifier transitions [M + H]⁺ m/z 867.6 →206.0 for wilforine and 664.1 →584.1 for IS. The main advantage of this method was the high sensitivity (a lower limit of quantification of 0.02 ng/mL) and the small amount of sample (0.1 mL plasma per sample). The method was fully validated to be accurate and precise with a linear range of 0.02–100 ng/mL, and successfully applied to a bioavailability study of wilforine in rats after intravenous and oral administration. The oral absolute bioavailability of wilforine in rats was estimated to be 84%. Copyright © 2014 John Wiley & Sons, Ltd.     

电感耦合等离子体-质谱法同时测定雷公藤中常量及微量元素

采用微波消解法对雷公藤进行消解制样,用电感耦合等离子体-质谱法(ICP-MS)同时测定了其常量及微量元素,并研究了常量及微量元素的含量特征.方法的相对标准偏差(RSD)＜9％,回收率在90.0％-103.0％之间.结果表明,中药雷公藤中含有比较丰富的K、Ca、Fe、Mg、Mn、Zn等元素,对人体有害的微量元素Pb、Cd...     

雷酚萜甲醚和雷酚萜的2DNMR研究

从雷公藤分离出二种新的萜化合物,利用¹H-¹H COSY,¹H-¹³H COSY和COLOC等2DNMR技术,分析了雷酚萜甲醚和雷酚萜的¹H和¹³C NMR谱,明确地指认出这三种化合物的全部¹H和¹³C共振峰.     

A new furanosteroid from Talaromyces sp. lgt-4, a fungal endophyte isolated from Tripterygium wilfordii

Wortmannolol (1), a new furanosteroid, along with five known compounds, wortmannolone (2), ergosterol (3), p-hydroxyphenyl ethanol (4), trans-6-dodecene (5), (2Z, 4E) -5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo [3.2.1] octan-8-yl) -3-methylpenta-2,4-dienoic acid (6) were isolated from a fungal endophyte Talaromyces sp. lgt-4. Their structures were elucidated by IR, MS, 1D and 2D NMR spectra. Compound 1 show weak monoamine oxidase inhibitory activity.