Wilfordine

Simultaneous determination of seven effective components of Tripterygium glycosides in human biological matrices by ultra performance liquid chromatography-triple quadrupole mass spectrometry.[Pubmed:30877981]

J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Apr 15;1113:1-13.

This paper developed a novel, sensitive, and selective ultra-performance liquid chromatography-triple quad mass spectrometry method to simultaneously determine seven effective constituents (triptolide, triptophenolide, celastrol, wilforgine, wilforine, Wilfordine and wilfortrine) of Tripterygium glycosides (GTW) in human serum and urine. The chromatographic separation was performed on the C18 column using an ammonium acetate buffer solution-acetonitrile (both containing 0.1% formic acid) in a gradient program with a flow rate of 0.3mL/min. Monitoring reaction mode was applied to target compounds quantitative analysis in the positive electrospray ionization (ESI) mode. The analysis process took 11min in total. This method was fully validated with a linear range of 1-200ng/mL for triptolide, 0.4-80ng/mL for celastrol, 0.1-20ng/mL for triptophenolide, wilforgine, wilforine, Wilfordine, and wilfortrine. The intra-day and inter-day accuracy and precision of the target compounds all met the 15% criterion in both serum and urine. Extraction recovery, matrix effect, and dilution integrity were also validated. The short-term and long-term stability results indicated that all the constituents were stable in human serum and urine under the investigated storage conditions. 10 patients' specimens were collected and analyzed. Most of the compounds exhibited the tendency of higher concentration in urine than that in serum. The concentration that was detected in the serum and in the urine of alkaloids showed a positive-correlation property. This is the first time that triptophenolide was quantified in human bio-matrices. The method is feasible for multi-components therapeutic monitoring or pharmacokinetics study in clinical pharmaceutical research of Tripterygium glycosides.

Separation and simultaneous determination of seven bioactive components in Tripterygium wilfordii Hook. F. and Tripterygium preparations by micellar electrokinetic capillary chromatography.[Pubmed:30511389]

Electrophoresis. 2019 Feb;40(4):547-554.

A simple, comprehensive, and highly selective MEKC method has been developed for simultaneous analysis of seven bioactive components (triptolide, wilfortrine, Wilfordine, wilforgine, wilforine, triptophenolide, and triptonide) in the root extracts of Tripterygium wilfordii Hook. F. (TWHF) and Tripterygium preparations (TPs). Optimal BGE consisted of 10 mM sodium tetraborate, 30 mM SDS, and 30% v/v methanol. The separation voltage was 20 kV and the temperature was 25 degrees C. A DAD was used and the detection wavelength was at 218 nm. Under the optimum conditions, the baseline separation of seven components was achieved in less than 26 min. Excellent precision, good stability, and accuracy were obtained. For all analytes, linear calibrations were established within 10-100 mug/mL. The LOD and LOQ were within 1.2-4.2 mug/mL and 4.0-14 mug/mL, respectively. The developed method was suitable for the determination of key components in TWHF and TPs.

Three new abietane-type diterpene glycosides from the roots of Tripterygium wilfordii.[Pubmed:28602481]

Fitoterapia. 2017 Jul;120:126-130.

Three new abietane-type diterpene glycosides named as tripterycoside A (1), tripterycoside B (2), tripterycoside C (3), along with two known ones, 11-O-beta-d-glucopyranosyl-neotritophenolide (4), wilfordoside A (5), and nine other known compounds, 5-hydroxymethylmellein (6),1,2-bis-(3-methoxy-4-hydroxyphenyl)-1,3-propanediol (7), leptolepisol C (8), icariol A2 (9), tripfordine A (10), 16alpha-hydroxy-ent-kauran-19-oic acid (11),wilforine (12), Wilfordine (13), 3-acetyloleanolic acid (14),were isolated from the roots of Tripterygium wilfordii. Their structures have been elucidated on the basis of NMR and MS data. To the best of our knowledge, abietane-type diterpene glycosides were rarely reported natural products, especially abietane-type diterpene glycoside containing 7-oxo group (compound 3) was reported here for the first time. Furthermore, compounds 6, 7, 8 and 14 were isolated from this plant for the first time. Compounds 1-5 showed statistically significant inhibitory effects on IL-1beta secretion in LPS-induced rat primary synovial fibroblasts at 10muM.

Molecular Cloning and Characterisation of Farnesyl Pyrophosphate Synthase from Tripterygium wilfordii.[Pubmed:25938487]

PLoS One. 2015 May 4;10(5):e0125415.

Farnesylpyrophosphate synthase (FPS) catalyzes the biosynthesis of farnesyl pyrophosphate (FPP), which is an important precursor of sesquiterpenoids such as artemisinin and Wilfordine. In the present study, we report the molecular cloning and characterization of two full-length cDNAs encoding FPSs from Tripterygium wilfordii (TwFPSs). TwFPSs maintained their capability to synthesise FPP in vitro when purified as recombinant proteins from E. coli. Consistent with the endogenous role of FPS in FPP biosynthesis, TwFPSs were highly expressed in T. wilfordii roots, and were up-regulated upon methyl jasmonate (MeJA) treatment. The global gene expression profiles suggested that the TwFPSs might play an important regulatory role interpenoid biosynthesis in T. wilfordii, laying the groundwork for the future study of the synthetic biology of natural terpene products.

[Study on chemical constituents from the root bark of Tripterygium hypoglaucum].[Pubmed:23252270]

Zhong Yao Cai. 2012 Jul;35(7):1083-7.

OBJECTIVE: To study the chemical constituents of the root bark of Tripterygium hypoglaucum. METHODS: Column chromatography was used to separate the chemical constituents. The structures were determined by application of spectroscopic (NMR, MS) and chemical methods. RESULTS: Eleven compounds were isolated and identified as 4'-0-(-) methylepigallocatechin (1),3,4-dimethoxyphenyl-beta-D-glucopyranoside (2), 3,4,5-trimethoxyphenyl-f-D-glucopyranoside (3), (2R,3R)-3,5,7,3',5'-pentahydroxyflavan (4), 2-O-deacetyleuonine (5), tripfordine C (6), peritassine A (7) hypoglaunine C (8), wilfortrine (9), wilforgine (10) and Wilfordine (11). CONCLUSION: Compounds 1-6 are isolated from this plant for the first time.

Determination of four pyridine alkaloids from Tripterygium wilfordii Hook. f. in human plasma by high-performance liquid chromatography coupled with mass spectrometry.[Pubmed:21982911]

J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Nov 15;879(30):3516-22.

A novel liquid chromatography-atmospheric-pressure chemical ionization-mass spectrometry (LC-APCI/MS) method was developed and validated for the simultaneous determination of four sesquiterpene pyridine alkaloids (wilfortrine, Wilfordine, wilforgine and wilforine) in human plasma. The chromatographic separation was performed on a Shim-pack XR-ODS column using an ammonium acetate buffer solution-acetonitrile in a gradient program. The detection was achieved by an ion trap mass spectrometry in the positive selected ion monitoring (SIM) mode. The method utilized acetonitrile as protein precipitation solvent and followed by solid-phase extraction (SPE). Calibration curves were linear for the four alkaloids over the range of 0.5-100.0 mug/L with the limits of quantification of 0.5 mug/L, while the method exhibited the recovery of 86.5-98.6%, intra- and inter-day RSDs of less than 8.2% and 12.8%, respectively. Methodology was validated in line with the EU requirements (Commission Decision 2002/657/EC). Results of incurred samples demonstrated excellent reproducibility. To our knowledge, this is the first analytical method for simultaneous determination of the four sesquiterpene pyridine alkaloids in plasma. The method was applicable to clinical pharmaceutical research of alkaloids in rheumatoid arthritis volunteer patients after oral administrations.

Simultaneous determination of four sesquiterpene alkaloids in Tripterygium wilfordii Hook. F. extracts by high-performance liquid chromatography.[Pubmed:17623366]

Phytochem Anal. 2007 Jul-Aug;18(4):320-5.

Wilfortrine, Wilfordine, wilforgine and wilforine are four major bioactive sesquiterpene alkaloids in Tripterygium wilfordii Hook. F. The first analytical determination of the four major bioactive alkaloids is described. The four alkaloids are well-resolved within 15 min using the developed HPLC method. The identity of the analytes was confirmed by an HPLC-MS experiment, with all compounds being clearly assignable by atmospheric pressure chemical ionization (APCI) positive mode analysis. The method was validated for limit of qualification, linearity and inter-day variation of precision and accuracy. Seven T. wilfordii samples (extracts and commercial product) were successfully analysed.

Constituents of the root wood of Austroplenckia populnea var. ovata.[Pubmed:16933883]

J Nat Prod. 2006 Aug;69(8):1225-7.

The root wood of Austroplenckia populnea var. ovata was extracted successively with chloroform and methanol. Lapachol and dehydro-beta-lapachone were isolated from the chloroform extract, and euonine, alatusinine, Wilfordine, 2-O-deacetyleuonine (1), 7-O-deacetyleuonine (2), and austronine (3) from the methanol extract. The structures of the new compounds 1-3 were elucidated by spectroscopic data interpretation. Lapachol, dehydro-beta-lapachone, euonine, alatusinine, and Wilfordine are known compounds that are newly identified from root wood of Austroplenckia populnea.

Insecticidal sesquiterpene pyridine alkaloids from Maytenus chiapensis.[Pubmed:14738378]

J Nat Prod. 2004 Jan;67(1):14-8.

The new sesquiterpene pyridine alkaloids chiapenines ES-I (1), ES-II (2), ES-III (3), and ES-IV (4), in addition to the known alkaloids Wilfordine (5), alatamine (6), wilforidine (7), alatusinine (8), euonine (9), euonymine (10), ebenifoline E-I (11), forrestine (12), mayteine (13), and 4-hydroxy-7-epi-chuchuhuanine E-V (14), were isolated from the leaves of Maytenus chiapensis. Their structures were elucidated by 1D and 2D NMR spectroscopy, including homonuclear and heteronuclear correlation (COSY, ROESY, HSQC, and HMBC) experiments. Wilfordine, alatusinine, and euonine exhibited strong antifeedant activity against Spodoptera littoralis.

[Long-term effect of Schonlein-Henoch nephritis with nephritic-nephrotic syndrome in children by traditional Chinese medicine and Western medicine].[Pubmed:1421973]

Zhongguo Zhong Xi Yi Jie He Za Zhi. 1992 Jun;12(6):340-2, 324.

21 cases are fully agreed with the diagnosis standard of Schonlein-Henoch nephritis. Biopsy on the kidney of 5 cases with resistant duration was made and all were diagnosed as mesenteric hyperplastic glomerular nephritis, among them, one with segmental sclerosis, one with segmental sclerosis and crescents in some glomerulus. 13 cases were treated with prednisone, cyclophosphamide and Traditional Chinese herbs. 8 cases with Wilfordine adding and/or traditional Chinese herbs. The results showed that 15 of 21 cases were cured, one case perfect remission, 4 cases part remission. All of the cases were followed-up from 2 years and 10 months to 12 years and 4 months, average 7.34 years. The late results: Group A, 16 cases with symptom, physical exam, urine routine normal. Group B, 4 cases with microscopic hematuria and/or "a little-(+)" urinary protein. Group C, one case with "+2" urinary protein and/or hypertension, urinary creatinine clearance rate normal. Of 5 cases, whose biopsies of kidney were made, one with glomerular segmental sclerosis belonged to Group B. 13 of 21 cases had recurrence for 1-6 times, which was closed related with up respiratory tract infection.