PREPARATIVE ISOLATION OF TETRANDRINE AND FANGCHINOLINE FROM RADIX <i>STEPHANIA TETRANDRA</i> USING REVERSED-PHASE FLASH CHROMATOGRAPHY

Xie, Zhihui; Xu, Xinjun; Xie, Chunyan; Liang, Zhikun; Yang, Mei; Huang, Junyi; Yang, Dongzi

doi:10.1080/10826076.2012.745139

Cited by 8 publications

(4 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Focusing first on the results obtained for S. tetrandra , two molecular features were detected with m / z values of 609.33 and 623.33 ([M + H] + ions) in the LC-MS data, which were tentatively attributed to the bisbenzylisoquinoline metabolites fangchinoline ( 15 ) and tetrandrine ( 16 ), respectively (Scheme ). Those assertions were further supported based on consideration of the biogenic source, UV–vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites. , LC-MS data obtained from testing the M. dauricum extract supported the presence of two active compounds based on the appearance of [M + H] + ions exhibiting m / z values of 611.50 and 625.42, which were preliminarily identified as daurisoline ( 17 ) and dauricine ( 18 ), respectively (Scheme ). Likewise, those assignments were buttressed by evidence derived from considerations of the biogenic source, UV–vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites. , The preliminary structure assignments of 15 – 18 were subsequently confirmed based on comparisons of their 1 H NMR spectroscopic data, specific rotation values, and MS features with reported data. ,− The DNA-binding activities of purified 15 – 18 were subsequently confirmed using the LLAMAS method (Figure S7, Supporting Information).…”

Section: Resultsmentioning

confidence: 85%

“…Those assertions were further supported based on consideration of the biogenic source, UV− vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites. 53,54 LC-MS data obtained from testing the M. dauricum extract supported the presence of two active compounds based on the appearance of [M + H] + ions exhibiting m/z values of 611.50 and 625.42, which were preliminarily identified as daurisoline (17) and dauricine (18), respectively (Scheme 1). Likewise, those assignments were buttressed by evidence derived from considerations of the biogenic source, UV−vis spectroscopic data, their reported DNA binding activities, and MS/MS data for the two metabolites.…”

Section: ■ Results and Discussionmentioning

confidence: 88%

See 1 more Smart Citation

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

et al. 2020

View full text Add to dashboard Cite

A fundamental factor in natural product drug discovery programs is the necessity to identify the active component(s) from complex chemical mixtures. Whereas this has traditionally been accomplished using bioassay-guided fractionation, we questioned whether alternative techniques could supplement and, in some cases, even supplant this approach. We speculated that a combination of ligand-fishing methods and modern analytical tools (e.g., LC-MS and online natural product databases) offered a route to enhance natural product drug discovery. Herein, a candidate solution referred to as the lickety-split ligand-affinity-based molecular angling system (LLAMAS) is described. This approach utilizes an ultrafiltration-based LC-PDA-MS/MS-guided DNAbinding assay in combination with the (i) Global Natural Products Social Molecular Networking, (ii) Dictionary of Natural Products, and (iii) SciFinder platforms to identify DNA binders in complex chemical mixtures. LLAMAS was initially vetted in tests using known small-molecule DNA binders and then optimized to a 96-well plate-based format. A set of 332 plant samples used in traditional Chinese medicine was screened for DNA-binding activity with LLAMAS, resulting in the identification of seven DNAbinding molecules, including berberine (12), palmatine (13), coptisine (14), fangchinoline (15), tetrandrine (16), daurisoline (17), and dauricine (18). These results demonstrate that LLAMAS is an effective natural product discovery platform for the efficient identification and dereplication of DNA-binding molecules from complex mixtures.N atural products are an important source of therapeutic drug leads due to the incredible diversity of their structures and bioactivities. 1−3 Many of the success stories to emerge from natural product drug development are legendary: the discovery of the antibiotic penicillin in 1928, 4 the identification and subsequent clinical approval of the anticancer drug Taxol (paclitaxel) in 1992, 5 the development of the antimalarial drug artemisinin (a discovery that was acknowledged by the 2015 Nobel Prize in Physiology or Medicine), 6 and more. 7 These milestones in drug discovery established natural products as an unparalleled resource for identifying therapeutically useful compounds to combat a wide range of diseases.Strikingly, a majority of these and other iconic natural products that are used as medicines 1,8,9 were discovered using the well-established, yet powerful technique known as bioassay-guided purification. 10,11 This approach relies on subjecting mixtures of compounds (e.g., extracts and fractions) to iterative steps of fractionation and biological testing with the

show abstract

Section: Resultsmentioning

confidence: 85%

Section: ■ Results and Discussionmentioning

confidence: 88%

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The 1 H‐NMR spectra measured in deuterated DMSO were employed to investigate the host–guest interaction between tetrandrine and SC6A/SC8A. As shown in Figure 10, 1 H‐NMR spectrum of tetrandrine displayed four different types of methyl protons H‐12 (3.80 ppm, s, 3H), H‐13 (3.67 ppm, s, 3H), H‐15 (3.29 ppm, s, 3H) and H‐16 (3.03 ppm, s, 3H), 37,38 the signals displayed an obvious shift upon interaction with SCnA, indicating that tetrandrine inserted into the cavity of SCnA via its methoxy group. The spectrum of SC6A has a singlet peak at 3.85 ppm for the methylene protons (H‐a) and a singlet peak at 7.26 ppm for the aromatic protons (H‐b), 39 the two signals do not shift appreciably upon inclusion of nuciferine (Δδ < 0.04 ppm).…”

Section: Resultsmentioning

confidence: 96%

An innovative extraction strategy for herbal medicine by adopting p‐sulphonatocalix[6]/[8]arenes

Wang

Ren

et al. 2022

Phytochemical Analysis

View full text Add to dashboard Cite

Introduction: Alkaloids exist in various herbal medicine widely and exhibit diverse biological and pharmacological activities. p-Sulphonatocalix[6]arenes (SC6A) and p-sulphonatocalix[8]arenes (SC8A) are water-soluble supramolecular macrocycles and are applied to the extraction of alkaloids from herbal products.Objective: In this study, an innovative method of SC6A/SC8A assisted extraction of the alkaloids from herbs was established.Methods: SC6A and SC8A were designed to extract 27 alkaloids from seven herbal medicines. Based on the significant solubilisation and extraction effect, Stephaniae Tetrandrae Radix (Fangji, FJ) was selected to obtain the optimal extraction process by adopting single factor test and orthogonal experiment. Then, the alkaloids and SC6A/SC8A were separated by one-step alkalisation and SCnA were reused. The host-guest complexes between alkaloids and SCnA were determined by competitive fluorescence titration, differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) and proton nuclear magnetic resonance ( 1 H-NMR) analysis. Results:The optimum condition for SC6A assisted extraction was 5:1:80 (g/g/mL) for herbs/SC6A/solution ratio, 355-250 μm particle size and ultrasonicate 0.5 h, whilst 10:1:40 (g/g/mL) for herbs/SC8A/solution ratio, 355-250 μm particle size and ultrasonicate 0.5 h for SC8A assisted extraction. The total yield of alkaloids (fangchinoline and tetrandrine) from FJ was increased by 4.87 times and 5.97 times with SC6A and SC8A. Moreover, a good reusability of SC6A/SC8A was achieved by alkalisation dissociation. Host-guest complexes were determined by competitive fluorescence titration at a molar ratio of 1:1 between most alkaloids (25/27, except evodiamine and rutaecarpine) and SC6A/SC8A. The complex structure was proved by DSC, FTIR and 1 H-NMR analysis. Conclusion:The study provided an effective eco-friendly and energy-saving extraction method of alkaloids from herbal medicine.

show abstract

“…In the last few decades, alternative medicine has increased in importance for the management of chronic disorders, including DN. Fangchinoline is an alkaloid isolated from Stephania tetrandra Radix (Stephania), which is traditionally used as a medicine in Japan and China [8]. Fangchinoline has been reported to exhibit anti-inflammatory, anti-oxidant, anti-hyperglycemic, and anti-cancer activities [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Fangchinoline Protects Against Renal Injury in Diabetic Nephropathy by Modulating the MAPK Signaling Pathway

Jiang

Liu

Zhou

et al. 2018

Exp Clin Endocrinol Diabetes

View full text Add to dashboard Cite

In this study, we evaluated the nephroprotective effects of fangchinoline in rats with diabetic nephropathy (DN). DN was induced by feeding a high-fat diet for 4 weeks and administering a single dose of streptozotocin (STZ) (30 mg/kg) intraperitoneally. The rats were split into groups; one group received oral fangchinoline (3 mg/kg) per day for 8 weeks. After completion of the 8-week study period, biomedical and inflammatory markers were evaluated in serum and urine, and oxidative stress was estimated in kidney tissues. In addition, Western blot assays, reverse transcription-polymerase chain reaction, and immunohistochemical analyses were performed in the kidney tissues of DN rats. The results suggest that treatment with fangchinoline attenuated the biochemical marker changes induced by DN in blood and urine. Moreover, a significant (p<0.01) reduction in inflammatory markers in serum was found in the fangchinoline group compared to the controls. Immunohistochemical analyses also revealed that treatment with fangchinoline significantly reduced the expression of collagen IV and CD31 in the kidneys compared to the control group. The expression of p38 MAPK, TNF-α, COX-2, and MMP-9 was also attenuated by fangchinoline treatment in the kidney tissues of DN rats. Together, the results of this study suggest that fangchinoline protects against nephron damage by attenuating alterations in the p38 MAPK pathway, thereby reducing oxidative stress and inflammation in DN rats.

show abstract

PREPARATIVE ISOLATION OF TETRANDRINE AND FANGCHINOLINE FROM RADIX STEPHANIA TETRANDRA USING REVERSED-PHASE FLASH CHROMATOGRAPHY

Cited by 8 publications

References 8 publications

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

An Integrated Strategy for the Detection, Dereplication, and Identification of DNA-Binding Biomolecules from Complex Natural Product Mixtures

An innovative extraction strategy for herbal medicine by adopting p‐sulphonatocalix[6]/[8]arenes

Fangchinoline Protects Against Renal Injury in Diabetic Nephropathy by Modulating the MAPK Signaling Pathway

Contact Info

Product

Resources

About