Sinapine thiocyanate

The seeds of Raphanus sativus L.

Sinapine is an alkaloid from seeds of the cruciferous species which shows favorable biological activities such as antioxidant and radio-protective activities.

In Vitro:Sinapine increases the sensitivity of Caco-2 cells to doxorubicin in a dose-dependent manner, whereas no or less effect is observed in the cells treated with doxorubicin alone. The combination of Sinapine and doxorubicin has a synergistic effect and increased the cytotoxicity of doxorubicin against Caco-2 cells. Results indicate that Sinapine plays an important role in the down-regulation of P-glycoprotein expression through suppression of FGFR4-FRS2a-ERK1/2 signaling pathway[1]. Sinapine can effectively protect against OH-induced damages to DNA and MSCs, thereby it may have a therapeutic potential in MSCs transplantation[2].

In Vivo:During the first 8 days, the dry matter intake and live weight gain of the rats are significantly reduced by the intake of sinapine and other phenolic compounds. However, after this adaptation period their performances are similar to those of the control group[3].

References:
[1]. Guo Y, et al. Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein. Food Chem Toxicol. 2014 May;67:187-92. [2]. Li X, et al. Protective Effect of Sinapine against Hydroxyl Radical-Induced Damage to Mesenchymal Stem Cells and Possible Mechanisms. Chem Pharm Bull (Tokyo). 2016;64(4):319-25. [3]. Vermorel M, et al. Valorization of rapeseed meal. 5. Effects of sinapine and other phenolic compounds on food intake and nutrient utilization in growing rats. Reprod Nutr Dev. 1987;27(4):781-90.

Systematic screening and characterization of Qi-Li-Qiang-Xin capsule-related xenobiotics in rats by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry.[Pubmed:29787993]

J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jul 15;1090:56-64.

Qi-Li-Qiang-Xin capsule (QLQX), a well-known traditional Chinese medicine prescription (TCMP), is consisted of eleven commonly used herbal medicines, has been widely used for the treatment of chronic heart failure (CHF). However, the absorbed components and related metabolites after oral administration of QLQX are still remaining unknown. In the present work, a reliable and effective method using ultra performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS) was established to identify QLQX-related xenobiotics in rats. Based on a representative structure based homologous xenobiotics identification (RSBHXI) strategy, a total of eleven compounds (salvianolic acid B, formononetin, benzoylmesaconine, alisol A, Sinapine thiocyanate, naringin, tanshinone IIA, ginsenoside Rg1, ginsenoside Rb1, astragaloside IV and periplocin), bearing different chemical core structures, were selected and investigated for their metabolism in vivo. And then, comprehensive metabolic profiles of the holistic multi-ingredients in QLQX were achieved. As a result, a total of 121 QLQX-related xenobiotics (47 prototypes and 74 metabolites) were identified or tentatively characterized, among them eight prototypes (mesaconine, hypaconine, songorine, fuziline, neoline, talatizamine formononetin, neocryptotanshinone) and two metabolites (calycosin-gluA, formononetin-guA) were relatively the main existing xenobiotics exposed in blood. All absorbed prototype constituents were mainly from six composed herbal medicines (Aconiti lateralis radix, Astragali radix, Ginseng radix, Alismatis rhizoma, Salvia miltiorrhiza radix, Periploca cortex). The main metabolic reactions were methylation, hydrogenation, hydroxylation, oxidization, sulfation and glucuronidation. This is the first study on in vivo metabolism of QLQX. These results enabled us to focus on several high exposure ingredients in the discovery of effective substances of QLQX, however further pharmacokinetic study on these QLQX-related xenobiotics are needed to be carried out.

Mechanism of the protective effects of the combined treatment with rhynchophylla total alkaloids and sinapine thiocyanate against a prothrombotic state caused by vascular endothelial cell inflammatory damage.[Pubmed:28587383]

Exp Ther Med. 2017 Jun;13(6):3081-3088.

The aim of the present study was to investigate the effect and the underlying mechanism of the combined treatment of rhynchophylla total alkaloids (RTA) and Sinapine thiocyanate for protection against a prothrombotic state (PTS) associated with the tumor necrosis factor-alpha (TNF-alpha)-induced inflammatory injury of vascular endothelial cells (VECs). A TNF-alpha-induced VEC inflammatory injury model was established, and cell morphology of VECs was evaluated using scanning electron microscopy. In addition, reverse transcription-quantitative polymerase chain reaction and western blot analysis were performed to examine the mRNA and protein expression of coagulation-related factors, including nuclear factor-kappaB (NF-kappaB), transforming growth factor-beta1 (TGF-beta1), tissue factor (TF), plasminogen activator inhibitor (PAI-1), protease-activation receptors (PAR-1) and protein kinase C (PKC-alpha) in VECs. Combined treatment with RTA and Sinapine thiocyanate was demonstrated to reduce, to a varying extent, the mRNA and protein expression of NF-kappaB, TGF-beta1, TF, PAR-1, PKC-alpha and PAI-1. Furthermore, combined treatment with RTA and Sinapine thiocyanate was able to downregulate the expression of coagulation-related factors in injured VECs, thereby inhibiting the PTS induced by vascular endothelial injury. The underlying mechanism is partially associated with the TF-mediated activation of the thrombin-receptor signaling pathway that suppresses coagulation during inflammation and balances fibrinolysis in order to inhibit fibrin generation and deposition.

[Chemical mechanisms involved in slow fire processing and pulverization of Brassica juncea].[Pubmed:25850264]

Zhongguo Zhong Yao Za Zhi. 2014 Nov;39(22):4345-8.

This article dealed with the effects of processing method and duration on the major bioactive components (sinigrin and Sinapine thiocyanate) in Brassica juncea. The contents of sinigrin and Sinapine thiocyanate in decoctions of raw and processed B. juncea were determined and compared by high performance liquid chromatography on a Alltima C18 column (4.6 mm x 250 mm, 5 microm) at 35 degrees C with the acetonitrile-0.1% phosphoric acid as the mobile phrase in gradient elution. The detection wavelength of sinigrin and Sinapine thiocyanate was set at 227 nm and 326 nm, and the flow rate was 1.0 mL x min(-1). It was found that with the extended processing duration, the contents of sinigrin and Sinapine thiocyanate first increased and then decreased: i.e., 0-2 minutes they increased gradually (for sinigrin, by 9.65% in processed products and 356. 10% in powder; for Sinapine thiocyanate, by 12.82% in processed products and 3.41% in powder), and achieved their highest content at 2 min; then, decreased during the next 5 minutes (for sinigrin, by 80.35% in processed products and 82.09% in powder; for Sinapine thiocyanate, by 14.29% in processed products and 17.54% in powder), suggesting that processing duration could significantly affect the contents of bioactive components in B. juncea, enzymatic hydrolysis of sinigrin when the seed is crushed in the present of moisture may be responsible for the content change. It is recommended that the slow fire should be the best processing method and the raw seed could be used directly in the water extracts related industrial production.

Skin penetration of topically applied white mustard extract and its effects on epidermal Langerhans cells and cytokines.[Pubmed:24076395]

Int J Pharm. 2013 Nov 30;457(1):136-42.

White mustard (Sinapis alba L.), a traditional Chinese medicine, is widely used in China for clinical prevention and treatment of the common winter diseases of asthma and bronchitis by percutaneous administration in the summer. The present study is to investigate the skin penetration behavior of white mustard extract to elucidate the possible mechanism underlying its immune regulation activity. The principle active compound of the extract, Sinapine thiocyanate (ST), was used as a marker. The skin penetration of ST in white mustard extract was examined in vitro and in vivo. In vitro study on excised guinea pig hairless skin using Franz diffusion cell revealed ST can permeate through the skin and also accumulate in the skin. In vivo study was carried out on the guinea pig hairless skin for 24 h, and then skin was excised for frozen section, ST from the sections were extracted to quantify the amount of drug in different skin layers. The detailed distribution of ST showed that it accumulated in the epidermis, especially in the stratum corneum. After treatment with white mustard extract for 24h, the skin was stained with ATPase, and the morphometric parameters of epidermal LCs were compared to the untreated control through image-analysis system. A statistically significant reduction in LC density and increase in shape factor were observed. Cytokines related to LCs migration including interleukin 1beta (IL-1beta) and tumor necrosis factor alpha (TNF-alpha) were also measured after white mustard extract treated at different time points. Compared to the untreated group, white mustard extract significantly enhanced the release of IL-1beta and TNFalpha. The morphometric changes of LCs and the local cytokine release after topical white mustard treatment may explain the activity of the white mustard extract against asthma and bronchitis.

Sinapine thiocyanate is an alkaloid from seeds of the cruciferous species which shows favorable biological activities such as antioxidant and radio-protective activities.

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