Isolation and structure characterization of related impurities in Sodium Tanshinone IIA Sulfonate by LC/ESI-MSn and NMR

Wang, Baolin; Wang, En; Yan, Wenjing; Ye, Wen‐Cai; Li, Ping

doi:10.1016/j.jpba.2012.04.029

Cited by 14 publications

(5 citation statements)

References 10 publications

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“…1A), a water-soluble derivative of tanshinone IIA, is synthesized and widely used for treatment of cardiovascular diseases [16,20]. However, various impurities are formatted in the process of storage or synthesis of STS [22,23]. In our present study, an array of compounds are derived from sodium 9-hydroxyltanshinone IIA sulfonate, which is one of major impurities of STS during storage [23].…”

Section: Introductionmentioning

confidence: 99%

“…However, various impurities are formatted in the process of storage or synthesis of STS [22,23]. In our present study, an array of compounds are derived from sodium 9-hydroxyltanshinone IIA sulfonate, which is one of major impurities of STS during storage [23]. We conduct several biological evaluations of these compounds, and in the course of these evaluations, a novel derivative sodium 9-acetoxyltanshinone IIA sulfonate (ZY-1A4, Fig.…”

Section: Introductionmentioning

confidence: 99%

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Induction of Heme Oxygenase-1 by Sodium 9-Hydroxyltanshinone IIA Sulfonate Derivative Contributes to Inhibit LPS-Mediated Inflammatory Response in Macrophages

Liu

Wang

Xiao

et al. 2015

Cell Physiol Biochem

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Background/Aim: Sodium 9-acetoxyltanshinone IIA sulfonate (ZY-1A4), a novel compound derived from sodium 9-hydroxyltanshinone IIA sulfonate, was synthesized with potential biological activities. This study aimed to explore the effects of ZY-1A4 on lipopolysaccharide (LPS)-triggered inflammatory response and the underlying mechanisms. Methods: Activation of RAW264.7 macrophages was induced by LPS. The effects of ZY-1A4 on inducible nitric oxide synthase (iNOS) expression, nitric oxide (NO) generation, nuclear factor-κB (NF-κB) activation, heme oxygenase-1 (HO-1) expression, and nuclear factor-erythroid 2 related factor 2 (Nrf2) pathway were evaluated to elucidate its underlying mechanisms on inflammatory responses. Results: ZY-1A4 concentration-dependently reduced iNOS expression and NO production, and inhibited c-Jun-N-terminal kinase 1/2 (JNK1/2) phosphorylation and NF-κB activation in LPS-stimulated macrophages. In addition, ZY-1A4 concentration- and time-dependently induced HO-1 expression associated with degradation of Kelch-like ECH-associated protein 1 (Keap1) and nuclear translocation of Nrf2, while the effect of ZY-1A4 was abolished by a phosphoinositide 3-kinase (PI3K) inhibitor LY294002. Intriguingly, pharmacological inactivation of HO-1 with zinc protoporphyrin IX reversed anti-inflammatory effect of ZY-1A4, but the anti-inflammatory effect of ZY-1A4 was largely mimicked by HO-1 by-products carbon monoxide and bilirubin. Furthermore, the inhibitory effect of ZY-1A4 on LPS-induced iNOS expression and NO release was abolished by HO-1 siRNA or LY294002. Conclusion: Our results demonstrated that ZY-1A4 suppressed LPS-induced iNOS expression and NO generation via modulation of NF-κB activation and HO-1 expression. This new finding might shed light to the prevention and therapy of cardiovascular diseases.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Induction of Heme Oxygenase-1 by Sodium 9-Hydroxyltanshinone IIA Sulfonate Derivative Contributes to Inhibit LPS-Mediated Inflammatory Response in Macrophages

Liu

Wang

Xiao

et al. 2015

Cell Physiol Biochem

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“…As an injection, STS is widely and successfully used in China for treating cardiovascular diseases. In the analysis of STS bulk drug, eight related impurities were observed and isolated by column chromatography, which structure was established employing a combined NMR and LC-ESI/MS approach [92]. NMR experiments ( 1 H, 13 C, HMBC, HSQC, COSY) were crucial for unequivocally establishing structural features, where MS was not useful, allowing to propose a possible mechanism for the formation of the impurities.…”

Section: Impurities Resulting From Isolation In Naturally Occurring Apismentioning

confidence: 99%

Pharmaceutical impurities and degradation products: Uses and applications of NMR techniques

Maggio

Calvo

Vignaduzzo

et al. 2014

Journal of Pharmaceutical and Biomedical Analysis

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“…Because terpenoids generally have low polarity, they are often extracted with chloroform, ethyl acetate or petroleum ether. For some slightly more polar compounds, the plant roots are usually first degreased and then extracted with a polar solvent such as acetone (Wang et al, 2012) and n-butanol (Pang et al, 2016). Although the alcohol extraction method is a relatively traditional extraction process, it is still widely used in the market for its simple and easy operation, and modern ideas have been incorporated to optimize the method.…”

Section: Extraction and Separation Methods Of Tanshinonesmentioning

confidence: 99%

Tanshinones, Critical Pharmacological Components in Salvia miltiorrhiza

2019

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Salvia miltiorrhiza Bunge, a member of the Lamiaceae family, is valued in traditional Chinese Medicine. Its dried root (named Danshen) has been used for hundreds of years, primarily for the treatment of cardiovascular and cerebrovascular diseases. Tanshinones are the main active ingredients in S. miltiorrhiza and exhibit significant pharmacological activities, such as antioxidant activity, anti-inflammatory activity, cardiovascular effects, and antitumor activity. Danshen dripping pill of Tianshili is an effective drug widely used in the clinical treatment of cardiovascular diseases. With the increasing demand for clinical drugs, the traditional method for extracting and separating tanshinones from medicinal plants is insufficient. Therefore, in combination with synthetic biological methods and strategies, it is necessary to analyze the biosynthetic pathway of tanshinones and construct high-yield functional bacteria to obtain tanshinones. Moreover, the biosynthesis of tanshinones has been studied for more than two decades but remains to be completely elucidated. This review will systematically present the composition, extraction and separation, pharmacological activities and biosynthesis of tanshinones from S. miltiorrhiza, with the intent to provide references for studies on other terpenoid bioactive components of traditional Chinese medicines and to provide new research strategies for the sustainable development of traditional Chinese medicine resources.

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Isolation and structure characterization of related impurities in Sodium Tanshinone IIA Sulfonate by LC/ESI-MSn and NMR

Cited by 14 publications

References 10 publications

Induction of Heme Oxygenase-1 by Sodium 9-Hydroxyltanshinone IIA Sulfonate Derivative Contributes to Inhibit LPS-Mediated Inflammatory Response in Macrophages

Induction of Heme Oxygenase-1 by Sodium 9-Hydroxyltanshinone IIA Sulfonate Derivative Contributes to Inhibit LPS-Mediated Inflammatory Response in Macrophages

Pharmaceutical impurities and degradation products: Uses and applications of NMR techniques

Tanshinones, Critical Pharmacological Components in Salvia miltiorrhiza

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