Simultaneous determination of tanshinone IIA and cryptotanshinone in rat plasma by liquid chromatography-electrospray ionisation-mass spectrometry

Li, Jing; Wang, Guangji; Li, Peng; Hao, Haiping

doi:10.1016/j.jchromb.2005.07.048

Cited by 49 publications

(32 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…TSA (20 M) was incubated in reaction mixture consisting of 0.2 mg of S9 protein, 2 mM UDPGA, 1 mM saccharic acid 1,4-lactone, 5 mM MgCl 2 , an NADPH-regenerating system containing 0.2 mM NADP, 1.9 mM glucose 6-phosphate, 1.2 U/ml glucose-6-phosphate dehydrogenase, and 100 mM potassium phosphate buffer, pH 7.4, in a final volume of 200 l. After preincubation for 5 min at 37°C, the reaction was started by adding UDPGA. All the reactions were incubated at 37°C for 30 min, terminated by ice-cold acetonitrile, followed by centrifugation at 20,000g for 10 min to obtain the supernatants, and then analyzed by HPLC and liquid chromatography/tandem mass spectrometry according to our previous reports (Li et al, 2005;Hao et al, 2006bHao et al, , 2007.…”

Section: Methodsmentioning

confidence: 99%

“…We previously conducted comprehensive studies on TSA pharmacokinetics and disposition both in vivo and in vitro based on developing some established bioanalytical methods (Li et al, 2005;Hao et al, 2006b). TSA bioavailability was found to be extremely poor because of its poor solubility and membrane permeability (Hao et al, 2006a) and especially because of the extensive intestinal first-pass metabolism (Hao et al, 2007).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Regioselective Glucuronidation of Tanshinone IIa after Quinone Reduction: Identification of Human UDP-Glucuronosyltransferases, Species Differences, and Interaction Potential

Wang¹,

Hao²,

Zhu³

et al. 2010

Drug Metab Dispos

Self Cite

View full text Add to dashboard Cite

ABSTRACT:We have previously identified that the predominant metabolic pathway for tanshinone IIa (TSA) in rat is the NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone reduction and subsequent glucuronidation. The present study contributes to further research on its glucuronidation enzyme kinetics, the identification of human UDP-glucuronosyltransferase (UGT) isoforms, and the interaction potential with typical UGT substrates. A pair of regioisomers (M1 and M2) of reduced TSA glucuronides was found from human, rat, and mouse, whereas only M1 was found in dog liver S9 incubations. The overall glucuronidation clearance of TSA in human liver S9 was 11.8 ؎ 0.8 l/min/mg protein, 0.7-, 0.8-, and 3-fold of that in the mouse, rat, and dog, respectively. Using intrinsic clearance M2/M1 as a regioselective index, opposite regioselectivity was found between human (0.7) and mouse (1.3), whereas no significant regioselectivity was found in rat. In a sequential metabolism system, by applying human liver cytosol as an NQO1 donor combined with a screening panel of 12 recombinant human UGTs, multiple UGTs were found involved in the M1 formation, whereas only UGT1A9 and, to a very minor extent, UGT1A1 and UGT1A3 contributed to the M2 formation. Further enzyme kinetics, correlation, and chemical inhibition studies confirmed that UGT1A9 played a major role in both M1 and M2 formation. In addition, TSA presented a potent inhibitory effect on the glucuronidation of typical UGT1A9 substrates propofol and mycophenolic acid, with an IC 50 value of 8.4 ؎ 1.8 and 8.9 ؎ 1.9 M, respectively. This study will help to guide future studies on characterizing the NQO1-mediated reduction and subsequent glucuronidation of other quinones.Quinones are a large group of compounds ubiquitous in nature and characterized with great biological, pharmacological, and/or toxicological significance. Humans are unavoidably exposed to many endogenous quinones such as coenzyme Q, vitamin K, oxidized products of endogenous phenols, and some xenobiotic quinones from foods, environmental pollutants, and drugs. The carbonyl group in the quinone structure is often a determining functional factor for their activities (Oppermann, 2007). For example, the quinone/hydroquinone interconversion of coenzyme Q plays an important role in the electron transport involved in cellular respiration, and the one-electron and/or two-electron reduction of the quinone carbonyl group-triggered redox cycle also largely explains the pharmacological or toxicological activities of many quinones. Note that the quinone carbonyl reduction and subsequent conjugation constitute the major biotransformation and metabolic elimination pathway of most quinones. Therefore, the biotransformation study of quinones is essential for understanding their bioactivation, detoxification, and/or inactivation process.Tanshinones are a class of diterpene phenanthrenequinone compounds isolated from the dried root of Salvia miltiorrhiza (Fam. Labiatae), which is a widely used traditional Chinese medicine with w...

show abstract

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Regioselective Glucuronidation of Tanshinone IIa after Quinone Reduction: Identification of Human UDP-Glucuronosyltransferases, Species Differences, and Interaction Potential

Wang¹,

Hao²,

Zhu³

et al. 2010

Drug Metab Dispos

Self Cite

View full text Add to dashboard Cite

show abstract

“…Concerning the pharmacokinetic of tashinones, there are several studies available in the literature on single tanshinones showing that CTS was metabolized to a major metabolite, TSIIA, and trace amounts of several hydroxyl-and dihydroxyl-CTS derivatives in rats [77][78][79][80]. Some showed that TSIIA was metabolized to TSIIB, and some hydroxylated derivatives, dehydrotanshinone IIA and tanshinaldehyde in rats [77,80,81]. It was also shown that DTSI was metabolized to TSI by dehydrogenation, hydroxyl derivatives, and a derivative by D-ring hydrolysis in rats [80].…”

mentioning

confidence: 99%

Effects of Salvia miltiorrhiza on CNS Neuronal Injury and Degeneration: A Plausible Complementary Role of Tanshinones and Depsides

Bonaccini

Karioti²,

Bergonzi

et al. 2015

Planta Med

View full text Add to dashboard Cite

show abstract

“…12,29,30) Some HPLC methods have also been described for the determination of Sal B in rat plasma. [31][32][33] These methods only determine TSIIA and Sal B, separately and it is not possible to simultaneously determine both of them in vivo.…”

mentioning

confidence: 99%

Pharmacokinetic Interaction between Tanshinones and Polyphenolic Extracts of Salvia miltinorrhiza BUNGE after Intravenous Administration in Rats

Guo

Zhang

Tang

et al. 2008

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

The dry roots of Salvia miltiorrhiza, also called "Danshen" in Chinese, are a well-known traditional Chinese medicinal herb. Because of its better performance and fewer side effects confirmed during the long-time clinical use, Danshen is widely used in traditional Chinese medicinal preparations to treat a number of coronary heart diseases, especially angina pectoris and myocardial infarction. [1][2][3][4] At present, a variety of Danshen products are commercially available, such as Fufang Danshen Tablets and Fufang Danshen Dripping pills, which are the two most commonly used ones in China and these have been officially listed in the Chinese Pharmacopoeia 2005. 5)According to their chemical structures, the major bioactive constituents in S. miltiorrhiza BUNGE can be classified into two groups: the tanshinone compounds, which belong to a group of lipid-soluble diterpenoids, and water-soluble polyphenolic compounds.6) The major lipophilic components are cryptotanshinone, tanshinone I and tanshinone IIA (TSIIA). Pharmacological tests have revealed that TSIIA possesses a variety of pharmacological activities including antioxidant effects, 7) prevention of angina pectoris and myocardial infarction, 8) as well as antineoplastic, 9) anticancer, 10,11) and anti-inflammatory effects.12) The major hydrophilic components include danshensu, protocatechuic aldehyde and salvianolic acid B (Sal B). Sal B is the most common component in the Salvia species and the most abundant in their aqueous extracts. 13,14) Different studies have shown that Sal B has a variety of biological activities including anti-oxidation, 15,16) antifibrotic, 17) and myocardial salvage effects 18) ; it also prevents hepatitis and uremia, 19) and improves blood circulation and renal function. [20][21][22][23][24][25] Considering their prominent pharmacological activities and high content in Danshen, both TSIIA and Sal B have been selected as marker components for the quality control of Danshen and many other medicinal preparations containing Danshen in the 2005 edition of Chinese Pharmacopoeia. 6,12,26) The chemical structures of TanIIA and Sal B are shown in Fig. 1. Recently, Song et al. 27) showed that the pharmacokinetics of cryptotanshinone and TSIIA in rats after oral intra-gavage of an extract of tanshinones was significantly affected by the co-present tanshinones. Also, Sal B had a lower effective concentration in vitro angiogenesis study than the crude extract. 28) In clinical practice, most Danshen products used consist of tanshinone and polyphenolic extracts at the same time.5) However, there have been no reports of pharmacokinetic interactions between tanshinones and polyphenolic extracts of S. miltiorrhiza BUNGE in vivo.To date, several methods have been established for the de- The objective of this study was to investigate the interaction between tanshinones and polyphenolic extracts of Salvia miltiorrhiza BUNGE in rats. The rats in the medium dose groups were given an intravenous administration of 10 mg/kg tanshinones extract-loaded emulsi...

show abstract

Simultaneous determination of tanshinone IIA and cryptotanshinone in rat plasma by liquid chromatography-electrospray ionisation-mass spectrometry

Cited by 49 publications

References 4 publications

Regioselective Glucuronidation of Tanshinone IIa after Quinone Reduction: Identification of Human UDP-Glucuronosyltransferases, Species Differences, and Interaction Potential

Regioselective Glucuronidation of Tanshinone IIa after Quinone Reduction: Identification of Human UDP-Glucuronosyltransferases, Species Differences, and Interaction Potential

Effects of Salvia miltiorrhiza on CNS Neuronal Injury and Degeneration: A Plausible Complementary Role of Tanshinones and Depsides

Pharmacokinetic Interaction between Tanshinones and Polyphenolic Extracts of Salvia miltinorrhiza BUNGE after Intravenous Administration in Rats

Contact Info

Product

Resources

About