Tanshinone IIB - CAS 17397-93-2
Catalog number: B0005-170092
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Molecular Formula:
C19H18O4
Molecular Weight:
310.4
COA:
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Chemical Family:
Quinones
Description:
Tanshinone IIB isolated from the roots of Salvia miltiorrhiza. It inhibits the uptake of digoxin and vinblastine in membrane vesicles containing PgP or MRP1, moderately stimulates PgP ATPase activity.
Ordering Information
Catalog Number Size Price Stock Quantity
B0005-170092 1 mg $499 In stock
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Purity:
0.97
Appearance:
Red powder
Synonyms:
(S)-6-(HydroxyMethyl)-1,6-diMethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione
MSDS:
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Application:
neuro-protective; antioxidant;
Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
1.The effect of yeast elicitor on the growth and secondary metabolism of hairy root cultures of Salvia miltiorrhiza.
Chen H;Chena F;Chiu FC;Lo CM Enzyme Microb Technol. 2001 Jan 2;28(1):100-105.
Hairy root cultures of Salvia miltiorrhiza transformed with Agrobacterium rhizogenes ATCC 15834 produced a tiny amount of tanshinones and a constituent level of phenolic acids under normal growth conditions. Upon elicitation with yeast elicitor, the production of both phenolic acids and tanshinones was enhanced. For example, the contents of two phenolic acids, rosmarinic acid and lithospermic acid B were elevated from 1.24% and 2.59% to 2.89% and 2.98% of dry wt, respectively while the intracellular content of cryptotanshinone increased from 0.001% to as much as 0.096% of dry wt. Yeast elicitor also improved the growth of hairy roots (from 3.9 g/l to 7.3 g/l on a dry wt basis). Liquid chromatography-mass spectrometry (LC-MS) was developed for simultaneous detection and identification of phenolic acids and tanshinones in the extracts of S. miltiorrhiza. Rosmarinic acid, lithospermic acid B, cryptotanshinone, tanshinone I, tanshinone IIA and tanshinone IIB were identified by comparison with standards available. Dihydrotanshinone I and methylenetanshiquinone were tentatively identified by the molecular weights and the elution comparable with the literature. An unknown compound with a molecular weight of 280 was found in yeast-elicitor treated hairy root cultures, which was one of the major tanshinones induced.
2.Characterization of metabolites of tanshinone IIA in rats by liquid chromatography/tandem mass spectrometry.
Li P;Wang GJ;Li J;Hao HP;Zheng CN J Mass Spectrom. 2006 May;41(5):670-84.
The metabolism of tanshinone IIA was studied in rats after a single-dose intravenous administration. In the present study, 12 metabolites of tanshinone IIA were identified in rat bile, urine and feces with two LC gradients using LC-MS/MS. Seven phase I metabolites and five phase II metabolites of tanshinone IIA were characterized and their molecular structures proposed on the basis of the characteristics of their precursor ions, product ions and chromatographic retention time. The seven phase I metabolites were formed, through two main metabolic routes, which were hydroxylation and dehydrogenation metabolism. M1, M4, M5 and M6 were supposedly tanshinone IIB, hydroxytanshinone IIA, przewaquinone A and dehydrotanshinone IIA, respectively, by comparing their HPLC retention times and mass spectral patterns with those of the standard compounds. The five phase II metabolites identified in this research were all glucuronide conjugates, all of which showed a neutral loss of 176 Da. M9 and M12 were more abundant than other identified metabolites in the bile, which was the main excretion path of tanshinone IIA and the metabolites. M12 was the main metabolite of tanshinone IIA. M9 and M12 were proposed to be the glucuronide conjugates of two different semiquinones and these semiquinones were the hydrogenation products of dehydrotanshinone IIA and tanshinone IIA, respectively.
3.Identification of tanshinone IIA metabolites in rat liver microsomes by liquid chromatography-tandem mass spectrometry.
Li P;Wang GJ;Li J;Hao HP;Zheng CN J Chromatogr A. 2006 Feb 3;1104(1-2):366-9. Epub 2006 Jan 10.
Tanshinone IIA, the major component extracted from Radix salvia miltiorrhiza, has been observed to possess various kinds of pharmacological activities including antioxidant, prevention of angina pectoris and myocardial infarction and anticancer. Tanshinone IIA was incubated with rat liver microsomes and the resulting metabolites were identified by liquid chromatography/tandem mass spectrometry. The results showed the formation of three main hydroxyl metabolites. The three hydroxyl metabolites of tanshinone IIA were proved to be tanshinone IIB, hydroxytanshinone IIA and przewaquinone A by comparing the tandem mass spectra and the chromatographic retention time with that of the respective authentic compounds. Tanshinone IIB, hydroxytanshinone IIA and przewaquinone A are all the chemical components of total tanshinones. It was reasonable to presume that the three hydroxy metabolites of tanshinone IIA were pharmacologically active the same as tanshinone IIA and the total tanshinones.
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CAS 17397-93-2 Tanshinone IIB

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