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MedKoo Cat#: 599032 | Name: Lithospermate B

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lithospermate B is a major biologically active component of dan shen; improves renal failure.

Chemical Structure

Lithospermate B
CAS#122021-74-3

Theoretical Analysis

MedKoo Cat#: 599032

Name: Lithospermate B

CAS#: 122021-74-3

Chemical Formula: C36H28MgO16

Exact Mass: 740.1228

Molecular Weight: 740.90

Elemental Analysis: C, 58.36; H, 3.81; Mg, 3.28; O, 34.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Lithospermate B; Magnesium lithospermate B; Magnesium tanshinoate B; Lithospermic acid B Mg complex;
IUPAC/Chemical Name
Magnesium, ((1R)-1-(carboxy-kappaO)-2-(3,4-dihydroxyphenyl)ethyl (2S,3S)-4-((1E)-3-((1R)-1-(carboxy-kappaO)-2-(3,4-dihydroxyphenyl)ethoxy)-3-(oxo-kappaO)-1-propenyl)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylato(2-)-kappaO3')-, (T-4)-
InChi Key
ANUBYMNVOPVATP-RBRJVDKYSA-L
InChi Code
InChI=1S/C36H30O16.Mg/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17;/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48);/q;+2/p-2/b10-5-;/t27-,28-,31+,32-;/m1./s1
SMILES Code
Oc1c(O)cc(C[C@H]2OC3=O[Mg+2]4([O-]C2=O)O=C([C@@H]5[C@@H](c6cc(O)c(O)cc6)Oc7c5c(/C=C\3)ccc7O)O[C@@H](C([O-]4)=O)Cc8cc(O)c(O)cc8)cc1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 740.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jiang F, Mao Y, Liu H, Xu P, Zhang L, Qian X, Sun X. Magnesium Lithospermate B Protects Neurons Against Amyloid β (1-42)-Induced Neurotoxicity Through the NF-κB Pathway. Neurochem Res. 2015 Sep;40(9):1954-65. doi: 10.1007/s11064-015-1691-1. Epub 2015 Aug 19. PubMed PMID: 26285901. 2: Jiang X, Jiang Y, Sun D, Rong L. Protective effect of magnesium lithospermate B against dextran sodiumsulfate induced ulcerative colitis in mice. Environ Toxicol Pharmacol. 2013 Jul;36(1):97-102. doi: 10.1016/j.etap.2013.03.010. Epub 2013 Mar 22. PubMed PMID: 23603461. 3: Quan W, Wei G, Zhou D, Zhu Y, Guo C, Wang Y, Weng Y, Xi M, Wen A. Magnesium lithospermate B reduces myocardial ischemia/reperfusion injury in rats via regulating the inflammation response. Pharm Biol. 2013 Nov;51(11):1355-62. doi: 10.3109/13880209.2013.791324. Epub 2013 Jul 18. PubMed PMID: 23863120. 4: Song S, Liu W, Liu F, Wang Z, Ding G, Guo W, Fu Z. Magnesium lithospermate B reduces inflammatory response in a mouse model of hepatic ischemia-reperfusion injury. Cell Biochem Biophys. 2014 Jun;69(2):347-55. doi: 10.1007/s12013-013-9806-2. PubMed PMID: 24385154. 5: Quan W, Liu F, Zhang Y, Xie C, Wu B, Yin J, Wang L, Zhang W, Zhang X, Wu Q. Antidepressant-like effects of magnesium lithospermate B in a rat model of chronic unpredictable stress. Pharm Biol. 2015 Aug;53(8):1168-75. doi: 10.3109/13880209.2014.967783. Epub 2015 Apr 10. PubMed PMID: 25857699. 6: Jung YR, Kim DH, Kim SR, An HJ, Lee EK, Tanaka T, Kim ND, Yokozawa T, Park JN, Chung HY. Anti-wrinkle effect of magnesium lithospermate B from Salvia miltiorrhiza BUNGE: inhibition of MMPs via NF-kB signaling. PLoS One. 2014 Aug 6;9(8):e102689. doi: 10.1371/journal.pone.0102689. eCollection 2014. PubMed PMID: 25099178; PubMed Central PMCID: PMC4123883. 7: Quan W, Wu B, Bai Y, Zhang X, Yin J, Xi M, Guan Y, Shao Q, Chen Y, Wu Q, Wen A. Magnesium lithospermate B improves myocardial function and prevents simulated ischemia/reperfusion injury-induced H9c2 cardiomyocytes apoptosis through Akt-dependent pathway. J Ethnopharmacol. 2014;151(1):714-21. doi: 10.1016/j.jep.2013.11.036. Epub 2013 Dec 1. PubMed PMID: 24296090. 8: Jung YR, Lee EK, Kim DH, Park CH, Park MH, Jeong HO, Yokozawa T, Tanaka T, Im DS, Kim ND, Yu BP, Mo SH, Chung HY. Upregulation of Collagen Expression via PPARβ/δ Activation in Aged Skin by Magnesium Lithospermate B from Salvia miltiorrhiza. J Nat Prod. 2015 Aug 28;78(8):2110-5. doi: 10.1021/acs.jnatprod.5b00348. Epub 2015 Aug 17. PubMed PMID: 26280594. 9: Jiang X, Zhong L, Sun D, Rong L. Magnesium lithospermate B acts against dextran sodiumsulfate-induced ulcerative colitis by inhibiting activation of the NRLP3/ASC/Caspase-1 pathway. Environ Toxicol Pharmacol. 2016 Jan;41:72-7. doi: 10.1016/j.etap.2015.10.009. Epub 2015 Nov 10. PubMed PMID: 26650800. 10: Chang CZ, Wu SC, Kwan AL, Lin CL. Magnesium Lithospermate B Implicates 3'-5'-Cyclic Adenosine Monophosphate/Protein Kinase A Pathway and N-Methyl-d-Aspartate Receptors in an Experimental Traumatic Brain Injury. World Neurosurg. 2015 Oct;84(4):954-63. doi: 10.1016/j.wneu.2015.05.075. Epub 2015 Jun 18. PubMed PMID: 26093361. 11: Chung YC, Hsieh FC, Lin YJ, Wu TY, Lin CW, Lin CT, Tang NY, Jinn TR. Magnesium lithospermate B and rosmarinic acid, two compounds present in Salvia miltiorrhiza, have potent antiviral activity against enterovirus 71 infections. Eur J Pharmacol. 2015 May 15;755:127-33. doi: 10.1016/j.ejphar.2015.02.046. Epub 2015 Mar 13. PubMed PMID: 25773498. 12: Cao ZQ, Quan W, Hou SX, Guo C, Ma SB, Zhang W, Li X. The natural therapeutic magnesium lithospermate B potently provides neuroprotective effects on cerebral ischemia/reperfusion injury in rats. J Ethnopharmacol. 2015 Mar 13;162:191-8. doi: 10.1016/j.jep.2014.12.048. Epub 2015 Jan 2. PubMed PMID: 25560670. 13: Yang ZB, Luo XJ, Ren KD, Peng JJ, Tan B, Liu B, Lou Z, Xiong XM, Zhang XJ, Ren X, Peng J. Beneficial effect of magnesium lithospermate B on cerebral ischemia-reperfusion injury in rats involves the regulation of miR-107/glutamate transporter 1 pathway. Eur J Pharmacol. 2015 Nov 5;766:91-8. doi: 10.1016/j.ejphar.2015.09.042. Epub 2015 Sep 28. PubMed PMID: 26420356. 14: Chang CZ, Wu SC, Kwan AL. Magnesium lithospermate B, an active extract of Salvia miltiorrhiza, mediates sGC/cGMP/PKG translocation in experimental vasospasm. Biomed Res Int. 2014;2014:272101. doi: 10.1155/2014/272101. Epub 2014 Apr 2. Erratum in: Biomed Res Int. 2016;2016:6240750. PubMed PMID: 24804208; PubMed Central PMCID: PMC3996929. 15: Cheng CC, Yang SP, Lin WS, Ho LJ, Lai JH, Cheng SM, Lin WY. Magnesium lithospermate B mediates anti-inflammation targeting activator protein-1 and nuclear factor-kappa B signaling pathways in human peripheral T lymphocytes. Int Immunopharmacol. 2012 Jul;13(3):354-61. doi: 10.1016/j.intimp.2012.04.011. Epub 2012 May 6. PubMed PMID: 22569344. 16: Chen YJ, Chung TY, Chen WY, Chen CY, Lee MR, Jinn TR, Tc Tzen J. Detecting metabolites of different transition metal-lithospermate B complexes after intravenous injection in rats. Acta Pharmacol Sin. 2014 Jul;35(7):937-44. doi: 10.1038/aps.2014.37. PubMed PMID: 24989253; PubMed Central PMCID: PMC4088287. 17: Xiao G, Hu W, Chen X. Magnesium lithospermate B protects neurons from N-methyl-D-aspartic acid injury and attenuates kainic acid-induced neurodegeration in FVB mice. J Mol Neurosci. 2013 Oct;51(2):550-7. doi: 10.1007/s12031-013-0023-7. Epub 2013 May 3. PubMed PMID: 23640537. 18: Quan W, Yin Y, Xi M, Zhou D, Zhu Y, Guan Y, Guo C, Wang Y, Duan J, Wen A. Antioxidant properties of magnesium lithospermate B contribute to the cardioprotection against myocardial ischemia/reperfusion injury in vivo and in vitro. J Tradit Chin Med. 2013 Feb;33(1):85-91. PubMed PMID: 23596818. 19: Lin NH, Chung TY, Li FY, Chen HA, Tzen JT. Enhancing the potency of lithospermate B for inhibiting Na+/K+-ATPase activity by forming transition metal ion complexes. Acta Pharmacol Sin. 2013 Jul;34(7):893-900. doi: 10.1038/aps.2013.32. Epub 2013 May 20. PubMed PMID: 23685954; PubMed Central PMCID: PMC4002613. 20: Paik YH, Yoon YJ, Lee HC, Jung MK, Kang SH, Chung SI, Kim JK, Cho JY, Lee KS, Han KH. Antifibrotic effects of magnesium lithospermate B on hepatic stellate cells and thioacetamide-induced cirrhotic rats. Exp Mol Med. 2011 Jun 30;43(6):341-9. PubMed PMID: 21499011; PubMed Central PMCID: PMC3128912.

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