Lithospermic acid | CAS#28831-65-4 | Biologically diverse polyphenol

MedKoo Cat#: 599019 | Name: Lithospermic acid

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Description:

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

Lithospermic acid is a polyphenol that has been found in S. miltiorrhiza and has diverse biological activities. It inhibits xanthine oxidase (IC50 = 5.2 µg/ml) and scavenges DPPH radicals in cell-free assays (IC50 = 23.2 µg/ml). It also inhibits the production of reactive oxygen species (ROS) induced by phorbol 12-myristate 13-acetate (PMA) in isolated human neutrophils in a concentration-dependent manner. Lithospermic acid inhibits 3'-processing and 3'-joining to target DNA by HIV-1 integrase in cell-free assays (IC50s = 0.83 and 0.48 µM, respectively). It also inhibits acute HIV-1 infection of H9 human lymphoma cells (IC50 = 2 µM) without inducing cytotoxicity. Lithospermic acid (100 mg/kg) prevents carbon tetrachloride-induced hepatic necrosis in mice.

Chemical Structure

Lithospermic acid

CAS#28831-65-4

Theoretical Analysis

MedKoo Cat#: 599019

Name: Lithospermic acid

CAS#: 28831-65-4

Chemical Formula: C27H22O12

Exact Mass: 538.1111

Molecular Weight: 538.46

Elemental Analysis: C, 60.23; H, 4.12; O, 35.65

Price and Availability

Size	Price	Availability
10mg	USD 285.00	2 Weeks
25mg	USD 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
250mg	USD 2,450.00	2 Weeks

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Synonym

Lithospermic acid; (+)-Lithospermic Acid; (+) Lithospermic Acid; Lithospermic Acid A; Lithospermic Acid-A;

IUPAC/Chemical Name

(2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy)-3-oxoprop-1-en-1-yl)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carboxylic acid

InChi Key

UJZQBMQZMKFSRV-RGKBJLTCSA-N

InChi Code

InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4+/t20-,23+,24-/m1/s1

SMILES Code

O=C([C@@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=C(O)C=CC(/C=C/C(O[C@@H](C(O)=O)CC4=CC=C(O)C(O)=C4)=O)=C13)O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lithospermic acid ((+)-Lithospermic acid) is a plant-derived polycyclic phenolic carboxylic acid isolated from Salvia miltiorrhiza, and has the anti-oxidative and hepatoprotective activity on carbon tetrachloride (CCl4)-induced acute liver damage in vitro and in vivo.

In vitro activity:

To further explore the role of LA (lithospermic acid) in H9C2 cells, in vitro experiments were performed with the HR model (Supplementary Figure S3). In addition, LA attenuated HR-induced upregulation of GP91 and p67 phox and triggered the transcription of SOD2 in H9C2 cells (Supplementary Figure S4). Reference: Front Pharmacol. 2021 Nov 26;12:794982. https://pubmed.ncbi.nlm.nih.gov/34899356/

In vivo activity:

LA (lithospermic acid) reduced HBV DNA, HBsAg/HBeAg, and HBcAg levels in the serum/liver tissues of HBV-HDI C57BL/6 mice during the 3-week treatment and suppressed the withdrawal rebound of HBV DNA and HBsAg in the mice serum. LA inhibited the activation of AKT and mammalian target of rapamycin (mTOR) induced by HBV, which was reversed by IGF-1 (an agonist of the PI3K/AKT/mTOR signaling pathway), indicating that LA elicited autophagy through hampering the PI3K/AKT/mTOR signaling pathway. Reference: J Ethnopharmacol. 2023 Feb 10;302(Pt A):115896. https://pubmed.ncbi.nlm.nih.gov/36334815/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	55.71
	DMSO	30.0	55.71
	Ethanol	30.0	55.71
	PBS (pH 7.2)	5.0	9.29
	Water	66.7	123.82

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 538.46 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.

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

Formulation protocol:

1. Zhang M, Wei L, Xie S, Xing Y, Shi W, Zeng X, Chen S, Wang S, Deng W, Tang Q. Activation of Nrf2 by Lithospermic Acid Ameliorates Myocardial Ischemia and Reperfusion Injury by Promoting Phosphorylation of AMP-Activated Protein Kinase α (AMPKα). Front Pharmacol. 2021 Nov 26;12:794982. doi: 10.3389/fphar.2021.794982. PMID: 34899356; PMCID: PMC8661697. 2. Chan KW, Ho WS. Anti-oxidative and hepatoprotective effects of lithospermic acid against carbon tetrachloride-induced liver oxidative damage in vitro and in vivo. Oncol Rep. 2015 Aug;34(2):673-80. doi: 10.3892/or.2015.4068. Epub 2015 Jun 16. PMID: 26081670. 3. Zhu S, Wen H, Wang W, Chen Y, Han F, Cai W. Anti-hepatitis B virus activity of lithospermic acid, a polyphenol from Salvia miltiorrhiza, in vitro and in vivo by autophagy regulation. J Ethnopharmacol. 2023 Feb 10;302(Pt A):115896. doi: 10.1016/j.jep.2022.115896. Epub 2022 Nov 2. PMID: 36334815. 4. Lin YL, Tsay HJ, Lai TH, Tzeng TT, Shiao YJ. Lithospermic acid attenuates 1-methyl-4-phenylpyridine-induced neurotoxicity by blocking neuronal apoptotic and neuroinflammatory pathways. J Biomed Sci. 2015 May 28;22(1):37. doi: 10.1186/s12929-015-0146-y. PMID: 26018660; PMCID: PMC4445499.

In vitro protocol:

In vivo protocol:

1. Zhu S, Wen H, Wang W, Chen Y, Han F, Cai W. Anti-hepatitis B virus activity of lithospermic acid, a polyphenol from Salvia miltiorrhiza, in vitro and in vivo by autophagy regulation. J Ethnopharmacol. 2023 Feb 10;302(Pt A):115896. doi: 10.1016/j.jep.2022.115896. Epub 2022 Nov 2. PMID: 36334815. 2. Lin YL, Tsay HJ, Lai TH, Tzeng TT, Shiao YJ. Lithospermic acid attenuates 1-methyl-4-phenylpyridine-induced neurotoxicity by blocking neuronal apoptotic and neuroinflammatory pathways. J Biomed Sci. 2015 May 28;22(1):37. doi: 10.1186/s12929-015-0146-y. PMID: 26018660; PMCID: PMC4445499.

1: Lin YL, Tsay HJ, Lai TH, Tzeng TT, Shiao YJ. Lithospermic acid attenuates 1-methyl-4-phenylpyridine-induced neurotoxicity by blocking neuronal apoptotic and neuroinflammatory pathways. J Biomed Sci. 2015 May 28;22:37. doi: 10.1186/s12929-015-0146-y. PubMed PMID: 26018660; PubMed Central PMCID: PMC4445499. 2: Xiuli W, Wei G, Mao S. Pharmacokinetic investigation on interaction between hydrophilic lithospermic acid B and lipophilic tanshinone IIA in rats: an experi- mental study. J Tradit Chin Med. 2015 Apr;35(2):206-10. PubMed PMID: 25975054. 3: Chan KW, Ho WS. Anti-oxidative and hepatoprotective effects of lithospermic acid against carbon tetrachloride-induced liver oxidative damage in vitro and in vivo. Oncol Rep. 2015 Aug;34(2):673-80. doi: 10.3892/or.2015.4068. Epub 2015 Jun 16. PubMed PMID: 26081670. 4: Murata T, Oyama K, Fujiyama M, Oobayashi B, Umehara K, Miyase T, Yoshizaki F. Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon. Fitoterapia. 2013 Dec;91:51-59. doi: 10.1016/j.fitote.2013.08.009. Epub 2013 Aug 23. PubMed PMID: 23978578. 5: Li Y, Guo ZT, Gong XC, Qu HB. [Simultaneous determination of danshensu, hydroxysafflor yellow A, rosmarinic acid, lithospermic acid, salvianolic acid B in water extract of mixed salviae miltiorrhizae radix et rhizoma and carthami flos by HPLC]. Zhongguo Zhong Yao Za Zhi. 2013 Jun;38(11):1653-6. Chinese. PubMed PMID: 24010270. 6: Jin CJ, Yu SH, Wang XM, Woo SJ, Park HJ, Lee HC, Choi SH, Kim KM, Kim JH, Park KS, Jang HC, Lim S. The effect of lithospermic acid, an antioxidant, on development of diabetic retinopathy in spontaneously obese diabetic rats. PLoS One. 2014 Jun 6;9(6):e98232. doi: 10.1371/journal.pone.0098232. eCollection 2014. PubMed PMID: 24905410; PubMed Central PMCID: PMC4048190. 7: Varadaraju TG, Hwu JR. Synthesis of anti-HIV lithospermic acid by two diverse strategies. Org Biomol Chem. 2012 Jul 28;10(28):5456-65. doi: 10.1039/c2ob25575h. Epub 2012 Jun 6. PubMed PMID: 22669348. 8: Ozturk H, Terzi EH, Ozgen U, Duran A, Ozturk H. Lithospermic acid and ischemia/reperfusion injury of the rat small intestine prevention. Adv Clin Exp Med. 2012 Jul-Aug;21(4):433-9. PubMed PMID: 23240448. 9: Guo YX, Shi CZ, Zhang L, Lv L, Zhang YY. Extraction and isolation of lithospermic acid B from Salvia miltiorrhiza Bunge using aqueous two-phase extraction followed by high-performance liquid chromatography. J Sep Sci. 2016 Sep;39(18):3624-30. doi: 10.1002/jssc.201600368. Epub 2016 Sep 6. PubMed PMID: 27484287. 10: Wang Y, Zhu J, Fu S, Zhu L, Zhang Y. [Study on chemical changes of salvianolic acid B and lithospermic acid aqueous under conditions of high temperature and high pressure]. Zhongguo Zhong Yao Za Zhi. 2011 Feb;36(4):434-8. Chinese. PubMed PMID: 21598535. 11: Pan J, Gong X, Qu H. Degradation Kinetics and Mechanism of Lithospermic Acid under Low Oxygen Condition Using Quantitative 1H NMR with HPLC-MS. PLoS One. 2016 Oct 24;11(10):e0164421. doi: 10.1371/journal.pone.0164421. eCollection 2016. PubMed PMID: 27776128; PubMed Central PMCID: PMC5077101. 12: Liu X, Chen R, Shang Y, Jiao B, Huang C. Lithospermic acid as a novel xanthine oxidase inhibitor has anti-inflammatory and hypouricemic effects in rats. Chem Biol Interact. 2008 Nov 25;176(2-3):137-42. doi: 10.1016/j.cbi.2008.07.003. Epub 2008 Jul 23. PubMed PMID: 18694741. 13: Wang L, Zhang Q, Li X, Lu Y, Xue Z, Xuan L, Wang Y. Pharmacokinetics and metabolism of lithospermic acid by LC/MS/MS in rats. Int J Pharm. 2008 Feb 28;350(1-2):240-6. Epub 2007 Sep 6. PubMed PMID: 17936527. 14: Ghosh AK, Cheng X, Zhou B. Enantioselective total synthesis of (+)-lithospermic acid. Org Lett. 2012 Oct 5;14(19):5046-9. doi: 10.1021/ol302273r. Epub 2012 Sep 14. PubMed PMID: 22978790; PubMed Central PMCID: PMC3482163. 15: Fischer J, Savage GP, Coster MJ. A concise route to dihydrobenzo[b]furans: formal total synthesis of (+)-lithospermic acid. Org Lett. 2011 Jul 1;13(13):3376-9. doi: 10.1021/ol201130h. Epub 2011 Jun 7. PubMed PMID: 21648396. 16: Li X, Yu C, Sun W, Liu G, Jia J, Wang Y. Simultaneous determination of magnesium lithospermate B, rosmarinic acid, and lithospermic acid in beagle dog serum by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(23):2878-82. PubMed PMID: 15517529. 17: Kim GD, Park YS, Jin YH, Park CS. Production and applications of rosmarinic acid and structurally related compounds. Appl Microbiol Biotechnol. 2015 Mar;99(5):2083-92. doi: 10.1007/s00253-015-6395-6. Epub 2015 Jan 27. Review. PubMed PMID: 25620368. 18: Thuong PT, Kang KW, Kim JK, Seo DB, Lee SJ, Kim SH, Oh WK. Lithospermic acid derivatives from Lithospermum erythrorhizon increased expression of serine palmitoyltransferase in human HaCaT cells. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1815-7. doi: 10.1016/j.bmcl.2009.01.052. Epub 2009 Jan 22. PubMed PMID: 19217780. 19: Watzke A, O'Malley SJ, Bergman RG, Ellman JA. Reassignment of the configuration of salvianolic acid B and establishment of its identity with lithospermic acid B. J Nat Prod. 2006 Aug;69(8):1231-3. PubMed PMID: 16933885. 20: Nagai M, Noguchi M, Iizuka T, Otani K, Kamata K. Vasodilator effects of des(alpha-carboxy-3,4-dihydroxyphenethyl)lithospermic acid (8-epiblechnic acid), a derivative of lithospermic acids in salviae miltiorrhizae radix. Biol Pharm Bull. 1996 Feb;19(2):228-32. PubMed PMID: 8850312.