Lithospermic Acid

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 (Cay-14805) 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, Cay-10008014) 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.Formal Name: (2S,3S)-4-[(1E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxo-1-propen-1-yl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-3-benzofurancarboxylic acid. CAS Number: 28831-65-4. Synonyms: (+)-Lithospermic Acid, Lithospermic Acid A. Molecular Formula: C27H22O12. Formula Weight: 538.5. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 30 mg/ml, PBS (pH 7.2): 5 mg/ml. SMILES: O=C(O[C@@H](C(O)=O)CC(C=C1)=CC(O)=C1O)/C=C/C(C=C2)=C3C(O[C@H](C4=CC=C(O)C(O)=C4)[C@H]3C(O)=O)=C2O. 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. InChi Key: UJZQBMQZMKFSRV-RGKBJLTCSA-N. Origin: Plant/Salvia miltiorrhiza root.