Geraniin

Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH, IC50s = 0.92 and 1.27 µM at pH 4.5 and 7.9, respectively), superoxide (IC50 = 2.65 µM), and hydroxyl radicals (IC50 = 1.44 µM) in cell-free assays. Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC50s = 35 and 18.4 µM, respectively). It inhibits angiotensin-converting enzyme (ACE) in vitro (IC50 = 13.22 µM) and reduces both systolic and diastolic blood pressure in spontaneously hypertensive rats when administered at a dose of 5 mg/kg. Geraniin (5, 10, and 20 µM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg.Formal Name: cyclic 2->7:4->5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate) cyclic 3,6-(4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-dicarboxylate) 1-(3,4,5-trihydroxybenzoate), beta-D-glucopyranose, stereoisomer. CAS Number: 60976-49-0. Synonyms: NSC 359346. Molecular Formula: C41H28O27. Formula Weight: 952.6. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 30 mg/ml, Ethanol:PBS (pH 7.2) (1:3): 0.25 mg/ml. lambdamax: 226, 280 nm. SMILES: OC1(C(C(C2=O)=CC3=O)C(C(OC13O)=C4O)=C(C=C4O)C(O[C@H](C5OC(C(C=C6O)=CC(O)=C6O)=O)[C@H](OC(C(C(C7=C8O)=C9O)=CC(O)=C9O)=O)[C@H]([C@H](COC(C7=CC(O)=C8O)=O)O5)O2)=O)O. InChi Code: InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2/t18-,23?,30-,32+,33-,39?,41?/m0/s1. InChi Key: JQQBXPCJFAKSPG-ZGTATTRASA-N. Origin: Plant/Phyllanthus urinaria.