A tannin with diverse biological activities
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Geraniin

Item No. 29924

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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), β-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(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $130

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    10 mg

    $236

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    50 mg

    $1,053

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    Cayman Chemical
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    Product Description

    Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities.1,2,3 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.1 Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC50s = 35 and 18.4 μM, respectively).2 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.1 Geraniin (5, 10, and 20 μM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells.3 It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, S.-Y., Wang, C.-C., Lu, Y.-L., et al. Antioxidant, anti-semicarbazide-sensitive amine oxidase, and anti-hypertensive activities of geraniin isolated from Phyllanthus urinaria. Food Chem. Toxicol. 46, 2485-2492 (2008).

    2. Yang, C.-M., Cheng, H.-Y., Lin, T.-C., et al. The in vitro activity of geraniin and 1,3,4,6-tetra-O-galloyl-β-D-glucose isolated from Phyllanthus urinaria against herpes simplex virus type 1 and type 2 infection. J. Ethnopharmacol. 110(3), 555-558 (2007).

    3. Li, J., Wang, S., Yin, J., et al. Geraniin induces apoptotic cell death in human lung adenocarcinoma A549 cells in vitro and in vivo. Can. J. Physiol. Pharmacol. 91(12), 1016-1024 (2013).