A lignan with diverse biological activities
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Lirioresinol B dimethyl ether

Item No. 44937

Technical Information
Formal Name
(1S,3aR,4S,6aR)-tetrahydro-1,4-bis(3,4,5-trimethoxyphenyl)-1H,3H-furo[3,4-c]furan
CAS Number
13060-14-5
Synonyms
  • LBDE
  • (+)-Yangambin
Molecular Formula
C24H30O8
Formula Weight
Purity
≥98%
A solid
Acetonitrile: Slightly soluble: 0.1-1 mg/mlDMSO: Slightly soluble: 0.1-1 mg/ml
SMILES
COC1=C(OC)C=C([C@H]2OC[C@@]3([C@H](OC[C@@]32[H])C4=CC(OC)=C(OC)C(OC)=C4)[H])C=C1OC
InChi Code
InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3/t15-,16-,21+,22+/m0/s1
InChi Key
HRLFUIXSXUASEX-RZTYQLBFSA-N
Origin
Plant/Polygala japonica Houtt.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Lirioresinol B dimethyl ether is a lignan originally isolated from L. tulipifera that has diverse biological activities.1,2,3,4 It scavenges DPPH (Item No. 14805) radicals in a cell-free assay (IC50 = 110.9 µM) and reduces the levels of NF-κB and COX-2 in HepG2 hepatocellular carcinoma cells when used at a concentration of 40 µM.2 Lirioresinol B dimethyl ether (50 mg/kg per day) also reduces intratumoral levels of NF-κB and COX-2 in a mouse model of hepatocellular carcinoma induced by carbon tetrachloride (CCl4) and diethylnitrosamine (DEN). It reduces liver damage and improves hepatic function in mice in the same model. Lirioresinol B dimethyl ether (40 and 80 µM) reduces the production of parathyroid hormone-related protein (PTHrP) in MDA-MB-231 breast cancer cells and inhibits RANKL-induced differentiation of bone marrow-derived macrophages (BMDMs; IC50 = 8.88 µM).3 Lirioresinol B dimethyl ether is also active against L. amazonensis and L. braziliensis intracellular amastigotes (IC50s = 43.9 and 76 µM, respectively).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dickey, E.E. Liriodendrin, a new lignan diglucoside from the inner bark of yellow poplar (Liriodendron tulipifera L.). The Journal of Organic Chemistry 23(2), 179-184 (1958).

    2. Shehzad, A., Rehmat, S., Ul-Islam, S., et alLirioresinol B dimethyl ether inhibits NF-κB and COX-2 and activates IκBα expression in CCl4-induced hepatic fibrosis. BMC Complement Med. Ther. 20(1), 49 (2020).

    3. Jun, A.Y., Kim, H.-J., Park, K.-K., et alTetrahydrofurofuran-type lignans inhibit breast cancer-mediated bone destruction by blocking the vicious cycle between cancer cells, osteoblasts and osteoclasts. Invest. New Drugs 32(1), 1-13 (2014).

    4. Rebouças-Silva, J., Santos, G.F., Filho, J.M.B., et alIn vitro leishmanicidal effect of Yangambin and Epi-yangambin lignans isolated from Ocotea fasciculata (Nees) Mez. Front Cell. Infect. Microbiol. 12, 1045732 (2022).