A coumarin with anticancer activity
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Marmesin

Item No. 25049

Technical Information
Formal Name
(2S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
13849-08-6
Synonyms
  • (+)-Marmesin
  • (S)-Marmesin
  • NSC 340840
Molecular Formula
C14H14O4
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 50 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 2 mg/ml
λmax
224, 336 nm
SMILES
O=C(C=C1)OC2=C1C=C(C[C@@H](C(O)(C)C)O3)C3=C2
InChi Code
InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m0/s1
InChi Key
FWYSBEAFFPBAQU-LBPRGKRZSA-N
Origin
Plant/Angelica citriodora Hance
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Marmesin is a coumarin originally isolated from the mature bark of A. marmelos.1 Marmesin decreases proliferation and cell invasion induced by fetal bovine serum (FBS) in H1299 non-small cell lung cancer cells (NSCLCs) when used at a concentration of 10 µM.2 It decreases VEGF secretion in A549 and H1299 cells and inhibits capillary-like structure formation by human umbilical vein endothelial cells (HUVECs). Marmesin also decreases proliferation of U937 human leukemia cells (IC50 = 40 µM).3 It halts the cell cycle at the G2/M phase, increases the ratio of Bax to Bcl-2 protein, induces apoptosis, and inhibits cell migration. Marmesin reduces tumor growth in a U937 mouse xenograft model when administered at a dose of 30 mg/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chatterjee, A., and Mitra, S.S. On the constitution of the active principles isolated from the mature bark of Aegle marmelos, Correâ. J. Am. Chem. Soc. 71(2), 606-609 (1949).

    2. Kim, J.H., Kim, M.S., Lee, B.H., et alMarmesin-mediated suppression of VEGF/VEGFR and integrin β1 expression: Its implication in non-small cell lung cancer cell responses and tumor angiogenesis. Oncol. Rep. 37(1), 91-97 (2017).

    3. Dong, L., Xu, W.W., Li, H., et alIn vitro and in vivo anticancer effects of marmesin in U937 human leukemia cells are mediated via mitochondrial-mediated apoptosis, cell cycle arrest, and inhibition of cancer cell migration. Oncol. Rep. 39(2), 597-602 (2018).