A chromone with diverse biological activities
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5-O-Methylvisammioside

Item No. 39250

Technical Information
Formal Name
(2S)-2-[1-(β-D-glucopyranosyloxy)-1-methylethyl]-2,3-dihydro-4-methoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
CAS Number
84272-85-5
Synonyms
  • 4′-O-β-D-glucosyl-5-O-Methylvisamminol
Molecular Formula
C22H28O10
Formula Weight
Purity
≥98%
A solid
Acetonitrile: SolubleMethanol: Soluble
SMILES
COC1=C(C[C@H]2C(C)(C)O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]([C@H]3O)CO)C(O2)=CC(OC(C)=C4)=C1C4=O
InChi Code
InChI=1S/C22H28O10/c1-9-5-11(24)16-13(29-9)7-12-10(20(16)28-4)6-15(30-12)22(2,3)32-21-19(27)18(26)17(25)14(8-23)31-21/h5,7,14-15,17-19,21,23,25-27H,6,8H2,1-4H3/t14-,15+,17-,18+,19-,21+/m1/s1
InChi Key
QVGFPTYGKPLXPK-OOBAEQHESA-N
Origin
Plant/Saposhnikovia divaricata (Turcz.) Schischk
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    5-O-Methylvisammioside is a chromone that has been found in S. diviaricata and has diverse biological activities.1,2,3,4 It inhibits the protein-protein interaction between histone H3 and 14-3-3ε and phosphorylation of histone H3, as well as induces cell cycle arrest at the G2/M phase, in HT-29 colon cancer cells when used at a concentration of 10 µM.1 5-O-Methylvisammioside (10-100 µM) inhibits histamine release induced by the mast cell degranulator compound 48/80 (Item No. 22173) in LAD 2 mast cells.2 It reduces LPS-induced increases in nitric oxide (NO), malondialdehyde (MDA), and nuclear NF-κB levels in BV-2 microglia and decreases immobility time in the tail suspension and forced swim tests in mice.3 5-O-Methylvisammioside (400 µg/kg) inhibits perivascular adventitia leukocyte infiltration and improves neurological deficits in a rat model of subarachnoid hemorrhage-induced vasospasm.4 It has been used as a quality control marker of S. diviaricata roots.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kang, J.-S., Chin, Y.-W., Lee, K., et alIdentification of 4'-O-β-D-glucosyl-5-O-methylvisamminol as a novel epigenetic suppressor of histone H3 phosphorylation at Ser10 and its interaction with 14-3-. Bioorg. Med. Chem. Lett. 24(19), 4763-4767 (2014).

    2. Jia, Q., Sun, W., Zhang, L., et alScreening the anti-allergic components in Saposhnikoviae Radix using high-expression Mas-related G protein-coupled receptor X2 cell membrane chromatography online coupled with liquid chromatography and mass spectrometry. J. Sep. Sci. 42(14), 2351-2359 (2019).

    3. Sun, X., Zhang, T., Zhao, Y., et alThe protective effect of 5-O-methylvisammioside on LPS-induced depression in mice by inhibiting the over activation of BV-2 microglia through Nf-κB/IκB-α pathway. Phytomedicine 79:153348, (2020).

    4. Chang, C.-Z., Wu, S.-C., Kwan, A.-L., et al4'-O-β-D-glucosyl-5-O-methylvisamminol, an active ingredient of Saposhnikovia divaricata, attenuates high-mobility group box 1 and subarachnoid hemorrhage-induced vasospasm in a rat model. Behav. Brain Funct. 11(1), 28 (2015).

    5. Yang, J.-M., Jiang, H., Dai, H.-L., et alFeeble antipyretic, analgesic, and anti-inflammatory activities were found with regular dose 4'-O-β-D-glucosyl-5-O-methylvisamminol, one of the conventional marker compounds for quality evaluation of Radix Saposhnikoviae. Pharmacogn. Mag. 13(49), 168-174 (2017).