A cyclized isoflavonoid with anti-inflammatory and antiallergenic activities
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Maackiain

Item No. 40215

Technical Information
Formal Name
6aR,12aR-dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-ol
CAS Number
2035-15-6
Synonyms
  • (–)-Maackiain
  • Trifolirhizin aglycone
Molecular Formula
C16H12O5
Formula Weight
Purity
≥95%
A solid
Acetonitrile: SolubleChloroform: Soluble
SMILES
OC1=CC=C([C@@]2([H])[C@](CO3)([H])C4=CC(OCO5)=C5C=C4O2)C3=C1
InChi Code
InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m0/s1
InChi Key
HUKSJTUUSUGIDC-ZBEGNZNMSA-N
Origin
Plant/Sophora flavescens Ait.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Maackiain is a cyclized isoflavonoid that has been found in S. flavescens and has anti-inflammatory and antiallergenic activities.1,2,3 It inhibits increases in the levels of mRNA encoding the histamine H1 receptor induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in serum-starved HeLa cells when used at concentrations of 10, 20, or 30 µM and inhibits PMA-induced increases in the levels of mRNA encoding Il-4 in RBL-2H3 cells at 50 or 150 µM.1 Maackiain decreases LPS-induced increases in nitric oxide (NO) production in RAW 264.7 macrophages (IC50 = 27 µM).2 It increases survival in a mouse model of sepsis induced by cecal ligation and puncture (CLP) when administered at doses of 2.5 or 5 mg/kg.3 Maackiain (20 mg/kg per day) reduces the number of sneezes and the extent of nasal redness, swelling, and watery rhinorrhea in a rat model of allergies induced by toluene-2,4-diisocyanate (TDI).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mizuguchi, H., Nariai, Y., Kato, S., et alMaackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes. Pharmacol. Res. Perspect. 3(5), e00166 (2015).

    2. Lee, J.W., Lee, J.H., Lee, C., et alInhibitory constituents of Sophora tonkinensis on nitric oxide production in RAW 264.7 macrophages. Bioorg. Med. Chem. Lett. 25(4), (2015).

    3. Bai, X., Zhu, Y., Jie, J., et alMaackiain protects against sepsis via activating AMPK/Nrf2/HO-1 pathway. Int. Immunopharmacol. 108, 108710 (2022).