A flavonolignan with diverse biological activities
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Silydianin

Item No. 39248

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,3aR,6R,7aR,8R)-4-[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-4-oxo-2H-1-benzopyran-2-yl]-2,3,3a,7a-tetrahydro-7a-hydroxy-8-(4-hydroxy-3-methoxyphenyl)-3,6-methanobenzofuran-7(6H)-one
CAS Number
29782-68-1
Synonyms
  • Silidianin
Molecular Formula
C25H22O10
Formula Weight
482.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleMethanol: Soluble
SMILES
O[C@@]12[C@]3([H])[C@@](CO2)([H])[C@@H](C4=CC(OC)=C(C=C4)O)[C@@](C1=O)([H])C=C3[C@H]5OC6=CC(O)=CC(O)=C6C([C@@H]5O)=O
InChi Code
InChI=1S/C25H22O10/c1-33-16-4-9(2-3-14(16)27)18-11-7-12(20-13(18)8-34-25(20,32)24(11)31)23-22(30)21(29)19-15(28)5-10(26)6-17(19)35-23/h2-7,11,13,18,20,22-23,26-28,30,32H,8H2,1H3/t11-,13-,18+,20+,22+,23-,25-/m1/s1
InChi Key
CYGIJEJDYJOUAN-JSGXPVSSSA-N
Origin
Plant/Silybum marianum (L.) Gaertn
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $43

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    5 mg

    $172

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    10 mg

    $280

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    25 mg

    $590

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    Product Description

    Silydianin is a flavonolignan that has been found in S. marianum and has diverse biological activities.1,2,3,4 It inhibits tyrosinase (IC50 = 2.6 µM for the mushroom enzyme) and scavenges DPPH (Item No. 14805) radicals in a cell-free assay (IC50 = 66.8 µM).1,2 Silydianin (100 µM) protects against cytotoxicity induced by allyl alcohol, carbon tetrachloride, paracetamol (acetaminophen; Item No. 10024), or D-galactosamine (Item No. 22981) in primary human hepatocytes.2 It inhibits the proliferation of DU145 and PC3 prostate cancer cells when used at a concentration of 90 µM.3 Silydianin (1%) prevents methacholine-induced airway hyperresponsiveness (AHR) and reduces blood and bronchoalveolar lavage fluid (BALF) levels of eosinophils in an ovalbumin-sensitized mouse model of allergic asthma when administered via inhalation.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kim, J.Y., Kim, J.Y., Jenis, J., et al. Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle). Bioorg. Med. Chem. 27(12), 2499-2507 (2019).

    2. Dvorák, Z., Kosina, P., Walterová, D., et al. Primary cultures of human hepatocytes as a tool in cytotoxicity studies: Cell protection against model toxins by flavonolignans obtained from Silybum marianum. Toxicol. Lett. 137(3), 201-2012 (2003).

    3. Davis-Searles, P.R., Nakanishi, Y., Kim, N.C., et al. Milk thistle and prostate cancer: Differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells. Cancer Res. 65(10), 4448-4457 (2005).

    4. Nasab, E.M., Athari, S.M., Ghafarzade, S., et al. Immunomodulatory effects of two silymarin isomers in a Balb/c mouse model of allergic asthma. Allergol. Immunopathol. (Madr) 48(6), 646-653 (2020).