A lignan with diverse biological activities
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(+)-Pinoresinol

Item No. 27700

Technical Information
Formal Name
4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-phenol
CAS Number
487-36-5
Synonyms
  • NSC 35444
Molecular Formula
C20H22O6
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:1): 0.50 mg/mlDMSO: 1 mg/mlEthanol: 1 mg/ml
λmax
233, 278, 328 nm
SMILES
OC(C=C1)=C(OC)C=C1[C@@H]2[C@@]3([H])CO[C@H](C4=CC(OC)=C(O)C=C4)[C@@]3([H])CO2
InChi Code
InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19+,20+/m0/s1
InChi Key
HGXBRUKMWQGOIE-AFHBHXEDSA-N
Origin
Plant/Eucommia ulmoides Oliver
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    (+)-Pinoresinol is a lignan that has been found in Forsythia and virgin olive oils and has diverse biological activities, including antioxidant, anticancer, and anti-inflammatory properties.1,2,3,4 It is an inhibitor of α-glucosidase and maltase (IC50s = 492 and 34.3 µM in Baker’s yeast and rat small intestine, respectively).3 (+)-Pinoresinol scavenges ABTS (Item No. 27317), but not 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805), radicals in cell-free assays (IC50s = 13.43 and >200 µg/ml, respectively).2 It is cytotoxic to A549, HepG2, and MCF-7, but not U251 and Bcap-37, cells with IC50 values of 29.35, 62.35, 75.32, >80, and >80 µM, respectively. (+)-Pinoresinol prevents cell death induced by glutamate in HT22 cells (EC50 = 6.96 µM) and inhibits LPS-induced nitric oxide production in RAW 264.7 cells (IC50 = 7.89 µM).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. López-Biedma, A., Sánchez-Quesada, C., Delgado-Rodríguez, M., et alThe biological activities of natural lignans from olives and virgin olive oils: A review. J. Funct. Foods 26, 36-47 (2016).

    2. Li, D.-Q., Wang, D., Zhou, L., et alAntioxidant and cytotoxic lignans from the roots of Bupleurum chinense. J. Asian Nat. Prod. Res. 19(5), 519-527 (2017).

    3. Wikul, A., Damsud, T., Kataoka, K., et al(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase. Bioorg. Med. Chem. Lett. 22(16), 5215-5217 (2012).

    4. In, S.-J., Seo, K.-H., Song, N.-Y., et alLignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity. Arch. Pharm. Res. 38(1), 26-34 (2015).