A pyranocoumarin with diverse biological activities
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(+)-Praeruptorin B

Item No. 37536

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2Z,2′Z)-2-methyl-2-butenoic acid, (9S,10S)-9,10-dihydro-8,8-dimethyl-2-oxo-2H,8H-benzo[1,2-b:3,4-b′]dipyran-9,10-diyl ester
CAS Number
73069-28-0
Synonyms
  • (+)-Anomalin
Molecular Formula
C24H26O7
Formula Weight
426.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/ml
SMILES
C/C=C(C)\C(O[C@H]1C2=C(OC(C)([C@H]1OC(/C(C)=C\C)=O)C)C=CC(C=C3)=C2OC3=O)=O
InChi Code
InChI=1S/C24H26O7/c1-7-13(3)22(26)29-20-18-16(11-9-15-10-12-17(25)28-19(15)18)31-24(5,6)21(20)30-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7-,14-8-/t20-,21-/m0/s1
InChi Key
PNTWXEIQXBRCPS-UWOGZXHISA-N
Origin
Plant/Peucedanum praeruptorum Dunn
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    50 mg

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    Product Description

    (+)-Praeruptorin B is a pyranocoumarin that has been found in P. praeruptorum and has diverse biological activities.1,2,3,4 It inhibits RANKL-induced osteoclastogenesis of primary mouse bone marrow-derived macrophages (BMDMs) when used at a concentration of 10 µM and LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages at 100 µM.2,1 (+)-Praeruptorin B inhibits platelet aggregation induced by platelet-activating factor (PAF) in isolated rabbit platelet-rich plasma (IC50 = 50 µM) and contractions of isolated guinea pig ileum induced by histamine (Item No. 22328) or leukotriene D4 (pD2s = 4.84 and 4.34, respectively).3 It decreases ovariectomy-induced bone loss in a mouse model of osteoporosis when administered at a dose of 10 mg/kg. (+)-Praeruptorin B (10 µmol/animal) reduces the number of tumors initiated by 7,12-dimethylbenz[a]anthracene (DMBA; Item No. 30383) and promoted by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in a mouse two-stage model of skin carcinogenesis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, J., Lee, Y.J., Kim, J., et al. Pyranocoumarins from root extracts of Peucedanum praeruptorum Dunn with multidrug resistance reversal and anti-inflammatory activities. Molecules 20(12), 20967-20978 (2015).

    2. Xu, K., Chen, Z., Hou, J., et al. Praeruptorin B inhibits osteoclastogenesis by targeting GSTP1 and impacting on the S-glutathionylation of IKKβ. Biomed. Pharmacother. 154, 113529 (2022).

    3. Aida, Y., Kasama, T., Takeuchi, N., et al. The antagonistic effects of khellactones on platelet-activating factor, histamine, and leukotriene D4. Chem. Pharm. Bull. (Tokyo) 43(5), 859-867 (1995).

    4. Nishino, H., Okuyama, T., Takata, M., et al. Studies on the anti-tumor-promoting activity of naturally occurring substances. IV. Pd-II [(+)anomalin, (+)praeruptorin B], a seselin-type coumarin, inhibits the promotion of skin tumor formation by 12-O-tetradecanoylphorbol-13-acetate in 7,12-dimethylbenz[a]anthracene-initiated mice. Carcinogenesis 11(9), 1557-1561 (1990).