A lignan with diverse biological activities
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Sauchinone

Item No. 19577

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5aR,7R,8S,8aR,14aS,14bR)-5a,6,7,8,8a,14b-hexahydro-7,8-dimethyl-5H-benzo[kl]bis[1,3]dioxolo[4,5-b:4',5'-g]xanthen-5-one
CAS Number
177931-17-8
Molecular Formula
C20H20O6
Formula Weight
356.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mLDMF:PBS (pH 7.2)(1:3): 0.25 mg/mLDMSO: 2 mg/mL
λmax
238, 299 nm
SMILES
O=C1[C@]2([H])C[C@@H](C)[C@H](C)[C@]3([H])[C@@]2([H])[C@@]4(OC5=C3C=C6C(OCO6)=C5)C(OCO4)=C1
InChi Code
InChI=1S/C20H20O6/c1-9-3-11-13(21)5-17-20(25-8-24-17)19(11)18(10(9)2)12-4-15-16(23-7-22-15)6-14(12)26-20/h4-6,9-11,18-19H,3,7-8H2,1-2H3/t9-,10+,11+,18+,19+,20+/m1/s1
InChi Key
GMTJIWUFFXGFHH-WPAOEJHSSA-N
Origin
Plant/Saururaceae
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sauchinone is a lignan that has been found in S. chinensis and has diverse biological activities.1,2,3,4 It inhibits LPS-induced expression of the genes encoding inducible nitric oxide synthase (iNOS), TNF-α, and COX-2 (IC50s = ≤10 µM for all), as well as LPS-induced activation of NF-κB and nuclear translocation of NF-κB p65 in RAW 264.7 cells.5 Sauchinone reduces hydrogen peroxide-induced increases in heat shock protein 70 (Hsp70) levels and cell death in C2C12 mouse skeletal muscle myoblasts.2 In vivo, sauchinone (10 and 30 mg/kg) reduces hepatic formation of thiobarbituric acid reactive substances (TBARS), plasma levels of alanine aminotransferase (ALT), and hepatocyte cell death in a mouse model of iron overload-induced liver injury.3 Sauchinone (10 mg/kg) reduces infarct size and heart levels of phosphorylated p38 MAPK and JNK in a rat model of myocardial ischemia-reperfusion injury.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lee, A.K., Sung, S.H., Kim, Y.C., et al. Inhibition of lipopolysaccharide-inducible nitric oxide synthase, TNF-α and COX-2 expression by sauchinone effects on I-κBα phosphorylation, C/EBP and AP-1 activation. Br. J. Pharmacol. 139, 11-20 (2003).

    2. Jung, M.H., Song, M.C., Bae, K., et al. Sauchinone attenuates oxidative stress-induced skeletal muscle myoblast damage through the down-regulation of ceramide. Biol. Pharm. Bull. 34(4), 575-579 (2011).

    3. Kim, Y.W., Lee, S.M., Shin, S.M., et al. Efficacy of sauchinone as a novel AMPK-activating lignan for preventing iron-induced oxidative stress and liver injury. Free Radic. Biol. Med. 47(7), 1082-1092 (2009).

    4. Kim, S.J., Jeong, C.W., Bae, H.B., et al. Protective effect of sauchinone against regional myocardial ischemia/reperfusion injury: inhibition of p38 MAPK and JNK death signaling pathways. J. Korean Med. Sci. 27(5), 572-575 (2012).

    5. Bhandari, K., Srivastava, S., and Shankar, G. Synthesis of tetrahydronaphthyl thioureas as potent appetite suppressants. Bioorg. Med. Chem. 12(15), 4189-4196 (2004).