A steroidal sapogenin with diverse biological activities
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Isomer(s)
24973Sarsasapogenin
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Tigogenin

Item No. 30137

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,25R)-spirostan-3-ol
CAS Number
77-60-1
Synonyms
  • NSC 93754
Molecular Formula
C27H44O3
Formula Weight
416.6
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2mg/mL
SMILES
O[C@H]1CC[C@@]2(C)[C@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])C[C@@]5([H])[C@]4([H])[C@H](C)[C@]6(OC[C@H](C)CC6)O5)([H])C1
InChi Code
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
InChi Key
GMBQZIIUCVWOCD-MFRNJXNGSA-N
Origin
Natural/Source unknown
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $49

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    50 mg

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    100 mg

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    250 mg

    $820

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    Product Description

    Tigogenin is a steroidal sapogenin that has been found in A. sisalana and has diverse biological activities.1,2,3,4 It increases the proliferation rate of, as well as mRNA levels of genes encoding the osteoblastic differentiation markers Cbfa1, collagen type I, and osteocalcin in, mouse bone marrow stromal cells (BMSCs) in a concentration-dependent manner.2 It also increases matrix calcium deposition in BMSCs when used at concentrations of 30 and 90 μM. Tigogenin is active against the fungus A. fumigatus (MIC50 = 16 μg/ml).3 It inhibits carrageenan-induced paw edema in rats when administered at a dose of 4.2 μg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cripps, A.L., and Blunden, G. A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalana. Steroids 31(5), 661-669 (1978).

    2. Zhou, H., Yang, X., Wang, N., et al. Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. Mol. Cell Endocrinol. 270(1-2), 17-22 (2007).

    3. Upadhyay, S.K., Creech, C.C., Bowdy, K.L., et al. Synthesis and antifungal activity of functionalized 2,3-spirostane isomers. Bioorg. Med. Chem. Lett. 21(10), 2826-2831 (2011).

    4. Peana, A.T., Moretti, M.D., Manconi, V., et al. Anti-inflammatory activity of aqueous extracts and steroidal sapogenins of Agave americana. Planta Med. 63(3), 199-202 (1997).