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Structure Database (LMSD)

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Common Name

Tigogenin

Systematic Name

(25R)-5α-spirostan-3β-ol

Synonyms

LM ID

LMST01080009

Formula

C₂₇H₄₄O₃

Exact Mass

Calculate m/z

416.329045

Sum Composition

ST 27:2;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

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

This information has been provided by Cayman Chemical

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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Digitalis purpurea (#4164)

Magnoliopsida (#3398)

Steroid saponins,
Phytochemistry, 1982

DOI: 10.1016/S0031-9422(00)82400-0

String Representations

InChiKey (Click to copy)

GMBQZIIUCVWOCD-MFRNJXNGSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@@]2([H])C[C@@H](O)C1)CC[C@@H](C)CO6)C