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Structure Database (LMSD)

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Common Name

Diosgenin

Systematic Name

(25R)-spirost-5-en-3β-diol

Synonyms

LM ID

LMST01080037

Formula

C₂₇H₄₂O₃

Exact Mass

Calculate m/z

414.313395

Sum Composition

ST 27:3;O3

Status

Curated

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Classification

Biological Context

Diosgenin is a natural steroid sapogenin that has diverse biochemical and physiological actions. It has antioxidant and anti-inflammatory activities, is protective against metabolic and cardiovascular diseases, and can have immunomodulatory and estrogenic effects.^1,2,3,4

This information has been provided by Cayman Chemical

References

1. Fuller, S., and Stephens, J.S. Diosgenin, 4-hydroxyisoleucine, and fiber from fenugreek: Mechanisms of actions and potential effects on metabolic syndrome. Adv. Nutr. 6(2), 189-197 (2015).

2. Chen, Y., Tang, Y.M., Yu, S.L., et al. Advances in the pharmacological activities and mechanisms of diosgenin. Chin. J. Nat. Med. 13(8), 578-587 (2015).

3. Lee, K.J., Oh, Y.C., Cho, W.K., et al. Antioxidant and anti-inflammatory activity determination of one hundred kinds of pure chemical compounds using offline and online screening HPLC assay. Evid. Based Complement. Alternat. Med. 165457 (2015).

4. Sung, B., Prasad, S., Yadav, V.R., et al. Cancer cell signaling pathways targeted by spice-derived nutraceuticals. Nutr. Cancer 64(2), 173-197 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ophiopogon japonicus (#100506)

Magnoliopsida (#3398)

Steroid saponins,
Phytochemistry, 1982

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

String Representations

InChiKey (Click to copy)

WQLVFSAGQJTQCK-VKROHFNGSA-N

InChi (Click to copy)

InChI=1S/C27H42O3/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/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

SMILES (Click to copy)

C1[C@H](O)CC2[C@@](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=2)CC[C@@H](C)CO6)C)C1