Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O3 |
| Molecular Weight | 416.6365 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]16CC[C@@H](C)CO6
InChI
InChIKey=GMBQZIIUCVWOCD-MFRNJXNGSA-N
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
| Molecular Formula | C27H44O3 |
| Molecular Weight | 416.6365 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Tigogenin is a saponin and acts as a natural plant steroid which induces apoptosis in rheumatoid arthritis fibroblast-like synoviocytes. This action is associated with overexpression of COX-2 correlated with overproduction of endogenous PGE2. In addition, it was found that through the inhibition of PPAR gamma and via the p38 MAPK pathway tigogenin has the potential to prevent the development of osteoporosis and the related disorders.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells. | 2007-05-30 |
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| Tigogenin and ursolic acid from Cestrum diurnum Linn. | 1964-04-15 |
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| A new source for tigogenin. | 1962-04 |
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| Steroidal sapogenins; magogenin and cacogenin and their biogenesis to chlorogenin and tigogenin. | 1947-10 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Tigogenin was more effective than hecogenin in inducing apoptosis in human Rheumatoid arthritis (RA) fibroblast-like synoviocytes (FLS) which was caspase dependent but poly(ADP-ribose) polymerase independent and characterized by DNA fragmentation. It was demonstrated, that tigogenin-induced apoptosis through activation of p38 without affecting the JNK and ERK pathways. Indeed, pretreatment with a p38 inhibitor decreased saponin-induced apoptosis with a significant decrease in DNA fragmentation. Furthermore, the rate of apoptosis induced by tigogenin was associated with overexpression of COX-2 correlated with overproduction of endogenous PGE2.
Unknown
| Substance Class |
Chemical
Created
by
admin
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Edited
Mon Mar 31 22:29:42 GMT 2025
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admin
on
Mon Mar 31 22:29:42 GMT 2025
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| Record UNII |
4SMU15RR44
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| Record Status |
Validated (UNII)
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201-041-9
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DTXSID40903920
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9595
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4SMU15RR44
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99516
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93754
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m10861
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77-60-1
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