Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H44O4 |
| Molecular Weight | 432.6359 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 13 / 13 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)[C@H](O)C[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2
InChI
InChIKey=FWCXELAAYFYCSR-RYKNUXCGSA-N
InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-23(31-27)12-20-18-6-5-17-11-21(28)22(29)13-26(17,4)19(18)8-9-25(20,24)3/h15-24,28-29H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,22-,23+,24+,25+,26+,27-/m1/s1
Gitogenin was first extracted from the herbs of Agave Americana. This compound was found to be a selective inhibitor of UDP- glucuronosyltransferase 1A4 and α-glucosidase, and does not exhibit any inhibition of the major human CYP isoforms. In vitro experiments revealed that gitogenin moderated stimulation for the release of growth hormone from rat pituitary cells.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P22310 Gene ID: 54657.0 Gene Symbol: UGT1A4 Target Organism: Homo sapiens (Human) |
|||
Target ID: O43451 Gene ID: 8972.0 Gene Symbol: MGAM Target Organism: Homo sapiens (Human) |
37.2 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Presence of chlorogenin beside the diosgenin and gitogenin in Tribulus terrestris L]. | 1968 |
|
| Longipetalosides A-C, new steroidal saponins from Tribulus longipetalus. | 2014 May |
|
| Drug interaction study of natural steroids from herbs specifically toward human UDP-glucuronosyltransferase (UGT) 1A4 and their quantitative structure activity relationship (QSAR) analysis for prediction. | 2016 Aug |
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Longipetalosides and gitogenin were isolated from the methanolic extract of the whole plant of Tribulus longipetalus. The structures of these compounds were established by using 1D ((1)H, (13)C) and 2D NMR (HMQC, HMBC, COSY, NOESY) spectroscopy, and mass spectrometry (ESIMS, HRESIMS), and in comparison with literature data reported for related compounds. Compounds were evaluated for their inhibitory activities against enzymes α-glucosidase, lipoxygenase, acetylcholinesterase, and butyrylcholinesterase. Only the compounds 4 and 5 (gitogenin) were found as the inhibitors of enzyme α-glucosidase with IC50 values of 33.5±0.22 and 37.2±0.18μM, respectively
Unknown
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441887
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511-96-6
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SUBSTANCE RECORD
