| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H22O9 |
| Molecular Weight | 418.394 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)[C@@H]2C3=CC(CO)=CC(O)=C3C(=O)C4=C2C=CC=C4O
InChI
InChIKey=AFHJQYHRLPMKHU-OSYMLPPYSA-N
InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2/t13-,14+,17-,19+,20-,21+/m1/s1
| Molecular Formula | C21H22O9 |
| Molecular Weight | 418.394 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
The ALOIN A (barbaloin) is considered to be the most specific secondary phytoconstituent in Aloe species, widely distributed throughout the world. Barbaloin has been found to have a strong inhibitory effect on histamine release from mast cells. Orally administered barbaloin is poorly absorbed but is metabolized by intestinal microflora to aloe emodin, which is readily absorbed. Barbaloin is the main medicinal constituent of aloe vera, which has anti-inflammatory activity. Moreover, it has strong anti-oxidant and anti-tumor properties. For example, barbaloin inhibited the proliferation and metastasis of non-small cell lung carcinoma cells in vivo and in vitro. Barbaloin demonstrated a cardioprotective potential: barbaloin pretreatment attenuates myocardial ischemia-reperfusion injury. Plus, it might be used as an antiarrhythmic drug.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Application of barbaloin (100, 200 uM/L) decreased ATX II-enhanced late sodium current (INa.L) by 36.6% and 71.8%, respectively. However, barbaloin up to 800 uM/L did not affect the inward rectifier potassium current (Ik1) or the rapidly activated delayed rectifier potassium current (Ikr) in ventricular myocytes.
