Details
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
[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@]2([H])C3=CC=CC(O)=C3C(=O)C4=C2C=C(CO)C=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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0038066 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28656293 |
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Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28673785 |
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Target ID: Calcium and sodium voltage-gated ion channels (rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29072259 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28673785
Rat: 20 mg/kg/d for 5 days
Route of Administration:
Intragastric
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29072259
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.
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m1573
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648RW354S9
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SUBSTANCE RECORD