Stereochemistry | ABSOLUTE |
Molecular Formula | C15H20O4 |
Molecular Weight | 264.3169 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O
InChI
InChIKey=JLIDBLDQVAYHNE-YKALOCIXSA-N
InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m1/s1
Molecular Formula | C15H20O4 |
Molecular Weight | 264.3169 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
Abscisic Acid ((2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid) is a plant hormone and growth regulator that is involved in several physiological mechanisms including seed dormancy, leaf abscission, stomatal movement, and plant stress responses. Through complex interactions with several intracellular signaling systems, it can regulate the expression of hundreds of plant genes. Abscisic Acid has also been found to be present in metazoans, from sponges up to mammals including humans. Currently, its biosynthesis and biological role in animals is poorly known. Abscisic acid has recently been shown to elicit potent anti-inflammatory and anti-diabetic effects in mouse models of diabetes/obesity, inflammatory bowel disease, atherosclerosis, and influenza infection. Many biological effects in animals have been studied using Abscisic Acid as a nutraceutical or pharmacognostic drug, but Abscisic Acid is also generated endogenously by some cells. There are also conflicting conclusions from different studies, where some claim that Abscisic acid is essential for pro-inflammatory responses whereas other show anti-inflammatory effects. Like with many natural substances with medical properties, Abscisic Acid has become popular also in naturopathy. While Abscisic Acid clearly has beneficial biological activities and many naturopathic remedies will contain high levels of Abscisic Acid (such as wheatgrass juice, fruits, and vegetables), some of the health claims made may be exaggerated or overly optimistic. In mammalian cells Abscisic Acid targets a protein known as lanthionine synthetase C-like 2 (LANCL2), triggering an alternative mechanism of activation of peroxisome proliferator-activated receptor gamma (PPAR gamma).
Approval Year
PubMed
Patents
Sample Use Guides
US adult would consume an average of 184 µg of ABA per day derived from the 2.79 servings/day of fruits and vegetables.
Route of Administration:
Oral
RAW 264.7 macrophages were cultured with DMEM containing 10% fetal bovine serum and grown until 60–70% confluence. Cells were cotransfected in each well with 0.6 mkg plasmid of DNA and 10 ng of pRL reporter control using F-2 transfection reagents (Targeting Systems, Santee, CA) according to the manufacturer’s protocol. After 24 h, transfected cells were seeded into white, opaque 96-well plates (BD Biosciences) at a concentration of 25,000 cells/well. To determine NF-_B reporter activity, cells were then transfected with 0.2 mkg of pNF-kappaB reporter and 0.2 mkg of pRL reporter control using the Lipofectamine 2000 transfection reagent (Invitrogen). Transfected cells were then treated in replicates of eight with rosiglitazone (Ros 1 mkM; Cayman Chemical, Ann Arbor, MI), (+)-ABA (1.25, 2.5, 5, and 10 mkM, Sigma), (-)-ABA (1.25, 2.5, 5, and 10 mkM, Sigma), or vehicle (DMSO) and placed in a 37 °C incubator with 5% CO2. After 20 h, cells were harvested
in reporter lysis reagent. Luciferase activity, normalized to pRL activity in the cell extracts, was determined by using the Dual-Luciferase II reporter assay system (Promega, Madison, WI) using a Modulus 96-well luminometer.