Stereochemistry | ABSOLUTE |
Molecular Formula | C30H48O5 |
Molecular Weight | 488.6991 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 12 / 12 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)C[C@@H](O)[C@H](O)[C@@]2(C)CO
InChI
InChIKey=JXSVIVRDWWRQRT-UYDOISQJSA-N
InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21-,22-,23+,24+,26+,27+,28-,29-,30+/m1/s1
Molecular Formula | C30H48O5 |
Molecular Weight | 488.6991 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 12 / 12 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Asiatic acid is a triterpene aglycone originally found in Centella; it exhibits cardioprotective, hepatoprotective, anti-inflammatory, antioxidative, antihypertensive, anticancer, anti-fibrotic, and anti-osteoporotic activities. In vitro and in vivo, asiatic acid inhibits TGF-β1-induced and overload-induced cardiac hypertrophy, decreasing production of TGF-β1 and activation of NF-κB, ERK1/2, and p38 MAPK. In high fat diet-fed rats, asiatic acid decreases expression of NF-κB, p38 MAPK, IL-1β, ROS, IL-6, and TNF-α and increases activity of glutathione peroxidase and catalase, preventing hepatic steatosis. Additionally, asiatic acid inhibits L-NAME-induced hypertension, increasing levels of NO and improving vascular function. In multiple myeloma cells, this compound induces G2/M phase cell cycle arrest, decreases expression of FAK, and inhibits cell proliferation. Asiatic acid inhibits adipogenesis, suppresses activation of G3PDH, and modulates differentiation in bone marrow stromal cells. In animal models of fibrosis, this compound decreases tubular injury and fibroblast activation by suppressing activation of Smad2/3, regulating PPARγ activation, and decreasing levels of α-SMA and TGF-β1. Asiatic acid stimulates wound healing by increasing collagen production. Asiatic acid is considered to be the most therapeutically active ingredient of Madecassol, marketed in Korea as wound healing agent for traumatic or surgical wounds, burns, skin grafts, fistulas, abnormal retractile or decubitus scars, cutaneomucous lesions in ENT, gynaecology, ulcerous lesions in leprosy, striae distensae, cellulitis, varicose leg ulcers, haemorrhoid.