Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C48H78O20 |
Molecular Weight | 975.1209 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 28 / 28 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC=C3[C@]4([H])[C@@H](C)[C@H](C)CC[C@@]4(CC[C@@]3(C)[C@]1(C)C[C@@H](O)[C@@]5([H])[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]25C)C(=O)O[C@@H]6O[C@H](CO[C@@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O
InChI
InChIKey=BNMGUJRJUUDLHW-HCZMHFOYSA-N
InChI=1S/C48H78O20/c1-19-10-11-48(13-12-46(6)22(28(48)20(19)2)8-9-27-44(4)14-24(52)39(61)45(5,18-50)38(44)23(51)15-47(27,46)7)43(62)68-42-35(59)32(56)30(54)26(66-42)17-63-40-36(60)33(57)37(25(16-49)65-40)67-41-34(58)31(55)29(53)21(3)64-41/h8,19-21,23-42,49-61H,9-18H2,1-7H3/t19-,20+,21+,23-,24-,25-,26-,27-,28+,29+,30-,31-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42+,44-,45+,46-,47-,48+/m1/s1
Molecular Formula | C48H78O20 |
Molecular Weight | 975.1209 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 28 / 28 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Madecassoside is a triterpenoid compound found in Centella asiatica (Gotu kola), a medicinal herb used in traditional Chinese medicine (TCM), Ayurvedic medicine, and traditional African medicine. Madecassoside has a wide range of reported biological activities including, anti-inflammatory, wound healing, and anti-oxidant activities. It has been reported to suppress LPS-induced TNF-alpha production via inhibition of ERK, p38, and NF-kappaB activity. Madecassoside, a triterpenoid derivative isolated from Centella asiatica, exhibits anti-inflammatory and antioxidant activities. Madecassoside significantly reduced brain infarct area, resolved neurological deficit, and ameliorated neuronal apoptosis. It also significantly reduced the levels of malondialdehyde and nitric oxide, and augmented the antioxidant activity in rats subjected to cerebral I/R. Moreover, the levels of pro-inflammatory cytokines and NF-κB p65 significantly reduced after madecassoside treatment. Madecassoside is neuroprotective and may be useful in reducing the damage caused by stroke. Madecassoside has being shown to inhibits melanin synthesis by blocking ultraviolet-induced inflammation.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25106808 | https://www.ncbi.nlm.nih.gov/pubmed/23876367
Curator's Comment: Madecassoside demonstrated protective activity against cognitive impairment induced by D-galactose in mice.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21349323 |
539.04 µM [IC50] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21349323 |
453.32 µM [IC50] | ||
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22829481 |
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Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19135346 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/27588048 |
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | 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/24278045
Mice: Oral
administration of madecassoside at doses of 6 mg/kg,
12 mg/kg and 24 mg/kg to mice facilitated wound closure
in a time-dependent manner and complete wound closure
took place on the 20th day in the group receiving 24 mg/kg
of madecassoside.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22829481
Madecassoside (10, 30, 100 umol/L) could reverse morphological changes, elevate cell viability, increase glutathione levels, and decrease lactate dehydrogenase and malondialdehyde levels caused by H(2)O(2) in a concentration-dependent manner.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 20:33:10 GMT 2023
by
admin
on
Fri Dec 15 20:33:10 GMT 2023
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Record UNII |
CQ2F5O6YIY
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Constituent of Centella asiatica aerial parts.
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