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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
Structure of MADECASSOSIDE

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

HIDE SMILES / InChI

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

Curator's Comment: Madecassoside demonstrated protective activity against cognitive impairment induced by D-galactose in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
539.04 µM [IC50]
453.32 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Madecassoside attenuates inflammatory response on collagen-induced arthritis in DBA/1 mice.
2009 Jun
In vitro inhibitory effects of asiaticoside and madecassoside on human cytochrome P450.
2011 Jun
Madecassoside, a triterpenoid saponin isolated from Centella asiatica herbs, protects endothelial cells against oxidative stress.
2012 Oct
Patents

Sample Use Guides

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
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 Fri Dec 15 20:33:10 UTC 2023
Edited
by admin
on Fri Dec 15 20:33:10 UTC 2023
Record UNII
CQ2F5O6YIY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MADECASSOSIDE
INCI   WHO-DD  
INCI  
Official Name English
Madecassoside [WHO-DD]
Common Name English
Urs-12-en-28-oic acid, 2,3,6,23-tetrahydroxy-, O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, (2α,3β,4α,6β)-
Systematic Name English
MADECASSOSIDE (CONSTITUENT OF CENTELLA ASIATICA) [DSC]
Common Name English
ASIATICOSIDE A
Common Name English
MADECASSOSIDE [INCI]
Common Name English
REDERMIC
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
252-076-1
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
CAS
34540-22-2
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
SMS_ID
100000151623
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
DAILYMED
CQ2F5O6YIY
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID40956057
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
DRUG BANK
DB15532
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
RXCUI
87855
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY RxNorm
FDA UNII
CQ2F5O6YIY
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
PUBCHEM
24825675
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
EVMPD
SUB125894
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
CHEBI
66651
Created by admin on Fri Dec 15 20:33:10 UTC 2023 , Edited by admin on Fri Dec 15 20:33:10 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Constituent of Centella asiatica aerial parts.