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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H68O13
Molecular Weight 780.9815
Optical Activity UNSPECIFIED
Defined Stereocenters 21 / 21
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAIKOSAPONIN D

SMILES

[H][C@@]12CC(C)(C)CC[C@@]13CO[C@@]24C=C[C@]5([H])[C@@]6(C)CC[C@H](O[C@]7([H])O[C@H](C)[C@H](O)[C@H](O[C@]8([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)[C@@](C)(CO)[C@]6([H])CC[C@@]5(C)[C@]4(C)C[C@H]3O

InChI

InChIKey=KYWSCMDFVARMPN-LCSVLAELSA-N
InChI=1S/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21-,22-,23-,24-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1

HIDE SMILES / InChI

Molecular Formula C42H68O13
Molecular Weight 780.9815
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 21 / 21
E/Z Centers 0
Optical Activity UNSPECIFIED

Saikosaponin D is a triterpene saponin found in Bupleurum that exhibits antioxidative, immunomodulatory, anti-fibrotic, anti-angiogenic, anticancer, and chemopreventive activities. Saikosaponin D increases activity of superoxide dismutase, catalase, and glutathione peroxidase and decreases activity of malondialdehyde in cellular models of oxidative damage. In other in vitro models, saikosaponin D increases secretion of IL-12, maturation of dendritic cells, and proliferation of lymphocytes. Saikosaponin D inhibits SERCA, increasing intracellular Ca2+ and inducing autophagy. In vivo, this compound decreases severity of fibrosis. In embryos, saikosaponin D decreases microvessel formation. Additionally, this compound decreases tumor formation in DEN-treated animal models and suppresses expression of CEBP-β and COX-2. Saikosaponin D also induces apoptosis and activation of caspases 3 and 7 in hepatocellular carcinoma cells. Saikosaponin D is a Glucocorticoid receptor agonist. It is a COX-2 and iNOS inhibitor.

CNS Activity

Curator's Comment: Saikosaponin D relieves chronic mild stress induced depressive-like behavior in rats. In rats saikosaponin D significantly reduced cocaine self-administration without affecting food consumption.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cytotoxicity and anti-hepatitis B virus activities of saikosaponins from Bupleurum species.
2003 Aug
Patents

Sample Use Guides

Mice: oral gavage of saikosaponin-d (5 mg/kg, 10 mg/kg and 20 mg/kg body weight/day).
Route of Administration: Oral
In order to investigate the anti-proliferative effect of saikosaponin d, ATC cells were cultured in the presence of various concentrations of saikosaponin-d (5 umol/L, 10 umol/L, 15 umol/L and 20 umol/L). MTT assay showed that saikosaponin-d treatment significantly inhibited the proliferation of ARO, 8305C and SW1736 in a time- and dose-dependent manner.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:11:51 GMT 2023
Edited
by admin
on Fri Dec 15 18:11:51 GMT 2023
Record UNII
UR635J3F00
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAIKOSAPONIN D
Common Name English
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,4.ALPHA.,16.ALPHA.)-13,28-EPOXY-16,23-DIHYDROXYOLEAN-11-EN-3-YL 6-DEOXY-3-O-.BETA.-D-GLUCOPYRANOSYL-
Common Name English
Code System Code Type Description
CAS
20874-52-6
Created by admin on Fri Dec 15 18:11:51 GMT 2023 , Edited by admin on Fri Dec 15 18:11:51 GMT 2023
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FDA UNII
UR635J3F00
Created by admin on Fri Dec 15 18:11:51 GMT 2023 , Edited by admin on Fri Dec 15 18:11:51 GMT 2023
PRIMARY
PUBCHEM
107793
Created by admin on Fri Dec 15 18:11:51 GMT 2023 , Edited by admin on Fri Dec 15 18:11:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID301317467
Created by admin on Fri Dec 15 18:11:51 GMT 2023 , Edited by admin on Fri Dec 15 18:11:51 GMT 2023
PRIMARY