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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 A

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-MSSMMRRTSA-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 A is a triterpene saponin found in Bupleurum that exhibits anti-inflammatory, analgesic, neuromodulatory, anticancer, and immunosuppressive activities. Saikosaponin A decreases production of TNF-α, IL-1β, and IL-2 and increases mechanical withdrawal thresholds and thermal withdrawal thresholds in animal models of chronic constructive injury. Saikosaponin A also decreases self-administration of cocaine and morphine. In colon carcinoma cells, saikosaponin A causes activation of caspases 2, 3, 8, and 9 and PARP, induces apoptosis, and decreases expression of Bcl-2 and XIAP. Additionally, this compound inhibits the proliferation and activation of ConA-treated T cells, inducing G0/G1 phase cell cycle arrest and decreasing expression of TNF-α, IL-2, and IFN-γ.

CNS Activity

Curator's Comment: Saikosaponin A alleviates symptoms of attention deficit hyperactivity disorder in spontaneous hypertensive rats.

Approval Year

PubMed

PubMed

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

Sample Use Guides

Rats were administered saikosaponin a (6.25, 12.50 and 25.00 mg/kg intraperitoneal, once daily) for 14 days.
Route of Administration: Oral
Saikosaponin A showed the most potent cytotoxicity against human cancer cells (gastric cancer, AGS cells; breast cancer, MCF-7 cells; and hepatoma, HepG2 cells) after 24 h. The IC50 values for the above three cell types were 34.6, 33.3, and 23.4 umol/L, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:22:20 GMT 2023
Edited
by admin
on Sat Dec 16 01:22:20 GMT 2023
Record UNII
09O6CAG7JV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAIKOSAPONIN A
Common Name English
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.,4.ALPHA.,16.BETA.)-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
EPA CompTox
DTXSID00942951
Created by admin on Sat Dec 16 01:22:20 GMT 2023 , Edited by admin on Sat Dec 16 01:22:20 GMT 2023
PRIMARY
CAS
20736-09-8
Created by admin on Sat Dec 16 01:22:20 GMT 2023 , Edited by admin on Sat Dec 16 01:22:20 GMT 2023
PRIMARY
FDA UNII
09O6CAG7JV
Created by admin on Sat Dec 16 01:22:20 GMT 2023 , Edited by admin on Sat Dec 16 01:22:20 GMT 2023
PRIMARY
PUBCHEM
167928
Created by admin on Sat Dec 16 01:22:20 GMT 2023 , Edited by admin on Sat Dec 16 01:22:20 GMT 2023
PRIMARY
MESH
C025759
Created by admin on Sat Dec 16 01:22:20 GMT 2023 , Edited by admin on Sat Dec 16 01:22:20 GMT 2023
PRIMARY