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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O12
Molecular Weight 496.4621
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYPAEONIFLORA

SMILES

C[C@]12C[C@@]3([C@]4([H])C[C@]1([C@]4(COC(=O)c5ccc(cc5)O)[C@]([H])(O2)O3)O[C@@]6([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O6)O)O)O)O

InChI

InChIKey=FCHVXNVDFYXLIL-WRJNSLSBSA-N
InChI=1S/C23H28O12/c1-20-8-22(30)13-6-23(20,33-18-16(28)15(27)14(26)12(7-24)32-18)21(13,19(34-20)35-22)9-31-17(29)10-2-4-11(25)5-3-10/h2-5,12-16,18-19,24-28,30H,6-9H2,1H3/t12-,13-,14-,15+,16-,18+,19-,20+,21+,22-,23+/m1/s1

HIDE SMILES / InChI

Molecular Formula C23H28O12
Molecular Weight 496.4621
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Oxypaeoniflorin is a natural product derived from Radix Paeoniae Rubra and Radix Paeoniae Alba. Oxypaeoniflora had protective effects on AGEs-induced mesangial cell damage. The pretreatment with oxypaeoniflora (10-8-10-4 M) significantly increased advanced glycation end product-induced glutathione peroxidase and catalase activities in mesangial cells HBZY-1. Oxypaeniflora attenuated markedly advanced glycation end products-induced inflammation cytokines interleukin-6 and monocyte chemoattractant protein-1 levels in ELISA and western blot analysis in a dose-dependent manner. Oxypaeniflora was able to attenuate advanced glycation end products-induced oxidative damage and inflammation in mesangial cells. Oxypaeniflora might therefore have a beneficial effect in the treatment of diabetic nephropathy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro synergistic antioxidant activity and identification of antioxidant components from Astragalus membranaceus and Paeonia lactiflora.
2014
Patents

Sample Use Guides

Rats: Aqueous solutions of Radix Paeoniae Rubra and Radix Paeoniae Alba were given to rats at a dose of containing 0.2 g/g crude drug. After dosing for 5, 10, 15, 20, 30, 60, 90, 120, 180, 240, 360, 540 min, 0.2 ml venous blood samples were collected in 1.5 ml heparinized tubes by eye puncture. Oxypaeoniflorin is a component of extracts of Radix Paeoniae Rubra and Radix Paeoniae Alba. After oral gavage of Radix Paeoniae Rubra and Radix Paeoniae Alba at the same amount of crude drug, the content of oxypaeoniflorin in plasma reached themaximum at 0.33 ± 0.06 h and 0.67 ± 0.23 h, respectively, which showed great significance.
Route of Administration: Oral
The pretreatment with Oxypaeoniflora (10−6, 10−5, 10−4 M) also decreased seriously the macrophage migration to 0.19 ± 0.05, 0.15 ± 0.03, and 0.14 ± 0.02, respectively, in a dose-dependent manner. The pretreatment with Oxypaeoniflora (10−5–10−4 M) could significantly inhibit the level of MCP-1. The IC50 values of paeoniflorin and oxypaeoniflora for inhibiting 2,2'-azinobis-(3-thylbenzothiazoline-6-sulfonic acid) formation were 4.197 × 10-4 M and 1.002 × 10-4 M, respectively.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:43:30 UTC 2021
Edited
by admin
on Sat Jun 26 13:43:30 UTC 2021
Record UNII
3A7O4NBD5S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYPAEONIFLORA
Common Name English
((2S,3R,5R,6R,8S)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-HYDROXY-8-METHYL-9,10-DIOXATETRACYCLO(4.3.1.02,5.03,8)DEC-2-YL)METHYL 4-HYDROXYBENZOATE
Systematic Name English
.BETA.-D-GLUCOPYRANOSIDE, TETRAHYDRO-5-HYDROXY-5B-(((4-HYDROXYBENZOYL)OXY)METHYL)-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL, (1AR-(1A.ALPHA.,2.BETA.,3A.ALPHA.,5.ALPHA.,5A.ALPHA.,5B.ALPHA.))-
Systematic Name English
OXYPAEONIFLORIN
Common Name English
(((1AR)-3A.BETA.,5,5A.BETA.,5B-TETRAHYDRO-5.BETA.-HYDROXY-5B.BETA.-(((4-HYDROXYBENZOYL)OXY)METHYL)-2-METHYL-2.ALPHA.,5-METHANO-3,4-DIOXA-1H-CYCLOBUTA(CD)PENTALEN)-1A.BETA.(2H)-YL).BETA.-D-GLUCOPYRANOSIDE
Systematic Name English
J17.727J
Code English
OXYPEONIFLORIN
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (1AR,2S,3AR,5R,5AR,5BS)-TETRAHYDRO-5-HYDROXY-5B-(((4-HYDROXYBENZOYL)OXY)METHYL)-2-METHYL-2,5-METHANO-1H-3,4-DIOXACYCLOBUTA(CD)PENTALEN-1A(2H)-YL
Systematic Name English
NSC-258310
Code English
Code System Code Type Description
FDA UNII
3A7O4NBD5S
Created by admin on Sat Jun 26 13:43:30 UTC 2021 , Edited by admin on Sat Jun 26 13:43:30 UTC 2021
PRIMARY
CAS
39011-91-1
Created by admin on Sat Jun 26 13:43:30 UTC 2021 , Edited by admin on Sat Jun 26 13:43:30 UTC 2021
PRIMARY
PUBCHEM
21631105
Created by admin on Sat Jun 26 13:43:30 UTC 2021 , Edited by admin on Sat Jun 26 13:43:30 UTC 2021
PRIMARY
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