OXYPAEONIFLORA

Possibly Marketed Outside US

First approved in 2021

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H28O12
Molecular Weight	496.4612
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@]4(O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1(COC(=O)C5=CC=C(O)C=C5)[C@@]6([H])O[C@]2(O)C[C@]4(C)O6

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	496.4612
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23881455 | https://www.ncbi.nlm.nih.gov/pubmed/20580804

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

Primary Target	Pharmacology	Condition	Potency
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23881455	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Diabetic nephropathy 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23881455	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro synergistic antioxidant activity and identification of antioxidant components from Astragalus membranaceus and Paeonia lactiflora.	2014	24816851

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Dec 16 07:55:50 UTC 2023` Edited by `admin` on `Sat Dec 16 07:55:50 UTC 2023`
Record UNII	3A7O4NBD5S
Record Status	`Validated (UNII)`
Record Version

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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

NSC

258310