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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2369
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SULFURETIN

SMILES

OC1=CC=C2C(=O)\C(OC2=C1)=C\C3=CC(O)=C(O)C=C3

InChI

InChIKey=RGNXWPVNPFAADO-NSIKDUERSA-N
InChI=1S/C15H10O5/c16-9-2-3-10-13(7-9)20-14(15(10)19)6-8-1-4-11(17)12(18)5-8/h1-7,16-18H/b14-6-

HIDE SMILES / InChI

Molecular Formula C15H10O5
Molecular Weight 270.2369
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Sulfuretin, one of the major flavonoid glycosides found in the stem bark of Albizzia julibrissin and heartwood of Rhus verniciflua, is a known anti-oxidant. Sulfuretin is also known to have anti-inflammatory effects. Sulfuretin suppressed the chemokine production, matrix metalloproteinase secretion, and cell proliferation induced by tumor necrosis factor-α in rheumatoid FLS. In addition, sulfuretin inhibited the osteoclast differentiation induced by macrophage colony-stimulating factor and receptor activator of NF-κB ligand in bone marrow macrophages. In mice with CIA, early intervention with sulfuretin prevented joint destruction, as evidenced by a lower cumulative disease incidence and an absence of diverse disease features based on hind paw thickness, radiologic and histopathologic findings, and inflammatory cytokine levels. In mice with established arthritis, sulfuretin treatment significantly reduced synovial inflammation and joint destruction. The in vitro and in vivo protective effects of sulfuretin were mediated by inhibition of the NF-κB signaling pathway.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of in vitro activity of aurones and related compounds against Cryptosporidium parvum.
2001 Nov
Sulfuretin, a major flavonoid isolated from Rhus verniciflua, ameliorates experimental arthritis in mice.
2012 May 22
Patents

Sample Use Guides

Rats: Oral administration (30 mg/kg) of sulfuretin and fustin, which were isolated from the EtOAc extract by activity-guided separation, significantly decreased RA and CRP factors.
Route of Administration: Oral
RA-FLS (2 × 10(6) cells) were pretreated with 30 uM sulfuretin for 1 h and then treated with TNF-α (10 ng/ml). Pretreatment with sulfuretin significantly diminished TNF-α-mediated chemokines production in a concentration-dependent manner.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:39 GMT 2023
Edited
by admin
on Sat Dec 16 01:37:39 GMT 2023
Record UNII
M6410VY6MI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFURETIN
MI  
Common Name English
ISOLIQUIRITIGENIN METABOLITE M3
Common Name English
SULFURETIN [MI]
Common Name English
3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-HYDROXY-, (Z)-
Systematic Name English
3(2H)-BENZOFURANONE, 2-(3,4-DIHYDROXYBENZYLIDENE)-6-HYDROXY-
Systematic Name English
3',4',6-TRIHYDROXYBENZALCOUMARANONE
Common Name English
3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-HYDROXY-, (2Z)-
Systematic Name English
SULPHURETIN
Common Name English
3',4',6-TRIHYDROXYAURONE
Common Name English
2-(3,4-DIHYDROXYBENZYLIDENE)-6-HYDROXY-3(2H)-BENZOFURANONE
Systematic Name English
Code System Code Type Description
CAS
120-05-8
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID30877681
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-366-4
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
MESH
C054989
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
PUBCHEM
5281295
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
CHEBI
9355
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
FDA UNII
M6410VY6MI
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY
MERCK INDEX
m10372
Created by admin on Sat Dec 16 01:37:39 GMT 2023 , Edited by admin on Sat Dec 16 01:37:39 GMT 2023
PRIMARY Merck Index
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