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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H26O13
Molecular Weight 594.5196
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TILIROSIDE

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C5=CC=C(O)C=C5)[C@H](O)[C@H]1O

InChI

InChIKey=DVGGLGXQSFURLP-VWMSDXGPSA-N
InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+/t21-,24-,26+,27-,30+/m1/s1

HIDE SMILES / InChI

Molecular Formula C30H26O13
Molecular Weight 594.5196
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26498393 | https://www.ncbi.nlm.nih.gov/pubmed/28539736 | https://www.ncbi.nlm.nih.gov/pubmed/28704976 | https://www.ncbi.nlm.nih.gov/pubmed/27347085

Tiliroside is a glycosidic flavonoid, which possesses anti-inflammatory, antioxidant, anticarcinogenic and hepatoprotective activities. In vitro Tiliroside shows antidiabetic properties by enhancing glucose consumption by insulin resistant HepG2 cells, antihypertensive and vasorelaxant effects in resis¬tance arteries, antihyperglycemic, antihyperlipidemic and antioxidant activities; as well as an inhibitory effect on important human liver cytochrome p450 enzymes. In vivo, Tiliroside significantly inhibited the mouse paw edema induced by phospholipase A and the mouse ear inflammation induced by 12 O tetradecanoylphorbol- 13-acetate. Tiliroside can be found in the hairy shields and young leaves of plants growing in tropical regions of the world. Tiliroside protects these plants from UV-induced and environmental stress and can be used as anti-aging and anti-inflammatory agent for cosmetic applications.

Originator

Sources: Naturwissenschaften (1959), 46, 358.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.6 nM [Ki]
5468.7 nM [Ki]
134.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena.
1996 Dec 4
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2003 Dec
Flavonol 3-O-glycoside hydroxycinnamoyltransferases from Scots pine (Pinus sylvestris L.).
2005 Mar
Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death.
2007 Mar 21
Patents

Sample Use Guides

The formulation (Tiliroside 0.1 % w/v) were applied twice daily (morning and evening) in normal conditions of use during 28 days.
Route of Administration: Topical
To determine the effect of tiliroside on cell viability, RAW 264.7 cells were cultured in 96 well plates at a density of 2x10^5 cells/well. Following a 24 h incubation period, the cells were then treated with seri¬ally diluted tiliroside at concentrations of 1.5625 100 μM. The mitochondrial dependent reduction of MTT to formazan was used to measure cell respiration as an indicator of cell viability
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:47:24 GMT 2023
Edited
by admin
on Fri Dec 15 19:47:24 GMT 2023
Record UNII
15M04TXR9M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TILIROSIDE
INCI  
INCI  
Official Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-3-((6-O-((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-
Common Name English
TILIROSIDE [INCI]
Common Name English
KAEMPFEROL 3-O-(6''-O-P-COUMAROYL)GLUCOSIDE
Common Name English
2-PROPENOIC ACID, 3-(4-HYDROXYPHENYL)-, 6'-ESTER WITH 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE, (E)-
Common Name English
KAEMPFEROL-3-O(-6-O-TRANS-P-COUMAROYL-.BETA.-GLUCOPYRANOSIDE
Common Name English
3-O-KAEMPFEROL 6-O-(TRANS-P-COUMAROYL)-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
RONACARE TILIROSIDE
Brand Name English
KAEMPFEROL 3-O-(6''-O-(E)-P-COUMAROYL)-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
POTENGRIFFIOSIDE A
Common Name English
KAEMPFEROL 3-O-(6''-O-(TRANS-P-COUMAROYL))-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
TRANS-TILIROSIDE
Common Name English
KAEMPFEROL 3-O-.BETA.-D-(6-O-TRANS-P-COUMAROYL)GLUCOPYRANOSIDE
Common Name English
ASTRAGALIN-6''-TRANS-P-COUMARATE
Common Name English
Code System Code Type Description
FDA UNII
15M04TXR9M
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID601021936
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
RXCUI
1423792
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY RxNorm
PUBCHEM
5320686
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
CAS
20316-62-5
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
DAILYMED
15M04TXR9M
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
SMS_ID
300000008663
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY
MESH
C052083
Created by admin on Fri Dec 15 19:47:24 GMT 2023 , Edited by admin on Fri Dec 15 19:47:24 GMT 2023
PRIMARY