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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H24O12
Molecular Weight 516.4509
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CYNARINE

SMILES

O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1O)(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)=O

InChI

InChIKey=YDDUMTOHNYZQPO-RVXRWRFUSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H24O12
Molecular Weight 516.4509
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Cynarine (Cynarin) is the most noteworthy active ingredient of the artichoke, and is considered a medicinal foodstuff due to its beneficial effect on the organism, derived from its condition as a stimulant of bile secretion (choleretic effect). Cynarine is present in artichoke leaves and has a beneficial effect on the control of gallstones, helps control cholesterol levels and improves gallbladder function. Chlorogenic acid and cynarin have been shown to have activity against oxidative stress in human leukocytes, whereas cynarin has also been shown to have hypocholesterolemic, hepatoprotective, and, more recently, antihuman immunodeficiency virus-1 (anti-HIV-1; 44) activities. Cynarin had marked antioxidant, anticholinergic, reducing ability, radical-scavenging, and metal-binding activities.

Originator

Curator's Comment: Cynarin, isolated from artichoke, was characterized for the first time by Panizzi and Scarpati.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Humans, oral: Many artichoke supplements recommend a dosage of around 1500 mg to 2000 mg. http://www.nutragreenbio.com/product/artichoke-extract
Cynarin (100 and 200 mg/kg body weight) administered intravenously to rabbits, lowered serum cholesterol by about 20% Triton WR 1339-induced hypercholesterolaemia. In rats it was significantly lowered (p=0.05-0.02) by cynarin after intraperitoneal administration (2*200 mg/kg body weight).
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: Cynarin demonstrated 87.72% inhibition of linoleic acid lipid peroxidation at 30 ug/mL concentration. https://www.ncbi.nlm.nih.gov/pubmed/25792498
Cynarin and caffeic acid showed significant cytoprotective activity (p<0.01 at 1 mg/ml) against carbon tetrachloride in isolated rat hepatocytes, reducing leakage of the liver enzymes glutamine oxaloacetic transaminase and glutamic pyrovic transaminase.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:48 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:48 GMT 2023
Record UNII
85D81U9JAV
Record Status Validated (UNII)
Record Version
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Name Type Language
CYNARINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
PLEMOCIL
Brand Name English
1-CARBOXY-4,5-DIHYDROXY-1,3-CYCLOHEXYLENEBIS-(3,4-DIHYDROXYCINNAMATE)
Common Name English
cynarine [INN]
Common Name English
CYNARINE [MI]
Common Name English
(1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-1,3-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-4,5-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID
Common Name English
CYCLOHEXANECARBOXYLIC ACID, 1,3-BIS(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-4,5-DIHYDROXY-, (1R,3R,4S,5R)-
Systematic Name English
CYNARINE [MART.]
Common Name English
3,4-DIHYDROXYCINNAMIC ACID 1-CARBOXY-4,5-DIHYDROXY-1,3-CYCLOHEXYLENE ESTER
Common Name English
1,3-DICQA
Common Name English
1,3-DICAFFEOYLQUINIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS) [DSC]
Common Name English
3,4-DIHYDROXYCINNAMIC ACID, 1-CARBOXY-4,5-DIHYDROXY-1,3-CYCLOHEXYLENE ESTER
Common Name English
LISTROCOL
Brand Name English
1,3-DICAFFEOYLQUINIC ACID
Common Name English
Cynarine [WHO-DD]
Common Name English
(1R,3R,4S,5R)-1,3-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-4,5-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID
Systematic Name English
CAFFEIC ACID 1-CARBOXY-4,5-DIHYDROXY-1,3-CYCLOHEXYLENE ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66913
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
Code System Code Type Description
FDA UNII
85D81U9JAV
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
SMS_ID
100000083760
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
DRUG CENTRAL
3124
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
INN
3276
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
EVMPD
SUB06870MIG
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105478
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
WIKIPEDIA
CYNARINE
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
PUBCHEM
5281769
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
MESH
C100257
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
MERCK INDEX
m4033
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY Merck Index
CAS
30964-13-7
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C81041
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
CAS
212891-05-9
Created by admin on Fri Dec 15 16:20:48 GMT 2023 , Edited by admin on Fri Dec 15 16:20:48 GMT 2023
PRIMARY
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