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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=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C3=CC=C(O)C(O)=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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
243.67 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Palliative
Cynara scolymus
Palliative
Cynara scolymus

Cmax

ValueDoseCo-administeredAnalytePopulation
27.9 ng/mL
300 mg single, oral
CYNARINE plasma
Homo sapiens
12.8 ng/mL
300 mg single, oral
1,5-DIFERULOYLQUINIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
151 ng × h/mL
300 mg single, oral
CYNARINE plasma
Homo sapiens
94 ng × h/mL
300 mg single, oral
1,5-DIFERULOYLQUINIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.6 h
300 mg single, oral
CYNARINE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
85D81U9JAV
Record Status Validated (UNII)
Record Version