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
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
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
Sources: http://www.organic-herb.com/Product/552.html
Curator's Comment: Cynarin, isolated from artichoke, was characterized for the first time by Panizzi and Scarpati.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP2708 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8824943 |
|||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25792498 |
243.67 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Palliative | Cynara scolymus Approved UseDigestive complaints, Dyspepsia |
|||
Palliative | Cynara scolymus Approved UseHyperlipidemia |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Herbal_-_HMPC_assessment_report/2011/12/WC500119940.pdf
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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Herbal_-_HMPC_assessment_report/2011/12/WC500119940.pdf
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
Edited
Fri Dec 15 16:20:48 GMT 2023
by
admin
on
Fri Dec 15 16:20:48 GMT 2023
|
Record UNII |
85D81U9JAV
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |