Compounds > isoline
Page last updated: 2024-12-08

isoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

isoline: a major retronecine-type pyrrolizidine alkaloid from Ligularia duciformis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
LigulariagenusA genus of ornamental plants in the family ASTERACEAE, often found near water.[MeSH]AsteraceaeA large plant family of the order Asterales, subclass Asteridae, class Magnoliopsida. The family is also known as Compositae. Flower petals are joined near the base and stamens alternate with the corolla lobes. The common name of daisy refers to several genera of this family including Aster; CHRYSANTHEMUM; RUDBECKIA; TANACETUM.[MeSH]

Cross-References

ID SourceID
PubMed CID185716
MeSH IDM0472339

Synonyms (14)

Synonym
30000-36-3
unii-kge82edn24
isoline
ruwenine
(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 6-(acetyloxy)-3-ethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro-3-hydroxy-5,6-dimethyl-, (3r,5r,6s,14ar,14br)-
isoline (alkaloid)
kge82edn24 ,
isolin
(3r,5r,6s,9a1r,14ar)-3-ethyl-3-hydroxy-5,6-dimethyl-2,7-dioxo-2,3,4,5,6,7,9,9a1,11,13,14,14a-dodecahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-6-yl acetate
[(1r,4r,6r,7s,17r)-4-ethyl-4-hydroxy-6,7-dimethyl-3,8-dioxo-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-en-7-yl] acetate
(3r,5r,6s,14ar,14br)-6-(acetyloxy)-3-ethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro-3-hydroxy-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione
DTXSID80952412
15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate
AKOS040752118

Research Excerpts

Overview

Isoline is a retronecine-type pyrrolizidine alkaloid (PA) isolated from the traditional Chinese medicinal herb Ligularia duciformis. Male mice demonstrated more higher serum ALT/AST levels, less GSH amounts, lower GCL and GPx activities and proteins induced by isoline as compared to female.

ExcerptReferenceRelevance
"Isoline is a retronecine-type pyrrolizidine alkaloid (PA) isolated from the traditional Chinese medicinal herb Ligularia duciformis. "( Pyrrolizidine alkaloid isoline-induced oxidative injury in various mouse tissues.
Chen, Y; Ji, LL; Liu, TY; Wang, ZT; Wang, ZY, 2010)		2.11
"Isoline is a natural HPA, our further results showed that male mice demonstrated more higher serum ALT/AST levels, less GSH amounts, lower GCL and GPx activities and proteins induced by isoline as compared to female."( The gender-dependent difference of liver GSH antioxidant system in mice and its influence on isoline-induced liver injury.
Ji, L; Jiang, P; Liang, Q; Min, Y; Sheng, Y; Wang, Z; Xia, Y, 2011)		1.31

Toxicity

ExcerptReferenceRelevance
"Isoline, a major retronecine-type pyrrolizidine alkaloid (PA) from the Chinese medicinal herb Ligularia duciformis, was suggested to be the most toxic known PA."( In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors.
Akao, T; Hattori, M; Nakamura, N; Sasahara, M; Takagawa, K; Tang, J; Wang, ZT, 2007)		2.09
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's5 (55.56)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 61.60

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index61.60 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index98.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (61.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (10.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (90.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenylmethylsulfonyl fluoride
Phenylmethylsulfonyl Fluoride: An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.. phenylmethanesulfonyl fluoride : An acyl fluoride with phenylmethanesulfonyl as the acyl group.		2.0310acyl fluorideserine proteinase inhibitor
proadifen
Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.		2.0310diarylmethane
tri-o-cresyl phosphate
tri-o-cresyl phosphate: see also related IMOL S-140		2.0310
2-ethylhexanol
[no description available]		2.4110primary alcoholplant metabolite;
volatile oil component
1-hexanol
1-hexanol: RN given refers to parent cpd. hexanol : A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of six carbon atoms.. hexan-1-ol : A primary alcohol that is hexane substituted by a hydroxy group at position 1.		7.4110hexanol;
primary alcohol		alarm pheromone;
antibacterial agent;
fragrance;
plant metabolite
diphenhydramine hydrochloride
Antitussive Agents: Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.. diphenhydramine hydrochloride : The hydrochloride salt of diphenhydramine.		2.0310hydrochloride;
organoammonium salt		anti-allergic agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
sedative
monocrotaline
Monocrotaline: A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment.		2.0310pyrrolizidine alkaloid
lignoceric acid
lignoceric acid: RN given refers to parent cpd; structure. tetracosanoic acid : A C24 straight-chain saturated fatty acid.		2.0410straight-chain saturated fatty acid;
very long-chain fatty acid		Daphnia tenebrosa metabolite;
human metabolite;
plant metabolite;
volatile oil component
alpha-naphthoflavone
alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).		2.0310extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist;
aryl hydrocarbon receptor antagonist;
EC 1.14.14.14 (aromatase) inhibitor
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0610acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
glutathione disulfide
Glutathione Disulfide: A GLUTATHIONE dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized.		2.0610glutathione derivative;
organic disulfide		Escherichia coli metabolite;
mouse metabolite
isoscopoletin
isoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.		2.0410aromatic ether;
hydroxycoumarin		plant metabolite
lupeol
[no description available]		2.0410pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
scopoletin
[no description available]		2.0410hydroxycoumarinplant growth regulator;
plant metabolite
senecionine
senecionine: RN given refers to parent cpd; structure. senecionine : A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio.		2.0610lactone;
pyrrolizidine alkaloid;
tertiary alcohol		plant metabolite
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.0410benzenes;
hydroxycoumarin;
methyl ketone
clivorine
clivorine: isolated from Ligularia dentata; structure in first source		2.4520
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Liver Injury, Drug-Induced
[description not available]		02.7630
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.7630
Weight Gain
Increase in BODY WEIGHT over existing weight.		03.4211