Compounds > geigerin
Page last updated: 2024-12-07

geigerin

Description

Geigerin is a naturally occurring sesquiterpene lactone isolated from the plant *Senecio geigeri*. It exhibits a range of biological activities, including cytotoxic, anti-inflammatory, and antimicrobial properties. Its synthesis involves a complex series of reactions, often starting from readily available starting materials. Geigerin's cytotoxic activity has led to investigations of its potential as a cancer chemotherapeutic agent. Its anti-inflammatory properties are attributed to its ability to inhibit the production of pro-inflammatory mediators. The study of geigerin is driven by its potential therapeutic applications and its unique structural features. Research efforts are focused on understanding its biological mechanisms, developing synthetic routes, and exploring its therapeutic potential.'

geigerin: from Geigeria; RN given refers to (3aR-(3alpha,3aalpha,4alpha,7abeta,8beta,9aalpha))-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID101676
MeSH IDM0150990

Synonyms (4)

Synonym
436-45-3
geigerin
(1r,3ar,5s,5ar,9s,9as)-9-hydroxy-1,5,8-trimethyl-1,3a,4,5,5a,6,9,9a-octahydroazuleno[6,5-b]furan-2,7-dione
azuleno(6,5-b)furan-2,6(3h,4h)-dione, 3a,7,7a,8,9,9a-hexahydro-4-hydroxy-3,5,8-trimethyl-, (3r-(3alpha,3aalpha,4alpha,7abeta,8beta,9aalpha))-

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The toxic principles contained by the toxic plants are believed to be several sesquiterpene lactones, such as geigerin, vermeeric acid and vermeerin, which cause striated muscle lesions in small stock."( Geigerin-induced cytotoxicity in a murine myoblast cell line (C2C12).
Botha, CJ; Clift, SJ; Ferreira, GCH; Masango, MG, 2017)		2.11
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's2 (40.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 72.44

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 Index72.44 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index116.32 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (72.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		1.9710maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
helenalin
helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.		1.9710cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite
hymenovin
hymenovin: major toxic constituent of poisonous range plant Hymenoxys odorate; shown to be mutagenic; structure		1.9710oxanes
p-methoxy-n-methylphenethylamine
p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.		1.9710aromatic ether;
secondary amino compound		metabolite
tenulin
tenulin: toxic constituent of Helenium amarum (bitter sneezeweed); structure		1.9710sesquiterpene lactone
thapsigargin
Thapsigargin: A sesquiterpene lactone found in roots of THAPSIA. It inhibits SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES.. thapsigargin : An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.		1.9710butyrate ester;
organic heterotricyclic compound;
sesquiterpene lactone		calcium channel blocker;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
sesquiterpenes
[no description available]		3.1550
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9710cysteiniumfundamental metabolite
thapsigargicin
thapsigargicin: a hexaoxygenated tetraacylated sesquiterpene lactone tetraester isolated from roots of Thapsia garganica; structure given in first source; it induces mast cell degranulation and histamine release; it (and thapsitranstagin) is an analog of thapsigargin;		1.9710
odoratin
odoratin: structure; RN given refers to cpd without isomeric designation		1.9710
ivalin
ivalin: from vomiting bush Geigeria; RN given refers to (3aR-(3aalpha,4aalpha,7alpha,8abeta,9aalpha))-isomer; structure given in first source		2.4220
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1510
Plant Poisoning
Poisoning by the ingestion of plants or its leaves, berries, roots or stalks. The manifestations in both humans and animals vary in severity from mild to life threatening. In animals, especially domestic animals, it is usually the result of ingesting moldy or fermented forage.		02.1510
Ovine Diseases
[description not available]		02.1510
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