Page last updated: 2024-11-05

galegine

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

Description

Galegine is an alkaloid found in the seeds of the plant Galega officinalis, commonly known as goat's rue. It is a potent hypoglycemic agent, meaning it lowers blood sugar levels. Galegine has been studied for its potential therapeutic applications in managing diabetes, particularly type 2 diabetes. It works by stimulating the release of insulin from pancreatic beta cells. However, its clinical use is limited due to its toxicity and potential side effects. Research continues to explore its potential therapeutic value, particularly in combination with other agents. Its synthesis involves complex organic chemistry methods, starting from naturally derived precursors.'

galegine: structure given in first source; from Verbesina encelioides and Gelega oficinalis plants; toxic to livestock [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
VerbesinagenusA plant genus of the family ASTERACEAE. Members contain galegine (GUANIDINES).[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]
Verbesina encelioidesspecies[no description available]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 CID10983
CHEMBL ID111469
CHEBI ID5265
SCHEMBL ID868430
SCHEMBL ID8342952
MeSH IDM0200693

Synonyms (34)

Synonym
NCI60_041670
n-3,3-dimethylallylguanidine
galegin
guanidine, (3-methyl-2-butenyl)-
brn 1754651
(3-methylbut-2-enyl)guanidine
isopentenyl guanidine
galegine
C08303 ,
543-83-9
AKOS000276789
2-(3-methylbut-2-enyl)guanidine
chebi:5265 ,
CHEMBL111469
3-04-00-00465 (beilstein handbook reference)
dimethylallylguanidine
r469kqg1ef ,
isoamylene guanidine
unii-r469kqg1ef
guanidine, n-(3-methyl-2-buten-1-yl)-
3-methyl-2-butenylguanidine
n-(3-methyl-2-buten-1-yl)guanidine
galegine [mi]
1-guanidino-3-methyl-butene-2
isoamyleneguanidine
SCHEMBL868430
SCHEMBL8342952
DTXSID10202659 ,
n-3,3-dimethylallylguanidin
1-(3-methylbut-2-en-1-yl)guanidine
Q27106696
n-(3-methylbut-2-en-1-yl)guanidine
EN300-317748
dtxcid90125150

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The minimum toxic dose of 5-6 g/kg indicates a high toxicity when compared to other poisonous plants of the southeastern area of Buenos Aires province, Argentina."( Experimental toxicity of verbesina encelioides in sheep and isolation of galegine.
Campero, CM; Caracino, M; Chayer, R; Cosentino, B; Lopez, TA, 1996
)
0.53

Dosage Studied

ExcerptRelevanceReference
" The higher dosed sheep became recumbent a few hours later and died 60 h after dosing without showing further signs."( Experimental toxicity of verbesina encelioides in sheep and isolation of galegine.
Campero, CM; Caracino, M; Chayer, R; Cosentino, B; Lopez, TA, 1996
)
0.53
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
guanidinesAny organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID193687Percent change in diastolic blood pressure (mmHg)in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID352979Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.5 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352975Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.60 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID421872Cytotoxicity against human SF295 cells after 3 days by MTT assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Cytotoxic guanidine alkaloids from Pterogyne nitens.
AID352977Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.54 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374700Antiobesity activity in high fat diet-induced obese BALB/c mouse model assessed as change in average daily body weight at 0.38 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID193703Percent change in tidal volume expressed in microL in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID374697Hypoglycemic activity in ob/ob mouse model assessed as blood glucose level at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352938Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.57 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID1177547Antimicrobial activity against methicillin-resistant Staphylococcus aureus EMRSA-16 assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID352984Antiobesity activity in ob/ob mouse model assessed as change in average daily weight at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352939Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.70 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352978Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.62 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID193699Percent change in systolic blood pressure (mmHg)in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID1177546Antimicrobial activity against methicillin-resistant Staphylococcus aureus EMRSA-15 assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID352940Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.59 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352937Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.51 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374704Antiobesity activity in high fat diet-induced obese BALB/c mouse model assessed as change in average daily food intake at 0.38 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID193681Maximum rate of rise of the left ventricular isovolumetric pressure in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID352974Antiobesity activity in lean normal BALB/c mouse assessed as change in average daily weight at 0.5 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID1177548Bactericidal activity against multi-drug-resistant Staphylococcus aureus SA-1199B expressing NorA efflux pump incubated for 18 hrs followed by transfer to Petri dishes and measured after 24 hrs2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID352963Antiobesity activity in lean normal BALB/c mouse assessed as change in average daily food intake at 0.5 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID421869Cytotoxicity against human HL60 cells after 3 days by MTT assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Cytotoxic guanidine alkaloids from Pterogyne nitens.
AID352941Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.52 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID1177542Antimicrobial activity against multi-drug-resistant Staphylococcus aureus SA-1199B expressing NorA efflux pump assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID352976Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.72 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352936Toxicity in lean normal BALB/c mouse assessed as overt signs of behavioural changes at equimolar dose of 0.5 mmol/kg galegine administered daily through diet for 7 days2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352942Hypoglycemic activity in lean normal BALB/c mouse assessed as blood glucose level at 0.5 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID1177544Antimicrobial activity against methicillin-resistant Staphylococcus aureus XU212 assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID421870Cytotoxicity against human HCT8 cells after 3 days by MTT assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Cytotoxic guanidine alkaloids from Pterogyne nitens.
AID193688Percent change in heart rate expressed in beats / min in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID1177543Antimicrobial activity against methicillin-resistant Staphylococcus aureus RN4220 assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID421871Cytotoxicity against human MDA-MB-435 cells after 3 days by MTT assay2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Cytotoxic guanidine alkaloids from Pterogyne nitens.
AID352948Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.40 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374708Hypoglycemic activity in high fat diet-induced obese BALB/c mouse model assessed as blood glucose level at 0.38 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID193697Percent change in respiratory frequency (RF) expressed in beats / min in anesthetized rats by i.v. administration1999Bioorganic & medicinal chemistry letters, Nov-15, Volume: 9, Issue:22
Further hypotensive metabolites from Verbesina caracasana.
AID1177545Antimicrobial activity against Staphylococcus aureus ATCC25943 assessed as absence of growth after 18 hrs by MTT assay2014Journal of natural products, Aug-22, Volume: 77, Issue:8
In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues.
AID352987Antiobesity activity in ob/ob mouse model assessed as change in average daily food intake at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (14.29)18.7374
1990's4 (28.57)18.2507
2000's4 (28.57)29.6817
2010's1 (7.14)24.3611
2020's3 (21.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 53.11

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 Index53.11 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.20 (4.65)
Search Engine Demand Index79.73 (26.88)
Search Engine Supply Index2.03 (0.95)

This Compound (53.11)

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%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]