Compounds > kotalanol
Page last updated: 2024-11-13

kotalanol

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

Description

Kotalanol: a sulfated thiosugar from Salacia plant genus; alpha-glucosidase inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
SalaciagenusA plant genus of the family Celastraceae. Members contain friedelane-type TRITERPENES and SESQUITERPENES, EUDESMANE.[MeSH]CelastraceaeA plant family of the order Celastrales, subclass Rosidae, class Magnoliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID42632210
CHEMBL ID1093264
MeSH IDM0295267

Synonyms (10)

Synonym
kotalanol
(1s,2r,3r,4s)-1-{(1s)-2-[(2r,3s,4s)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydrothiophenium-1-yl]-1-hydroxyethyl}-2,3,4,5-tetrahydroxypentyl sulfate
214491-07-3
CHEMBL1093264 ,
1,4-dideoxy-1,4-[[2s,3s,4r,5r,6s-2,4,5,6,7-pentahydroxy-3-(sulfooxy)heptyl]-(r-)epi-sulfoniumylidine]-d-arabinitol
bdbm50316179
(2s,3s,4r,5r,6s)-1-[(2r,3s,4s)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-2,4,5,6,7-pentahydroxyheptan-3-yl sulfate (non-preferred name)
DTXSID10655282
[(2s,3s,4r,5r,6s)-1-[(2r,3s,4s)-3,4-dihydroxy-2-(hydroxymethyl)thiolan-1-ium-1-yl]-2,4,5,6,7-pentahydroxyheptan-3-yl] sulfate
Q27462126

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In human studies, Salacia extracts have been shown to decrease plasma glucose and insulin levels, decrease HbA1c, and modulate serum lipid levels with no adverse effects being reported."( Anti-diabetic and Anti-hyperlipidemic Effects and Safety of Salacia reticulata and Related Species.
Ray, S; Stohs, SJ, 2015)		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Maltase-glucoamylase, intestinalHomo sapiens (human)Ki0.19000.17001.86737.3000AID472416; AID536212
Sucrase-isomaltase, intestinalRattus norvegicus (Norway rat)IC50 (µMol)3.15000.04001.848310.0000AID343501; AID343502; AID578320; AID578321; AID593349; AID593353; AID696530; AID696531
Sucrase-isomaltase, intestinalRattus norvegicus (Norway rat)Ki2.31000.20001.48004.2000AID343501; AID343502
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)IC50 (µMol)7.05000.08002.50619.8500AID343500; AID578319; AID593351; AID696532
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)Ki0.54000.00871.09573.5000AID343500
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
maltose catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
starch catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
dextrin catabolic processMaltase-glucoamylase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
catalytic activityMaltase-glucoamylase, intestinalHomo sapiens (human)
glucan 1,4-alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
alpha-1,4-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
protein bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
amylase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
carbohydrate bindingMaltase-glucoamylase, intestinalHomo sapiens (human)
maltose alpha-glucosidase activityMaltase-glucoamylase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
apical plasma membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
extracellular exosomeMaltase-glucoamylase, intestinalHomo sapiens (human)
tertiary granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
ficolin-1-rich granule membraneMaltase-glucoamylase, intestinalHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID620761Inhibition of mouse his-tagged ctMGAM-N20 expressed in Sf9 cells assessed as amount of glucose produced using maltose as a substrate after 45 mins by glucose oxidase assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID620760Inhibition of mouse his-tagged ctMGAM-N2 expressed in Sf9 cells assessed as amount of glucose produced using maltose as a substrate after 45 mins by glucose oxidase assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID343502Inhibition of rat intestinal isomaltase2008Journal of natural products, Jun, Volume: 71, Issue:6
Alpha-glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT).
AID593353Inhibition of rat small intestinal isomaltase after 30 mins2011Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor.
AID620768Selectivity ratio of Ki for human ntMGAM to Ki for mouse ctMGAM-N202011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID620766Selectivity ratio of Ki for human ntSI to Ki for mouse ctMGAM-N22011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID578321Inhibition of rat intestinal isomaltase2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.
AID472416Inhibition of recombinant human maltase glucoamylase N-terminal catalytic domain2010Bioorganic & medicinal chemistry, Apr-15, Volume: 18, Issue:8
Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor.
AID343501Inhibition of rat intestinal sucrase2008Journal of natural products, Jun, Volume: 71, Issue:6
Alpha-glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT).
AID696532Inhibition of rat small intestinal maltase after 30 mins by glucose-oxidase method2012Bioorganic & medicinal chemistry, Nov-01, Volume: 20, Issue:21
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2.
AID620772Selectivity ratio of Ki for human ntSI to Ki for mouse ctSI2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID593349Inhibition of rat small intestinal sucrase after 30 mins2011Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor.
AID620765Selectivity ratio of Ki for human ntMGAM to Ki for mouse ctMGAM-N22011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID696530Inhibition of rat small intestinal isomaltase after 30 mins by glucose-oxidase method2012Bioorganic & medicinal chemistry, Nov-01, Volume: 20, Issue:21
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2.
AID578320Inhibition of rat intestinal sucrase2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.
AID620771Selectivity ratio of Ki for human ntMGAM to Ki for mouse ctSI2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID343500Inhibition of rat intestinal maltase2008Journal of natural products, Jun, Volume: 71, Issue:6
Alpha-glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT).
AID593351Inhibition of rat small intestinal maltase after 30 mins2011Bioorganic & medicinal chemistry, Apr-01, Volume: 19, Issue:7
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor.
AID578319Inhibition of rat intestinal maltase2011Bioorganic & medicinal chemistry, Mar-15, Volume: 19, Issue:6
Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors.
AID620769Selectivity ratio of Ki for human ntSI to Ki for mouse ctMGAM-N202011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID696531Inhibition of rat small intestinal sucrase after 30 mins by glucose-oxidase method2012Bioorganic & medicinal chemistry, Nov-01, Volume: 20, Issue:21
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2.
AID620764Inhibition of human ntSI expressed in Drosophila S2 cells assessed as amount of glucose produced using maltose as a substrate after 45 mins by glucose oxidase assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID620763Inhibition of mouse his-tagged ctSI expressed in Sf9 cells assessed as amount of glucose produced using maltose as a substrate after 45 mins by glucose oxidase assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
AID536212Inhibition of human recombinant N-terminal subunit of maltase-glucoamylase after 60 mins by glucose oxidase assay2010Bioorganic & medicinal chemistry, Nov-15, Volume: 18, Issue:22
Probing the active-site requirements of human intestinal N-terminal maltase-glucoamylase: Synthesis and enzyme inhibitory activities of a six-membered ring nitrogen analogue of kotalanol and its de-O-sulfonated derivative.
AID620762Inhibition of human ntMGAM expressed in Drosophila S2 cells assessed as amount of glucose produced using maltose as a substrate after 45 mins by glucose oxidase assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.56)18.2507
2000's5 (27.78)29.6817
2010's12 (66.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.99

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.99 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index5.40 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (15.79%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (84.21%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
thiophenes
Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.		3.1210mancude organic heteromonocyclic parent;
monocyclic heteroarene;
thiophenes;
volatile organic compound		non-polar solvent
mannose
mannopyranose : The pyranose form of mannose.		2.0510D-aldohexose;
D-mannose;
mannopyranose		metabolite
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		2.46202-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
castanospermine
castanospermine: indolizidine alkaloid from seeds of Australian legume, Castanospermum australe. castanospermine : A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).		210indolizidine alkaloidanti-HIV-1 agent;
anti-inflammatory agent;
EC 3.2.1.* (glycosidase) inhibitor;
metabolite
procyanidin
Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.		3.2110proanthocyanidin
proanthocyanidin
proanthocyanidin: RN given refers to proanthocyanidin A; Cannabinoid Receptor CB1 antagonist. proanthocyanidin : A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.		3.2110
tagetitoxin
tagetitoxin: chlorosis-inducing phytoxin produced by Pseudomonas syringae pv. tagetis; inhibits RNA synthesis directed by chloroplast RNA polymerase		3.1210
erythritol
[no description available]		210butane-1,2,3,4-tetrolantioxidant;
human metabolite;
plant metabolite
arabinose
[no description available]		210L-arabinoseEscherichia coli metabolite;
mouse metabolite
glucosamine
D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.		2.0510D-glucosamineEscherichia coli metabolite;
geroprotector;
mouse metabolite
miglitol
[no description available]		2.4620piperidines
ao 128
AO 128: alpha-glucosidase inhibitor; structure given in first source		2.4720organic molecular entity
acarbose
[no description available]		2.7630amino cyclitol;
glycoside
mangiferin
shamimin: isolated from the leaves of Bombax ceiba; structure in first source		3.2110C-glycosyl compound;
xanthones		anti-inflammatory agent;
antioxidant;
hypoglycemic agent;
plant metabolite
sulfur
Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.		2.0410chalcogen;
nonmetal atom		macronutrient
salacinol
salacinol: a sulfated thiosugar from Salacia reticulata (CELASTRACEAE); structure in first source		5.61130
ponkoranol
ponkoranol: isolated from the plant Salacia reticulata; structure in first source		2.4720
neosalacinol
[no description available]		2.0610
thiolactomycin
thiolactomycin: from actinomycetes; structure given in first source		3.1210
ConditionIndicatedRelationship StrengthStudiesTrials
Diabetes Mellitus, Adult-Onset
[description not available]		03.6730
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1110
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		03.6730
Diabetes Mellitus
A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.		03.3620