Page last updated: 2024-12-07

sesaminol

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

Description

Sesaminol is a lignan compound found in sesame seeds. It is a potent antioxidant and has been shown to have various beneficial effects on human health, including anti-inflammatory, anti-cancer, and neuroprotective properties. Sesaminol is synthesized from sesamin, another lignan found in sesame seeds, through a series of enzymatic reactions. It is often studied due to its potential for therapeutic applications in various diseases and conditions. Sesaminol is a promising compound with potential health benefits, and further research is needed to fully understand its mechanisms of action and clinical applications.'

sesaminol: structure given in first source; RN given from CAS Index Guide 1990; RN given refers to the (1S-(alpha,3aalpha,4alpha,6aalpha))-isomer; RN for cpd without isomeric designation not available 11/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

sesaminol : A furofuran that is cis-tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 6-hydroxy-1,3-benzodioxol-5-yl group at position 1S and a 1,3-benzodioxol-5-yl group at position 4S. It is metabolite found in sesame seeds. [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]

Cross-References

ID Source	ID
PubMed CID	94672
CHEBI ID	145778
SCHEMBL ID	12600772
MeSH ID	M0181294

Synonyms (15)

Synonym
sesaminol
(1s-(1alpha,3aalpha,4alpha,6aalpha))-6-(4-(1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-1,3-benzodioxol-5-ol
74061-79-3
(+)-sesaminol
CHEBI:145778
6-[(1s,3ar,4s,6ar)-4-(1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-1,3-benzodioxol-5-ol
justisolin
6-[(3s,3ar,6s,6ar)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxol-5-ol
1,3-benzodioxol-5-ol, 6-(4-(1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-, (1s-(1alpha,3aalpha,4alpha,6aalpha))-
SCHEMBL12600772
DTXSID50995513
6-[4-(2h-1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-2h-1,3-benzodioxol-5-ol
1,3-benzodioxol-5-ol, 6-[(1s,3ar,4s,6ar)-4-(1,3-benzodioxol-5-yl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-
sesaminol, (+)-
QTS6XJP5LC

Research Excerpts

Overview

Sesaminol triglucoside is a major lignin in sesame meal. It has a methylenedioxyphenyl group and multiple functions in vivo.

Excerpt	Reference	Relevance
"Sesaminol triglucoside is a major lignin in sesame meal and has a methylenedioxyphenyl group and multiple functions in vivo. "	( Gene expression profiling of sesaminol triglucoside and its tetrahydrofuranoid metabolites in primary rat hepatocytes. Jan, KC; Liu, TC; Yang, BB, 2014)	2.14

Bioavailability

Excerpt	Reference	Relevance
" These findings indicate that sesame sesaminol and its epimer are poorly absorbed prior to reaching the rectum and that substantial amounts pass from the small to the large intestine, where they are metabolized by the colonic microflora to tetrahydrofuranoid metabolites."	( Intestinal distribution and excretion of sesaminol and its tetrahydrofuranoid metabolites in rats. Chu, YH; Ho, CT; Hwang, LS; Jan, KC; Ku, KL, 2011)	0.91

Dosage Studied

Excerpt	Relevance	Reference
" In Experiment 2, we examined whether sesaminol caused enhanced absorption of alpha-tocopherol and alpha-tocotrienol in a dosage regimen supplying T-mix and sesaminol on alternating days and observed significantly higher levels of alpha-tocopherol and alpha-tocotrienol in rats fed sesaminol, even without simultaneous intake, compared to those in rats without sesaminol."	( Effect of sesaminol on plasma and tissue alpha-tocopherol and alpha-tocotrienol concentrations in rats fed a vitamin E concentrate rich in tocotrienols. Iizuka, Y; Ikeda, I; Ikeda, S; Yamashita, K, 2002)	0.99

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antioxidant	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
[role 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]

Drug Classes (3)

Class	Description
benzodioxoles
furofuran	Organic heterobicyclic compounds containing a two furan rings ortho-fused to each other.
organic hydroxy compound	An organic compound having at least one hydroxy group attached to a carbon atom.
[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]

Pathways (1)

Pathway	Proteins	Compounds
sesaminol glucoside biosynthesis	5	8
sesaminol glucoside biosynthesis	5	12

Research

Studies (38)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	7 (18.42)	18.2507
2000's	14 (36.84)	29.6817
2010's	10 (26.32)	24.3611
2020's	7 (18.42)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.36

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.

Metric	This Compound (vs All)
Research Demand Index	29.36 (24.57)
Research Supply Index	3.69 (2.92)
Research Growth Index	4.70 (4.65)
Search Engine Demand Index	36.71 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (29.36)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (2.63%)	5.53%
Reviews	2 (5.26%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	35 (92.11%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
nitrites Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)	2.03	1	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species	human metabolite
dapi DAPI: RN given refers to parent cpd.	2.02	1	indoles	fluorochrome
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	2.1	1	butan-4-olide	metabolite; neurotoxin
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	7.1	1	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.04	1	UDP-D-glucose	fundamental metabolite
thiazoles [no description available]	2.02	1	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.41	1	dialdehyde	biomarker
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.25	6	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
azoxymethane Azoxymethane: A potent carcinogen and neurotoxic compound. It is particularly effective in inducing colon carcinomas.	7.03	1
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	3.91	12	D-glucopyranose	epitope; mouse metabolite
thiazolyl blue thiazolyl blue: RN & II refers to bromide. 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide : The bromide salt of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium.	2.02	1	organic bromide salt	colorimetric reagent; dye
sesamol sesamol: constituent of sesame oil; RN given refers to parent cpd; structure in first source	3.58	2	benzodioxoles
sesamin (+)-sesamin : A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity.	5	12	benzodioxoles; furofuran; lignan	antineoplastic agent; neuroprotective agent; plant metabolite
2,2'-azobis(2,4-dimethylvaleronitrile) 2,2'-azobis(2,4-dimethylvaleronitrile): free radical initiator in liposome systems	6.99	1
gamma-tocopherol gamma-Tocopherol: A natural tocopherol with less antioxidant activity than ALPHA-TOCOPHEROL. It exhibits antioxidant activity by virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus. As in BETA-TOCOPHEROL, it also has three methyl groups on the 6-chromanol nucleus but at different sites.. gamma-tocopherol : A tocopherol in which the chroman-6-ol core is substituted by methyl groups at positions 7 and 8. It is found particularly in maize (corn) oil and soya bean (soybean) oils.	2.03	1	tocopherol; vitamin E	algal metabolite; food antioxidant; plant metabolite
glycidyl nitrate glycidyl nitrate: a nitric oxide donor; structure in first source. peptidoglycan : A peptidoglycosaminoglycan formed by alternating residues of beta-(1->4)-linked N-acetylglucosamine and N-acetylmuramic acid {2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose} residues. Attached to the carboxy group of the muramic acid is a peptide chain of three to five amino acids.	2.1	1
sesamolin sesamolin: constituent of sesame oil; RN given refers to the (1S-(1alpha,3aalpha,4alpha,6aalpha)-isomer); inhibits proliferation of human lymphocytic leukemia cells in culture	4.33	5	benzodioxoles
2,3-bis(3'-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone: lignan isolated from urine of humans & other mammals; RN given refers to cpd without isomeric designation; structure given in second source	2.1	1	lignan
2,3-bis(3'-hydroxybenzyl)butane-1,4-diol 2,3-bis(3'-hydroxybenzyl)butane-1,4-diol: lignan isolated from urine of humans & other mammals	2.1	1	lignan
diaminopimelic acid Diaminopimelic Acid: A diamino derivative of heptanedioic acid with amino groups at C-2 and C-6 and the general formula (COOH)CH(NH2)CH2CH2CH2CH(NH2)(COOH).. LL-2,6-diaminopimelic acid : A 2,6-diaminopimelic acid in which both chiral centres have S configuration. It is a component of bacterial cell wall.	2.1	1	2,6-diaminopimelic acid; amino acid zwitterion	Escherichia coli metabolite
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	10.34	17
coniferyl alcohol coniferyl alcohol: structure. coniferol : A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring.	3.41	1	guaiacols; phenylpropanoid	animal metabolite; monolignol; mouse metabolite; pheromone; plant metabolite; volatile oil component
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.02	1
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	1.99	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
leukotriene b4 Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.	1.99	1	dihydroxy monocarboxylic acid; hydroxy polyunsaturated fatty acid; leukotriene; long-chain fatty acid	human metabolite; mouse metabolite; plant metabolite; vasoconstrictor agent
tocotrienol, alpha alpha-tocotrienol : A tocotrienol that is chroman-6-ol substituted by methyl groups at positions 2, 5, 7 and 8 and a farnesyl chain at position 2. It has been found in palm oil derived from Elaeis guineensis.	2.01	1	tocotrienol; vitamin E	ferroptosis inhibitor; human metabolite; neuroprotective agent; plant metabolite
tocotrienols tocotrienol : A tocol in which the hydrocarbon chain at position 2 contains three double bonds.	7.01	1	diterpenoid
hydroxymatairesinol hydroxymatairesinol: a plant lignan from Norway spruce (Picea abies); structure in first source	7.03	1
deoxyguanosine [no description available]	2.02	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	2.49	2	guanosines	biomarker

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	2.41	1	0
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.41	1	0
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.41	1	0
Insulin Sensitivity [description not available]	2.25	1	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.25	1	0
Weight Gain Increase in BODY WEIGHT over existing weight.	2.61	2	0
Cognitive Decline [description not available]	3.7	1	1
Acute Confusional Senile Dementia [description not available]	3.98	2	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	3.98	2	1
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	3.7	1	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.13	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.13	1	0
Cognition Disorders Disorders characterized by disturbances in mental processes related to learning, thinking, reasoning, and judgment.	2.05	1	0
Academic Disorder, Developmental [description not available]	2.05	1	0
Learning Disabilities Conditions characterized by a significant discrepancy between an individual's perceived level of intellect and their ability to acquire new language and other cognitive skills. These may result from organic or psychological conditions. Relatively common subtypes include DYSLEXIA, DYSCALCULIA, and DYSGRAPHIA.	2.05	1	0
Extravascular Hemolysis [description not available]	2.4	2	0
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.4	2	0
Cancer of Colon [description not available]	2.03	1	0
Condition, Preneoplastic [description not available]	2.03	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.03	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2.03	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2	1	0
Elevated Cholesterol [description not available]	2	1	0
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	2	1	0
Leukemia, Lymphocytic [description not available]	2	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	2	1	0

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