sesamolin
Description
Sesamolin is a lignan found in sesame seeds. It is a natural antioxidant and has been shown to have a variety of biological activities, including anti-inflammatory, anti-cancer, and neuroprotective effects. Sesamolin is synthesized in plants through the shikimate pathway. It is thought to be a valuable ingredient in sesame seeds for its antioxidant properties, helping protect against oxidative stress and its harmful effects. Sesamolin is studied for its potential health benefits, including its ability to protect against heart disease, cancer, and neurodegenerative diseases. More research is needed to fully understand the effects of sesamolin on human health.'
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 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 101746 |
CHEMBL ID | 2059646 |
CHEBI ID | 175751 |
SCHEMBL ID | 163696 |
MeSH ID | M0153020 |
Synonyms (28)
Synonym |
---|
5-[[(3s,3ar,6r,6ar)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrouro[3,4-c]uran-6-yl]oxy]-1,3-benzodioxole |
CHEBI:175751 |
526-07-8 |
sesamolin |
5-[[(3s,3ar,6r,6ar)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole |
ai3-20978 |
unii-7a90tj149g |
1,3-benzodioxole, 5-(4-(1,3-benzodioxol-5-yloxy)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-, (1s-(1alpha,3a alpha,4alpha,6a alpha))- |
7a90tj149g , |
CHEMBL2059646 |
1,3-benzodioxol-5-yl (1r,3ar,4s,6ar)-4-(1,3-benzodioxol-5-yl)perhydrofuro(3,4-c)furan-1-yl ether |
sesamolin [mi] |
(1s,3ar,4r,6ar)-5-(4-(1,3-benzodioxol-5-yloxy)tetrahydro-1h,3h-furo(3,4-c)furan-1-yl)-1,3-benzodioxole |
SCHEMBL163696 |
5-(((1r,3ar,4s,6ar)-4-(benzo[d][1,3]dioxol-5-yl)hexahydrofuro[3,4-c]furan-1-yl)oxy)benzo[d][1,3]dioxole |
AC-35092 |
Q-100595 |
A1-06842 |
AS-74827 |
5-[(1s,3ar,4r,6ar)-4-(2h-1,3-benzodioxol-5-yloxy)-hexahydrofuro[3,4-c]furan-1-yl]-2h-1,3-benzodioxole |
AKOS030573689 |
DTXSID90878472 , |
HY-N0809 |
mfcd04112844 |
Q15720551 |
CS-0009814 |
1,3-benzodioxole,5-[4-(1,3-benzodioxol-5-yloxy)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-,(1s,3ar,4r,6ar)- |
dtxcid301323428 |
Research Excerpts
Overview
Sesamolin is a lignan compound isolated from sesame seeds. It has several beneficial properties, including potential for melanin inhibition.
Excerpt | Reference | Relevance |
---|---|---|
"Sesamolin is a lignan compound isolated from sesame seeds with several beneficial properties, including potential for melanin inhibition." | ( Inhibitory Effect of Sesamolin on Melanogenesis in B16F10 Cells Determined by In Vitro and Molecular Docking Analyses. Baek, SH; Kang, MG; Park, D, 2020) | 1.6 |
Actions
Excerpt | Reference | Relevance |
---|---|---|
"Sesamolin was able to inhibit H2O2-induced p38 MAPK and caspase-3 activation and cell death." | ( Oxidative toxicity in BV-2 microglia cells: sesamolin neuroprotection of H2O2 injury involving activation of p38 mitogen-activated protein kinase. Chen, YS; Hou, RC; Huang, JR; Jeng, KC; Wu, CC, 2005) | 1.31 |
Toxicity
Excerpt | Reference | Relevance |
---|---|---|
" These findings demonstrated that, among three sesame lignans tested, sesamin protected against Aβ toxicity by reducing toxic Aβ oligomers." | ( Sesamin and sesamolin reduce amyloid-β toxicity in a transgenic Caenorhabditis elegans. Bunargin, W; Keowkase, R; Shoomarom, N; Sitthithaworn, W; Weerapreeyakul, N, 2018) | 0.86 |
Bioavailability
differences in bioavailability may contribute to the divergent effects of sesamin and sesamolin on hepatic fatty acid oxidation. However, the bioavailability of sedamolin was poor in mice.
Excerpt | Reference | Relevance |
---|---|---|
" The increased bioavailability of tocopherols in the presence of dietary lignans might be due to the regeneration of oxidized tocopherols." | ( Dietary sesame oils inhibits iron-induced oxidative stress in rats [corrected]. Hemalatha, S; Raghunath, M, 2004) | 0.32 |
" Differences in bioavailability may contribute to the divergent effects of sesamin and sesamolin on hepatic fatty acid oxidation." | ( Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. Adachi, Y; Ide, T; Lim, JS; Takahashi, Y, 2007) | 0.81 |
" However, the bioavailability of sesamin and sesamolin was poor in mice." | ( Using Turmeric Oil as a Solvent Improves the Distribution of Sesamin-Sesamolin in the Serum and Brain of Mice. Iwamoto, K; Makino, S; Matsumura, S; Moriyama, T; Yamamoto, A; Yoshioka, Y; Zaima, N, 2019) | 1.01 |
Drug Classes (1)
Class | Description |
---|---|
benzodioxoles | |
[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 |
---|---|---|
sesamin biosynthesis | 0 | 15 |
Bioassays (4)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID673419 | Inhibition of rat intestinal sucrase using sucrose as substrate at 10 mg/ml preincubated for 10 mins before substrate addition by glucose oxidase method | 2012 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16 | (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase. |
AID673421 | Inhibition of rat intestinal maltase using maltose as substrate at 10 mg/ml preincubated for 10 mins before substrate addition by glucose oxidase method | 2012 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16 | (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase. |
AID779150 | Inhibition of Wnt/beta-catenin signaling pathway in human HEK293 cells at 20 uM after 24 hrs by dual luciferase reporter gene assay relative to vehicle-treated control | 2013 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 23, Issue:20 | Anti-proliferative activity of hydnocarpin, a natural lignan, is associated with the suppression of Wnt/β-catenin signaling pathway in colon cancer cells. |
AID673424 | Inhibition of bakers yeast alpha-glucosidase using p-nitrophenyl-(alpha-D-glucopyranoside) as substrate preincubated for 10 mins before substrate addition by microplate reader | 2012 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16 | (+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (56)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (1.79) | 18.7374 |
1990's | 2 (3.57) | 18.2507 |
2000's | 12 (21.43) | 29.6817 |
2010's | 23 (41.07) | 24.3611 |
2020's | 18 (32.14) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 34.75
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.
| This Compound (34.75) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 4 (7.02%) | 6.00% |
Case Studies | 1 (1.75%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 52 (91.23%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |