sigmoidin A: isolated from Erythrina sigmoidea; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
sigmoidin A : A tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and prenyl groups at positions 2' and 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities. [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]
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Erythrina | genus | A genus of leguminous shrubs or trees, mainly tropical, yielding useful compounds such as ALKALOIDS and PLANT LECTINS.[MeSH] | Fabaceae | The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH] |
| Erythrina sigmoidea | species | [no description available] | Fabaceae | The large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH] |
| ID Source | ID |
|---|---|
| PubMed CID | 73204 |
| CHEMBL ID | 229506 |
| CHEBI ID | 66482 |
| MeSH ID | M0176989 |
| Synonym |
|---|
| 4h-1-benzopyran-4-one, 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5- ,7-dihydroxy-, (s)- |
| sigmoidin a |
| (2s)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chroman-4-one |
| 87746-48-3 |
| chebi:66482 , |
| CHEMBL229506 , |
| (2s)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one |
| (2s)-2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-2,3-dihydro-4h-chromen-4-one |
| bdbm50212392 |
| 5,7,3',4'-tetrahydroxy-2',5'-diprenylflavone |
| (2s)- 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-4h-1-benzopyran-4-one |
| 4h-1-benzopyran-4-one, 2-(3,4-dihydroxy-2,5-bis(3-methyl-2-butenyl)phenyl)-2,3-dihydro-5,7-dihydroxy-, (s)- |
| sigmoidin-a |
| DTXSID20236607 |
| Q27135083 |
| XS161554 |
Sigmoidin A (SGN) is a prenylated flavanone derivative of eriodictyol (ERD) SGN has moderate antioxidant, antimicrobial and anti-inflammatory activity.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Sigmoidin A (SGN) is a prenylated flavanone derivative of eriodictyol (ERD) with reported moderate antioxidant, antimicrobial and anti-inflammatory activity. " | ( Comparative antioxidant, prooxidant and cytotoxic activity of sigmoidin A and eriodictyol. Dagne, E; Habtemariam, S, 2010) | 2.04 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Dose-response inhibitor potency was established for sigmoidin A (IC (50) = 31 microM)." | ( Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Fomum, ZT; Giner, RM; Kamanyi, A; Máñez, S; Mbafor, JT; Mbanya, JC; Njamen, D; Recio, MC; Ríos, JL, 2004) | 0.83 |
| Role | Description |
|---|---|
| metabolite | Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. |
| anti-inflammatory agent | Any compound that has anti-inflammatory effects. |
| radical scavenger | A role played by a substance that can react readily with, and thereby eliminate, radicals. |
| anti-obesity agent | Any substance which is used to reduce or control weight. |
| antibacterial agent | A substance (or active part thereof) that kills or slows the growth of bacteria. |
| [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] | |
| Class | Description |
|---|---|
| tetrahydroxyflavanone | A hydroxyflavanone with atleast four hydroxy substituents. |
| 4'-hydroxyflavanones | Any hydroxyflavanone having a hydroxy substituent located at position 4'. |
| [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] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Tyrosine-protein phosphatase non-receptor type 1 | Homo sapiens (human) | IC50 (µMol) | 14.4000 | 0.0005 | 3.4984 | 9.7600 | AID288630 |
| Delta-type opioid receptor | Mus musculus (house mouse) | IC50 (µMol) | 14.4000 | 0.0001 | 0.7298 | 10.0000 | AID288630 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID288630 | Inhibition of human recombinant PTP1B | 2007 | Journal of natural products, Jun, Volume: 70, Issue:6 | Isoprenylated flavonoids from the stem bark of Erythrina abyssinica. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (20.00) | 18.2507 |
| 2000's | 2 (40.00) | 29.6817 |
| 2010's | 2 (40.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 weak demand-to-supply ratio for research on this compound.
| This Compound (12.87) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||