(S)-4',5,7-Trihydroxy-6-prenylflavanone, also known as **naringenin chalcone**, is a natural compound belonging to the flavonoid family. It's found in various plants, including citrus fruits (like grapefruit and oranges) and other fruits like berries.
Here's a breakdown of its importance in research:
**1. Antioxidant Properties:** Naringenin chalcone is a potent antioxidant, meaning it can neutralize free radicals and protect cells from damage. This property is crucial for research on:
* **Age-related diseases:** Research explores its potential role in preventing or slowing down age-related diseases like Alzheimer's and Parkinson's, where oxidative stress plays a role.
* **Cardiovascular health:** Studies investigate its ability to protect against heart disease by reducing inflammation and improving blood vessel function.
* **Cancer prevention:** Naringenin chalcone has shown promise in inhibiting cancer cell growth and promoting apoptosis (programmed cell death) in laboratory settings.
**2. Anti-inflammatory Effects:** Research indicates that naringenin chalcone can suppress inflammation by interfering with various inflammatory pathways in the body. This makes it relevant for studying:
* **Autoimmune diseases:** Its potential to modulate immune responses is being investigated for conditions like rheumatoid arthritis and inflammatory bowel disease.
* **Chronic pain:** Research explores its ability to reduce pain associated with chronic inflammatory conditions.
* **Skin health:** Studies examine its potential in managing inflammatory skin conditions like psoriasis and eczema.
**3. Other Biological Activities:** Naringenin chalcone has been found to exhibit various other biological activities, including:
* **Antimicrobial properties:** Research explores its potential to combat bacterial and fungal infections.
* **Neuroprotective effects:** Studies investigate its potential to protect brain cells from damage caused by stroke, trauma, or neurodegenerative diseases.
* **Metabolic regulation:** Research examines its influence on blood sugar levels and lipid metabolism.
**4. Research on its Mechanism of Action:** A significant area of research focuses on understanding how naringenin chalcone exerts its effects at the molecular level. This includes:
* **Target identification:** Identifying the specific proteins and enzymes that naringenin chalcone interacts with.
* **Signal transduction pathways:** Understanding how naringenin chalcone impacts various cellular signaling pathways involved in its diverse biological activities.
**5. Development of Pharmaceuticals and Supplements:** The promising biological activities of naringenin chalcone have led to research focused on:
* **Developing new drugs:** Investigating its potential as a therapeutic agent for various diseases.
* **Formulating dietary supplements:** Investigating its safety and efficacy as a natural health supplement.
**Overall:** (S)-4',5,7-Trihydroxy-6-prenylflavanone is a fascinating natural compound with a wide range of potential health benefits. Continued research is essential to fully understand its mechanisms of action and develop safe and effective applications for treating various diseases and improving overall health.
| ID Source | ID |
|---|---|
| PubMed CID | 3519901 |
| CHEMBL ID | 1537093 |
| CHEBI ID | 174571 |
| SCHEMBL ID | 145713 |
| Synonym |
|---|
| CHEBI:174571 |
| 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| MEGXP0_001752 |
| ACON1_000068 |
| MLS000863575 , |
| smr000440733 |
| NCGC00168825-01 |
| BRD-A11775589-001-01-8 |
| HMS2271K08 |
| SCHEMBL145713 |
| 2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-5,7-bis(oxidanyl)-2,3-dihydrochromen-4-one |
| 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)-3,4-dihydro-2h-1-benzopyran-4-one |
| cid_3519901 |
| 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methylbut-2-enyl)chroman-4-one |
| bdbm58016 |
| CHEMBL1537093 |
| (2r/s)-6-png |
| 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-4h-1-benzopyran-4-one |
| 68682-01-9 |
| 6png |
| 6 png; 6-png |
| BCP31580 |
| k 07047 |
| F82679 |
| MS-25192 |
| 6-png |
| HY-115681 |
| CS-0120480 |
| 6-prenyl-rac-naringenin |
| Class | Description |
|---|---|
| flavanones | Members of the class of flavans with a 3,4-dihydro-2-aryl-2H-1-benzopyran-4-one skeleton and its substituted derivatives. |
| [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 (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 5.0119 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 8.9125 | 0.0447 | 17.8581 | 100.0000 | AID485341 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 89.1251 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 26.8545 | 0.0072 | 15.7588 | 89.3584 | AID588342 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 12.5893 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
| TDP1 protein | Homo sapiens (human) | Potency | 19.7347 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| Microtubule-associated protein tau | Homo sapiens (human) | Potency | 14.1254 | 0.1800 | 13.5574 | 39.8107 | AID1468 |
| Smad3 | Homo sapiens (human) | Potency | 25.1189 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| nonstructural protein 1 | Influenza A virus (A/WSN/1933(H1N1)) | Potency | 19.9526 | 0.2818 | 9.7212 | 35.4813 | AID2326 |
| glucocerebrosidase | Homo sapiens (human) | Potency | 15.8489 | 0.0126 | 8.1569 | 44.6684 | AID2101 |
| serine-protein kinase ATM isoform a | Homo sapiens (human) | Potency | 1.0000 | 0.7079 | 25.1119 | 41.2351 | AID485349 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 35.4813 | 0.0398 | 16.7842 | 39.8107 | AID1454 |
| histone-lysine N-methyltransferase 2A isoform 2 precursor | Homo sapiens (human) | Potency | 3,162.2800 | 0.0103 | 23.8567 | 63.0957 | AID2662 |
| geminin | Homo sapiens (human) | Potency | 5.1735 | 0.0046 | 11.3741 | 33.4983 | AID624296 |
| histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 6.3096 | 0.2512 | 15.8432 | 39.8107 | AID504327 |
| neuropeptide S receptor isoform A | Homo sapiens (human) | Potency | 12.5893 | 0.0158 | 12.3113 | 615.5000 | AID1461 |
| Rap guanine nucleotide exchange factor 4 | Homo sapiens (human) | Potency | 35.4813 | 3.9811 | 46.7448 | 112.2020 | AID720708 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Voltage-dependent T-type calcium channel subunit alpha-1G | Homo sapiens (human) | IC50 (µMol) | 1.0000 | 0.0370 | 0.8915 | 2.5000 | AID1398114 |
| Voltage-dependent T-type calcium channel subunit alpha-1H | Homo sapiens (human) | IC50 (µMol) | 1.0000 | 0.0320 | 1.0479 | 3.6000 | AID1398109 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| glycogen synthase kinase-3 beta isoform 1 | Homo sapiens (human) | EC50 (µMol) | 300.0000 | 0.2125 | 22.1562 | 83.9400 | AID434954 |
| streptokinase A precursor | Streptococcus pyogenes M1 GAS | EC50 (µMol) | 78.0420 | 0.0600 | 8.9128 | 130.5170 | AID1902; AID1914 |
| Estrogen receptor | Homo sapiens (human) | EC50 (µMol) | 0.4000 | 0.0000 | 0.5305 | 4.4000 | AID1379240 |
| Estrogen receptor | Rattus norvegicus (Norway rat) | EC50 (µMol) | 150.0000 | 0.0060 | 22.3670 | 130.5170 | AID1914 |
| Estrogen receptor beta | Rattus norvegicus (Norway rat) | EC50 (µMol) | 150.0000 | 0.0060 | 22.3670 | 130.5170 | AID1914 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| NAD(P)H dehydrogenase [quinone] 1 | Mus musculus (house mouse) | CD | 30.0000 | 0.0002 | 0.2389 | 2.6500 | AID1379242 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID1398108 | Inhibition of human CaV3.2 expressed in HEK293 cells assessed as suppression of T-current amplitude by measuring remaining activity at 3 uM after 10 mins by whole cell patch clamp method relative to control | 2018 | Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15 | Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers. |
| AID1379242 | Induction of NQO1 activity in mouse Hepa1c1c7 cells after 48 hrs by MTT reduction assay | 2017 | Journal of natural products, 08-25, Volume: 80, Issue:8 | DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women's Health. |
| AID1423945 | Effect on barrier function in human Caco2 cells assessed as LY transport at 10 uM pre-treated on apical side for 1 hr and measured after 48 hrs | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| AID1379240 | Estrogenic activity at estrogen receptor alpha in human Ishikawa cells assessed as induction of alkaline phosphatase activity using p-Nitrophenol phosphate as substrate pretreated for 96 hrs followed by substrate addition measured every 15 secs by scannin | 2017 | Journal of natural products, 08-25, Volume: 80, Issue:8 | DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women's Health. |
| AID1398110 | Antihyperalgesic activity in ddY mouse assessed as suppression of partial sciatic nerve ligation-induced mechanical allodynia at 10 mg/kg, ip administered 7 days by Von Frey test | 2018 | Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15 | Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers. |
| AID1379241 | Cytotoxicity against human Ishikawa cells after 96 hrs by SRB assay | 2017 | Journal of natural products, 08-25, Volume: 80, Issue:8 | DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women's Health. |
| AID1398114 | Inhibition of human CaV3.1 expressed in HEK293 cells assessed as suppression of T-current after 10 mins by whole cell patch clamp method | 2018 | Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15 | Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers. |
| AID1423947 | Inhibition of TNFalpha induced barrier dysfunctionin human Caco2 cells assessed as increase in transepithelial electrical resistance at 10 uM pre-treated on apical side for 1 hr before TNFalpha stimulation on basolateral side for 72 hrs by cellZScope moni | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| AID1423941 | Cytotoxicity in human Caco2 cells assessed as reduction in ATP metabolism at 1 to 50 uM incubated for 24 hrs by cell-titer-Glo luminescent cell viability assay | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| AID1379243 | Cytotoxicity against mouse Hepa1c1c7 cells after 48 hrs by crystal violet staining based assay | 2017 | Journal of natural products, 08-25, Volume: 80, Issue:8 | DESIGNER Extracts as Tools to Balance Estrogenic and Chemopreventive Activities of Botanicals for Women's Health. |
| AID1423948 | Inhibition of TNFalpha induced barrier dysfunctionin human Caco2 cells assessed as increase in transepithelial electrical resistance at 10 uM treated on apical side for 1 hr post TNFalpha stimulation on basolateral side for 24 hrs and measured after 72 hr | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| AID1423940 | Cytotoxicity in human Caco2 cells assessed as reduction in ATP metabolism at 100 uM incubated for 24 hrs by cell-titer-Glo luminescent cell viability assay | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| AID1398109 | Inhibition of human CaV3.2 expressed in HEK293 cells assessed as suppression of T-current amplitude after 10 mins by whole cell patch clamp method | 2018 | Bioorganic & medicinal chemistry, 08-15, Volume: 26, Issue:15 | Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers. |
| AID1423946 | Increase in transepithelial electrical resistance in human Caco2 cells at 10 uM pre-treated on apical side and measured after 36 to 72 hrs | 2017 | Journal of natural products, 04-28, Volume: 80, Issue:4 | Effect of Hops Derived Prenylated Phenols on TNF-α Induced Barrier Dysfunction in Intestinal Epithelial Cells. |
| [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 | 0 (0.00) | 18.2507 |
| 2000's | 1 (12.50) | 29.6817 |
| 2010's | 6 (75.00) | 24.3611 |
| 2020's | 1 (12.50) | 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 (12.25) 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 | 8 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||