20784-50-3
(2E)-1-[2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
CAS: 20784-50-3
Molecular Formula: C20H20O4
20784-50-3 - Names and Identifiers
| Name | (2E)-1-[2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one |
| Synonyms | CS-446 Corylifolinin ISOBAVACHALCONE Isobavachalcone Isobacachalcone iso-Bavachalcone (E)-4,2',4'-Trihydroxy-3'-prenylchalcone 2',4,4'-Trihydroxy-3'-prenyl-trans-chalcone (E)-1-[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one 2-Propen-1-one,1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-, (2E)- (2E)-1-[2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one 2-propen-1-one, 1-[2,4-dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(4-hydroxyphenyl)-, (2E)- |
| CAS | 20784-50-3 |
| InChI | InChI=1/C20H20O4/c1-13(2)3-9-16-19(23)12-10-17(20(16)24)18(22)11-6-14-4-7-15(21)8-5-14/h3-8,10-12,21,23-24H,9H2,1-2H3/b11-6+ |
20784-50-3 - Physico-chemical Properties
| Molecular Formula | C20H20O4 |
| Molar Mass | 324.37 |
| Density | 1.243±0.06 g/cm3(Predicted) |
| Melting Point | 156.8-157.8 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3)) |
| Boling Point | 549.0±50.0 °C(Predicted) |
| Flash Point | 299.9°C |
| Solubility | Soluble in chloroform, methanol |
| Vapor Presure | 1.15E-12mmHg at 25°C |
| Appearance | Yellow or red powder or crystal |
| pKa | 7.99±0.40(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.658 |
| MDL | MFCD00902090 |
| Physical and Chemical Properties | Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from psoralen PsoraleacorylifoliaLinn.. |
| In vitro study | Isobavachalcone (6.0-48.0 μM; 72 hours; OVCAR-8, PC3, A549, MCF-7, L-02 and HUVEC cells) treatment inhibits the proliferation of human cancer cells. Isobavachalcone inhibits PC3, A549, MCF-7, L-02 and HUVEC cells growth with IC50 values of 15.06 μM, 32.2 μM, 28.29 μM, 31.61 μM and 31.3 μM, respectively. Isobavachalcone (0-18 μM; 6 hours; OVCAR-8 and PC3 cells) treatment results in a concentration-and time-dependent down-regulation of the Ser-473 phosphorylation of Akt and GSK3b phosphorylation. Isobavachalcone (0-18 μM; 72 hours; OVCAR-8 and PC3 cells) treatment causes apoptosis via caspase- and ROS-involved mitochondrial pathway. Cell Proliferation Assay Cell Line: OVCAR-8, PC3, A549, MCF-7, L-02 and HUVEC cells Concentration: 6.0-48.0 μM Incubation Time: 72 hours Result: Inhibited the proliferation of human cancer cells. Western Blot Analysis Cell Line: OVCAR-8 or PC3 cells Concentration: 0 μM, 6 μM, 12 μM, and 18 μM Incubation Time: 6 hours Result: A concentration-and time-dependent down-regulation of the Ser-473 phosphorylation of Akt. GSK3b phosphorylation was also inhibited in a concentration- and time-dependent manner. Apoptosis Analysis Cell Line: OVCAR-8 cells and PC3 cells Concentration: 0 μM, 6 μM, 12 μM, and 18 μM Incubation Time: 72 hours Result: Led to dose dependent increase of apoptosis. |
| In vivo study | Isobavachalcone (20 mg/kg; intraperitoneal injection; for 0.5-24 hours; female Kunming mice) treatment results in an increase in blood glucose levels, reaching a maximum within 1 hour and maintaining until 4 hours post-dosing. Animal Model: Seven-week-old specific pathogen-free female Kunming mice (18-22 g) Dosage: 20 mg/kg Administration: Intraperitoneal injection; for 0.5, 1, 2, 4, 6, 8, 12, 24 hours Result: Increased in blood glucose levels. |
20784-50-3 - Reference
| Reference Show more | 1. Ding Liyan, Guo Yanhua, Huang Ting, et al. Study on the evaluation method of processing anti-osteoporosis components based on psoralea [J]. Chinese patent medicine, 2013, 35(002):346-349. 2. Ding Liyan, Guo Yanhua, Huang Ting, et al. Optimization of processing technology of psoralea [J]. Modern Chinese medicine, 2013, 15(1). 3. Zheng Nan, Guo Yanhua, Liu Kui, et al. Fingerprint Study of Different Procured Products of Psoralea barb [J]. Liaoning Journal of Traditional Chinese Medicine, 2015(04):157-159. 4. Ding Liyan, Zhou Lu, Wang Lina, et al. Determination of the content of different types of components in psoralea [J]. Chinese Journal of Experimental Prescritique 2013 19(5):152-154. 5. Huang Ting, Guo Yanhua, Ding Liyan, et al. Effect of medicinal juice preparation of psoralea on its anti-OP chemical composition [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2013(05):62-64. 6. Fan Lingqiu Xinsong Gaoyang et al. Simultaneous Determination of 10 Components in Psoralea chinensis by HPLC [J]. Journal of Qiqihar Medical College 2018 39(16):73-76. 7. Chen, Zhi-Jing, et al. "Dietary total prenylflavonoids from the Psoralea corylifolia L. prevents age-related cognitive deficits and down-regulates Alzheimer's markers in SAMP8 mICE." Molecules 23.1 (2018): 196.https://doi.org/10.3390/molecules230 8. Chen, Xiumin, Yanfang Yang, and Yingtao Zhang. "Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro." Febs Letters 587.18 (2013): 2930-2935.https:// doi.org/10.1016/j.febslet. 2013.07. 9. [IF=3.935] Tiehua Zhang et al."Quantitative structure-activity relationship for estrogenic flavonoids from Psoralea corylifolia."J Pharmaceut Biomed. 2018 Nov;161:129 10. [IF=3.267] Zhi-Jing Chen et al."Dietary Total Prenylflavonoids from the Fruits of Psoralea corylifolia L. Prevents Age-Related Cognitive Deficits and Down-Regulates Alzheimer's Markers in SAMP8 Mice."Molecules. 2018 Jan;23(1):196 11. [IF=2.675] Xiumin Chen et al."Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro."Febs Lett. 2013 Sep;587(18):2930-2935 |
20784-50-3 - Reference Information
| biological activity | Isobavachalcone (corylifolin) is derived from Psoralea corylifolia, which is a potent inhibitor of Akt signaling pathway, it can induce apoptosis of human cancer cells (inhibit the growth of cancer cells by OVCAR-8 with IC50 value of 7.92 μm), and has anti-cancer and anti-proliferative activities. Isobavachalcone was also able to induce the production of reactive oxygen species in OVCAR-8 of cells. |
| Target | IC50: 7.92 μm (OVCAR-8 cell) |
| in vitro study | Isobavachalcone (6.0-48.0 μm; 72 hours; OVCAR-8, PC3, A549, MCF-7, l-02 and HUVEC cells) treatment inhibitors of human cancer cells. Isobavachalcone inhibitors PC3, A549, MCF-7, L-02 and HUVEC cells growth with IC50 values of 15.06 μm, 32.2 μm, 28.29 μm, 31.61 μM and 31.3 μM, respectively. Isobavachalcone (0-18 μM; 6 hours; OVCAR-8 and PC3 cells) treatment results in a concentration-and time-dependent down-regulation of the Ser-473 phosphorylation of Akt and GSK3b phosphorylation. Isobavachalcone (0-18 μM; 72 hours; OVCAR-8 and PC3 cells) treatment causes apoptosis via caspase- and ROS-involved mitochondrial pathway. Cell Proliferation Assay Cell Line: OVCAR-8, PC3, A549, MCF-7, L-02 and HUVEC cells Concentration: 6.0-48.0 μM Incubation Time: 72 hours Result: Inhibited the proliferation of human cancer cells. Western Blot Analysis Cell Line: OVCAR-8 or PC3 cells Concentration: 0 μM 6 μM, 12 μM, and 18 μM Incubation Time: 6 hours Result: A concentration-and time-dependent down-regulation of the Ser-473 phosphorylation of Akt. GSK3b phosphorylation was also inhibited in a concentration- and time-dependent manner. Apoptosis Analysis Cell Line: OVCAR-8 cells and PC3 cells Concentration: 0 μM, 6 μM, 12 μM and 18 μM Incubation Time: 72 hours Result: Led to dose dependent increase of apoptosis. |
| Cell Line: | OVCAR-8, PC3, A549, MCF-7, L-02 and HUVEC cells OVCAR-8 or PC3 cells OVCAR-8 cells and PC3 cells |
| Concentration: | 6.0-48.0 μM 0 μM, 6 μM, 12 μM, and 18 μM 0 μM, 6 μM, 12 μM, and 18 μM |
| Incubation Time: | 72 hours 6 hours 72 hours |
| Result: | Inhibited the proliferation of human cancer cells. A concentration-and time-dependent down-regulation of the Ser-473 phosphorylation of Akt. GSK3b phosphorylation was also inhibited in a concentration- and time-dependent manner. Led to dose dependent increase of apoptosis. Increased in blood glucose levels. |
| in vivo studies | Isobavachalcone (20 mg/kg; Intraperional injection; for 0.5-24 hours; female Kunming mice) treatment results in an independent in blood glucose levels, reaching a maximum within 1 hour and maintaining until 4 hours post-doing. Animal Model: Seven-week-old specific pathogen-free female Kunming mice (18-22g) Dosage: 20 mg/kg Administration: Intraperitoneal injection; for 0.5, 1, 2, 4, 6, 8, 12, 24 hours Result: Increased in blood glucose levels. |
| Animal Model: | Seven-week-old specific pathogen-free female Kunming mice (18-22 g) |
| Dosage: | 20 mg/kg |
| Administration: | Intraperitoneal injection; for 0.5, 1, 2, 4, 6, 8, 12, 24 hours |
| Chemical properties | yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Psoralea coryfolialinn.. |
| Usage | psoralen B has antibacterial and anticancer pharmacological activities. inhibition of lipopolysaccharide-induced icam-1 expression and leukocyte adhesion to brain endothelial cells |
Last Update：2024-04-09 21:21:28
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