Isobavachalcone

Last updated
Isobavachalcone
Isobavachalcone structure.png
Identifiers
  • (E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
CAS Number
PubChem CID
Chemical and physical data
Formula C20H20O4
Molar mass 324.376 g·mol−1
3D model (JSmol)
  • CC(=CCC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)C
  • InChI=1S/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+
  • Key:DUWPGRAKHMEPCM-IZZDOVSWSA-N

Isobavachalcone is a natural product from the prenylated chalconoid family. It can be isolated from numerous medicinal plant species including Psoralea corylifolia , Fructus psoraleae , and Angelica keiskei . It has antiiflammatory, antiviral and anti-cancer properties in vitro and plants containing isobavachalcone are used in Chinese herbal medicine for the treatment of osteoporosis and other aging-related diseases. [1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13]

See also


References

  1. ↑ Kuete V, Sandjo LP. Isobavachalcone: an overview. Chin J Integr Med. 2012 Jul;18(7):543-7. doi : 10.1007/s11655-012-1142-7 PMID   22772918
  2. ↑ Zhou YT, Zhu L, Yuan Y, Ling S, Xu JW. Effects and Mechanisms of Five Psoralea Prenylflavonoids on Aging-Related Diseases. Oxid Med Cell Longev. 2020 Jun 17;2020:2128513. doi : 10.1155/2020/2128513 {{doi}}: unflagged free DOI (link) PMID   32655760
  3. ↑ Dong WH, Chu QQ, Liu SQ, Deng DT, Xu Q. Isobavachalcone ameliorates diabetic nephropathy in rats by inhibiting the NF-κB pathway. J Food Biochem. 2020 Sep;44(9):e13405. doi : 10.1111/jfbc.13405 PMID   32710574
  4. ↑ Solnier J, Fladerer JP. Flavonoids: A complementary approach to conventional therapy of COVID-19? Phytochem Rev. 2021;20(4):773-795. doi : 10.1007/s11101-020-09720-6 PMID   32982616
  5. ↑ Wang M, Lin L, Lu JJ, Chen X. Pharmacological review of isobavachalcone, a naturally occurring chalcone. Pharmacol Res. 2021 Mar;165:105483. doi : 10.1016/j.phrs.2021.105483 PMID   33577976
  6. ↑ Zhou K, Yang S, Li SM. Naturally occurring prenylated chalcones from plants: structural diversity, distribution, activities and biosynthesis. Nat Prod Rep. 2021 Dec 15;38(12):2236-2260. doi : 10.1039/d0np00083c PMID   33972962
  7. ↑ Shin S, Park J, Lee YE, Ko H, Youn HS. Isobavachalcone suppresses the TRIF-dependent signaling pathway of Toll-like receptors. Arch Pharm (Weinheim). 2022 Mar;355(3):e2100404. doi : 10.1002/ardp.202100404 PMID   34964142
  8. ↑ Xing N, Meng X, Wang S. Isobavachalcone: A comprehensive review of its plant sources, pharmacokinetics, toxicity, pharmacological activities and related molecular mechanisms. Phytother Res. 2022 Aug;36(8):3120-3142. doi : 10.1002/ptr.7520 PMID   35684981
  9. ↑ Liu X, Xu X, Li J, Shi L, Zeng Y, Tang S, Liu W, Jia L, Li Y, Zhang J. Isobavachalcone inhibits RANKL-induced osteoclastogenesis via miR-193-3p/NF-κB/NFATc1 signaling pathway in BMMs cells. Biosci Biotechnol Biochem. 2023 Aug 23;87(9):960-971. doi : 10.1093/bbb/zbad075 PMID   37291698
  10. ↑ Ren YL, Lei JT, Zhang TR, Lu P, Cui DD, Yang B, Zhao GY, Peng F, Cao ZX, Peng C, Li YZ. Isobavachalcone, a natural sirtuin 2 inhibitor, exhibits anti-triple-negative breast cancer efficacy in vitro and in vivo. Phytother Res. 2024 Apr;38(4):1815-1829. doi : 10.1002/ptr.8143 PMID   38349045
  11. ↑ Kour D, Khajuria P, Sharma K, Sharma A, Sharma A, Ali SM, Wazir P, Ramajayan P, Sawant SD, Nandi U, Ahmed Z, Kumar A. Isobavachalcone ameliorates Alzheimer disease pathology by autophagy-mediated clearance of amyloid beta and inhibition of NLRP3 inflammasome in primary astrocytes and 5x-FAD mice. Front Pharmacol. 2025 Mar 20;16:1525364. doi : 10.3389/fphar.2025.1525364 {{doi}}: unflagged free DOI (link) PMID   40183098
  12. ↑ Xie F, Zhu C, Sun L, Lin Q, Fang P, Li A, Lai T, Ma C, Zhang Y, Lu Y, Chen Y, Zhang Y, Xiao S, Yang X, Yin G, Lv G. Isobavachalcone inhibits α-synuclein fibrillogenesis and its Parkinson's disease variants, disassembles the mature fibrils and alleviates cellular toxicity. Int J Biol Macromol. 2025 Sep;322(Pt 1):146541. doi : 10.1016/j.ijbiomac.2025.146541 PMID   40763859
  13. ↑ Lee EJ, Shaikh S, Ahmad K, Lee SH, Choi JM, Lee YH, Choi I. Isobavachalcone reduces blood glucose and promotes muscle development via dipeptidyl peptidase-4 inhibition. Int J Biol Macromol. 2025 Dec 22;339(Pt 1):149858. doi : 10.1016/j.ijbiomac.2025.149858 PMID   41443458


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