Chalcone Scaffolds, Bioprecursors of Flavonoids: Chemistry, Bioactivities, and Pharmacokinetics.

Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE

Original Publication: Basel, Switzerland : MDPI, c1995-

Chalcone/*metabolism ; Flavonoids/*chemistry ; Plants, Edible/*chemistry ; Plants, Medicinal/*chemistry; Chalcone/chemistry ; Chalcone/pharmacokinetics ; Chalcone/therapeutic use ; Flavonoids/biosynthesis ; Flavonoids/pharmacokinetics ; Flavonoids/therapeutic use ; Humans ; Tissue Scaffolds/chemistry

Chalcones are secondary metabolites belonging to the flavonoid (C 6 -C 3 -C 6 system) family that are ubiquitous in edible and medicinal plants, and they are bioprecursors of plant flavonoids. Chalcones and their natural derivatives are important intermediates of the flavonoid biosynthetic pathway. Plants containing chalcones have been used in traditional medicines since antiquity. Chalcones are basically α,β-unsaturated ketones that exert great diversity in pharmacological activities such as antioxidant, anticancer, antimicrobial, antiviral, antitubercular, antiplasmodial, antileishmanial, immunosuppressive, anti-inflammatory, and so on. This review provides an insight into the chemistry, biosynthesis, and occurrence of chalcones from natural sources, particularly dietary and medicinal plants. Furthermore, the pharmacological, pharmacokinetics, and toxicological aspects of naturally occurring chalcone derivatives are also discussed herein. In view of having tremendous pharmacological potential, chalcone scaffolds/chalcone derivatives and bioflavonoids after subtle chemical modification could serve as a reliable platform for natural products-based drug discovery toward promising drug lead molecules/drug candidates.

Phytochemistry. 2003 Apr;62(8):1225-9. (PMID: 12648541)
J Med Chem. 2018 Apr 26;61(8):3277-3292. (PMID: 28956609)
Nat Prod Commun. 2012 Dec;7(12):1589-90. (PMID: 23413559)
J Nat Prod. 2004 Mar;67(3):481-4. (PMID: 15043439)
J Ethnopharmacol. 2010 Sep 15;131(2):502-4. (PMID: 20603209)
Drug Metab Dispos. 2001 Mar;29(3):223-31. (PMID: 11181488)
Planta Med. 2012 Jun;78(10):995-1001. (PMID: 22618373)
J Enzyme Inhib Med Chem. 2016;31(1):23-30. (PMID: 25683083)
Acta Pharmacol Sin. 2020 Jan;41(1):82-92. (PMID: 31371781)
Phytochemistry. 2004 May;65(9):1287-90. (PMID: 15184014)
Z Naturforsch C J Biosci. 2001 Nov-Dec;56(11-12):969-72. (PMID: 11837685)
Phytochemistry. 2000 Feb;53(4):511-3. (PMID: 10731031)
Phytochemistry. 2002 Apr;59(8):877-83. (PMID: 11937170)
Molecules. 2021 Jun 22;26(13):. (PMID: 34206687)
J Cosmet Dermatol. 2017 Dec;16(4):512-519. (PMID: 28421656)
Bioorg Med Chem Lett. 2011 Jan 1;21(1):294-8. (PMID: 21123068)
Phytochemistry. 2006 Jul;67(14):1539-46. (PMID: 16806328)
Pharmacogn Rev. 2017 Jan-Jun;11(21):27-30. (PMID: 28503050)
Bioorg Med Chem. 2003 Jul 3;11(13):2729-38. (PMID: 12788347)
J Nat Prod. 1993 Oct;56(10):1718-22. (PMID: 8277311)
Planta Med. 2001 Feb;67(1):87-9. (PMID: 11270732)
Oxid Med Cell Longev. 2016;2016:9156510. (PMID: 27668038)
Curr Med Chem. 2005;12(4):481-99. (PMID: 15720256)
Planta Med. 1984 Jun;50(3):271-2. (PMID: 17340312)
Int J Oncol. 2016 Feb;48(2):843-53. (PMID: 26692364)
Biochem Pharmacol. 2001 Apr 15;61(8):939-46. (PMID: 11286985)
Am J Cancer Res. 2020 Nov 01;10(11):3721-3736. (PMID: 33294263)
Eur J Med Chem. 2015 Mar 6;92:839-65. (PMID: 25638569)
Phytochemistry. 2008 May;69(8):1745-9. (PMID: 18406436)
J Agric Food Chem. 2007 Jun 13;55(12):4691-7. (PMID: 17516657)
Phytochemistry. 2004 Nov;65(22):3029-32. (PMID: 15504437)
Molecules. 2017 Aug 24;22(9):. (PMID: 28837100)
Molecules. 2017 Jul 25;22(8):. (PMID: 28757583)
Antiviral Res. 2004 Dec;64(3):189-94. (PMID: 15550272)
Food Chem. 2008 Mar 15;107(2):813-819. (PMID: 22359426)
Int Immunopharmacol. 2009 Apr;9(4):499-507. (PMID: 19291859)
Planta Med. 2007 Aug;73(10):1074-80. (PMID: 17628836)
Biol Pharm Bull. 2010;33(9):1489-93. (PMID: 20823562)
J Agric Food Chem. 2004 Jun 2;52(11):3297-300. (PMID: 15161186)
Photochem Photobiol Sci. 2017 Jul 1;16(7):1162-1173. (PMID: 28594010)
J Oral Sci. 2009 Mar;51(1):87-95. (PMID: 19325204)
J Mol Med (Berl). 2008 Nov;86(11):1287-95. (PMID: 18825356)
FEBS Lett. 2001 Mar 2;491(3):252-6. (PMID: 11240137)
Biochim Biophys Acta. 1998 Jun 15;1392(2-3):291-9. (PMID: 9630680)
Am J Epidemiol. 1995 Dec 15;142(12):1269-78. (PMID: 7503047)
Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13. (PMID: 12083758)
Microbiol Immunol. 2014 Mar;58(3):180-7. (PMID: 24397541)
J Agric Food Chem. 2008 Apr 9;56(7):2436-41. (PMID: 18318499)
Antimicrob Agents Chemother. 1995 Dec;39(12):2742-8. (PMID: 8593012)
J Nat Prod. 2002 Apr;65(4):624-7. (PMID: 11975520)
Antiviral Res. 2004 Jan;61(1):57-62. (PMID: 14670594)
Z Naturforsch C J Biosci. 2008 May-Jun;63(5-6):361-5. (PMID: 18669021)
J Agric Food Chem. 2011 Apr 13;59(7):3180-5. (PMID: 21375300)
Yao Xue Xue Bao. 1992;27(10):748-51. (PMID: 1293921)
Bioorg Med Chem Lett. 2011 Dec 15;21(24):7431-3. (PMID: 22047698)
Phytother Res. 2003 Feb;17(2):155-9. (PMID: 12601679)
J Nat Med. 2019 Sep;73(4):847-854. (PMID: 31218551)
J Agric Food Chem. 2000 Sep;48(9):3876-84. (PMID: 10995285)
Free Radic Biol Med. 2010 Jul 15;49(2):214-26. (PMID: 20398749)
Food Chem Toxicol. 2013 Oct;60:147-52. (PMID: 23891701)
Biol Pharm Bull. 2003 Jan;26(1):61-5. (PMID: 12520174)
Br J Pharmacol. 2007 Sep;152(1):9-20. (PMID: 17549047)
Bioorg Med Chem. 2010 Jan 15;18(2):962-70. (PMID: 20022509)
J Agric Food Chem. 2007 Jul 25;55(15):6013-7. (PMID: 17583349)
Fitoterapia. 2020 Oct;146:104717. (PMID: 32877711)
Antimicrob Agents Chemother. 2002 May;46(5):1226-30. (PMID: 11959549)
Clin Exp Pharmacol Physiol. 2005 Jan-Feb;32(1-2):19-23. (PMID: 15730429)
Phytochemistry. 2000 Nov;55(5):447-56. (PMID: 11140606)
Life Sci. 2007 Sep 29;81(16):1272-9. (PMID: 17915259)
Phytochemistry. 2002 Jan;59(2):169-73. (PMID: 11809452)
Planta Med. 1990 Jun;56(3):254-8. (PMID: 2118267)
Nat Prod Res. 2021 Jun;35(12):2056-2059. (PMID: 31401870)
Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1326-9. (PMID: 15516755)
Mol Nutr Food Res. 2009 Sep;53 Suppl 2:S184-93. (PMID: 19035558)
Arch Pharm Res. 2011 Mar;34(3):437-42. (PMID: 21547675)
Phytochemistry. 2002 Dec;61(8):931-6. (PMID: 12453520)
Free Radic Res. 2021 Jan;55(1):53-70. (PMID: 33267705)
Gene. 1996 Nov 7;179(1):61-71. (PMID: 8955630)
Bioorg Med Chem. 2006 Mar 15;14(6):1710-4. (PMID: 16263298)
Curr Pharm Des. 2019;25(23):2526-2539. (PMID: 31333090)
J Agric Food Chem. 2001 Jun;49(6):3046-50. (PMID: 11410007)
Eur J Cancer. 2005 Sep;41(13):1941-54. (PMID: 15953717)
Phytomedicine. 2011 Jun 15;18(8-9):795-801. (PMID: 21315569)
Mol Cell Endocrinol. 2010 Jul 29;323(2):208-14. (PMID: 20363289)
Molecules. 2018 Jan 04;23(1):. (PMID: 29300354)
Evid Based Complement Alternat Med. 2020 Mar 16;2020:3821248. (PMID: 32256642)
J Nutr Biochem. 2012 Jul;23(7):759-67. (PMID: 21840191)
Biol Pharm Bull. 2005 Dec;28(12):2253-7. (PMID: 16327160)
Plants (Basel). 2020 Jun 20;9(6):. (PMID: 32575698)
J Chromatogr A. 2013 Nov 5;1316:78-91. (PMID: 24120027)
Mol Pharmacol. 2005 May;67(5):1444-50. (PMID: 15703376)
J Agric Food Chem. 2016 Oct 26;64(42):8062-8070. (PMID: 27696846)
J Nat Prod. 1995 Aug;58(8):1160-6. (PMID: 7595585)
Evid Based Complement Alternat Med. 2015;2015:451870. (PMID: 25883671)
J Nat Prod. 1998 Oct;61(10):1274-6. (PMID: 9784166)
Phytochemistry. 1998 May;48(1):125-9. (PMID: 9621457)
Phytochemistry. 2009 Oct-Nov;70(15-16):1728-38. (PMID: 19559450)
Nat Prod Res. 2014;28(4):245-50. (PMID: 24099509)
Biomed Pharmacother. 2020 Dec;132:110809. (PMID: 33049584)
Bioorg Med Chem Lett. 2019 Oct 1;29(19):126589. (PMID: 31427220)
J Agric Food Chem. 2003 May 21;51(11):3309-12. (PMID: 12744659)
J Am Diet Assoc. 2009 Apr;109(4):656-67. (PMID: 19328261)
Antibiotics (Basel). 2020 Jun 20;9(6):. (PMID: 32575738)
J Nat Prod. 2017 Feb 24;80(2):334-346. (PMID: 28140583)
J Nat Prod. 2003 Aug;66(8):1061-4. (PMID: 12932124)
Mol Nutr Food Res. 2009 Oct;53(10):1263-80. (PMID: 19764067)
Biopharm Drug Dispos. 2014 Oct;35(7):382-90. (PMID: 24903704)
Biomolecules. 2021 Jun 16;11(6):. (PMID: 34208562)
Molecules. 2021 Jun 30;26(13):. (PMID: 34209338)
Int J Mol Sci. 2014 Jan 15;15(1):1080-95. (PMID: 24434621)
J Agric Food Chem. 2001 Feb;49(2):1035-41. (PMID: 11262068)
J Agric Food Chem. 2006 Jun 14;54(12):4176-85. (PMID: 16756344)
Drug Test Anal. 2017 Aug;9(8):1124-1136. (PMID: 27794181)
J Sep Sci. 2015 Dec;38(24):4180-6. (PMID: 26472171)
JAMA. 2004 Aug 18;292(7):805-6. (PMID: 15315994)
Biomed Pharmacother. 2015 Mar;70:140-5. (PMID: 25776492)
Proteomics. 2015 May;15(9):1608-21. (PMID: 25594392)
Proteins. 2021 Feb;89(2):185-192. (PMID: 32875607)
PLoS One. 2012;7(5):e38103. (PMID: 22666456)
Chem Rev. 2017 Jun 28;117(12):7762-7810. (PMID: 28488435)
J Pharm Sci. 2021 May;110(5):2285-2294. (PMID: 33610566)
Nat Prod Rep. 2010 Jun;27(6):809-38. (PMID: 20358127)
Braz J Med Biol Res. 2012 Jun;45(6):524-30. (PMID: 22358425)
Nat Commun. 2020 Feb 13;11(1):870. (PMID: 32054839)
Bioorg Med Chem Lett. 2005 May 16;15(10):2453-5. (PMID: 15929201)
Clin Exp Pharmacol Physiol. 2007 Mar;34(3):238-43. (PMID: 17250645)
Phytochemistry. 2007 May;68(9):1312-20. (PMID: 17397884)
Eur J Med Chem. 2015 Jun 15;98:69-114. (PMID: 26005917)
Phytochemistry. 2012 Jun;78:120-5. (PMID: 22459967)

Keywords: bioactivities; biosynthesis; chalcone; chemistry; flavonoids; pharmacokinetics

0 (Flavonoids)
5S5A2Q39HX (Chalcone)

Date Created: 20211210 Date Completed: 20220214 Latest Revision: 20240404

20240404

PMC8659147

10.3390/molecules26237177

34885754