Chalcones: Synthetic Chemistry Follows Where Nature Leads
Abstract
:1. Introduction
2. Chalcone Synthesis
3. Molecular Mechanisms of Chalcone Actions
3.1. Activation of Nuclear Factor-Erythroid 2 p45 Subunit-Related Factor 2 Pathway and Cellular Defence Genes
3.2. Activation of the Nuclear Factor-Kappa B (NF-κB) PI3K/Akt Signaling Pathway
3.3. Effects on the Cell Cycle
3.4. Effects on Apoptosis
3.5. Binding with the Estrogenic Receptor (ER)
4. Bioactivity of Chalcones
4.1. Anticancer and Cancer Chemopreventive Activity
4.2. Antidiabetic Activity
4.3. Anti-Inflammatory Activity
4.4. Antimicrobial Activity
4.4.1. Antibacterial Activity
4.4.2. Antifungal Activity
4.4.3. Antiviral Activity
4.5. Antioxidant Activity
4.6. Antiparasitic Activity
4.7. Immunoregulatory Activity
5. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Approach | Compound 1 | Compound 2 | Reaction Conditions | Synthesize Chalcone and Its Derivatives |
---|---|---|---|---|
Microwave | NaOH/MeOH, microwave radiation at 110 W, 55 °C | (1) | ||
I2-Al2O3, microwave radiation for 80 s | ||||
Ionic liquids | HBr, Bmim(OTs), 12 h, 100 °C | |||
Claisen-Schmidt | Base | |||
Using SOCl2 | SOCl2/EtOH | |||
Alkynes and aldehydes | Amberlyst-15, DCM, at r.t. | (2) | ||
Sonogashira coupling | [PdCl2(PPh3)2], Et3N, THF, heat | (3) | ||
Cross-coupling | [PdCl2(dtbpf)], K2CO3, 1,4-dioxane, microwave radiation for 30 min at 140 °C | (4) | ||
Wittig reaction | Br-, NaOEt, toluene, microwave radiation for 5 min | (2) | ||
Claisen-Schmidt | Zeolite ultrasound | (5) | ||
NaOH base | (6) | |||
Solvent free | SiO2, H2SO4, 80 °C | (7) | ||
Suzuki reaction | (PPh3)4Pd(0), Cs2CO3, toluene | (8) | ||
PdCl2, Na2CO3, water/acetone | (1) | |||
Pd | (1) | |||
Base-driven | KOH/EtOH, heat, 1–5 h | (9) | ||
NaOH | (10) |
Bioactivities | Chalcones | Sources | References | |
---|---|---|---|---|
Anti-acetylcholinesterase | Isosalipurposide (66) Naringenin chalcone (78) | Acacia cyanophylla | [50] | |
Anti-arthritic | Cardamonin (48) | Boesenbergia rotunda | [51] | |
Anticancer | Butein (16) | Toxicodendron vernicifluum | [52] | |
Butea dahlia | [22,53] | |||
Calomelanone (17) | Stevia lucida | |||
Deoxydihydroxanthoangelol H (49) | Angelica keiskei | [54] | ||
2,6-Dihydroxy-4-methoxychalcone (52) | ||||
Dimethyl-cardamonin (27) | Syzygium campanulatum | [55] | ||
Echinantin (59) | Piper methysticum & Alpinia pricei | [56] | ||
Flavokawain A (60) | Piper methysticum | |||
Flavokawain B (28) | ||||
Flavokawain B (28) | Alpinia pricei | [57] | ||
Flavokawain C (18) | Piper methysticum | [22,53] | ||
Homobutein (19) | Butea frondosa | |||
2′-Hydroxy-4′,5′-dimethoxychalcone (61) | Sarcandra hainanensis | [58] | ||
4-Hydroxychalcone (20) | Glycyrrhiza glabra | [22,53] | ||
4′-Hydroxychalcone (21) | ||||
4-Hydroxyderricin (62) | Angelica keiskei | [59] | ||
Isobavachalcone (63) | [54] | |||
Isobavachalcone (63) | Psoralea corylifolia | [60] | ||
Isoliquiritigenin (22) | Piper methysticum | [57] | ||
Alpinia pricei | ||||
Glycyrrhiza glabra | [22,53] | |||
Isosalipurposide (66) | Helichrysum maracandicum | [61] | ||
Lonchocarpin (41) | Pongamia pinnata | [41] | ||
Marein (77) | Glycyrrhiza glabra | [22,53] | ||
4-Methoxychalcone (2) | ||||
Phloretin (23) | Stevia lucida | [22,53] | ||
2,3,4-Trimethoxy-2′-hydroxychalcone (82) | Piper methysticum | [62] | ||
Xanthoangelol (83) | Angelica keiskei | [59] | ||
Xanthoangelol I (91) | [54] | |||
Xanthoangelol J (92) | ||||
Antidiabetic | 2′,6′-Dihydroxy-4′-methoxychalcone (54) | Piper claussenianum | [63] | |
4-Hydroxyderricin (62) | Angelica keiskei | [64] | ||
Xanthoangelol (83) | ||||
Anti-inflammatory | Flavokawain B (28) | Alpinia pricei | [65] | |
Isoliquiritigenin (22) | ||||
Licoagrochalcone A (70) | Glycyrrhiza inflata | [66] | ||
Licochalcone B (68) | ||||
Licochalcone C (71) | Glycyrrhiza glabra | [67] | ||
Mallotophilippens C (74) | Mallotus philippinensis | [68] | ||
Mallotophilippens D (75) | ||||
Mallotophilippens E (76) | ||||
Antimicrobial | ||||
Antibacterial | 2′,4′-Dihydroxychalcone (51) | Zuccagnia punctata | [69] | |
3,2′-Dihydroxy-2,4,4′,6′-tetramethoxychalcone (55) | Piper hispidum | [70] | ||
2′-Hydroxy-2,4,4′,6′-tetramethoxychalcone (56) | ||||
2′-Hydroxy-2,3,4,4′,6′-pentamethoxychalcone (57) | ||||
Isoliquiritigenin (22) | Apis mellifera | [71] | ||
Antifungal | 1-(5,7-Dihydroxy-2,2,6-trimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one [58] | Mallotus philippinensis | [72] | |
3,2′-Dihydroxy-2,4,4′,6′-tetramethoxychalcone (55) | Piper hispidum | [70] | ||
2′-Hydroxy-2,4,4′,6′-tetramethoxychalcone (56) | ||||
2′-Hydroxy-2,3,4,4′,6′-pentamethoxychalcone (57) | ||||
4′-Hydroxyrottlerin (64) | Mallotus philippinensis | [72] | ||
Isoliquiritigenin (22) | Apis mellifera | [71] | ||
Kamalachalcone E (67) | Mallotus philippinensis | [72] | ||
Rottlerin (65) | ||||
2′,3,4,4′-Tetrahydroxy-3′-geranylchalcone (85) | Artocarpus nobilis | [73] | ||
2′,3,4,4′-Tetrahydroxy-3′-(6-hydroxy-3,7-dimethyl-7-octadienyl)chalcone (79) | ||||
2′,4′,4-Trihydroxy-3′-geranylchalcone (83) [xanthoangelol] | ||||
2′,4′,4-Trihydroxy-3′-(6-hydroxy-3,7-dimethyl-7-octadienyl)chalcone (80) | ||||
2′,4′,4-Trihydroxy-3′-[2-hydroxy-7-methyl-3-methylene-6-octenyl-chalcone] (81) | ||||
Antiviral | Dihydrochalcone diglycoside (50) | Thalassodendrin ciliatum | [74] | |
Echinantin (59) | Glycyrrhiza inflata | [75] | ||
Isoliquiritigenin (22) | ||||
Licochalcone A (40) | Quercus coccifera | [76] | ||
Glycyrrhiza inflata | [75] | |||
Licochalcone B (68) | Quercus coccifera | [76] | ||
Licochalcone D (72) | Glycyrrhiza inflata Quercus coccifera | [76] | ||
Licochalcone G (73) | ||||
Tetrahydroxy-methoxychalcone (69) | [76] | |||
Xanthoangelol (83) | Angelica keiskei | [77] | ||
Xanthoangelol F (84) | ||||
Xanthoangelol D (89) | ||||
Xanthoangelol E (90) | ||||
Xanthoangelol B (86) | ||||
Xanthoangelol G (87) | ||||
Xanthodeistal A (88) | ||||
Antioxidant | Licochalcone C (71) | Glycyrrhiza glabra | [67] | |
Isosalipurposide (66) Naringenin chalcone (78) | Acacia cyanophylla | [50] | ||
Antiparasitic | (E)-1-(2,4-Dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)-3-phenylprop-2-en-1-one (53) | Lonchocarpus sp. | [78] | |
Flavokawain B (28) | Polygonum ferrugineum | [79] | ||
Licochalcone C (71) | Glycyrrhiza glabra | [80] | ||
Licoagrochalcone A (70) | Erythrina abyssinica | [81] | ||
Immunoregulatory | Mallotophilippens C (74) | Mallotus philippinensis | [68] | |
Mallotophilippens D (75) | ||||
Mallotophilippens E (76) |
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Jasim, H.A.; Nahar, L.; Jasim, M.A.; Moore, S.A.; Ritchie, K.J.; Sarker, S.D. Chalcones: Synthetic Chemistry Follows Where Nature Leads. Biomolecules 2021, 11, 1203. https://doi.org/10.3390/biom11081203
Jasim HA, Nahar L, Jasim MA, Moore SA, Ritchie KJ, Sarker SD. Chalcones: Synthetic Chemistry Follows Where Nature Leads. Biomolecules. 2021; 11(8):1203. https://doi.org/10.3390/biom11081203
Chicago/Turabian StyleJasim, Hiba A., Lutfun Nahar, Mohammad A. Jasim, Sharon A. Moore, Kenneth J. Ritchie, and Satyajit D. Sarker. 2021. "Chalcones: Synthetic Chemistry Follows Where Nature Leads" Biomolecules 11, no. 8: 1203. https://doi.org/10.3390/biom11081203