Table 2.
Overview of the main physico-chemical properties and biological activities of compounds 1–15.
| Compound | Name (Other Trivial Names) | CAS Number | MW | Acidity 1 | Log P 1 | Log D 1 (pH 7.4) | Most Studied Biological Activities |
|---|---|---|---|---|---|---|---|
| 1 | Limonin (citrolimonin, dictamnolactone, evodin, obaculactone) | 1180-71-8 | 470 | pKa > 8 | 1.66 | 1.66 | Analgesic [45], anticancer [46,47,48,49,50,51,52,53,54,55,56,57,58,59], anti-inflammatory [45,60,61,62], antibacterial [63,64], antioxidant [4,65,66], antiviral [67], larvicidal [68,69] |
| 2 | Nomilin | 1063-77-0 | 514 | pKa > 8 | 2.47 | 2.47 | Anticancer [46,47,58,59,70], anti-hyperglycemic [71], anti-inflammatory [25,62], antioxidant [4,65,66], antiviral [67], larvicidal [68,69], osteoclastogenesis inhibition [72] |
| 3 | Obacunone (casimirolide, obacunon, tricoccin S3) | 753-03-1 | 454 | pKa > 8 | 2.91 | 2.91 | Anticancer [46,47,58,73,74,75], antibacterial [76,77] anti-hyperglycemic [78], antioxidant [66], larvicidal [79,80] |
| 4 | Deacetylnomilin (isolimonin, deacetylnomilinate) | 3264-90-2 | 472 | pKa > 8 | 1.57 | 1.57 | Anticancer [58,70], antioxidant [66] |
| 5 | Limonexic acid (limonexin, shihulimonin A, substance X) 2 | 99026-99-0 | 502 | 6 ≤ pKa ≤ 8 | −0.93 | −0.7 | Anticancer [28,48,52,81], antioxidant [28], hepatoprotection [82] |
| 6 | Isolimonexic acid 3 | 113164-90-2 | 502 | 6 ≤ pKa ≤ 8 | −0.93 | −0.7 | Anticancer [48,52] |
| 7 | Citrusin 3 | 108943-57-3 | 546 | 6 ≤ pKa ≤ 8 | −0.04 | 0.24 | Anti-inflammatory [25] |
| 8 | Ichangin | 10171-61-6 | 488 | pKa > 8 | 0.13 | 0.13 | Antibacterial [83,84] |
| 9 | Isoobacunoic acid (iso-obacunoic acid) | 751-28-0 | 472 | 4 ≤ pKa < 6 | 2.33 | −1.03 | Antibacterial [83] |
| 10 | Deoxylimonin (desoxylimonin) | 989-23-1 | 454 | pKa > 8 | 2.34 | 2.34 | Analgesic [45], anti-inflammatory [45] |
| 11 | Limonin 17-β-d-glucoside (limonin 17-β-d-glucopyranoside, glucosyl-limonin) | 123564-61-4 | 650 | 4 ≤ pKa < 6 | −0.46 | −3.66 | Anticancer [52,85,86,87], antioxidant [66,86], hepatoprotection [88] |
| 12 | Obacunone 17-β-d-glucoside (obacunone 17-β-d-glucopyranoside) 4 | 123564-64-7 | 635 | 4 ≤ pKa < 6 | 0.79 | −2.61 | Anticancer [75,76,86,89], antioxidant [86,89] |
| 13 | Deacetylnomilinic acid 17-β-d-glucoside (deacetylnomilinic acid 17-β-d-glucopyranoside) 4 | 125107-16-6 | 671 | pKa < 4 | −2.2 | −5.9 | Anticancer [89], antioxidant [89] |
| 14 | Nomilinic acid 17-β-d-glucoside (nomilinic acid 17-β-d-glucopyranoside) 4 | 125107-15-5 | 713 | pKa < 4 | 0.04 | −4.42 | Anticancer [46,89], antioxidant [89] |
| 15 | Isoobacunoic acid 17-β-d-glucoside (isoobacunoic acid 17-β-d-glucopyranoside) 4 | 125225-95-8 | 653 | pKa < 4 | 0.21 | −3.49 | Antibacterial [83] |
1 Predicted data generated using the ACD/Labs Percepta Platform—PhysChem Module (ACD/Labs, Toronto, ON, Canada); 2 Experimental; 3 pKa was assumed to be similar to that of limonexic acid (5); 4 pKa value from ChemAxon (https://chemicalize.com/#/calculation).