Table 28.
Cytotoxic activity of compounds from the genus Croton.
| Compounds | Tumor Cell Line | Activity (IC50) | Ref |
|---|---|---|---|
| Methyl 15,16-epoxy-3,13(16),14-ent-clerodatrien-18,19-olide-17-carboxylate (6) | HuCCA-1 | 36.0 μg/mL | [29] |
| KB | 26.0 μg/mL | [29] | |
| HeLa | 30.0 μg/mL | [29] | |
| MDA-MB231 | 29.0 μg/mL | [29] | |
| T47D | 10.0 μg/mL | [29] | |
| Dimethyl-15,16-epoxy-12-oxo-3,13 (16)14-ent-clerodatriene-17,18-dicarboxylate (7) | HuCCA-1 | 39.0 μg/mL | [29] |
| KB | 27.0 μg/mL | [29] | |
| HeLa | 29.0 μg/mL | [29] | |
| MDA-MB231 | 27.0 μg/mL | [29] | |
| T47D | 25.0 μg/mL | [29] | |
| Laevigatbenzoate (8) | HeLa | 45.4 μM | [13] |
| Crotonolide A (23) | HL-60 | 9.42 μM | [21] |
| P-388 | 7.45 μM | [21] | |
| 15-oxo-17(10′-α-pinenyl)-kauran-18-oic acid (181) | HCT-116 | 7.14 μg/mL | [35] |
| OVCAR-8 | 8.19 μg/mL | [35] | |
| SF-295 | >10.0 μg/mL | [35] | |
| Launine K (67) | HeLa | 14.5 μM | [37] |
| MCF-7 | 62.5 μM | [37] | |
| Crassin H (75) | HL-60 | 11.8 ± 2.1 μM | [17] |
| A549 | 5.2 ± 0.4 μM | [17] | |
| Crassifolius A (76) | Hep3B | 17.91 μM | [38] |
| HepG2 | 42.04 μM | [38] | |
| Cracroson D (339) | T24 | 14.48 ± 0.65 μM | [40] |
| A549 | 25.64 ± 2.14 μM | [40] | |
| Cracroson E (87) | T24 | 22.99 ± 1.76 μM | [40] |
| A549 | 51.88 ± 14.07μM | [40] | |
| Hela | 3.9 μM | [48] | |
| DU145 | 7.2 μM | [48] | |
| A549 | 5.8 μM | [48] | |
| SGC-7091 | 13 μM | [48] | |
| H1975 | 10 μM | [48] | |
| HL60 | 12 μM | [48] | |
| 293T | 291.6 μM | [48] | |
| LX-2 | >500.0 μM | [48] | |
| 12-O-benzoylphorbol-13-(2-methyl)butyrate (114) | K562 | 15 μM | [48] |
| MOLT-4 | 12 μM | [48] | |
| U937 | 17 μM | [48] | |
| MCF-7 | 20 μM | [48] | |
| Hela | 4.6 μM | [48] | |
| DU145 | 4.3 μM | [48] | |
| A549 | 6.9 μM | [48] | |
| SGC-7091 | 10 μM | [48] | |
| H1975 | 3.3 μM | [48] | |
| HL60 | 6.8 μM | [48] | |
| 293T | 420.4 μM | [48] | |
| LX-2 | >500.0 μM | [48] | |
| 12-O-tiglyl-7-oxo-5-ene-phorbol-13-(2-methyl)butyrate (115) | K562 | 17 μM | [48] |
| MOLT-4 | 4.8 μM | [48] | |
| U937 | 21 μM | [48] | |
| MCF-7 | 20 μM | [48] | |
| Hela | 5.0 μM | [48] | |
| DU145 | 10 μM | [48] | |
| A549 | 19 μM | [48] | |
| SGC-7091 | 23 μM | [48] | |
| H1975 | 10 μM | [48] | |
| HL60 | 10 μM | [48] | |
| 293T | 455.3 μM | [48] | |
| LX-2 | >500.0 μM | [48] | |
| 13-O-(2-metyl)butyryl-4-deoxy-4a-phorbol (116) | K562 | 8.0 μM | [48] |
| MOLT-4 | 9.9 μM | [48] | |
| U937 | 18 μM | [48] | |
| MCF-7 | 24 μM | [48] | |
| H1975 | 10 μM | [48] | |
| HL60 | 10 μM | [48] | |
| 293T | 455.3 μM | [48] | |
| LX-2 | >500.0 μM | [48] | |
| Hela | 10 μM | [48] | |
| DU145 | 10 μM | [48] | |
| A549 | 4.5 μM | [48] | |
| SGC-7091 | 5.4 μM | [48] | |
| H1975 | 3.3 μM | [48] | |
| HL60 | 9.8 μM | [48] | |
| 293T | 191.0 μM | [48] | |
| LX-2 | >500.0 μM | [48] | |
| Crotignoid A (117) | HL-60 | 1.61 μM | [49] |
| A549 | 2.85 μM | [49] | |
| Crotignoid B (118) | HL-60 | 22.1 μM | [49] |
| A549 | 31.0 μM | [49] | |
| Crotignoid C (119) | HL-60 | 32.3 μM | [49] |
| A549 | 5.03 μM | [49] | |
| Crotignoid D (120) | HL-60 | 19.8 μM | [49] |
| A549 | 10.2 μM | [49] | |
| Crotignoid F (122) | HL-60 | 44.6 μM | [49] |
| A549 | 6.96 μM | [49] | |
| Crotignoid G (123) | HL-60 | 22.1 μM | [49] |
| A549 | 3.89 μM | [49] | |
| Crotignoid H (124) | HL-60 | 9.97 μM | [49] |
| A549 | 8.08 μM | [49] | |
| Crotignoid I (125) | HL-60 | 14.8 μM | [49] |
| A549 | 24.4 μM | [49] | |
| Crotignoid J (126) | HL-60 | 14.2 μM | [49] |
| A549 | 29.5 μM | [49] | |
| Crotusin A (128) | HL-60 | 12.53 ± 0.37 μM | [44] |
| SMMC-7721 | 7.06 ± 0.72 μM | [44] | |
| A549 | 9.69 ± 0.41 μM | [44] | |
| MCF-7 | 9.56 ± 0.76 μM | [44] | |
| SW480 | 14.88 ± 0.43 μM | [44] | |
| Crotusin B (129) | HL-60 | 19.39 ± 0.46 μM | [44] |
| SMMC-7721 | 21.13 ± 0.29 μM | [44] | |
| A549 | 14.66 ± 1.66 μM | [44] | |
| MCF-7 | 1.49 ± 0.23 μM | [44] | |
| SW480 | 31.21 ± 3.20 μM | [44] | |
| Crotusin C (130) | HL-60 | 4.19 ± 0.15 μM | [44] |
| SMMC-7721 | 3.87 ± 0.12 μM | [44] | |
| A549 | 2.44 ± 0.35 μM | [44] | |
| MCF-7 | 0.49 ± 0.04 μM | [44] | |
| SW480 | 2.89 ± 0.01 μM | [44] | |
| 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-acetate (131) | SNU387 | 59.5 ± 2.1 μM | [50] |
| SNU398 | 43.7 ± 1.5 μM | [50] | |
| 12-O-tiglylphorbol-4-deoxy-4β-phorbol-13-hexadecanoate (132) | SNU387 | 30.2 ± 1.4 μM | [50] |
| SNU398 | 91.2 ± 3.7 μM | [50] | |
| 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-oleate (133) | SNU387 | 1.9 ± 0.2 μM | [50] |
| SNU398 | 13.5 ± 1.1 μM | [50] | |
| 13-O-acetylphorbol-4-deoxy-4β-phorbol-20-linoleate (134) | SNU387 | 0.71 ± 0.08 μM | [50] |
| SNU398 | 18.2 ± 1.7 μM | [50] | |
| 4-deoxy-20-oxophorbol 12-tiglyl 13-acetate (135) | K562 | 0.03 μM | [51] |
| A549 | 6.88 μM | [51] | |
| Huh-7 | 3.85 μM | [51] | |
| 7-oxo-5-ene-phorbol-13-(2-methylbutyrate) (136) | K562 | 0.03 μM | [51] |
| A549 | 6.33 μM | [51] | |
| Huh-7 | 20.9 μM | [51] | |
| 7-hydroxyl-phorbol-5-ene-13-(2-methyl)butyrate (137) | K562 | 0.07 μM | [51] |
| A549 | 8.86 μM | [51] | |
| Huh-7 | 11.6 μM | [51] | |
| 13-O-(2-metyl)butyryl-phorbol (139) | K562 | 0.05 μM | [51] |
| A549 | 43.5 μM | [51] | |
| Huh-7 | 34.2 μM | [51] | |
| 7-keto-12-O-tiglylphorbol-13-acetate (140) | HL-60 | 6.22 ± 3.24 μg/mL | [52] |
| A549 | 18.0 ± 9.48 μg/mL | [52] | |
| Phorbol-13-isobutyrate (148) | HL-60 | 0.22 ± 0.15 μg/mL | [52] |
| 14-epi-hyalic acid (159) | HL-60 | 8.2 μM | [63] |
| Kongeniod A (178) | HL-60 | 1.27 ± 0.24 μM | [59]] |
| A549 | 5.74 ± 0.25 μM | [59] | |
| Kongeniod B (179) | HL-60 | 0.47 ± 0.04 μM | [59] |
| A549 | 3.25 ± 0.91 μM | [59] | |
| Kongeniod C (180) | HL-60 | 0.58 ± 0.17 μM | [59] |
| Crotonkinensin D (188) | MCF-7 | 9.4 ± 1.7 μM | [61] |
| MCF-7/TAMR | 2.6 ± 0.9 μM | [61] | |
| MCF-7/ADR | 18.9 ± 0.6 μM | [61] | |
| MDA-MB-231 | 22.0 ± 0.9 μM | [61] | |
| EBC-162 (207) | HL-60 | 15 μg/mL | [74] |
| HT29 | 15 μg/mL | [74] | |
| MCF-7 | 30 μg/mL | [74] | |
| MM96 | 10 μg/mL | [74] | |
| NNF | 20 μg/mL | [74] | |
| K562 | 50 μg/mL | [74] | |
| EBC-233 (208) | HL-60 | 10 μg/mL | [74] |
| HT29 | 80 μg/mL | [74] | |
| MCF-7 | 20 μg/mL | [74] | |
| MM96 | 6 μg/mL | [74] | |
| NNF | 50 μg/mL | [74] | |
| K562 | 50 μg/mL | [74] | |
| EBC-300 (209) | HL-60 | 35 μg/mL | [74] |
| HT29 | 100 μg/mL | [74] | |
| MCF-7 | 100 μg/mL | [74] | |
| MM96 | 80 μg/mL | [74] | |
| NNF | 80 μg/mL | [74] | |
| K562 | 100 μg/mL | [74] | |
| EBC-240 (210) | HL-60 | 45 μg/mL | [74] |
| HT29 | 80 μg/mL | [74] | |
| MCF-7 | 50 μg/mL | [74] | |
| MM96 | 12 μg/mL | [74] | |
| NNF | 80 μg/mL | [74] | |
| K562 | 60 μg/mL | [74] | |
| EBC-241 (211) | HL-60 | 40 μg/mL | [74] |
| HT29 | 80 μg/mL | [74] | |
| MCF-7 | 40 μg/mL | [74] | |
| MM96 | 12 μg/mL | [74] | |
| NNF | 75 μg/mL | [74] | |
| K562 | 60 μg/mL | [74] | |
| Furanocembranoid 1 (266) | BT474 | 7.8 μg/mL | [83] |
| CHAGO | 7.0 μg/mL | [83] | |
| Hep-G2 | 5.6 μg/mL | [83] | |
| KATO-3 | 5.9 μg/mL | [83] | |
| SW-620 | 6.3 μg/mL | [83] | |
| Furanocembranoid 2 (267) | BT474 | 9.5 μg/mL | [83] |
| CHAGO | >10 μg/mL | [83] | |
| Hep-G2 | >10 μg/mL | [83] | |
| KATO-3 | 6.8 μg/mL | [83] | |
| SW-620 | 9.9 μg/mL | [83] | |
| Furanocembranoid 3 (268) | BT474 | 9.6 μg/mL | [83] |
| CHAGO | 7.1 μg/mL | [83] | |
| Hep-G2 | 5.7 μg/mL | [83] | |
| KATO-3 | 8.2 μg/mL | [83] | |
| SW-620 | 5.6 μg/mL | [83]] | |
| Furanocembranoid 4 (269) | BT474 | 9.6 μg/mL | [83] |
| CHAGO | 9.3 μg/mL | [83] | |
| Hep-G2 | 6.1 μg/mL | [83] | |
| KATO-3 | 8.1 μg/mL | [83] | |
| SW-620 | 6.0 μg/mL | [83] | |
| Laevigatlactone B (272) | Hela | 38.4 μM | [84] |
| (+)-[1R*,2S*,7S*,8S*,12R*]-7,8-Epoxy-2,12-cyclocembra-3E,10Zdien-20,10-olide (276) | PEO1 | 132 nM | [85] |
| PEO1TaxR | 200 nM | [85] | |
| (+)-[1R*,4S*,10R*]-4-Hydroxycembra-2E,7E,11Z-trien-20,10-olide (278) | PEO1 | 125 nM | [85] |
| PEO1TaxR | 135 nM | [85] | |
| Crotontomentosin A (294) | Hela | 24.0 ± 2.6 μM | [88] |
| Hep G2 | 87.9 ± 4.5 μM | [88] | |
| MDA-MB-231 | 54.1 ± 2.1 μM | [88] | |
| A549 | 40.6 ± 3.9 μM | [88] | |
| Crotontomentosin B (295) | Hela | >100 μM | [88] |
| Hep G2 | 28.1 ± 2.1 μM | [88] | |
| MDA-MB-231 | 28.7 ± 3.4 μM | [88] | |
| A549 | 29.1 ± 5.2 μM | [88] | |
| Crotontomentosin C (297) | Hela | 47.9 ± 3.3 μM | [88] |
| Hep G2 | 83.3 ± 5.3 μM | [88] | |
| MDA-MB-231 | >100 μM | [88] | |
| A549 | >100 μM | [88]] | |
| Crotontomentosin D (296) | Hela | 59.7 ± 4.5 μM | [88] |
| Hep G2 | >100 μM | [88] | |
| MDA-MB-231 | 49.3 ± 2.8 μM | [88] | |
| A549 | >100 μM | [88] | |
| Crotolaevigatone B (300) | A549 | 21.2 μM | [89] |
| MDA-MB-231 | 33.4 μM | [89] | |
| Crotolaevigatone G (305) | A549 | 25.6 μM | [89] |
| MDA-MB-231 | 32.7 μM | [89] | |
| EBC-324 (311) | MCF-7 | 40 μM | [92] |
| NFF | 50 μM | [92] | |
| K562 | 6 μM | [92] | |
| EBC-329 (312) | MCF-7 | 13 μM | [92] |
| NFF | 40 μM | [92] | |
| K562 | 0.6 μM | [92] | |
| ent-3β-hydroxypimara-8(14),9,15-trien-12-one (319) | NFF | 23 μg/mL | [98] |
| Hela | 13 μg/mL | [98] | |
| HT 29 | 13 μg/mL | [98] | |
| MCF-7 | 16 μg/mL | [98] | |
| MM96L | 2.8 μg/mL | [98] | |
| K562 | 17 μg/mL | [98] | |
| EBC-325 (321) | MCF-7 | 20 μM | [99] |
| NFF | 6 μM | [99] | |
| K562 | 3 μM | [99] | |
| EBC-326 (322) | MCF-7 | 14 μM | [99] |
| NFF | 6 μM | [99] | |
| K562 | 6 μM | [99] | |
| EBC-327 (323) | MCF-7 | 10 μM | [99] |
| NFF | 10 μM | [99] | |
| K562 | 10 μM | [99] | |
| 3-hydroxycleistantha-13(17),15-diene (325) | KATO-3 | 6.0 μg/mL | [93] |
| SW-620 | >10 μg/mL | [93] | |
| BT474 | 6.1 μg/mL | [93] | |
| Hep-G2 | 0.5 μg/mL | [93] | |
| CHAGO | 5.5 μg/mL | [93] | |
| 3,4-seco-cleistantha-4(18),13(17),15-trien-3-oic acid (326) | KATO-3 | 9.6 μg/mL | [93] |
| SW-620 | >10 μg/mL | [93] | |
| BT474 | 10 μg/mL | [93] | |
| Hep-G2 | 8.6 μg/mL | [93] | |
| CHAGO | >10 μg/mL | [93] | |
| Crotobarin (330) | KB | 2.5 ± 0.10 μM | [101] |
| HT29 | 2.1 ± 0.60 μM | [101] | |
| A549 | 0.79 ± 0.15 μM | [101] | |
| HL60 | 0.56 ± 0.02 μM | [101] | |
| Crotogoudin (331) | KB | 1.5 ± 0.03 μM | [101] |
| HT29 | 1.9 ± 0.25 μM | [101] | |
| A549 | 0.54 ± 0.02 μM | [101] | |
| HL60 | 0.49 ± 0.01 μM | [101] | |
| Crotonpyrone A (381) | Hela | 10.21 μg/mL | [120] |
| NCI-446 | 6.59 μg/mL | [120] | |
| Crotonpyrone B (382) | Hela | 9.54 μg/mL | [120] |
| [1−9-NαC]-crourorb A1 (385) | NCI-ADR/RES | 4.8 μM | [123] |