Table 2.
Pharmacological activity of acylated oximes of triterpenes and their mother compounds
| Compound | Results | Activity | Literature |
|---|---|---|---|
| 13 (betulin) | IC50 = 43.7 μM | Antiviral (HIV acutely infected H9 lymphocytes) | Sun et al. (1998) |
| 15 (dioxime of 13) | IC50 = 5.47 μM | ||
| 16a (di-O-acyl deriv. of 15) | IC50 = 15.4 μM | ||
| 13 (betulin) | EC50 = 23.0 μM | Antiviral (HIV acutely infected H9 lymphocytes) | |
| 15 (dioxime of 13) | EC50 = 1.07 μM | ||
| 16a (di-O-acyl deriv. of 15) | EC50 = 4.57 μM | ||
| 13 (betulin) | VR = 7 % | Antiviral (SFV) | Pohjala et al. (2009) |
| 15 (dioxime of 13) | VR = 121 % | ||
| 16b (di-O-acyl deriv. of 15) | VR = 73 % | ||
| 13 (betulin) | CV = 83 % | ||
| 15 (dioxime of 13) | CV = 80 % | ||
| 16b (di-O-acyl deriv. of 15) | CV = 85 % | ||
| 20 (oxime of BA) | EC50 = 2.17 μM | Antiviral (influenza A) | Flekhter et al. (2004) |
| 21 (oxime of MB) | EC50 > 25.84 μM | ||
| 22 (oxime of 20-OAB) | EC50 = 150.54 μM | ||
| 20 (oxime of BA) | MTC/EC50 = 392.16 | ||
| 21 (oxime of MB) | MTC/EC50 < 1 | ||
| 22 (oxime of 20-OAB) | MTC/EC50 = 2.83 | ||
| 20 (oxime of BA) | EC50 = 81.56 μM | Antiviral (HSV 1) | |
| 21 (oxime of MB) | EC50 = 31.32 μM | ||
| 22 (oxime of 20-OAB) | EC50 = 160.07 μM | ||
| 20 (oxime of BA) | MTC/EC50 = 1.30 | ||
| 21 (oxime of MB) | MTC/EC50 = 6.60 | ||
| 22 (oxime of 20-OAB) | MTC/EC50 = 2.66 | ||
| 20 (oxime of BA) | EC50 = 4.19 μM | Antiviral (ECHO 6) | |
| 21 (oxime of MB) | EC50 = 36.84 μM | ||
| 22 (oxime of 20-OAB) | EC50 = 133.10 μM | ||
| 20 (oxime of BA) | MTC/EC50 = 6.09 | ||
| 21 (oxime of MB) | MTC/EC50 = 11.22 | ||
| 22 (oxime of 20-OAB) | MTC/EC50 = 1.60 | ||
| BA | ED50 = 1.23 μg/ml | Cytotoxic (MOLT-4) | Mukherjee et al. (2004) |
| 20 (oxime of BA) | ED50 = 2.1 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 2.2 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 2.7 μg/ml | ||
| BA | ED50 = 0.65 μg/ml | Cytotoxic (JurkatE6.1) | |
| 20 (oxime of BA) | ED50 = 1.8 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 2.9 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 4.9 μg/ml | ||
| BA | ED50 = 0.98 μg/ml | Cytotoxic (CEM.CM3) | |
| 20 (oxime of BA) | ED50 = 2.6 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 4.2 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 1.5 μg/ml | ||
| BA | ED50 = 0.84 μg/ml | Cytotoxic (BRISTOL8) | |
| 20 (oxime of BA) | ED50 = 1.6 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 3.4 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 3.3 μg/ml | ||
| BA | ED50 = 0.69 μg/ml | Cytotoxic (U937) | |
| 20 (oxime of BA) | ED50 = 2.4 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 5.5 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 4.8 μg/ml | ||
| BA | ED50 = 1.13 μg/ml | Cytotoxic (DU145) | |
| 20 (oxime of BA) | ED50 = 1.1 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 2.9 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 2.8 μg/ml | ||
| BA | ED50 > 10 μg/ml | Cytotoxic (PA-1) | |
| 20 (oxime of BA) | ED50 = 0.7 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 3.7 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 = 1.8 μg/ml | ||
| BA | ED50 > 10 μg/ml | Cytotoxic (A549) | |
| 20 (oxime of BA) | ED50 = 1.8 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 > 10 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 > 10 μg/ml | ||
| BA | ED50 = 1.3 μg/ml | Cytotoxic (L132) | |
| 20 (oxime of BA) | ED50 = 1.5 μg/ml | ||
| 23a (O-acyl deriv. of 20) | ED50 = 5.3 μg/ml | ||
| 23d (O-acyl deriv. of 20) | ED50 > 10 μg/ml | ||
| 20 (oxime of BA) | EC50 = 1.75 μM | Antidiabetic (TGR 5) | Genet et al. (2010) |
| 23a (O-acyl deriv. of 20) | EC50 = 5.00 μM | ||
| 23e (O-acyl deriv. of 20) | EC50 = 3.17 μM | ||
| 23f (O-acyl deriv. of 20) | EC50 = 7.88 μM | ||
| 23g (O-acyl deriv. of 20) | EC50 = 7.73 μM | ||
| 23h (O-acyl deriv. of 20) | EC50 = 3.65 μM | ||
| 20 (oxime of BA) | efficacy = 132 | ||
| 23a (O-acyl deriv. of 20) | efficacy = 159 | ||
| 23e (O-acyl deriv. of 20) | efficacy = 20 | ||
| 23f (O-acyl deriv. of 20) | efficacy = 139 | ||
| 23g (O-acyl deriv. of 20) | efficacy = 126 | ||
| 23h (O-acyl deriv. of 20) | efficacy = 13 | ||
| 1 (OA) | IC50 = 8.0 μM | Antiviral (HIV-1) | Ma et al. (2000) |
| 11 (oxime of OA) | IC50 = 5.5 μM | ||
| 12 (oxime of MO) | IC50 = 9.5. μM | ||
| 27a (O-acyl deriv. of 11) | IC50 = 5.5. μM | ||
| 28a (O-acyl deriv. of 12) | IC50 = 4.0 μM | ||
| 1 (OA) | IC50 = 8.0 μM | Antiviral (HIV-1 PR) | Ma et al. (2002) |
| 11 (oxime of OA) | IC50 = 5.5 μM | ||
| 12 (oxime of MO) | IC50 = 9.5 μM | ||
| 27a (O-acyl deriv. of 11) | IC50 = 5.5 μM | ||
| 27b (O-acyl deriv. of 11) | IC50 = 1.9 μM | ||
| 28a (O-acyl deriv. of 12) | IC50 = 4.0 μM | ||
| 28b (O-acyl deriv. of 12) | IC50 = 16 μM | ||
| 28c (O-acyl deriv. of 12) | IC50 > 100 μM | ||
| 1 (OA) | IC100 not effective | Antiviral (HIV-1 RT) | |
| 11 (oxime of OA) | IC100 not effective | ||
| 12 (oxime of MO) | IC100 not effective | ||
| 27a (O-acyl deriv. of 11) | IC100 not effective | ||
| 27b (O-acyl deriv. of 11) | IC100 = 1.84 μM | ||
| 28a (O-acyl deriv. of 12) | IC100 not effective | ||
| 28b (O-acyl deriv. of 12) | IC100 = 4.53 μM | ||
| 28c (O-acyl deriv. of 12) | IC100 not effective | ||
| 1 (OA) | CC0 ≥ 110 μM | Antiviral (HIV-1 RT) | |
| 11 (oxime of OA) | CC0 = 266 μM | ||
| 12 (oxime of MO) | CC0 = 51.8 μM | ||
| 27a (O-acyl deriv. of 11) | CC0 = 209 μM | ||
| 27b (O-acyl deriv. of 11) | CC0 = 29.6 μM | ||
| 28a (O-acyl deriv. of 12) | CC0 = 40.9 μM | ||
| 28b (O-acyl deriv. of 12) | CC0 = 145 μM | ||
| 28c (O-acyl deriv. of 12) | CC0 = 31.0 μM | ||
| 39 (dioxime of oleanonic | MGC = 1.20 g/100 cm3 (methylene chloride) | Gelation | Hu et al. (2009) |
| MGC = 0.37 g/100 cm3 (chloroform) | |||
| MGC = 2.08 g/100 cm3 (carbon tetrachloride) | |||
| MGC = 0.10 g/100 cm3 (benzene) | |||
| MGC = 0.20 g/100 cm3 (toluene) | |||
| 45d (O-acyl deriv. of 12) | GI50 = (1.55–12.80) × 10−6 the most sensitive cell line: HOP-92) | Anticancer (lung cancers) | Bednarczyk-Cwynar et al. (2011) |
| GI50 = (1.66–34.80) × 10−6 (the most sensitive cell line: HCT-116) | Anticancer (colon cancers) | ||
| GI50 = (1.56–2.67) × 10−6 (the most sensitive cell line: HS-578T2) | Anticancer (brest cancers) | ||
| GI50 = (1.67–16.50) × 10−6 (the most sensitive cell line: OVCAR-3) | Anticancer (ovary cancers) | ||
| GI50 = (2.02–2.78) × 10−6 (the most sensitive cell line: HL-60 TB) | Anticancer (leukemias) | ||
| GI50 = (1.49–2.60) × 10−6 (the most sensitive cell line: UO-31) | Anticancer (kidney cancers) | ||
| GI50 = (1.47–11.50) × 10−6 (the most sensitive cell line: LOX IMVI) | Anticancer (melanomas) | ||
| GI50 = (1.76–10.40) × 10−6 (the most sensitive cell line: SF-539) | Anticancer (CNS cancers) | ||
| TGI = (4.04–22.90) × 10−6 (the most sensitive cell line: HOP-92) | Anticancer (lung cancers) | ||
| TGI = (3.02–12.60) × 10−6 (the most sensitive cell line: HCC-2998) | Anticancer (colon cancers) | ||
| TGI = (4.29–14.20) × 10−6 (the most sensitive cell line: MCF-7) | Anticancer (brest cancers) | ||
| TGI = (3.08–30.40) × 10−6 (the most sensitive cell line: OVCAR-3) | Anticancer (ovary cancers) | ||
| TGI = (5.36–8.16) × 10−6 (the most sensitive cell line: HL-60 TB) | Anticancer (leukemias) | ||
| TGI = (2.93–16.30) × 10−6 (the most sensitive cell line: UO-31) | Anticancer (kidney cancers) | ||
| TGI = (2.94–24.40) × 10−6 (the most sensitive cell line: LOX IMVI) | Anticancer (melanomas) | ||
| TGI = (3.37–22.10) × 10−6 (the most sensitive cell line: U251) | Anticancer (CNS cancers) | ||
| LC50 = (11.50–100.00) × 10−6 (the most sensitive cell line: HOP-92) | Anticancer (lung cancers) | ||
| LC50 = (6.14–38.80) × 10−6 (the most sensitive cell line: HCT-116) | Anticancer (colon cancers) | ||
| LC50 = (11.10–46.80) × 10−6 (the most sensitive cell line: MCF-7) | Anticancer (brest cancers) | ||
| LC50 = (5.70–60.20) × 10−6 (the most sensitive cell line: OVCAR-3.) | Anticancer (ovary cancers) | ||
| LC50 = (2.62–100.00) × 10−6 (the most sensitive cell line: HL-60 TB) | Anticancer (leukemias) | ||
| LC50 = (5.79–57.20) × 10−6 (the most sensitive cell line: UO-31) | Anticancer (kidney cancers) | ||
| LC50 = (5.89–51.50) × 10−6 (the most sensitive cell line: LOX IMVI) | Anticancer (melanomas) | ||
| LC50 = (6.39–54.90) × 10−6 (the most sensitive cell line: U251) | Anticancer (CNS cancers) | ||
| 1 (OA) | MGIR = 22.4 % | Fungicidal (Candida albicans GlcN-6-P synthase inhibitor); conc. = 0.35 mM | Zhao et al. (2013) |
| 50a (O-acyl deriv. of 11) | MGIR = 29.4 % | ||
| 50b (O-acyl deriv. of 11) | MGIR = 37.2 % | ||
| 50c (O-acyl deriv. of 11) | MGIR = 40.8 % | ||
| 50d (O-acyl deriv. of 11) | MGIR = 19.2 % | ||
| 50e (O-acyl deriv. of 11) | MGIR = 30.8 % | ||
| 50f (O-acyl deriv. of 11) | MGIR = 29.1 % | ||
| 50 g (O-acyl deriv. of 11) | MGIR = 22.9 % | ||
| 50 h (O-acyl deriv. of 11) | MGIR = 24.8 % | ||
| 50i (O-acyl deriv. of 11) | MGIR = 21.0 % | ||
| 50j (O-acyl deriv. of 11) | MGIR = 20.5 % | ||
| 51a (O-acyl deriv. of 49) | MGIR = 8.7 % | ||
| 51b (O-acyl deriv. of 49) | MGIR = 12.2 % | ||
| 51c (O-acyl deriv. of 49) | MGIR = 19.8 % | ||
| 51d (O-acyl deriv. of 49) | MGIR = 16.2 % | ||
| 51e (O-acyl deriv. of 49) | MGIR = 20.2 % | ||
| 51f (O-acyl deriv. of 49) | MGIR = 34.2 % | ||
| 51 g (O-acyl deriv. of 49) | MGIR = 28.2 % | ||
| 51 h (O-acyl deriv. of 49) | MGIR = 12.7 % | ||
| 51i (O-acyl deriv. of 49) | MGIR = 19.3 % | ||
| 51j (O-acyl deriv. of 49) | MGIR = 13.2 % | ||
| 51 k (O-acyl deriv. of 49) | MGIR = 16.4 % | ||
| 51 l (O-acyl deriv. of 49) | MGIR = 33.0 % | ||
| 51 m (O-acyl deriv. of 49) | MGIR = 33.1 % | ||
| 51n (O-acyl deriv. of 49) | MGIR = 12.5 % | ||
| 51o (O-acyl deriv. of 49) | MGIR = 13.8 % | ||
| 1 (OA) | MGIR = 1.0–25.3 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | Fungicidal; conc. = 50 μg/ml | |
| 50a (O-acyl deriv. of 11) | MGIR = 1.8–61.2 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 50b (O-acyl deriv. of 11) | MGIR = 8.4–61.2 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 50c (O-acyl deriv. of 11) | MGIR = 3.1–42.7 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 50d (O-acyl deriv. of 11) | MGIR = 15.8–53.5 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 50e (O-acyl deriv. of 11) | MGIR = 6.5–73.0 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 50f (O-acyl deriv. of 11) | MGIR = 4.0–33.5 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 50 g (O-acyl deriv. of 11) | MGIR = 6.1–67.6 % (the most sensitive cell line: Phytophthora parasitica Dast) | ||
| 50 h (O-acyl deriv. of 11) | MGIR = 2.0–27.8 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 50i (O-acyl deriv. of 11) | MGIR = 1.4–25.1 % (the most sensitive cell line: Rice blast) | ||
| 50j (O-acyl deriv. of 11) | MGIR = 2.3–30.3 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51a (O-acyl deriv. of 49) | MGIR = 9.4–79.2 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51b (O-acyl deriv. of 49) | MGIR = 12.0–71.1 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51c (O-acyl deriv. of 49) | MGIR = 23.5–93.6 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51d (O-acyl deriv. of 49) | MGIR = 25.9–74.3 % (the most sensitive cell line: Rice blast) | ||
| 51e (O-acyl deriv. of 49) | MGIR = 17.4–84.1 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51f (O-acyl deriv. of 49) | MGIR = 18.1–73.1 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51 g (O-acyl deriv. of 49) | MGIR = 17.7–86.1 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51 h (O-acyl deriv. of 49) | MGIR = 21.7–67.8 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51i (O-acyl deriv. of 49) | MGIR = 25.3–74.4 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51j (O-acyl deriv. of 49) | MGIR = 23.5–68.2 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51 k (O-acyl deriv. of 49) | MGIR = 21.4–64.5 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51 l (O-acyl deriv. of 49) | MGIR = 28.2–69.5 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51 m (O-acyl deriv. of 49) | MGIR = 24.6–66.7 % (the most sensitive cell line: Sclerotinia sclerotiorum (Lib.) de Bary) | ||
| 51n (O-acyl deriv. of 49) | MGIR = 30.8–77.6 % (the most sensitive cell line: Rhizoctonia solani Kuhn) | ||
| 51o (O-acyl deriv. of 49) | MGIR = 28.7–85.5 % (the most sensitive cell line: Rice blast) | ||
| 1 (OA) | IC50 = 14.93 μM | Anticancer (KB) | |
| 53 (oxime of OM) | IC50 = 2.06 μM | Bednarczyk-Cwynar et al. (2012b) | |
| 54a (O-acyl deriv. of 53) | IC50 > 15.00 μM | ||
| 54b (O-acyl deriv. of 53) | IC50 = 9.42 μM | ||
| 54c (O-acyl deriv. of 53) | IC50 = 4.90 μM | ||
| 54d (O-acyl deriv. of 53) | IC50 = 0.72 μM | ||
| 54e (O-acyl deriv. of 53) | IC50 = 10.10 μM | ||
| 1 (OA) | IC50 = 13.95 μM | Anticancer (MCF-7) | |
| 53 (oxime of OM) | IC50 = 11.27 μM | ||
| 54a (O-acyl deriv. of 53) | IC50 > 15.00 μM | ||
| 54b (O-acyl deriv. of 53) | IC50 = 7.26 μM | ||
| 54c (O-acyl deriv. of 53) | IC50 = 3.76 μM | ||
| 54d (O-acyl deriv. of 53) | IC50 = 2.13 μM | ||
| 54e (O-acyl deriv. of 53) | IC50 = 9.28 μM | ||
| 1 (OA) | IC50 = 11.82 μM | Anticancer (MCF-7) | |
| 53 (oxime of OM) | IC50 = 1.34 μM | ||
| 54a (O-acyl deriv. of 53) | IC50 > 15.00 μM | ||
| 54b (O-acyl deriv. of 53) | IC50 = 9.19 μM | ||
| 54c (O-acyl deriv. of 53) | IC50 = 4.41 μM | ||
| 54d (O-acyl deriv. of 53) | IC50 = 1.87 μM | ||
| 54e (O-acyl deriv. of 53) | IC50 = 9.84 μM | ||
| 55 (GA) | GI50 = 63.2 μM | Anticancer (HL-60) | Liu et al. (2007) |
| 56 (oxime of GA) | GI50 = 63.9 μM | ||
| 57a (O-acyl deriv. of 56) | GI50 = 58.8 μM | ||
| 57b (O-acyl deriv. of 56) | GI50 = 57.7 μM | ||
| 55 (GA) | AC = 24.9 % | ||
| 56 (oxime of GA) | AC = 24.5 % | ||
| 57a (O-acyl deriv. of 56) | AC = 19.1 % | ||
| 57b (O-acyl deriv. of 56) | AC = 27.7 % |
BA betulinic acid, MB methyl betulinate, 20-OAB 20-oxoallobetulin, OA oleanolic acid, MO methyl oleanolate, GA glycyrrhetinic acid, IC 50 50 % inhibitory concentration, EC 50 50 % effective concentration, VR virus replication, CV cell viability, MTC maximum tolerable concentration, ED 50 50 % effective dose, IC 100 100 % inhibition concentration, CC 0 minimum cytotoxic concentration, MGC minimum gelator concentration, GI 50 50 % growth inhibition, TGI total growth inhibitor, LC 50 50 % lethal concentration, MGIR mycelium growth inhibition rate, AC amount of apoptotic cells