Table 1.
Cytotoxic activity of acetogenins in vitro in different cancer cell lines.
| Plant species | Acetogenin | Cytotoxicity/cancer cell line | Functional groups | References |
|---|---|---|---|---|
| Annona cornifolia A. St.-Hil |  |
Acetogenins isolated from A. cornifolia: squamocin M, annofolin, isolongimicin B, glaucanisin, and annotacin IC50 in the range of <3.0 × 10−1 to <3.2 × 10−1 µM/MCF-7 |
Annofolin the most active acetogenin of the group from A. cornifolia (IC50 = < 3.0 × 101) is a C-37 acetogenin with 9 carbon atoms between the OH-flanked THF and the γ-lactone and a stereochemical arrangement of erythro/trans/threo/
trans/threo around THF rings |
Lima et al., 2014 |
| Annona diversifolia Saff. |  |
Laherradurin: ED50 = 0.015 µg/ml/HeLa and SW480 Cherimolin-2: ED50 = 0.05 µg/ml/HeLa and SW480 |
Adjacent bis THF with β-hydroxy γ-methyl γ-lactone Non-adjacent bis THF γ-lactone |
Schlie-Guzmán et al., 2009 |
 |
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| Annona montana Macfad |  |
ED50 = 0.083 µg/ml/LLC | Terminal lactone unit α-acetonyl-α, β-unsaturated γ-lactone; three OH groups; mono-THF ring | Wang et al., 2002 |
| Annona muricata L. |  |
Annopentocin A: ED50 (µg/ml) = 0.17/A-549, 1.63/HT-29, 0.6/A-498, 1.14/PC-3, 0.03/PACA-2 | Compounds a, b, and c: penta hydroxylated mono-THF ring with one flanking OH on the side chain (hydrocarbon), and an OH on the lactone side | Zeng et al., 1996; Elisya et al., 2014; Moghadamtousi et al., 2015b |
 |
Annopentocin B: ED50 (µg/ml) = 0.02/A-549, 3.56/MCF-7, 1.64/HT-29, 0.38/A-498, 0.21/PC-3, 0.16/PACA-2 |
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Annopentocin C: ED50 (µg/ml) = 0.02/A549, 2.97/MCF-7, 1.24/HT-29, 0.26/A-498, 0.22/PC-3, 0.43/PACA-2 | |||
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Annomuricin D: ED50 (µg/ml) = < 0.01/A-549, 0.6/MCF-7, < 0.01/HT-29, 0.1/A-498, 1.32/PC-3, < 0.916/PACA-2 |
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IC50 = 1.62 + 0.24 µg/ml/HT-29 | Mono-THF bearing two flanking OH and an erythro-diol between the THF and the ketolactone rings |
Moghadamtousi et al., 2015b | |
| Annona squamosa L. |  |
IC50 (µg/ml) = 0.103/H460; 0.687/BGC803; 4.19/BEL7402; 0.43/HepG2; 6.56/SMMC-7721 |
Bis-THF and a 4-OH structure |
Miao et al., 2016a |
 |
Squamocin-IV: IC50 = 0.049 µg/ml/H460 12,15-cis-squamostatin-A: IC50 = 17.40 ± 2.09 µg/ml/A-549/taxol (resistant cell line) Squamostatin-D IC50 = 16.19 ± 1.98 µg/ml/A-549/taxol (resistant cell line) |
Squamocin-IV presence of an ana, β-unsaturated γ-lactone; adjacent bis-THF ring system with two flanking hydroxy groups and four OH groups, one at C-7 Functional groups in 12,15-cis-squamostatin-A and squamostatin-D: non-adjacent bis-THF and fewer hydroxy groups |
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Annosquatin A: IC50 = 6.3 × 10−2 µg/ml/MCF-7 Annosquatin B: IC50 = 8.4 × 10−2 µg/ml/A-549 |
The activity of compounds A and B is related to the three hydroxy groups, two flanking the THF rings and another located in the long hydrocarbon chain gives the cytotoxicity | Chen et al., 2012c | |
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| Goniothalamus undulatus Ridl. |  |
Annonacin: IC50 = 0.56 ± 0.02 µM/COR-L23 Goniothalamicin IC50 = 1.68 ± 0.09 µM/COR-L23 Cis-Goniothalamicin IC50 = 1.71 ± 0.27 µM/COR-L23 |
Functional groups annonacin: mono-THF ring with two flanking hydroxy groups |
Tantithanaporn et al., 2011; Yuan et al., 2003 |
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A-498 (human kidney carcinoma); A-549 (human lung carcinoma); A-549/taxol (lung carcinoma multidrug resistant to taxol); BEL7402 (human hepatocellular carcinoma); BGC803 (human gastric carcinoma); COR-L23 (human lung cancer); H460 (human lung carcinoma); HepG2 (human hepatocellular carcinoma); HT-29 (human colon adenocarcinoma); HCT-15 (adherent colon carcinoma); LLC (Lewis lung carcinoma mouse); MCF-7(human breast carcinoma), PACA-2 (human pancreatic carcinoma); PC-3 (human prostate adenocarcinoma); SMMC-7721 (human hepatocellular carcinoma); SW480 (colon adenocarcinoma)