Isoasatone A
(Synonyms: 异细辛酮 A) 目录号 : GC39106Isoasatone A 是一种从 Heterotropa takaoi M. 中分离得到的天然产物,具有抗虫活性。Isoasatone A 通过作用细胞色素 P450 单加氧酶和谷胱甘肽转移酶起抗 S. litura作用。
Cas No.:67451-73-4
Sample solution is provided at 25 µL, 10mM.
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Isoasatone A is a natural product isolated from the plant Heterotropa takaoi M., with anti-insect activity. Isoasatone A againsts S. litura by acting on cytochrome P450 monoxygenases and glutathione transferases[1][2].
[1]. Terada, Y., et al. ISOASATONE A AND ISOASATONE B, TWO NOVEL NEOLIGNANS, FROMHETEROTROPA TAKAOIM. Chemistry Letters. 1978.7(5), 553-554. [2]. Ling R, et al. Asatone and Isoasatone A Against Spodoptera litura Fab. by Acting on Cytochrome P450 Monoxygenases and Glutathione Transferases. Molecules. 2019 Oct 31;24(21).
Cas No. | 67451-73-4 | SDF | |
别名 | 异细辛酮 A | ||
Canonical SMILES | O=C1C(OC)(OC)[C@@]2([H])[C@@](C(OC)(OC)C3=O)([H])C(/C=C/C)=C[C@@]3(OC)C2(CC=C)C=C1OC | ||
分子式 | C24H32O8 | 分子量 | 448.51 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.2296 mL | 11.148 mL | 22.296 mL |
5 mM | 0.4459 mL | 2.2296 mL | 4.4592 mL |
10 mM | 0.223 mL | 1.1148 mL | 2.2296 mL |
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Asatone and Isoasatone A Against Spodoptera litura Fab. by Acting on Cytochrome P450 Monoxygenases and Glutathione Transferases
Molecules 2019 Oct 31;24(21):3940.PMID:31683670DOI:PMC6864857
Asatone and Isoasatone A from Asarum ichangense Cheng were determined to be defensive compounds to some insects in a previous investigation. However, the anti-insect activity mechanisms to caterpillar are still unclear. The compounds asatone and Isoasatone A from A. ichangense were induced by Spodoptera litura. The anti-insect activity of asatone and Isoasatone A to S. litura was further tested by weight growth rate of the insect through a diet experiment. Isoasatone A showed a more significant inhibitory effect on S. litura than asatone on the second day. The concentration of asatone was higher than Isoasatone A in the second instar larvae of S. litura after 12 h on the feeding test diet. Both compounds caused mid-gut structural deformation and tissue decay as determined by mid-gut histopathology of S. litura. Furthermore, some detoxification enzyme activity were measured by relative expression levels of genes using a qPCR detecting system. Asatone inhibited the gene expression of the cytochrome P450 monooxygenases (P450s) CYP6AB14. Isoasatone A inhibited the relative expression levels of CYP321B1, CYP321A7, CYP6B47, CYP6AB14, and CYP9A39. Asatone increased the relative gene expression of the glutathione transferases (GSTs) SIGSTe1 and SIGSTo1, in contrast, Isoasatone A decreased the relative gene expression of SIGSTe1 by about 33 fold. Neither compound showed an effect on acetylcholinesterase SIAce1 and SIAce2. The mechanism of anti-insect activity by both compounds could be explained by the inhibition of enzymes P450s and GSTs. The results provide new insights into the function of unique secondary metabolites asatone and Isoasatone A in genus Asarum, and a new understanding of why A. ichangense is largely free of insect pests.