Asatone and Isoasatone A Against Spodoptera litura Fab. by Acting on Cytochrome P450 Monoxygenases and Glutathione Transferases.

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.

Xanthones from the Pericarp of Garcinia mangostana.

Mangosteen (Garcinia mangostana L.) is one of the most popular tropical fruits (called the "Queen of Fruits"), and is a rich source of oxygenated and prenylated xanthone derivatives. In the present work, phytochemical investigation has resulted in one new prenylated xanthone and 13 known xanthones isolated from the pericarp of G. mangostana. Their structures were established by spectroscopic data analysis, including X-ray diffraction. The new one was further tested for cytotoxic activity against seven cancer cell lines (CNE-1, CNE-2, A549, H490, PC-3, SGC-7901, U87), displaying the half maximal inhibitory concentration (IC50) values 3.35, 4.01, 4.84, 7.84, 6.21, 8.09, and 6.39 µM, respectively. It is noteworthy that the new compound can promote CNE-2 cells apoptosis in late stage, having a remarkable inhibition effect on the side population growth of CNE-2 at 1.26 µM. The bioactive compound was also detected in extract from fresh mangosteen flesh, which indicated that the popular fruit could have potential cytotoxic activity for cancer cell lines.

A homoisoflavonoid and a fatty acid in common purslane (Portulaca oleracea L.) synergistically inhibit growth of Spodoptera litura larvae.

BACKGROUND: Portulaca oleracea L., common purslane, is an insecticidal plant that has been documented as a 'Chinese indigenous pesticide', and it is seldom visited by insects in the field. However, identification of anti-insect compounds and mechanisms of action are still unclear. RESULTS: Interplanting purslane with Chinese cabbage demonstrated that purslane may contain secondary compounds that S. litura avoids eating. Four compounds were isolated from P. oleracea by directed anti-insect activity, and their chemical structures were identified by NMR spectra as (9Z,11E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid (1), portulacanone A (2), portulacanone D (3), and a new natural product 2,4'-dihydroxy-3',5'-dimethoxychalcone (4). A combination of compound 1 and 2 possessed stronger activity than other combinations (compounds 1 + 3; 1 + 4; 2 + 3; 2 + 4; 3 + 4). Both active compounds were detected in all samples from 23 regions in China, and concentrations in samples collected from 17 regions were generally above 500 µg/kg. Concentrations of compounds 1 and 2 fluctuated greatly from April to November, and reached maximum concentrations of 45 951.44 µg/kg for compound 1 and 3739.09 µg/kg for compound 2 in November. The combination of these compounds (1 + 2) caused mid-gut structural deformation and tissue decay as determined by mid-gut histopathology of S. litura. CONCLUSION: In general, these active compounds coexisting contributed to partly protect purslane from insects. This research also provides new insights into the use of purslane as important ingredient of botanical pesticide alternatives to traditional chemical pesticides. © 2019 Society of Chemical Industry.