Studies On Chemical Constituents From The Seeds Of Annona Glabra L. And The Anti-tumor Activity

Annona glabra Linn. is a plant of Annona genus (Annonaceae). This plant is distributedmainly in tropical Americas and southeast Asia, it is introduced and cultivated in Guangdong,Yunnan, Hainan, Hong Kong and Guangxi provinces of China.109compounds have beenisolated from Annona glabra at present, including annonaceous acetogenins, terpenoids, cyclicpeptides, alkaloids and so on.These compounds have antitumor, antimalarial, antibacterial,immune suppression and insecticidal bioactivities in various degrees. Especially the compoundsof annonaceous acetogenins were paid closely attention for their antitumor founction. In theprevious work of our research group, the antitumor activity of different extracts from the seedsof Annona glabra grown in Hainan province had been screened in vitro, and the chemicalseparation work of the antitumor active fraction(F06) was carried out partly.But the study ofAnnona glabra is not sufficient enough, the pharmacodynamic material basis of its antitumoreffect still needs to be further researched.On the basis of the previous work, the chemical constituents in chloroform fraction of95%ethanol extract from seeds of Annona glabra were researched systematically.Twenty-onecompounds were isolated by silica gel, reverse phase C18silica gel, Sephadex LH-20columnchromatographies and pre-HPLC. The structures of ten compounds of those were identified onthe basis of morden spectroscopic and chemical derivatization methods (acetylation, TMSireaction and Mosher ester method), including eight annonaceous acetogenins:Squamocin-29-one(ZQ-1),29-Hydroxybullatacin(ZQ-2), Motrilin(ZQ-4), atemotetrolin(ZQ-3),cherimolin-2(ZQ-7), muricatetrocin B(ZQ-8), annopentocins C(ZQ-16)，10-hydroxyglabranin(ZQ-19); a cyclic peptide glabrin A(ZQ-12) and Organic acid ester dibutyl phthalate(ZQ-10).ZQ-1, ZQ-2and ZQ-19are new compounds, which are annonaceous acetogenins. CompoundsZQ-3and ZQ-16were isolated from this plant for the first time, and compounds ZQ-10wasisolated from this genus for the first time. The structural identification of the rest elevencompounds is still ongoing. These compounds are annonaceous acetogenins by analyzing theexisting1H NMR and13C NMR data.At the same time, we carried out antitumor activity screening in four kinds of humancancer cell lines(Human melanoma A375cells, Human melanoma A875cells, Human ovariancancer A2780cells, Human hepatocellular carcinoma Hep G2) in vitro on compound ZQ-1. Thetest result shows that the IC50values of new compound ZQ-1ranges from12.39to12.39g/mL, the new compound has different level of cytotoxic activity for the four kinds of human cancer cells lines...