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Molecules 2014, 19(7), 8762-8772; doi:10.3390/molecules19078762

Cytotoxic Aporphine Alkaloids from Leaves and Twigs of Pseuduvaria trimera (Craib)

1
Laboratory of Natural Products, Center for Innovation in Chemistry, Faculty of Science, Lampang Rajabhat University, Lampang 52100, Thailand
2
Science and Technology Research Institute, Chiang Mai University, Chiang Mai 53000, Thailand
3
The Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Ministry of Natural Resources and Environment, Bangkok 10220, Thailand
4
Department of Biochemistry, Faculty of Medicine, Chiang Mai University, Chiang Mai 53000, Thailand
*
Author to whom correspondence should be addressed.
Received: 21 May 2014 / Revised: 17 June 2014 / Accepted: 19 June 2014 / Published: 25 June 2014
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
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Abstract

From ethyl acetate-methanol extracts of leaves and twigs of Pseuduvaria trimera a new aporphine alkaloid; 8-hydroxy-1,4,5-trimethoxy-7-oxoaporphine or 8-hydroxyartabonatine C (1) was isolated, together with the known 1,2,3-trimethoxy-4,5-dioxo-6a,7-dehydroaporphine (ouregidione, 2). Their structures were elucidated by a combination of spectral methods; mainly 2D NMR; IR and MS. Compounds 1 and 2 exhibited cytotoxic activity with IC50 values of 26.36 ± 5.18 μM and 12.88 ± 2.49 μM, respectively, for human hepatocellular carcinoma HepG2 cells, and 64.75 ± 4.45 and 67.06 ± 3.5 μM, respectively, for human breast cancer MDA-MB231 cells. Both compounds displayed anti-cancer activity but less than that of doxorubicin; a conventional chemotherapeutic drug, the IC50 levels of which were 2.21 ± 1.72 and 1.83 ± 0.09 μM for HepG2 and MDA-MB231 cells, respectively. View Full-Text
Keywords: aporphine alkaloid; cytotoxicity; anti-cancer; Pseuduvaria trimera; Annonaceae aporphine alkaloid; cytotoxicity; anti-cancer; Pseuduvaria trimera; Annonaceae
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Sesang, W.; Punyanitya, S.; Pitchuanchom, S.; Udomputtimekakul, P.; Nuntasaen, N.; Banjerdpongchai, R.; Wudtiwai, B.; Pompimon, W. Cytotoxic Aporphine Alkaloids from Leaves and Twigs of Pseuduvaria trimera (Craib). Molecules 2014, 19, 8762-8772.

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