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J Agric Food Chem. 2017 Jun 21;65(24):4993-4999. doi: 10.1021/acs.jafc.7b01762. Epub 2017 Jun 9.

Meroterpenoids with Antitumor Activities from Guava (Psidium guajava).

Qin XJ1,2, Yu Q3, Yan H1,2, Khan A4, Feng MY1,2, Li PP1,2, Hao XJ1,2, An LK3, Liu HY1,2.

Author information

1
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, People's Republic of China.
2
Yunnan Key Laboratory of Natural Medicinal Chemistry , Kunming 650201, People's Republic of China.
3
Institute of Medicinal Chemistry and Chemical Biology, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
4
Department of Chemistry, COMSATS Institute of Information Technology , Abbottabad 22060, Pakistan.

Abstract

Psidium guajava L., a species native to South America, has been widely cultivated in the tropical and subtropical areas of China for its popular fruits. The preliminary analysis by liquid chromatography-ultraviolet (LC-UV) indicated the presence of meroterpenoids in the fruits of P. guajava (guava). Subsequent fractionation of the petroleum ether extract resulted in the identification of two new meroterpenoids, psiguajavadials A (1) and B (2), together with 14 previously described meroterpenoids (3-16). Their structures were fully elucidated by comprehensive spectroscopic techniques and theoretical calculations. All of the meroterpenoids showed cytotoxicities against five human cancer cell lines, with guajadial B (12) being the most effective having an IC50 value of 150 nM toward A549 cells. Furthermore, biochemical topoisomerase I (Top1) assay revealed that psiguajavadial A (1), psiguajavadial B (2), guajadial B (12), guajadial C (14), and guajadial F (16) acted as Top1 catalytic inhibitors and delayed Top1 poison-mediated DNA damage. The flow cytometric analysis indicated that the new meroterpenoids psiguajavadials A (1) and B (2) could induce apoptosis of HCT116 cells. These data suggest that meroterpenoids from guava fruit could be used for the development of antitumor agents.

KEYWORDS:

DNA topoisomerase I inhibitors; antiproliferative activity; cytotoxicity; guava; meroterpenoids

PMID:
28578580
DOI:
10.1021/acs.jafc.7b01762
[Indexed for MEDLINE]

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