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Molecules. 2015 Nov 27;20(12):21193-203. doi: 10.3390/molecules201219754.

Dihydrochalcone Compounds Isolated from Crabapple Leaves Showed Anticancer Effects on Human Cancer Cell Lines.

Author information

1
College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400716, China. vipqindada@163.com.
2
Beijing Key Laboratory for Agricultural Application and New Technique, Department of Plant Science and Technology, Beijing University of Agriculture, Beijing 102206, China. vipqindada@163.com.
3
Beijing Key Laboratory for Agricultural Application and New Technique, Department of Plant Science and Technology, Beijing University of Agriculture, Beijing 102206, China. 13521981395@163.com.
4
College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400716, China. zzqswu@yahoo.com.
5
College of Horticulture and Landscape Architecture, Southwest University, Chongqing 400716, China. yaoyc_20@126.com.
6
Beijing Key Laboratory for Agricultural Application and New Technique, Department of Plant Science and Technology, Beijing University of Agriculture, Beijing 102206, China. yaoyc_20@126.com.

Abstract

Seven dihydrochalcone compounds were isolated from the leaves of Malus crabapples, cv. "Radiant", and their chemical structures were elucidated by UV, IR, ESI-MS, ¹H-NMR and (13)C-NMR analyses. These compounds, which include trilobatin (A1), phloretin (A2), 3-hydroxyphloretin (A3), phloretin rutinoside (A4), phlorizin (A5), 6''-O-coumaroyl-4'-O-glucopyranosylphloretin (A6), and 3'''-methoxy-6''-O-feruloy-4'-O-glucopyranosyl-phloretin (A7), all belong to the phloretin class and its derivatives. Compounds A6 and A7 are two new rare dihydrochalcone compounds. The results of a MTT cancer cell growth inhibition assay demonstrated that phloretin and these derivatives showed significant positive anticancer activities against several human cancer cell lines, including the A549 human lung cancer cell line, Bel 7402 liver cancer cell line, HepG2 human ileocecal cancer cell line, and HT-29 human colon cancer cell line. A7 had significant effects on all cancer cell lines, suggesting potential applications for phloretin and its derivatives. Adding a methoxyl group to phloretin dramatically increases phloretin's anticancer activity.

KEYWORDS:

Malus crabapples; anticancer activity; dihydrochalcone compounds; human cancer cell lines; leaves

PMID:
26633321
PMCID:
PMC6332433
DOI:
10.3390/molecules201219754
[Indexed for MEDLINE]
Free PMC Article

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