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ORIGINAL ARTICLE
Gomphrenin-Based Decarboxylated and Acylated Pigments from Basella alba L. Fruit Extracts Impair Survival of Colorectal Cancer Cells but Not Normal Cells – In Vitro Study
1
Department C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Krakow, Poland
2
Faculty of Biotechnology and Horticulture, University of Agriculture in Krakow, al. 29 Listopada 54, 31-425 Krakow, Poland
3
Department of Analytical Chemistry and Biochemistry, Faculty of Materials Science and Ceramics, AGH University of Krakow, al. Adama Mickiewicza 30, 30-059 Krakow, Poland
4
Laboratory of Proteomics and Mass Spectrometry, Maj Institute of Pharmacology, Polish Academy of Sciences, ul. Smętna 12, 31-343 Krakow, Poland
5
Department of Clinical Immunology, Faculty of Medicine, Institute of Pediatrics, Jagiellonian University Medical College, ul. Wielicka 265, 30-688 Kraków, Poland
6
Department of Clinical Immunology, Faculty of Medicine, Institute of Pediatrics, Jagiellonian University Medical College, 30-688 Kraków, Poland
7
Department of Cell Biology, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, ul. Gronostajowa 7, 30-387 Kraków, Poland
8
NanoBioMedical Centre, Adam Mickiewicz University, ul. Wszechnicy Piastowskiej 3, 61-614 Poznan, Poland
9
Department C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155, Krakow, Poland
10
Faculty of Pharmacy, Jagiellonian University Medical College, ul. Medyczna 9, 30-688 Krakow, Poland
Submission date: 2024-07-20
Acceptance date: 2024-10-08
Online publication date: 2024-11-13
Publication date: 2024-11-13
Corresponding author
Sławomir Wybraniec
Department C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Krakow, Poland
Department C-1, Faculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Krakow, Poland
Pol. J. Food Nutr. Sci. 2024;74(4):350-362
KEYWORDS
acylated betacyaninsbetalainscolorectal adenocarcinomadecarboxylated gomphreninsdehydrogenated gomphreninsplant pigments
TOPICS
ABSTRACT
The fast-growing, soft-stemmed vine, Basella alba L., yields high quantities of gomphrenin pigments in its dark-violet fruits which can be converted to their decarboxylated derivatives while still possessing coloring properties. These pigments are much less investigated in terms of the health-promoting properties than their source counterparts. Hence, decarboxylated derivatives with potential health-promoting properties were generated by controlled thermal modifications of gomphrenin structure. Bioactivity experiments were performed on gomphrenin acylated (malabarin and globosin) and decarboxylated derivatives (17-decarboxy-gomphrenin, 2-decarboxy-gomphrenin, and 2,17-bidecarboxy-gomphrenin) derived from the fruit extracts using preparative HPLC. High-resolution mass spectrometric analyses of decarboxylated gomphrenins brought deep fragmentation patterns in the positive ionization mode. The combination of elimination pathways specific to 17-decarboxygomphrenin and 2-decarboxy-gomphrenin contributed to the generation of pyridinium, dihydroindolic, as well as indolic and dehydrated indolic derivative ions characteristic of the fragmentation spectra of 2,17-bidecarboxy-gomphrenin.First studies on two Duke’s type C colorectal adenocarcinoma cell lines were performed on the isolated pigments. HT-29 cell line was obtained from a primary (“in situ”) colon tumor, SW620 cancer cells was derived from a metastatic site, whereas non-cancerous CHO-K1 cell line served for comparative purposes. Gomphrenin, 2-decarboxy-gomphrenin and malabarin revealed the highest cytotoxic properties towards cancer cells, affecting cell proliferation and aggravating cancer cell survival due to programmed cell death. The obtained results show specific, beneficial health properties of decarboxylated and acylated gomphrenins.
FUNDING
This research was financed by Polish National Science Centre for years 2018-2021 (Project No. UMO-2017/27/B/NZ9/02831) except of the apoptosis/necrosis assay financed by Jagiellonian University Medical College (Project No. N/42/DBS/000284).
CONFLICT OF INTEREST
The authors declare that they have no conflicts of interest.
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