journal article·2024-03-13Open access

Phenolic Profiles and Antitumor Activity against Colorectal Cancer Cells of Seeds from Selected Ribes Taxa

Svetlana Lyashenko, Rosalía López-Ruiz, Ana Minerva García-Cervantes, Ignacio Rodríguez-García, Svetlana Yunusova, José Luis Guil-Guerrero

Applied Sciences· Volume 14· Issue 6

Abstract

Seeds from several Ribes taxa were surveyed for phenolic compounds and in vitro antiproliferative activity against HT-29 colorectal cancer cells. Total phenolic compounds were analyzed through the Folin–Ciocalteu procedure, while LC coupled to a single mass spectrometer (MS) Orbitrap using an electrospray interface (ESI) was performed to determine the phenolic profiles. Antitumor effects were established using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Total phenolics ranged from 11.4 in R. alpinum to 94.8 mg of caffeic acid equivalents (CAE)/g in R. nigrum ‘Koksa’. Concerning phenolic compounds, four were hydroxylated benzoic acids, four cinnamic acid derivatives, eight flavonoids, and nine flavonoid glycosides. The growth inhibition against HT-29 cancer cells was exercised much better by R. nigrum ‘Koksa’ and Ribes ‘Erkeeni’ (GI50 37 and 42 µg/mL). All Ribes extracts, except for R. nigrum ‘Hara katarlik’, showed higher activity than R. rubrum (GI50 at 72 h: 99 µg/mL). Interestingly, the extract from Ribes ‘Erkeeni’, which exhibited high bioactivity, contains all detected phenolic compounds, unlike R. nigrum ‘Koksa’, which lacks only populnin. Therefore, the high bioactivity found for such extracts could be due to a synergy of all detected compounds. This work constitutes a comprehensive action for expanding knowledge on the phenolic profiles and antitumor activity of GLA-rich Ribes seeds.
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Research context

OpenAlex topics: Phytochemicals and Antioxidant Activities · Plant Gene Expression Analysis · Biochemical and biochemical processes

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Food Technology, University of Almeria, 04120 Almeria, Spain

Department of Physical Chemistry, Analytical Chemistry of Contaminants, University of Almeria, 04120 Almeria, Spain

Department of Organic Chemistry, University of Almeria, 04120 Almeria, Spain

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054 Ufa, Russia

Funding

Junta de Andalucía · University of Almería · Campus de Excelencia Internacional Agroalimentario · Centro de Investigación en Agrosistemas Intensivos Mediterráneos y biotecnología Agroalimentaria · State Tasks

References (35)

Show source-provided references
1. Janick, J., and Moore, J.N. (1996). Fruit Breeding, Vol. II Vine and Small Fruit Crops, John Wiley & Sons. Inc.. Chapter 3.
2. Improving Fruit Quality in Rubus and Ribes Through Breeding
3. Antioxidant activity and phenolic profiles of the wild currant Ribes magellanicum from Chilean and Argentinean Patagonia
4. Changes in fruit quality parameters of four Ribes species during ripening10.1016/j.foodchem.2014.10.011 ↗
5. Disparate metabolic effects of blackcurrant seed oil in rats fed a basal and obesogenic diet10.1007/s00394-014-0775-z ↗
6. Oils from fruit seeds and their dietetic and cosmetic significance10.2478/hepo-2018-0026 ↗
7. Ribes taxa: A promising source of γ-linolenic acid-rich functional oils10.1016/j.foodchem.2019.125309 ↗
8. Gamma-linolenic acid and tocopherol contents in the seed oil of 47 accessions from several Ribes species10.1021/jf0006729 ↗
9. Characterization of Canadian black currant (Ribes nigrum L.) seed oils and residues10.1021/jf902161k ↗
10. Horwitz, W. (2000). Officials Methods of Analysis of AOAC International, AOAC. [17th ed.].
11. Lyashenko, S., González-Fernández, M.J., Gómez-Mercado, F., Yunusova, S., Denisenko, O., and Guil-Guerrero, J.L. (2021). Phenolic composition and in vitro antiproliferative activity of Borago spp. seed extracts on HT-29 cancer cells. Food Biosci., 42.10.1016/j.fbio.2021.101043 ↗
12. Analysis of total phenols and other oxidation substrates and antioxidants by means of folin-ciocalteu reagent10.1016/S0076-6879(99)99017-1 ↗
13. Various acylglycerols from common oils exert different antitumor activities on colorectal cancer cells10.1080/01635581.2016.1152382 ↗
14. Anti-proliferation and induction of mitochondria-mediated apoptosis by Garcinia hanburyi resin in colorectal cancer cells10.1016/j.heliyon.2023.e16411 ↗
15. Influence of filtering of cold pressed berry seed oils on their antioxidant profile and quality characteristics10.1016/j.foodchem.2011.01.134 ↗
16. Extraction of polyphenols from processed black currant (Ribes nigrum L.) residues10.1021/jf052999l ↗
17. Enzyme-assisted extraction of anthocyanins and other phenolic compounds from blackcurrant (Ribes nigrum L.) press cake: From processing to bioactivities10.1016/j.foodchem.2022.133240 ↗
18. Effects of latitude and weather conditions on phenolic compounds in currant (Ribes spp.) cultivars10.1021/jf4000456 ↗
19. Wójciak, M., Mazurek, B., Tyśkiewicz, K., Kondracka, M., Wójcicka, G., Blicharski, T., and Sowa, I. (2022). Blackcurrant (Ribes nigrum L.) seeds—A valuable byproduct for further processing. Molecules, 2.10.3390/molecules27248679 ↗
20. Natural flavonoids exhibit potent anticancer activity by targeting microRNAs in cancer: A signature step hinting towards clinical perfection10.1016/j.tranon.2022.101596 ↗
21. In vitro anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca
22. Flavonoids are determinants of freezing tolerance and cold acclimation in Arabidopsis thaliana10.1038/srep34027 ↗
23. Marcum, C.L. (2016). Fundamental Studies of Collision-Activated Dissociation (CAD) of Deprotonated Model Compounds Relevant to Lignin Degradation Products. [Ph.D. Thesis, Purdue University].
24. A fragmentation study of kaempferol using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution10.1016/j.ijms.2003.10.008 ↗
25. Dos Santos, C., Galaverna, R.S., Angolini, C.F.F., Nunes, V.V.A., De Almeida, L.F.R., Ruiz, A.L.T.G., De Carvalho, J.E., Duarte, R.M.T., Duarte, M.C.T., and Eberlin, M.N. (2018). Antioxidative, antiproliferative and antimicrobial activities of phenolic compounds from three Myrcia species. Molecules, 23.10.3390/molecules23050986 ↗
26. Characterization of flavone and flavonol aglycones by collision-induced dissociation tandem mass spectrometry10.1002/(SICI)1097-0231(199708)11:12<1357::AID-RCM983>3.0.CO;2-9 ↗
27. Identification of phenolic compounds in Myricaria bracteata leaves by high-performance liquid chromatography with a diode array detector and liquid chromatography with tandem mass spectrometry10.1016/j.bjp.2017.07.001 ↗
28. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry10.1016/S1044-0305(01)00226-4 ↗
29. Śliwka-Kaszyńska, M., Anusiewicz, I., and Skurski, P. (2022). The Mechanism of a Retro-Diels–Alder Fragmentation of Luteolin: Theoretical Studies Supported by Electrospray Ionization Tandem Mass Spectrometry Results. Molecules, 27.10.3390/molecules27031032 ↗
30. Dereplication of phenolic derivatives of three Erythroxylum species using liquid chromatography coupled with ESI-MSn and HRESIMS10.1002/pca.3043 ↗
31. Black currant (Ribes nigrum L.) extract induces apoptosis of MKN-45 and TE-1 cells through MAPK-and PI3K/Akt-mediated mitochondrial pathways10.1089/jmf.2015.3521 ↗
32. Hostettmann, K. (1990). Methods in Plant Biochemistry: Assays for Bioactivity, Academic Press.
33. Microwave-assisted extraction of an acidic polysaccharide from Ribes nigrum L.: Structural characteristics and biological activities10.1016/j.indcrop.2020.112249 ↗
34. Buglossoides spp. seeds, a land source of health-promoting n-3 PUFA and phenolic compounds10.1016/j.foodres.2022.111421 ↗
35. Peña-Morán, O.A., Villarreal, M.L., Álvarez-Berber, L., Meneses-Acosta, A., and Rodríguez-López, V. (2016). Cytotoxicity, post-treatment recovery, and selectivity analysis of naturally occurring podophyllotoxins from Bursera fagaroides var. fagaroides on breast cancer cell lines. Molecules, 21.10.3390/molecules21081013 ↗