Combined effect of flavonoid compounds and cytostatics in cancer treatment
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Aim. The aim of the study was to review the literature on the combination of cytostatics with flavonoids as a promising way to improve the cancer therapy. Material and methods. A review of Polish and foreign literature was performed. The following databases were searched: PubMed, Scopus, Science Direct, and Polish Medical Bibliography. Literature analysis. Effective strategies to inhibit the progression of cancer are needed. Compounds of natural origin, including plant polyphenols, are a part of our diet. Due to their availability, and antioxidant properties, they may serve as efficacious adjuvants in cancer therapy, enhancing the effectiveness of chemotherapeutics. Epidemiological studies have shown an inverse relationship between diets rich in fruits, vegetables, and supplements, and the risk of all causes of death from cancer. Based on their diverse biological activity, flavonoids may be potential adjuvant therapeutic agents that act synergistically with cytostatics for treatment of many types of cancer. This review of the results is a summary the research on anticancer activity of flavonoids and may also raise consciousness of consumers, who will be able to compose their diet armed with the knowledge of preventive and therapeutic anticancer properties of food ingredients. There is need for further research on polyphenols of plant origin, including interactions among food components that coexist. Another important aspect is to understand how the activity of phytocompounds depends on concentration and the presence of additional factors (e.g. microflore, metal ions), which could possibly make a compound harmful, instead of having positive theraputics effect. Elucidation of the mechanisms involved in biological activity of the described phytocompounds is essential for a better understanding of their influence on an organism.Keywords:
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Isoflavonoid
Enamine
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Six isoflavonoid derivatives among which three are new have been isolated from the stem heartwood of Lophira alata. The structures were elucidated from spectroscopic and chemical evidences. Two have unusual carbon skeletons, possibly resulting from a variant of isoflavonoid biogenesis. The two compounds form the first members of a new subclass of flavonoid compounds which we call "isobiflavonoids". The presence of these isoflavonoid compounds in this plant of the Ochnaceae family has important chemotaxonomic implications since it modifies the botanic distribution of isoflavonoid compounds in non-leguminous plants.
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Abstract Seven isoflavonoid phytoalexins were subjected to a series of screening tests used for the routine examination of potential fungicides. The phytoalexins had no appreciable effects on disease intensity in these assays, which encompassed five major crop plants and six pathogens. It seems unlikely that isoflavonoid phytoalexins could be used as conventional fungicides in control programmes against phytopathogens.
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Abstract The fungus-inoculated leaflets of Dalbergia sericea produce several isoflavonoid phytoalexins including the known pterocarpans, medicarpin and maackiain, ana the isoflavan, vestitol. A fourth, previously undescribed, phytoalexin has been identified as 7-methoxy-2′,4′-dihydroxyisoflavan (neovestitol) by comparison with synthetic material.
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Hairy root cultures are genetically and biochemically stable, and they regularly possess the same or better biosynthetic capabilities for specialized (secondary) metabolite production compared to the intact plant. Ononis species are well-known herbal remedies in ethnopharmacology and rich sources of isoflavonoids. Besides isoflavones, less prevalent isoflavones and pterocarpans with valuable biological effects can be found in Ononis species as well. As these plants are only collected but not cultivated, biotechnological methods could play a role in the larger-scale extraction of Ononis isoflavonoids. Regarding this information, we aimed to establish Ononis spinosa and Ononis arvensis hairy root cultures (HRCs) and analyze the isoflavonoid profile of hairy root cultures qualitatively and quantitatively, in order to define their capacity to produce biologically valuable isoflavonoids. During the qualitative description, beside isoflavonoids, two new phenolic lactones, namely, bulatlactone 2″- O -β -D- glucoside and ononilactone, were isolated, and their structures were characterized for the first time. Altogether, 29 compounds were identified by the means of UPLC-Orbitrap-MS/MS. Based on UHPLC-UV-DAD measurements, the isoflavonoid spectrum of the Ononis HRCs differed markedly from wild-grown samples, as they produce a limited range of the scaffolds. The most abundant compounds in the HRCs were medicarpin glucoside and sativanone glucoside. The overall isoflavonoid production of the cultures was comparable to wild-grown O. arvensis and approximately twice as high as in wild-grown O. spinosa samples. As the overall content of wild-grown samples include more isoflavonoid derivatives, the HRCs contain structurally less divergent isoflavonoids but in higher quantity.
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Secondary metabolite
Glucoside
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In this work, Astragalus membranaceus hairy root cultures (AMHRCs) were exposed to ultraviolet radiation (UV-A, UV-B, and UV-C) for promoting isoflavonoid accumulation. The optimum enhancement for isoflavonoid production was achieved in 34-day-old AMHRCs elicited by 86.4 kJ/m(2) of UV-B. The resulting isoflavonoid yield was 533.54 ± 13.61 μg/g dry weight (DW), which was 2.29-fold higher relative to control (232.93 ± 3.08 μg/g DW). UV-B up-regulated the transcriptional expressions of all investigated genes involved in isoflavonoid biosynthetic pathway. PAL and C4H were found to be two potential key genes that controlled isoflavonoid biosynthesis. Moreover, a significant increase was noted in antioxidant activity of extracts from UV-B-elicited AMHRCs (IC50 values = 0.85 and 1.08 mg/mL) in comparison with control (1.38 and 1.71 mg/mL). Overall, this study offered a feasible elicitation strategy to enhance isoflavonoid accumulation in AMHRCs and also provided a basis for metabolic engineering of isoflavonoid biosynthesis in the future.
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Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry
Abstract Ononis arvensis L. can be found overall in Europe and is used to treat infections of the urinary tract and skin diseases in ethnopharmacology. Flavonoids, hydroxycinnamic acids, oxycoumarin, scopoletin and scopolin, phytosterols, lectins, and some selected isoflavonoids were identified in O. arvensis till date; however, there is a lack of the detailed investigation of the isoflavonoid profile of the plant. With the application of high‐resolution tandem mass spectrometry, the fragmentation patterns of isoflavonoid derivatives found in O. arvensis roots and aerial parts were investigated and discussed. Isoflavonoid glucosides, glucoside malonates, aglycones, and beta amino acid derivatives were characterized, among which homoproline isoflavonoid glucoside esters were described for the first time. Besides the known isoflavonoid aglycones described earlier in other Ononis species, two 2′‐methoxy isoflavonoid derivatives were detected. The presence of licoagroside B was verified, and its structure was also corroborated by NMR experiments. Altogether, the high‐resolution fragmentation pattern of 47 isoflavonoids and glycosides is presented, and their relative quantity in the roots and the aerial parts can be evaluated. Based on this information, the chemotaxonomic relation of Ononis species and the biosynthesis of their compounds could be comprehended to a greater depth.
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