Sulfated flavanones and dihydroflavonols from willow

Dias, Clarice Noleto; Harflett, Claudia; Ward, Jane L.

doi:10.1016/j.phytol.2019.11.008

Cited by 11 publications

(6 citation statements)

References 30 publications

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“…As only mild cytotoxicity has been discovered in willow bark extracts, willows are a promising biomass for various health applications ( Ramos et al, 2019 ). However, because of the vast number of different willow species and their widespread ability to form hybrids, as well as recently identified compounds (e.g., Wu et al, 2016 ; Noleto-Dias et al, 2018 ; Noleto-Dias et al 2019 ; Noleto-Dias et al 2020 ; Ward et al, 2020 ), there is still much to explore regarding Salix spp. and their metabolites.…”

Section: Introductionmentioning

confidence: 99%

Salix spp. Bark Hot Water Extracts Show Antiviral, Antibacterial, and Antioxidant Activities—The Bioactive Properties of 16 Clones

Tienaho

Reshamwala

Sarjala

et al. 2021

Front. Bioeng. Biotechnol.

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Earlier studies have shown that the bark of Salix L. species (Salicaceae family) is rich in extractives, such as diverse bioactive phenolic compounds. However, we lack knowledge on the bioactive properties of the bark of willow species and clones adapted to the harsh climate conditions of the cool temperate zone. Therefore, the present study aimed to obtain information on the functional profiles of northern willow clones for the use of value-added bioactive solutions. Of the 16 willow clones studied here, 12 were examples of widely distributed native Finnish willow species, including dark-leaved willow (S. myrsinifolia Salisb.) and tea-leaved willow (S. phylicifolia L.) (3 + 4 clones, respectively) and their natural and artificial hybrids (3 + 2 clones, respectively). The four remaining clones were commercial willow varieties from the Swedish willow breeding program. Hot water extraction of bark under mild conditions was carried out. Bioactivity assays were used to screen antiviral, antibacterial, antifungal, yeasticidal, and antioxidant activities, as well as the total phenolic content of the extracts. Additionally, we introduce a fast and less labor-intensive steam-debarking method for Salix spp. feedstocks. Clonal variation was observed in the antioxidant properties of the bark extracts of the 16 Salix spp. clones. High antiviral activity against a non-enveloped enterovirus, coxsackievirus A9, was found, with no marked differences in efficacy between the native clones. All the clones also showed antibacterial activity against Staphylococcus aureus and Escherichia coli, whereas no antifungal (Aspergillus brasiliensis) or yeasticidal (Candida albicans) efficacy was detected. When grouping the clone extract results into Salix myrsinifolia, Salix phylicifolia, native hybrid, artificial hybrid, and commercial clones, there was a significant difference in the activities between S. phylicifolia clone extracts and commercial clone extracts in the favor of S. phylicifolia in the antibacterial and antioxidant tests. In some antioxidant tests, S. phylicifolia clone extracts were also significantly more active than artificial clone extracts. Additionally, S. myrsinifolia clone extracts showed significantly higher activities in some antioxidant tests than commercial clone extracts and artificial clone extracts. Nevertheless, the bark extracts of native Finnish willow clones showed high bioactivity. The obtained knowledge paves the way towards developing high value-added biochemicals and other functional solutions based on willow biorefinery approaches.

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Section: Introductionmentioning

confidence: 99%

Salix spp. Bark Hot Water Extracts Show Antiviral, Antibacterial, and Antioxidant Activities—The Bioactive Properties of 16 Clones

Tienaho

Reshamwala

Sarjala

et al. 2021

Front. Bioeng. Biotechnol.

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“…Several studies have shown that low water temperatures result in an increase in flavonoid production [ 14 , 15 , 43 ]. It seems, though, to be an increase in the occurrence of the sulfated flavonoids related to the longitude and colder climatic or harsher conditions, possibly reflecting the indicated physiological protective role of sulfated flavonoids in the seagrass [ 30 , 31 , 32 , 33 ]. However, in Zostera spp.…”

Section: Discussionmentioning

confidence: 99%

“…The physiological role of the sulfated flavonoids in plants and the factors that regulate flavonoid sulfate accumulation is unclear. However, some evidence implies physiological protection of the seagrass [ 30 , 31 , 32 , 33 ]. As for the phenolic acid content of Z. marina , zosteric acid (ZA), a sulfated phenolic acid only seen in Zostera species [ 11 ], has been found to prevent the settlement of marine bacteria, algae, barnacles and tubeworms [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

Variation in Phenolic Chemistry in Zostera marina Seagrass along Environmental Gradients

Dybsland

Bekkby

Enerstvedt

et al. 2021

Plants

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Chemical ecology has been suggested as a less time-consuming and more cost-efficient monitoring tool of seagrass ecosystems than traditional methods. Phenolic chemistry in Zostera marina samples was analyzed against latitude, sea depth, sample position within a seagrass meadow (periphery or center) and wave exposure. Multivariate data analysis showed that rosmarinic acid correlated moderately positively with depth, while the flavonoids had an overall strong negative correlation with increasing depth—possibly reflecting lack of stress-induced conditions with increasing depth, rather than a different response to light conditions. At a molecular level, the flavonoids were separated into two groups; one group is well described by the variables of depth and wave exposure, and the other group that was not well described by these variables—the latter may reflect biosynthetic dependencies or other unrevealed factors. A higher flavonoid/rosmarinic acid ratio was seen in the periphery of a seagrass meadow, while the contrary ratio was seen in the center. This may reflect higher plant stress in the periphery of a meadow, and the flavonoid/rosmarinic acid ratio may provide a possible molecular index of seagrass ecosystem health. Further studies are needed before the full potential of using variation in phenolic chemistry as a seagrass ecosystem monitoring tool is established.

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“…In contrast to the parent compounds, sulfated forms of silymarin constituents cannot be isolated from plant material. The only exception is taxifolin 7-O-sulfate, which was recently identified in a hybrid species of willow [22]. Several sulfated derivatives were, however, prepared by chemical [23] or enzymatic synthesis using the microbial aryl sulfotransferase from Desulfitobacterium hafniense (also see Section 4.1) [24][25][26], the aryl sulfotransferase IV from rat liver [27,28], or the fungus Cunninghamella blakesleeana [29].…”

Section: Discussionmentioning

confidence: 99%

Identification of Human Sulfotransferases Active towards Silymarin Flavonolignans and Taxifolin

et al. 2020

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Natural phenolic compounds are known to be metabolized by phase II metabolic reactions. In this study, we examined the in vitro sulfation of the main constituents of silymarin, an herbal remedy produced from the fruits of the milk thistle. The study focused on major flavonolignan constituents, including silybin A, silybin B, isosilybin A, isosilybin B, silychristin, and silydianin, as well as the flavonoid taxifolin. Using ultra-high-performance liquid chromatography coupled with tandem mass spectrometry (UHPLC-MS), individual flavonolignans and taxifolin were found to be sulfated by human liver and human intestinal cytosols. Moreover, experiments with recombinant enzymes revealed that human sulfotransferases (SULTs) 1A1*1, 1A1*2, 1A2, 1A3, 1B1, 1C4, and 1E1 catalyzed the sulfation of all of the tested compounds, with the exception of silydianin, which was not sulfated by SULT1B1 and SULT1C4. The sulfation products detected were monosulfates, of which some of the major ones were identified as silybin A 20-O-sulfate, silybin B 20-O-sulfate, and isosilybin A 20-O-sulfate. Further, we also observed the sulfation of the tested compounds when they were tested in the silymarin mixture. Sulfates of flavonolignans and of taxifolin were produced by incubating silymarin with all of the above SULT enzymes, with human liver and intestinal cytosols, and also with human hepatocytes, even though the spectrum and amount of the sulfates varied among the metabolic models. Considering our results and the expression patterns of human sulfotransferases in metabolic tissues, we conclude that flavonolignans and taxifolin can potentially undergo both intestinal and hepatic sulfation, and that SULTs 1A1, 1A3, 1B1, and 1E1 could be involved in the biotransformation of the constituents of silymarin.

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Sulfated flavanones and dihydroflavonols from willow

Cited by 11 publications

References 30 publications

Salix spp. Bark Hot Water Extracts Show Antiviral, Antibacterial, and Antioxidant Activities—The Bioactive Properties of 16 Clones

Salix spp. Bark Hot Water Extracts Show Antiviral, Antibacterial, and Antioxidant Activities—The Bioactive Properties of 16 Clones

Variation in Phenolic Chemistry in Zostera marina Seagrass along Environmental Gradients

Identification of Human Sulfotransferases Active towards Silymarin Flavonolignans and Taxifolin

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