Methoxylated flavones: occurrence, importance, biosynthesis

Berim, Anna; Gang, David R.

doi:10.1007/s11101-015-9426-0

Cited by 82 publications

(64 citation statements)

References 180 publications

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“…The identification of different flavonoid groups across land plants has been conducted for many years, both to further understand the evolutionary significance of flavonoid distribution by chemotaxonomy and for the discovery of novel bioactives (Markham, 1988;Asakawa, 2017;Jiang et al, 2016;de Vries et al, 2017;Yonekura-Sakakibara et al, 2019). Flavones and/or flavonols are almost ubiquitous across land plants (Berim, 2016) but variations in the specific types of flavonols or flavones produced have occurred during evolution, for example resulting in the rarity of flavone O-glycosides in leafy liverworts (Markham, 1988) or of polymethoxylated flavones in gymnosperms (Berim, 2016). Overall, it is probable that their biosynthesis was acquired very early during land plant evolution as an important stress adaptation.…”

Section: The Evolutionary Significance Of the Occurrence Of Differentmentioning

confidence: 99%

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

et al. 2020

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The flavonoid pathway is one of the best characterized specialized metabolite pathways of plants. In angiosperms, the flavonoids have varied roles in assisting with tolerance to abiotic stress and are also key for signaling to pollinators and seed dispersal agents. The pathway is thought to be specific to land plants and to have arisen during the period of land colonization around 550-470 million years ago. In this review we consider current knowledge of the flavonoid pathway in the bryophytes, consisting of the liverworts, hornworts, and mosses. The pathway is less characterized for bryophytes than angiosperms, and the first genetic and molecular studies on bryophytes are finding both commonalities and significant differences in flavonoid biosynthesis and pathway regulation between angiosperms and bryophytes. This includes biosynthetic pathway branches specific to each plant group and the apparent complete absence of flavonoids from the hornworts.

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Section: The Evolutionary Significance Of the Occurrence Of Differentmentioning

confidence: 99%

The Evolution of Flavonoid Biosynthesis: A Bryophyte Perspective

et al. 2020

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“…The structural diversity of flavonoids is achieved by a number of modifications, including hydroxylation, methylation, glycosylation, and malonylation [12]. In plants, flavonoid O-methylation on the hydroxy groups enhances the chemical stability and transportability of flavonoids, and is thus one of the most important modifications [13]. It has also been suggested that methylated flavonoids possess higher biological activity than unmethylated compounds [13].…”

Section: Introductionmentioning

confidence: 99%

“…In plants, flavonoid O-methylation on the hydroxy groups enhances the chemical stability and transportability of flavonoids, and is thus one of the most important modifications [13]. It has also been suggested that methylated flavonoids possess higher biological activity than unmethylated compounds [13]. O-methyltransferases (OMTs) can transfer the methyl group to specific hydroxy moieties of flavonoids by utilizing S-Adenosyl-l-methionine (SAM) as a methyl donor; thereby, the regioselective O-methylation of flavonoids can be catalyzed.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the In Vitro Cytotoxicity of Its Methylated Products

et al. 2020

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O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.

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“…This fragmentation pattern was consistent with a dihydroxy dimethoxy flavone. In fact, the occurrence of methoxylated flavonoids in plants belonging to the Lamiaceae family has been widely reported in the literature (Hossain, Rai, Brunton, Martin-Diana, & Barry-Ryan, 2010;Pacifico et al, 2016) and recently in Salvia species (Ayatollahi et al, 2015;Berim & Gang, 2016;Birtić , Dussort, Pierre, Bily, & Roller, 2015;Farjam, Rustaiyan, Ezzatzadeh, & Jassbi, 2013;Kharazian, 2014).…”

Section: Flavonoidsmentioning

confidence: 96%