Potent antiviral flavone glycosides from Ficus benjamina leaves

Yarmolinsky, Ludmila; Huleihel, Mahmoud; Zaccai, Michèle; Ben‐Shabat, Shimon

doi:10.1016/j.fitote.2011.11.014

Cited by 110 publications

(78 citation statements)

References 32 publications

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“…Although flavones are generally colorless, they can function as copigments with anthocyanins to alter the color of flowers (Goto and Kondo, 1991;Tanaka et al, 1998;Shiono et al, 2008;Kalisz et al, 2013;Tanaka and Brugliera, 2013) and leaves (Ishikura, 1981;Fossen et al, 2007). On the other hand, flavones as dietary constituents or supplements have beneficial effects, as they have antioxidant properties, they can prevent cancer, they reduce the risks of cardiovascular diseases, they decrease cholesterol levels, and they show antiviral activities (Bontempo et al, 2007;Cai et al, 2007;Liu et al, 2007;Park et al, 2007;Baek et al, 2009;Dharmarajan and Arumugam, 2012;Yarmolinsky et al, 2012;Dajas et al, 2013).…”

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confidence: 99%

The Identification of Maize and Arabidopsis Type I FLAVONE SYNTHASEs Links Flavones with Hormones and Biotic Interactions

et al. 2015

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Flavones are a major group of flavonoids with diverse functions and are extensively distributed in land plants. There are two different classes of FLAVONE SYNTHASE (FNS) enzymes that catalyze the conversion of the flavanones into flavones. The FNSI class comprises soluble Fe 2+ /2-oxoglutarate-dependent dioxygenases, and FNSII enzymes are oxygen-and NADPH-dependent cytochrome P450 membrane-bound monooxygenases. Here, we describe the identification and characterization of FNSI enzymes from maize (Zea mays) and Arabidopsis (Arabidopsis thaliana). In maize, ZmFNSI-1 is expressed at significantly higher levels in silks and pericarps expressing the 3-deoxy flavonoid R2R3-MYB regulator P1, suggesting that ZmFNSI-1 could be the main enzyme for the synthesis of flavone O-glycosides. We also show here that DOWNY MILDEW RESISTANT6 (AtDMR6), the Arabidopsis homologous enzyme to ZmFNSI-1, has FNSI activity. While dmr6 mutants show loss of susceptibility to Pseudomonas syringae, transgenic dmr6 plants expressing ZmFNSI-1 show similar susceptibility to wild-type plants, demonstrating that ZmFNSI-1 can complement the mutant phenotype. AtDMR6 expression analysis showed a tissue-and developmental stage-dependent pattern, with high expression in cauline and senescing leaves. Finally, we show that Arabidopsis cauline and senescing leaves accumulate apigenin, demonstrating that Arabidopsis plants have an FNSI activity involved in the biosynthesis of flavones. The results presented here also suggest cross talk between the flavone and salicylic acid pathways in Arabidopsis; in this way, pathogens would induce flavones to decrease salicylic acid and, hence, increase susceptibility.

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confidence: 99%

The Identification of Maize and Arabidopsis Type I FLAVONE SYNTHASEs Links Flavones with Hormones and Biotic Interactions

et al. 2015

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“…In plants, flavones play important physiological roles, including UV protection (Schmitz-Hoerner and Weissenböck, 2003), interactions with other organisms (Peters et al, 1986;Kong et al, 2007), regulation of auxin transport (Mathesius et al, 1998), and copigmentation in flowers (Goto and Kondo, 1991). On the other hand, flavones as dietary constituents or supplements have become increasingly popular due to their health-beneficial effects, such as cancer prevention (Bontempo et al, 2007;Cai et al, 2007;Liu et al, 2007), antioxidation (Park et al, 2007), antiviral activities (Yarmolinsky et al, 2012), reduction of risks of cardiovascular diseases (Baek et al, 2009), and suppression of cholesterol levels (Dharmarajan and Arumugam, 2012).…”

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Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

et al. 2014

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Flavones are a major class of flavonoids with a wide range of physiological functions in plants. They are constitutively accumulated as C-glycosides and O-linked conjugates in vegetative tissues of grasses. It has long been presumed that the two structural modifications of flavones occur through independent metabolic routes. Previously, we reported that cytochrome P450 93G2 (CYP93G2) functions as a flavanone 2-hydroxylase (F2H) that provides 2-hydroxyflavanones for C-glycosylation in rice (Oryza sativa). Flavone C-glycosides are subsequently formed by dehydratase activity on 2-hydroxyflavanone C-glycosides. On the other hand, O-linked modifications were proposed to proceed after the flavone nucleus is generated. In this study, we demonstrate that CYP93G1, the closest homolog of CYP93G2 in rice, is a bona fide flavone synthase II (FNSII) that catalyzes the direct conversion of flavanones to flavones. In recombinant enzyme assays, CYP93G1 desaturated naringenin and eriodictyol to apigenin and luteolin, respectively. Consistently, transgenic expression of CYP93G1 in Arabidopsis (Arabidopsis thaliana) resulted in the accumulation of different flavone O-glycosides, which are not naturally present in cruciferous plants. Metabolite analysis of a rice CYP93G1 insertion mutant further demonstrated the preferential depletion of tricin O-linked flavanolignans and glycosides. By contrast, redirection of metabolic flow to the biosynthesis of flavone C-glycosides was observed. Our findings established that CYP93G1 is a key branch point enzyme channeling flavanones to the biosynthesis of tricin O-linked conjugates in rice. Functional diversification of F2H and FNSII in the cytochrome P450 CYP93G subfamily may represent a lineage-specific event leading to the prevalent cooccurrence of flavone C-and O-linked derivatives in grasses today.

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“…Expression of transcripts was calculated in relation to the expression level of GAPDH and expressed as a fold change compared with mock-infected cells. infections in vitro (Yarmolinsky, Huleihel, Zaccai, & Ben-Shabat, 2012). In our study, we tested on a flavonoid compound, wogonin, as well as three polyphenolic compounds (honokiol, magnolol, and resveratrol) for antiviral activities against 2 different clinical strains of VZV.…”

Section: Fig 3 -Polymerase Chain Reaction (Pcr) Array In Vzv-infectementioning

confidence: 99%

Wogonin inhibits Varicella-Zoster (shingles) virus replication via modulation of type I interferon signaling and adenosine monophosphate-activated protein kinase activity

Choi

Lee

Kim

et al. 2015

Journal of Functional Foods

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Potent antiviral flavone glycosides from Ficus benjamina leaves

Cited by 110 publications

References 32 publications

The Identification of Maize and Arabidopsis Type I FLAVONE SYNTHASEs Links Flavones with Hormones and Biotic Interactions

The Identification of Maize and Arabidopsis Type I FLAVONE SYNTHASEs Links Flavones with Hormones and Biotic Interactions

Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice

Wogonin inhibits Varicella-Zoster (shingles) virus replication via modulation of type I interferon signaling and adenosine monophosphate-activated protein kinase activity

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