Molecular cloning and functional analysis of a biphenyl phytoalexin-specific O-methyltransferase from apple cell suspension cultures

Sarkate, Amol; Gaid, Mariam; Teotia, Deepa; Mir, Javid Iqbal; Agrawal, P. K.; Beerhues, Ludger; Sircar, Debabrata

doi:10.1007/s00425-018-3031-6

Cited by 13 publications

(5 citation statements)

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“…Moreover, pinpoint pits, the typical sign of a hypersensitive response (HR), were observed in ‘Shireen’ leaves. These pinpoint pits are associated with the scab resistance properties of ‘Shireen’, as observed previously in the scab‐resistant apple cultivar ‘Florina’ (Sarkate et al ., ). The expression of Md CNL in the V. inaequalis ‐infected stems of the two cultivars was measured in relation to that observed in mock‐inoculated stems over a time‐course of 16 days (384 h).…”

Section: Resultsmentioning

confidence: 97%

“…Moreover, the coordinated changes in Md PAL, Md CNL and Md BIS3 transcript levels (Figure a) argue for the involvement of these enzymes in the formation of biphenyl phytoalexins through intermediate formation of benzoic acid and its derivatives. The accumulation of biphenyls as a defence mechanism in apple was repeatedly reported in in vitro cultures (Sircar et al ., ; Sarkate et al ., ) and in greenhouse‐grown plants (Chizzali et al ., ,b; Sarkate et al ., ). Similarly, in our study, the level of biphenyls in the scab‐resistant ‘Shireen’ cultivar was almost 2.5‐fold higher than that in cv.…”

Section: Discussionmentioning

confidence: 99%

“…In planta , BZL activity has been biochemically identified in two plants other than Malus , namely Clarkia breweri and Hypericum androsaemum (Abd El‐Mawla and Beerhues, ; Beuerle and Pichersky, 2002a). Although the core biphenyl biosynthetic pathway is well studied in the Malinae (Chizzali et al ., 2012a; Khalil et al ., ; Sircar et al ., ; Sarkate et al ., ) , the formation of the precursor, benzoyl‐CoA, is not well understood.…”

Section: Introductionmentioning

confidence: 99%

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Cinnamate‐CoA ligase is involved in biosynthesis of benzoate‐derived biphenyl phytoalexin in Malus × domestica ‘Golden Delicious’ cell cultures

et al. 2019

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Apple (Malus sp.) and other genera belonging to the sub-tribe Malinae of the Rosaceae family produce unique benzoic acid-derived biphenyl phytoalexins. Cell cultures of Malus domestica cv. 'Golden Delicious' accumulate two biphenyl phytoalexins, aucuparin and noraucuparin, in response to the addition of a Venturia inaequalis elicitor (VIE). In this study, we isolated and expressed a cinnamate-CoA ligase (CNL)-encoding sequence from VIE-treated cell cultures of cv. 'Golden Delicious' (M. domestica CNL; MdCNL). MdCNL catalyses the conversion of cinnamic acid into cinnamoyl-CoA, which is subsequently converted to biphenyls. MdCNL failed to accept benzoic acid as a substrate. When scab-resistant (cv. 'Shireen') and moderately scab-susceptible (cv. 'Golden Delicious') apple cultivars were challenged with the V. inaequalis scab fungus, an increase in MdCNL transcript levels was observed in internodal regions. The increase in MdCNL transcript levels could conceivably correlate with the pattern of accumulation of biphenyls. The C-terminal signal in the MdCNL protein directed its N-terminal reporter fusion to peroxisomes in Nicotiana benthamiana leaves. Thus, this report records the cloning and characterisation of a cinnamoyl-CoA-forming enzyme from apple via a series of in vivo and in vitro studies. Defining the key step of phytoalexin formation in apple provides a biotechnological tool for engineering elite cultivars with improved resistance.

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Section: Resultsmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cinnamate‐CoA ligase is involved in biosynthesis of benzoate‐derived biphenyl phytoalexin in Malus × domestica ‘Golden Delicious’ cell cultures

et al. 2019

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“…Noraucuparin ( 2 ), aucuparin ( 3 ), and eriobofuran ( 53 ) inhibited conidial germination of V. inaequalis at 5 µM by 28%, 46%, and 34%, respectively. Interestingly, a combination of the three compounds synergistically inhibited the conidial germination of V. inaequalis by 74% (Sarkate et al 2018 ). This report is the only study to explore the synergistic effects of biphenyl and dibenzofuran phytoalexins upon combination.…”

Section: Antimicrobial Activity Against Phytopathogens and Structure–...mentioning

confidence: 99%

Biphenyls and dibenzofurans of the rosaceous subtribe Malinae and their role as phytoalexins

Busnena,

Beerhues,

Liu

2023

Planta

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Main conclusion Biphenyl and dibenzofuran phytoalexins are differentially distributed among species of the rosaceous subtribe Malinae, which includes apple and pear, and exhibit varying inhibitory activity against phytopathogenic microorganisms. Abstract Biphenyls and dibenzofurans are specialized metabolites, which are formed in species of the rosaceous subtribe Malinae upon elicitation by biotic and abiotic inducers. The subtribe Malinae (previously Pyrinae) comprises approximately 1000 species, which include economically important fruit trees such as apple and pear. The present review summarizes the current status of knowledge of biphenyls and dibenzofurans in the Malinae, mainly focusing on their role as phytoalexins. To date, 46 biphenyls and 41 dibenzofurans have been detected in 44 Malinae species. Structurally, 54 simple molecules, 23 glycosidic compounds and 10 miscellaneous structures were identified. Functionally, 21 biphenyls and 21 dibenzofurans were demonstrated to be phytoalexins. Furthermore, their distribution in species of the Malinae, inhibitory activities against phytopathogens, and structure–activity relationships were studied. The most widely distributed phytoalexins of the Malinae are the three biphenyls aucuparin (3), 2ʹ-methoxyaucuparin (7), and 4ʹ-methoxyaucuparin (9) and the three dibenzofurans α-cotonefuran (47), γ-cotonefuran (49), and eriobofuran (53). The formation of biphenyl and dibenzofuran phytoalexins appears to be an essential defense weapon of the Malinae against various stresses. Manipulating phytoalexin formation may enhance the disease resistance in economically important fruit trees. However, this approach requires an extensive understanding of how the compounds are formed. Although the biosynthesis of biphenyls was partially elucidated, formation of dibenzofurans remains largely unclear. Thus, further efforts have to be made to gain deeper insight into the distribution, function, and metabolism of biphenyls and dibenzofurans in the Malinae.

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“…The preliminary structural identification results based on high-resolution MS data further indicated that the differential compounds identified were mainly biphenyls, terpenes, nitrogencontaining heterocycles, and organic acids (Tables 1 and 2). Interestingly among different bioactive compounds, biphenyls (Sarkate et al, 2019) and terpenes (Liang et al, 2020)…”

Section: Secondary Metabolites Produced By S Pohuashanensis Cells Under Environmental Stressmentioning

confidence: 99%

High‐throughput screening of secondary metabolites by Sorbus pohuashanensis cells under environmental stress using UHPLC‐QTOF combined with AntDAS

Yang

et al. 2021

Physiologia Plantarum

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Environment stress can promote the synthesis and accumulation of a series of secondary metabolites, which are important quality factors in medicinal plants.However, the data related to metabolites is often too large, making it difficult to screen quickly, accurately and comprehensively various differential compounds. In this study, a high-throughput screening method for differential secondary metabolites produced by medicinal plants under environmental stress has been developed based on ultrahigh performance liquid chromatography-quadrupole time-offlight mass spectrometry (UHPLC-QTOF) and automatic data analysis strategy. This work uses Sorbus pohuashanensis cells with biotic stress (Harpin protein) and abiotic stress (Cd 2+ ) as potential environmental stress factors. The results showed that S. pohuashanensis cells could rapidly respond to both Harpin protein and Cd 2

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Molecular cloning and functional analysis of a biphenyl phytoalexin-specific O-methyltransferase from apple cell suspension cultures

Cited by 13 publications

References 44 publications

Cinnamate‐CoA ligase is involved in biosynthesis of benzoate‐derived biphenyl phytoalexin in Malus × domestica ‘Golden Delicious’ cell cultures

Cinnamate‐CoA ligase is involved in biosynthesis of benzoate‐derived biphenyl phytoalexin in Malus × domestica ‘Golden Delicious’ cell cultures

Biphenyls and dibenzofurans of the rosaceous subtribe Malinae and their role as phytoalexins

High‐throughput screening of secondary metabolites by Sorbus pohuashanensis cells under environmental stress using UHPLC‐QTOF combined with AntDAS

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