Biphenyl synthase, a novel type III polyketide synthase

Liu, B.; Raeth, Torben; Beuerle, Till; Beerhues, Ludger

doi:10.1007/s00425-006-0435-5

Cited by 63 publications

(75 citation statements)

References 27 publications

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“…The biphenyl scaffold is formed by biphenyl synthase (BIS), which catalyzes benzoyl-CoA and malonyl-CoA to generate 3,5-Dihydroxybiphenyl [9,19]. In recent studies, the biosynthetic pathway leading from 3,5-Dihydroxybiphenyl to Noraucuparin was clarified at the enzyme level in S. aucuparia [18].…”

Section: Discussionmentioning

confidence: 99%

Biphenyl Phytoalexin in Sorbus pohuashanensis Suspension Cell Induced by Yeast Extract

et al. 2016

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Biphenyls are unique phytoalexins de novo synthesized in plants in response to pathogen attack. These compounds are found in Maloideae, a subfamily of the Rosaceae. The anti-microbial activities of biphenyls have been reported in a number of studies and they appear to represent an important defense strategy against pathogens common in the Maloideae, such as species in Malus, Pyrus, Sorbus, and Chaenomeles. Here, cell suspension cultures of Sorbus pohuashanensis were established to study biphenyl phytoalexins formation after yeast extract (YE) treatment. An ultra-performance liquid chromatography (UPLC) method coupled with quadrupole time of flight mass spectrometry (Q-TOF-MS) LC−MS/MS was applied to determine the time course of these biphenyl biomarkers accumulation in YE-treated S. pohuashanensis suspension cells. The results of quantitative analyses show the content of Noraucuparin, 2 -Hydroxyaucuparin, and their glycosides initially increased, then decreased over time. The Noraucuparin content reached its highest (225.76 µg·g −1 ) at 18 h after treatment, 6 hours earlier than that of Noraucuparin 5-O-β-D-glucopyranoside. The content of 2 -Hydroxyaucuparin reached its highest (422.75 µg·g −1 ) at 30 h after treatment, also earlier than that of its glycoside. The understanding of phytoalexin metabolism in this study may provide a basis for improving Maloideae resistance to pathogens.

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Section: Discussionmentioning

confidence: 99%

Biphenyl Phytoalexin in Sorbus pohuashanensis Suspension Cell Induced by Yeast Extract

et al. 2016

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“…Aucuparin biosynthesis is initiated by BIS (Liu et al, 2004(Liu et al, , 2007. In apple, BIS is encoded by a gene family consisting of four differentially regulated subfamilies (Chizzali et al, 2012a).…”

Section: Discussionmentioning

confidence: 99%

“…The scaffold of this compound is formed by biphenyl synthase (BIS), a type III polyketide synthase, which catalyzes the condensation of the unusual starter substrate benzoyl-CoA with three molecules of malonylCoA to yield 3,5-dihydroxybiphenyl ( Fig. 1; Liu et al, 2004Liu et al, , 2007. The benzoyl moiety of the starter substrate stems from L-Phe, whose carbon skeleton is channeled into the phytoalexin biosynthetic pathway by the action of phenylalanine ammonia lyase (PAL; Hanson and Havir, 1981).…”

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confidence: 99%

“…Benzaldehyde dehydrogenase was detected in chitosan-treated rowan (Sorbus aucuparia) cell cultures, which serve as an in vitro system for studying biphenyl and dibenzofuran metabolism in the Malinae (Gaid et al, 2009;Hüttner et al, 2010). The first complementary DNA (cDNA) encoding BIS was isolated from these cell cultures after elicitor treatment (Liu et al, 2007). The elicitors that efficiently induce phytoalexin formation in rowan cell cultures include preparations from the fungus Venturia inaequalis, the causal agent of scab, and the bacterium Erwinia amylovora, the causal agent of fire blight (Hüttner et al, 2010).…”

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confidence: 99%

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Biphenyl 4-Hydroxylases Involved in Aucuparin Biosynthesis in Rowan and Apple Are Cytochrome P450 736A Proteins

Sircar¹,

Gaid

Chizzali

et al. 2015

Plant Physiol.

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Upon pathogen attack, fruit trees such as apple (Malus spp.) and pear (Pyrus spp.) accumulate biphenyl and dibenzofuran phytoalexins, with aucuparin as a major biphenyl compound. 4-Hydroxylation of the biphenyl scaffold, formed by biphenyl synthase (BIS), is catalyzed by a cytochrome P450 (CYP). The biphenyl 4-hydroxylase (B4H) coding sequence of rowan (Sorbus aucuparia) was isolated and functionally expressed in yeast (Saccharomyces cerevisiae). SaB4H was named CYP736A107. No catalytic function of CYP736 was known previously. SaB4H exhibited absolute specificity for 3-hydroxy-5-methoxybiphenyl. In rowan cell cultures treated with elicitor from the scab fungus, transient increases in the SaB4H, SaBIS, and phenylalanine ammonia lyase transcript levels preceded phytoalexin accumulation. Transient expression of a carboxyl-terminal reporter gene construct directed SaB4H to the endoplasmic reticulum. A construct lacking the amino-terminal leader and transmembrane domain caused cytoplasmic localization. Functional B4H coding sequences were also isolated from two apple (Malus 3 domestica) cultivars. The MdB4Hs were named CYP736A163. When stems of cv Golden Delicious were infected with the fire blight bacterium, highest MdB4H transcript levels were observed in the transition zone. In a phylogenetic tree, the three B4Hs were closest to coniferaldehyde 5-hydroxylases involved in lignin biosynthesis, suggesting a common ancestor. Coniferaldehyde and related compounds were not converted by SaB4H.

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“…During the last 10 years, scientists have had fascinating insights into the evolutionary creation of genetic diversity of secondary metabolism. The evolution of new genes by duplicating the genes of primary metabolism, followed by the functional diversification or new functionalization of the duplicates under the selection pressure of the environment (41,42), has been demonstrated for key biosynthetic enzymes of a number of classes of secondary metabolites, such as terpenoids (43), polyketides (44), phenolic esters (45), benzoxazinone alkaloids (46), and pyrrolizidine alkaloids (47). In conclusion, we see that the evolutionary ideas of Stahl and his contemporaries are confirmed by recent concepts of molecular evolution of plant secondary metabolism.…”

Section: Early Chemical Ecology: Why Neglected and Forgotten For Decamentioning

confidence: 99%

The lost origin of chemical ecology in the late 19th century

Hartmann

2008

Proc. Natl. Acad. Sci. U.S.A.

115

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The origin of plant chemical ecology generally dates to the late 1950s, when evolutionary entomologists recognized the essential role of plant secondary metabolites in plant-insect interactions and suggested that plant chemical diversity evolved under the selection pressure of herbivory. However, similar ideas had already flourished for a short period during the second half of the 19th century but were largely forgotten by the turn of the century. This article presents the observations and studies of three protagonists of chemical ecology: Anton Kerner von Marilaun (1831-1898, Innsbruck, Austria, and Vienna, Austria), who mainly studied the impact of geological, climatic, and biotic factors on plant distribution and survival; Lé o Errera (1858 -1906, Brussels, Belgium), a plant physiologist who analyzed the localization of alkaloids in plant cells and tissues histochemically; and Ernst Stahl (1848 -1919, Jena, Germany), likely the first experimental ecologist and who performed feeding studies with snails and slugs that demonstrated the essential role of secondary metabolites in plant protection against herbivores. All three, particularly Stahl, suggested that these ''chemical defensive means'' evolved in response to the relentless selection pressure of the heterotrophic community that surrounds plants. Although convincingly supported by observations and experiments, these ideas were forgotten until recently. Now, more than 100 years later, molecular analysis of the genes that control secondary metabolite production underscores just how correct Kerner von Marilaun, Errera, and, particularly, Stahl were in their view. Why their ideas were lost is likely a result of the adamant rejection of all things ''teleological'' by the physiologists who dominated biological research at the time.herbivore ͉ historical basis ͉ plant protection ͉ secondary metabolism C hemical ecology refers to chemically mediated interactions between organisms and their biotic and abiotic environment. It covers a broad range of chemical interactions and signaling processes; major facets are (i) the chemical communication (chemical language, e.g., pheromones) of animals, particularly expressed in arthropods; (ii) the mutualistic interactions of organisms, e.g., plants and animals (pollination), plants and fungi (mycorrhiza), and plants and bacteria (symbiotic nitrogen fixation); (iii) the chemical defenses of organisms, e.g., plant defenses against herbivores and pathogens, animal defenses against predators and parasitoids, and microorganism defenses against food competitors; and (iv) protection against abiotic stress, e.g., plant defenses against damage by UV light, drought, or cold.A major area of chemical ecology concerns the constant competition between the worlds of autotrophs and heterotrophs or simply plants and animals. During their evolution, plants have evolved sophisticated adaptations to cope with herbivores and pathogens while the latter developed similarly elaborated counteradaptations to overcome plants' defenses. Plants produce a...

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Biphenyl synthase, a novel type III polyketide synthase

Cited by 63 publications

References 27 publications

Biphenyl Phytoalexin in Sorbus pohuashanensis Suspension Cell Induced by Yeast Extract

Biphenyl Phytoalexin in Sorbus pohuashanensis Suspension Cell Induced by Yeast Extract

Biphenyl 4-Hydroxylases Involved in Aucuparin Biosynthesis in Rowan and Apple Are Cytochrome P450 736A Proteins

The lost origin of chemical ecology in the late 19th century

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