Biosynthesis of gallic acid in Rhus typhina: discrimination between alternative pathways from natural oxygen isotope abundance

Werner, Roland A.; Roßmann, A.; Schwarz, Christine; Bacher, Adelbert; Schmidt, Hanns‐Ludwig; Eisenreich, Wolfgang

doi:10.1016/j.phytochem.2004.08.020

Cited by 70 publications

(46 citation statements)

References 26 publications

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“…In persimmon, it has been suggested that the down-regulation of DkDHD/SDH expression reduced the content of PAs in the NA-type fruit (Ikegami et al, 2007Akagi et al, 2009). In addition, intermediates from the shikimate pathway serve as substrates for the biosynthesis of gallic acid (Werner et al, 2004;Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

DkMyb4 Is a Myb Transcription Factor Involved in Proanthocyanidin Biosynthesis in Persimmon Fruit

et al. 2009

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Proanthocyanidins (PAs) are secondary metabolites that contribute to the protection of the plant and also to the taste of the fruit, mainly through astringency. Persimmon (Diospyros kaki) is unique in being able to accumulate abundant PAs in the fruit flesh. Fruits of the nonastringent (NA)-type mutants lose their ability to produce PA at an early stage of fruit development, while those of the normal astringent (A) type remain rich in PA until fully ripened. The expression of many PA pathway genes was coincidentally terminated in the NA type at an early stage of fruit development. The five genes encoding the Myb transcription factor were isolated from an A-type cultivar (Kuramitsu). One of them, DkMyb4, showed an expression pattern synchronous to that of the PA pathway genes in A-and NA-type fruit flesh. The ectopic expression of DkMyb4 in kiwifruit (Actinidia deliciosa) induced PA biosynthesis but not anthocyanin biosynthesis. The suppression of DkMyb4 in persimmon calluses caused a substantial down-regulation of the PA pathway genes and PA biosynthesis. Furthermore, analysis of the DNA-binding ability of DkMyb4 showed that it directly binds to the MYBCORE cis-motif in the promoters of the some PA pathway genes. All our results indicate that DkMyb4 acts as a regulator of PA biosynthesis in persimmon and, therefore, suggest that the reduction in the DkMyb4 expression causes the NA-type-specific down-regulation of PA biosynthesis and resultant NA trait.

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Section: Resultsmentioning

confidence: 99%

DkMyb4 Is a Myb Transcription Factor Involved in Proanthocyanidin Biosynthesis in Persimmon Fruit

et al. 2009

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“…solvent was evaporated under reduced pressure to yield the crude extract (10.9 g),which exhibited cytotoxicity against the human U2OS cell line (IC 50 Biological Assays.C ytotoxicities of the compounds against the PC3, A549, A2780, MDA-MB-231, and HEPG2 cell lines were evaluated using the MTT assay [45], with cisplatin as positive control. Growth inhibitory activity against the fungus Candida albicans was assessed by the microdilutionm ethod [46], with fluconazole as positive control. Candida albicans was obtained from Affiliated QianfoshanHospital of Shandong University,P .R.C hina.…”

Section: Experimental Partmentioning

confidence: 99%

Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

Zhou

Zhu

et al. 2015

Chemistry & Biodiversity

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A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.

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“…In plants, gallic acid (54), which is biosynthesized via the shikimate pathway [67], was considered as the precursor of ellagitannins [68]. The ellagitannins would be transformed into ellagic acid (55), and then into a series of urolithins (Scheme 1) [6,7,63].…”

Section: Biosynthesis and Biotransformationmentioning

confidence: 99%

Natural Dibenzo-α-Pyrones and Their Bioactivities

Mao

Sun

et al. 2014

Molecules

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Natural dibenzo-α-pyrones are an important group of metabolites derived from fungi, mycobionts, plants and animal feces. They exhibit a variety of biological activities such as toxicity on human and animals, phytotoxicity as well as cytotoxic, antioxidant, antiallergic, antimicrobial, antinematodal, and acetylcholinesterase inhibitory properties. Dibenzo-α-pyrones are biosynthesized via the polyketide pathway in microorganisms or metabolized from plant-derived ellagitannins and ellagic acid by intestinal bacteria. At least 53 dibenzo-α-pyrones have been reported in the past few decades. This mini-review aims to briefly summarize the occurrence, biosynthesis, biotransformation, as well as their biological activities and functions. Some considerations related to synthesis, production and applications of dibenzo-α-pyrones are also discussed.

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Biosynthesis of gallic acid in Rhus typhina: discrimination between alternative pathways from natural oxygen isotope abundance

Cited by 70 publications

References 26 publications

DkMyb4 Is a Myb Transcription Factor Involved in Proanthocyanidin Biosynthesis in Persimmon Fruit

DkMyb4 Is a Myb Transcription Factor Involved in Proanthocyanidin Biosynthesis in Persimmon Fruit

Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

Natural Dibenzo-α-Pyrones and Their Bioactivities

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