Biosynthesis of the dimeric ellagitannin, cornusiin E, in Tellima grandiflora

First evidence for the in vitro synthesis of a dimeric ellagitannin has been obtained with cell-free extracts from the weed Tellima grandiflora (fringe cups, Saxifragaceae). Partially purified enzyme preparations from leaves of this plant catalyzed the oxidation of 1,2,3,4,6-pentagalloyl-beta-D-gluc...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2003-09, Vol.64 (1), p.109-114
Main Authors: Niemetz, R, Schilling, G, Gross, G.G
Format: Article
Language:English
Subjects:
biochemical pathways
Biological and medical sciences
chemical constituents of plants
cornusiin e
dimeric ellagitannin
Dimerization
ellagic acid
enzyme substrates
fringe cups
Fundamental and applied biological sciences. Psychology
gallic acid
Gallic Acid - analogs & derivatives
Gallic Acid - metabolism
glucose
Glucosides - metabolism
Hydrolyzable Tannins - analogs & derivatives
Hydrolyzable Tannins - metabolism
leaves
Magnetic Resonance Spectroscopy
Metabolism
Metabolism. Physicochemical requirements
Monophenol Monooxygenase - metabolism
oxidation
Oxidation-Reduction
pentagalloyl-beta-d-glucose
plant extracts
Plant Leaves - enzymology
Plant physiology and development
Saxifragaceae - metabolism
spectral analysis
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - methods
synthesis
tannins
Tannins - biosynthesis
Tannins - chemistry
Tellima
tellima grandiflora
tellimagrandin ii
weeds
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Summary:First evidence for the in vitro synthesis of a dimeric ellagitannin has been obtained with cell-free extracts from the weed Tellima grandiflora (fringe cups, Saxifragaceae). Partially purified enzyme preparations from leaves of this plant catalyzed the oxidation of 1,2,3,4,6-pentagalloyl-beta-D-glucose to the monomeric ellagitannin, tellimagrandin II, followed by oxidative coupling of two units of this intermediate to yield a dimeric derivative. Chemical degradation, MALDI-TOF mass spectrometry, 1H and 13C nuclear magnetic resonance, and CD spectroscopy were employed to identify this enzyme reaction product as cornusiin E which is characterized by a (S)-valoneoyl bridge between glucose-positions 2, 4' and 6'. This result was supported by comparison with data obtained for cornusiin E that had been isolated from leaves of intact T. grandiflora plants. No indication for the earlier proposed existence of rugosin D (an isomer with a 1,4',6'-bound valoneoyl unit) in T. grandiflora has been obtained in this investigation.
ISSN:0031-9422
1873-3700
DOI:10.1016/s0031-9422(03)00280-2