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Biosynthesis of the Dimeric Ellagitannin, Cornusiin E, in Tellima Grandiflora

Biosynthesis of the Dimeric Ellagitannin, Cornusiin E, in Tellima Grandiflora

Ruth Niemetz, Gerhard Schilling, Georg G Gross

Phytochemistry. 2003 Sep;64(1):109-114.

PMID: 12946409

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14937327	1,2,3,4,6-Pentagalloyl β-D-glucose		14937-32-7	Price

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