Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis

K.F. McCue; P.V. Allen; L.V.T. Shepherd; A. Blake; M.M. Maccree; D.R. Rockhold; R.G. Novy; D. Stewart; H.V. Davies; W.R. Belknap

doi:10.1016/j.phytochem.2006.10.025

Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis

K.F. McCue, P.V. Allen, L.V.T. Shepherd, A. Blake, M.M. Maccree, D.R. Rockhold, R.G. Novy, D. Stewart, H.V. Davies, W.R. Belknap

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Abstract

Steroidal glycoalkaloids (SGAs) are potentially harmful specialty metabolites found in Solanaceous plants. Two tri-glycosylated alkaloids, a-chaconine and a-solanine accumulate in potato tubers. Expressed sequence tags (ESTs) were identified in the available database by searching for protein homology to the Sgt1 (SOLtu:Sgt1) steriodalalkaloid galactosyltransferase. The EST sequence data was used to isolate Sgt3 cDNA sequences by polymerase chain reaction (PCR) from a wounded potato tuber cDNA library. The resulting 1515 bp open reading frame of Sgt3, encodes a predicted SGT3 amino acid sequence that is 18 residues longer than, 45% identical to, and 58% homologous to the SGT1 protein. The amino-terminal region of the Sgt3 cDNA was used to create an antisense transgene under control of the granule bound starch synthase, GBSS6, promoter and the ubiquitin, Ubi3, polyadenylation signal. Analysis of SGA metabolites in selected transgenic tubers revealed a dramatic decrease in the accumulation of a-chaconine and a-solanine. This decrease was compensated by an increase in ß-solanine and ß-chaconine with minor accumulation of a-SGAs. These results allowed the identification of the function for SGT3 as the ß-solanine/ß-chaconine rhamnosyl transferase, the terminal step in formation of the potato glycoalkaloid triose side chains.
© 2007 Elsevier

Original language	English
Pages (from-to)	327-334
Number of pages	8
Journal	Phytochemistry
Volume	68
Issue number	3
DOIs	https://doi.org/10.1016/j.phytochem.2006.10.025
Publication status	Published - Feb 2007

Keywords

solanum tuberosum
Solanaceae
potato
molecular genetics
steroidal glycoalkaloids
β-solanine/β-chaconine rhamnosyltransferase
Chaconine
Solanine
Sgt3

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10.1016/j.phytochem.2006.10.025

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title = "Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis",

abstract = "Steroidal glycoalkaloids (SGAs) are potentially harmful specialty metabolites found in Solanaceous plants. Two tri-glycosylated alkaloids, a-chaconine and a-solanine accumulate in potato tubers. Expressed sequence tags (ESTs) were identified in the available database by searching for protein homology to the Sgt1 (SOLtu:Sgt1) steriodalalkaloid galactosyltransferase. The EST sequence data was used to isolate Sgt3 cDNA sequences by polymerase chain reaction (PCR) from a wounded potato tuber cDNA library. The resulting 1515 bp open reading frame of Sgt3, encodes a predicted SGT3 amino acid sequence that is 18 residues longer than, 45% identical to, and 58% homologous to the SGT1 protein. The amino-terminal region of the Sgt3 cDNA was used to create an antisense transgene under control of the granule bound starch synthase, GBSS6, promoter and the ubiquitin, Ubi3, polyadenylation signal. Analysis of SGA metabolites in selected transgenic tubers revealed a dramatic decrease in the accumulation of a-chaconine and a-solanine. This decrease was compensated by an increase in {\ss}-solanine and {\ss}-chaconine with minor accumulation of a-SGAs. These results allowed the identification of the function for SGT3 as the {\ss}-solanine/{\ss}-chaconine rhamnosyl transferase, the terminal step in formation of the potato glycoalkaloid triose side chains.{\textcopyright} 2007 Elsevier",

keywords = "solanum tuberosum, Solanaceae, potato, molecular genetics, steroidal glycoalkaloids, β-solanine/β-chaconine rhamnosyltransferase, Chaconine, Solanine, Sgt3",

author = "K.F. McCue and P.V. Allen and L.V.T. Shepherd and A. Blake and M.M. Maccree and D.R. Rockhold and R.G. Novy and D. Stewart and H.V. Davies and W.R. Belknap",

year = "2007",

month = feb,

doi = "10.1016/j.phytochem.2006.10.025",

language = "English",

volume = "68",

pages = "327--334",

journal = "Phytochemistry",

publisher = "Elsevier",

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TY - JOUR

T1 - Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis

AU - McCue, K.F.

AU - Allen, P.V.

AU - Shepherd, L.V.T.

AU - Blake, A.

AU - Maccree, M.M.

AU - Rockhold, D.R.

AU - Novy, R.G.

AU - Stewart, D.

AU - Davies, H.V.

AU - Belknap, W.R.

PY - 2007/2

Y1 - 2007/2

N2 - Steroidal glycoalkaloids (SGAs) are potentially harmful specialty metabolites found in Solanaceous plants. Two tri-glycosylated alkaloids, a-chaconine and a-solanine accumulate in potato tubers. Expressed sequence tags (ESTs) were identified in the available database by searching for protein homology to the Sgt1 (SOLtu:Sgt1) steriodalalkaloid galactosyltransferase. The EST sequence data was used to isolate Sgt3 cDNA sequences by polymerase chain reaction (PCR) from a wounded potato tuber cDNA library. The resulting 1515 bp open reading frame of Sgt3, encodes a predicted SGT3 amino acid sequence that is 18 residues longer than, 45% identical to, and 58% homologous to the SGT1 protein. The amino-terminal region of the Sgt3 cDNA was used to create an antisense transgene under control of the granule bound starch synthase, GBSS6, promoter and the ubiquitin, Ubi3, polyadenylation signal. Analysis of SGA metabolites in selected transgenic tubers revealed a dramatic decrease in the accumulation of a-chaconine and a-solanine. This decrease was compensated by an increase in ß-solanine and ß-chaconine with minor accumulation of a-SGAs. These results allowed the identification of the function for SGT3 as the ß-solanine/ß-chaconine rhamnosyl transferase, the terminal step in formation of the potato glycoalkaloid triose side chains.© 2007 Elsevier

AB - Steroidal glycoalkaloids (SGAs) are potentially harmful specialty metabolites found in Solanaceous plants. Two tri-glycosylated alkaloids, a-chaconine and a-solanine accumulate in potato tubers. Expressed sequence tags (ESTs) were identified in the available database by searching for protein homology to the Sgt1 (SOLtu:Sgt1) steriodalalkaloid galactosyltransferase. The EST sequence data was used to isolate Sgt3 cDNA sequences by polymerase chain reaction (PCR) from a wounded potato tuber cDNA library. The resulting 1515 bp open reading frame of Sgt3, encodes a predicted SGT3 amino acid sequence that is 18 residues longer than, 45% identical to, and 58% homologous to the SGT1 protein. The amino-terminal region of the Sgt3 cDNA was used to create an antisense transgene under control of the granule bound starch synthase, GBSS6, promoter and the ubiquitin, Ubi3, polyadenylation signal. Analysis of SGA metabolites in selected transgenic tubers revealed a dramatic decrease in the accumulation of a-chaconine and a-solanine. This decrease was compensated by an increase in ß-solanine and ß-chaconine with minor accumulation of a-SGAs. These results allowed the identification of the function for SGT3 as the ß-solanine/ß-chaconine rhamnosyl transferase, the terminal step in formation of the potato glycoalkaloid triose side chains.© 2007 Elsevier

KW - solanum tuberosum

KW - Solanaceae

KW - potato

KW - molecular genetics

KW - steroidal glycoalkaloids

KW - β-solanine/β-chaconine rhamnosyltransferase

KW - Chaconine

KW - Solanine

KW - Sgt3

U2 - 10.1016/j.phytochem.2006.10.025

DO - 10.1016/j.phytochem.2006.10.025

M3 - Article

C2 - 17157337

VL - 68

SP - 327

EP - 334

JO - Phytochemistry

JF - Phytochemistry

IS - 3

ER -

Potato glycosterol rhamnosyltransferase, the terminal step in triose side-chain biosynthesis

Abstract

Keywords

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