Flavonoid compounds from pollen and stigma of Petunia hybrida: Inducers of the vir region of the Agrobacterium tumefaciens Ti plasmid

doi:10.1016/0168-9452(89)90192-1

Plant Science

Volume 62, Issue 1, 1989, Pages 83-91

https://doi.org/10.1016/0168-9452(89)90192-1 Get rights and content

Abstract

The Agrobacterium tumefaciens strain A348 (pSM358) carrying a gene fusion between the pTiA6 virE locus and the Escherichia coli lacZ gene was used to determine the vir inducing activity of extracts and diffusates of pollen and stigma of Petunia hybrida. Pollen and stigma contain vir inducing compounds, which are released in high concentrations only by pollen. In pollen extracts these compounds could be identified as the flavonol glycosides kaempferol 3-glucosylagalactoside and quercetin 3-glucosylgalactoside. The expression of the virE locus is also induced by other flavonoid compounds as rutin, myricetin 3-galactoside, narcissin and apigenin 7-glucoside, which are widespread in the plant kingdom. Together with other vir inducing factors like cinnamic acids such flavonoids could therefore play a more important role in the natural infection of plants by Agrobacterium than acetosyringone, which until now has been found only in tobacco.

References (39)

A. Janssens et al.
Plant cells induce transcription of the Agrobacterium tumefaciens nopaline pTiC58 virulence region
Plant Sci.
(1986)
D. Hess
Pollen-based techniques in genetic manipulation
Int. Rev. Cytol.
(1987)
D. Hess
Genetic effects in Petunia hybrida induced by pollination with pollen treated with lac transducing phages
Z. Pflanzenphysiol.
(1978)
O. Ceska et al.
Flavonoids from Zea mays pollen
Phytochemistry
(1984)
M.S. El Ridi et al.
Isolation of rutin from the pollen grain of the date palm (Dactylifera palma L.)
Arch. Biochem. Biophys.
(1952)
B. Meurer et al.
Phenylpropanoid patterns in Fagales pollen and their phylogenetic relevance
Phytochemistry
(1988)
F. Pratviel-Sosa et al.
Les sophorosides de flavonols de quelques pollens
Phytochemistry
(1972)
F. Sosa et al.
Le kempférol-3-O-rhamnodiglucoside, nouvel hétéroside du pollen de Populus yunnanensis
Phytochemistry
(1970)
D. Strack et al.
Quercetin 3-glucosylgalactoside from pollen of Corylus avellana
Phytochemistry
(1984)
D. Strack et al.
Pollen of Tulipa cv. “Apeldoorn” as an accumulation site of flavonol diand triglycosides
Z. Pflanzenphysiol.
(1981)

E. Wollenweber et al.

Occurrence and distribution of free flavonoid aglycones in plants

Phytochemistry

(1981)

P.M. Rogowsky et al.

Regulation of the vir genes of Agrobacterium tumefaciens plasmid pTiC58

J. Bacteriol.

(1987)

S.E. Stachel et al.

The genetic and transcriptional organization of the vir region of the A6 Ti plasmid of Agrobacterium tumefaciens

EMBO J.

(1986)

R.J.H. Okker et al.

Plant-inducible virulence promoter of the Agrobacgterium tumefaciens Ti plasmid

Nature

(1984)

S.E. Stachel et al.

A Tn3 lacZ transposon for the random generation of β-galactosidase gene fusions: application to the analysis of gene expression in Agrobacterium

EMBO J.

(1985)

S.E. Stachel et al.

Identification of the signal molecules produced by wounded plant cells that activate T-DNA transfer in Agrobacterium tumefaciens

Nature

(1985)

S.E. Stachel et al.

A plant cell factor induces Agrobacterium tumefaciens vir gene expression

G.W. Bolton et al.

Plant phenolic compounds induce expression of the Agrobacterium tumefaciens loci needed for virulence

Science

(1986)

D. Hess

Gene technology and plant breeding

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Flavonoid compounds from pollen and stigma of Petunia hybrida: Inducers of the vir region of the Agrobacterium tumefaciens Ti plasmid

Abstract

Plant Sci.

Int. Rev. Cytol.

Z. Pflanzenphysiol.

Phytochemistry

Arch. Biochem. Biophys.

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Z. Pflanzenphysiol.

Phytochemistry

Regulation of the vir genes of Agrobacterium tumefaciens plasmid pTiC58

J. Bacteriol.

The genetic and transcriptional organization of the vir region of the A6 Ti plasmid of Agrobacterium tumefaciens

EMBO J.

Plant-inducible virulence promoter of the Agrobacgterium tumefaciens Ti plasmid

Nature

A Tn3 lacZ transposon for the random generation of β-galactosidase gene fusions: application to the analysis of gene expression in Agrobacterium

EMBO J.

Identification of the signal molecules produced by wounded plant cells that activate T-DNA transfer in Agrobacterium tumefaciens

Nature

A plant cell factor induces Agrobacterium tumefaciens vir gene expression

Plant phenolic compounds induce expression of the Agrobacterium tumefaciens loci needed for virulence

Science

Gene technology and plant breeding