Ulrich Matern2008 Phytochemistry Pioneer Award

Ulrich Matern, Connie Nozollilo, Mamdouh AbouZaid(Bonn, 1990)

Ulrich Matern, et al.(PSNA Annual Meeting, 1998)

Massuo Kato and Ulrich Matern(PSNA Annual Meeting, 2008)

H2N NH2

O

Urea synthesis1828

Friedrich WohlerFriedrich Wohler

Adolph Wilhelm Hermann Kolbe Adolph Wilhelm Hermann Kolbe 1818 – 18841818 – 1884

OH

CO2H

Salicylic acid synthesis

Arthur Rudolf HantzschArthur Rudolf Hantzsch1857 – 19351857 – 1935

O O

Coumarin synthesis(1886)

Coumarins

Response to phytopathogens, abiotic stress, requirement of oxidation stress, and hormonal regulation

Furanocoumarins

OOO

OCH3

8-Methoxypsoralen

Heracleum mantegazzianum(Giant Hogweed )

N

N

CH3

O

OOO O

OO O

N

N

O

OCH3

OO O

N

N OO

H3C

OO O

N

N OO

N

N

O

OH3CCH3

Thymine Psoralen

+

UVA

UVA

Lactone Ring Formation of Coumarin.Lactone Ring Formation of Coumarin.

Brown, S.A. Brown, S.A. (1960) Zeitschrift fuer Naturforschung (1960) Zeitschrift fuer Naturforschung 15b:768-76915b:768-769

[14C]cinnamic acid [14C]coumarin&

7-OH-coumarin

OHO O

Umbelliferone:Dimethylallyltransferase of Umbelliferone:Dimethylallyltransferase of RutaRuta..

Dhillon, D.S. and Brown, S.A. Dhillon, D.S. and Brown, S.A. (1976) Arch. Biochem. (1976) Arch. Biochem. Biophys. 177:74-83Biophys. 177:74-83

OHO O CH2OPP

+

OHO O

Umbelliferone DMAPP Demethylsuberosin

PsoralenO OO

• 1986– Differential response of cultured parsley cells to elicitors

from two non-pathogenic strains of fungi. Microsomal conversion of (+)-marmesin into psoralen. Eur. J. Biochem. 161:391-398. Wendorff and Matern

• 1983– Differential response of cultured parsley cells and elicitors

from two non-pathogenic strains of fungi. 1. Identification of induced products as coumarin derivatives. Eur. J. Biochem. Tietjen, K.G. et al.

Furanocoumarins

• 1988– Biosynthesis of psoralen: Psoralen-5-monooxygenase

activity from elicitor treated Ammi majus cells (psoralen + bergaptol). FEBS Lett. 239:263-5. Hamershi et al.

– Elicitor-induced biosynthesis of psoralens in Ammi majus L. suspension cultures. Microsomal conversion of demethylsuberosin into (+)-marmesin and psoralen.

Eur. J. Biochem. 171:369-375. Hamershi et al.

Furanocoumarins

• 1990– Accumulation of coumarins in elicitor-treated cell

suspension cultures of Ammi majus. Phytochemistry, 29:1137-1142. Hamershi et al.

– Induction of two prenyl transferases for the accumulation of coumarin phytoalexins in elicitor-treated Ammi majus. Phytochemistry 29:1131-1135. Hamerihi et al.

Furanocoumarins

Furanocoumarins• 2007

– Molecular Cloning and Functional Characterization of Psoralen Synthase. J. Biol. Chem. Larbat et al.

• 2004– Furanocoumarin Biosynthesis in Ammi majus Bergaptol 5-OMT Bergapten. Eur. J. Biochem. Hehmann et al.

• 1999– Biosynthesis of Coumarins. Comprehensive Natural Products 1:623-637. Matern, Luer & Kruesch.

– Medicinal Potential and Biosynthesis, Plant Coumarins. RAP, 13:161-183. Matern, U.

5-OMT

• Flavone Synthase I• Flavanone 3-β-Hydroxylase

• Flavonol Synthase

• Molecular Evolution• Structural Biology

O2/Fe(II)2-oxoglutarate dependent dioxygenases

Acridone Biosynthesis

• 1995– Molecular cloning and heterologous expression of

acridone synthase from elicitated Ruta graveolens cells. Plant Mol. Biol. 27:681-692. Junghans et al.

• 1994– Acridone alkaloids from cell suspension culture of

Thamnosa montana. Planta Medica. 60:143-145. Baumert et al.

Acridone Biosynthesis

• 2001– Transformation of acridone synthase to chalcone

synthase. FEBS Lett. 508:413-417. Lukarin et al.

• 1999– Native acridone synthase I and II from Ruta graveolens.

FEBS Lett. 448:135-140. Lukarin et al.

Acridone Biosynthesis

• 2008– Anthranilate-N-methyltransferase, a branch point enzyme

of acridone synthesis. Plant J. 53:541-553. Rhode et al.

• 2006– Study and utilization of acridone alkaloids, the natural

bioactive compounds from Citrus. Quoshu Xuebao 20:276-282.

• 2005– Starter substrate specificities of wild-type and mutant

polyketide synthases from Rutaceae. Phytochemistry 66:277-284.

Pioneers in Monolignol/Lignin Pathway Pioneers in Monolignol/Lignin Pathway ResearchResearch

Eric Conn (PAL/C4H)

Meinhart Zenk (HCT)

Werner Heller (C3H)

S.A. Brown / R. Byerrum (OMT)

Ulrich Matern (CCoAOMT)

C. Grand / K. Fukushima (F5H)

Stewart Brown (4CL/CCR/CAD)

Georg Gross/ M. Zenk (4CL/CCR/CAD)

Hans Grisebach (4CL/CCR/CAD)

Michel Legrand (COMT)

Holgar Erdtman ( monolignol radical-radical coupling/ dehydrogenative polymerization)

Karl Freudenberg (monolignol coupling product identification)

David Goring (spatial/temporal deposition of monolignols)

Neil Towers (lignin pathway evolution)

Lewis and Davin (1999) CONAP, Vol. 3, 639-712Lewis et al. (1999) CONAP, Vol. 1, 617-745