» Articles » PMID: 21865488

Biosynthesis of the Major Tetrahydroxystilbenes in Spruce, Astringin and Isorhapontin, Proceeds Via Resveratrol and is Enhanced by Fungal Infection

Overview
Journal Plant Physiol
Specialty Physiology
Date 2011 Aug 26
PMID 21865488
Citations 35
Authors
Affiliations
Soon will be listed here.
Abstract

Stilbenes are dibenzyl polyphenolic compounds produced in several unrelated plant families that appear to protect against various biotic and abiotic stresses. Stilbene biosynthesis has been well described in economically important plants, such as grape (Vitis vinifera), peanut (Arachis hypogaea), and pine (Pinus species). However, very little is known about the biosynthesis and ecological role of stilbenes in spruce (Picea), an important gymnosperm tree genus in temperate and boreal forests. To investigate the biosynthesis of stilbenes in spruce, we identified two similar stilbene synthase (STS) genes in Norway spruce (Picea abies), PaSTS1 and PaSTS2, which had orthologs with high sequence identity in sitka (Picea sitchensis) and white (Picea glauca) spruce. Despite the conservation of STS sequences in these three spruce species, they differed substantially from angiosperm STSs. Several types of in vitro and in vivo assays revealed that the P. abies STSs catalyze the condensation of p-coumaroyl-coenzyme A and three molecules of malonyl-coenzyme A to yield the trihydroxystilbene resveratrol but do not directly form the dominant spruce stilbenes, which are tetrahydroxylated. However, in transgenic Norway spruce overexpressing PaSTS1, significantly higher amounts of the tetrahydroxystilbene glycosides, astringin and isorhapontin, were produced. This result suggests that the first step of stilbene biosynthesis in spruce is the formation of resveratrol, which is further modified by hydroxylation, O-methylation, and O-glucosylation to yield astringin and isorhapontin. Inoculating spruce with fungal mycelium increased STS transcript abundance and tetrahydroxystilbene glycoside production. Extracts from STS-overexpressing lines significantly inhibited fungal growth in vitro compared with extracts from control lines, suggesting that spruce stilbenes have a role in antifungal defense.

Citing Articles

Biosynthesis of Piceatannol from Resveratrol in Grapevine Can Be Mediated by Cresolase-Dependent -Hydroxylation Activity of Polyphenol Oxidase.

Martinez-Marquez A, Selles-Marchart S, Najera H, Morante-Carriel J, Martinez-Esteso M, Bru-Martinez R Plants (Basel). 2024; 13(18).

PMID: 39339576 PMC: 11434850. DOI: 10.3390/plants13182602.


Elevated nutrient supply can exert worse effects on Norway spruce than drought, viewed through chemical defence against needle rust.

Ganthaler A, Guggenberger A, Stoggl W, Kranner I, Mayr S Tree Physiol. 2023; 43(10):1745-1757.

PMID: 37405989 PMC: 10565715. DOI: 10.1093/treephys/tpad084.


Astringin protects LPS-induced toxicity by suppressing oxidative stress and inflammation via suppression of PI3K/AKT/NF-κB pathway for pediatric acute lung injury.

Wang L, Jiang S, Li X, Lin T, Qin T Naunyn Schmiedebergs Arch Pharmacol. 2023; 396(10):2369-2377.

PMID: 37193771 DOI: 10.1007/s00210-023-02439-z.


Bark Beetle Attack History Does Not Influence the Induction of Terpene and Phenolic Defenses in Mature Norway Spruce () Trees by the Bark Beetle-Associated Fungus .

Nagel R, Hammerbacher A, Kunert G, Phillips M, Gershenzon J, Schmidt A Front Plant Sci. 2022; 13:892907.

PMID: 35599904 PMC: 9120863. DOI: 10.3389/fpls.2022.892907.


Transcriptomic changes during the establishment of long-term methyl jasmonate-induced resistance in Norway spruce.

Wilkinson S, Dalen L, Skrautvol T, Ton J, Krokene P, Mageroy M Plant Cell Environ. 2022; 45(6):1891-1913.

PMID: 35348221 PMC: 9321552. DOI: 10.1111/pce.14320.


References
1.
Abdeen A, Miki B . The pleiotropic effects of the bar gene and glufosinate on the Arabidopsis transcriptome. Plant Biotechnol J. 2009; 7(3):266-82. DOI: 10.1111/j.1467-7652.2009.00398.x. View

2.
Raiber S, Schroder G, Schroder J . Molecular and enzymatic characterization of two stilbene synthases from Eastern white pine (Pinus strobus). A single Arg/His difference determines the activity and the pH dependence of the enzymes. FEBS Lett. 1995; 361(2-3):299-302. DOI: 10.1016/0014-5793(95)00199-j. View

3.
Li S, Niu X, Zahn S, Gershenzon J, Weston J, Schneider B . Diastereomeric stilbene glucoside dimers from the bark of Norway spruce (Picea abies). Phytochemistry. 2007; 69(3):772-82. DOI: 10.1016/j.phytochem.2007.08.033. View

4.
Franceschi V, Krokene P, Christiansen E, Krekling T . Anatomical and chemical defenses of conifer bark against bark beetles and other pests. New Phytol. 2005; 167(2):353-75. DOI: 10.1111/j.1469-8137.2005.01436.x. View

5.
Tamura K, Dudley J, Nei M, Kumar S . MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol. 2007; 24(8):1596-9. DOI: 10.1093/molbev/msm092. View