ArticleNature communications2023
Regioselective stilbene O-methylations in Saccharinae grasses.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 14 citations in OpenAlex.
- Cell-Free Synthesis of Cannabistilbene I: A Dual Acting Anti-Inflammatory fromJournal of natural products · 2026Article
- Structural dynamics of the π-stacking network governing cofactor-substrate cooperativity of SbSOMT methyltransferase.Communications chemistry · 2026Article
- Molecular Design with Artificial Intelligence: Progress and Perspectives for Small Molecules.Chemical reviews · 2026Review
- Structure-Guided Engineering of a Promiscuous O-Methyltransferase for a SAM Regeneration Biocatalysis Platform of Methylated Pharmaceuticals.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Characterization and In Vitro Prebiotic Activity of Pterostilbene/β-Cyclodextrin Inclusion Complexes.Molecules (Basel, Switzerland) · 2025Article
- The Interplay Between Autophagy and Apoptosis in the Mechanisms of Action of Stilbenes in Cancer Cells.Antioxidants (Basel, Switzerland) · 2025Review
- Review
- Evaluation of biocontrol agents for the management of sorghum anthracnose caused byFrontiers in plant science · 2025Article
- Identification of a polyphenol O-methyltransferase with broad substrate flexibility in Streptomyces albidoflavus J1074.Microbial cell factories · 2024Article
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Authors and funding
12 authors at 6 institutions in 6 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
O-Methylated stilbenes are prominent nutraceuticals but rarely produced by crops. Here, the inherent ability of two Saccharinae grasses to produce regioselectively O-methylated stilbenes is reported. A stilbene O-methyltransferase, SbSOMT, is first shown to be indispensable for pathogen-inducible pterostilbene (3,5-bis-O-methylated) biosynthesis in sorghum (Sorghum bicolor). Phylogenetic analysis indicates the recruitment of genus-specific SOMTs from canonical caffeic acid O-methyltransferases (COMTs) after the divergence of Sorghum spp. from Saccharum spp. In recombinant enzyme assays, SbSOMT and COMTs regioselectively catalyze O-methylation of stilbene A-ring and B-ring respectively. Subsequently, SOMT-stilbene crystal structures are presented. Whilst SbSOMT shows global structural resemblance to SbCOMT, molecular characterizations illustrate two hydrophobic residues (Ile144/Phe337) crucial for substrate binding orientation leading to 3,5-bis-O-methylations in the A-ring. In contrast, the equivalent residues (Asn128/Asn323) in SbCOMT facilitate an opposite orientation that favors 3'-O-methylation in the B-ring. Consistently, a highly-conserved COMT is likely involved in isorhapontigenin (3'-O-methylated) formation in wounded wild sugarcane (Saccharum spontaneum). Altogether, our work reveals the potential of Saccharinae grasses as a source of O-methylated stilbenes, and rationalize the regioselectivity of SOMT activities for bioengineering of O-methylated stilbenes.
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