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Article: Regioselective stilbene O-methylations in Saccharinae grasses

TitleRegioselective stilbene O-methylations in Saccharinae grasses
Authors
Issue Date12-Jun-2023
PublisherNature Research
Citation
Nature Communications, 2023, v. 14, n. 1 How to Cite?
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.


Persistent Identifierhttp://hdl.handle.net/10722/337013
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLui, ACW-
dc.contributor.authorPow, KC-
dc.contributor.authorLin, N-
dc.contributor.authorLam, LPY-
dc.contributor.authorLiu, G-
dc.contributor.authorGodwin, ID-
dc.contributor.authorFan, Z-
dc.contributor.authorKhoo, CJ-
dc.contributor.authorTobimatsu, Y-
dc.contributor.authorWang, L-
dc.contributor.authorHao, Q-
dc.contributor.authorLo, C-
dc.date.accessioned2024-03-11T10:17:22Z-
dc.date.available2024-03-11T10:17:22Z-
dc.date.issued2023-06-12-
dc.identifier.citationNature Communications, 2023, v. 14, n. 1-
dc.identifier.urihttp://hdl.handle.net/10722/337013-
dc.description.abstract<p>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.<br></p>-
dc.languageeng-
dc.publisherNature Research-
dc.relation.ispartofNature Communications-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.titleRegioselective stilbene O-methylations in Saccharinae grasses-
dc.typeArticle-
dc.identifier.doi10.1038/s41467-023-38908-5-
dc.identifier.scopuseid_2-s2.0-85161852363-
dc.identifier.volume14-
dc.identifier.issue1-
dc.identifier.eissn2041-1723-
dc.identifier.isiWOS:001007854800002-
dc.identifier.issnl2041-1723-

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