Regioselective stilbene O-methylations in Saccharinae grasses

Andy C. W. Lui, Kah Chee Pow, Nan Lin, Lydia Pui Ying Lam, Guoquan Liu, Ian D. Godwin, Zhuming Fan, Chen Jing Khoo, Yuki Tobimatsu, Lanxiang Wang, Quan Hao () and Clive Lo ()
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Andy C. W. Lui: The University of Hong Kong
Kah Chee Pow: The University of Hong Kong
Nan Lin: The University of Hong Kong
Lydia Pui Ying Lam: Akita University, Tegata Gakuen-machi 1-1, Akita City
Guoquan Liu: The University of Queensland
Ian D. Godwin: The University of Queensland
Zhuming Fan: The University of Hong Kong
Chen Jing Khoo: The University of Hong Kong
Yuki Tobimatsu: Kyoto University, Gokasho, Uji
Lanxiang Wang: Chinese Academy of Sciences
Quan Hao: The University of Hong Kong
Clive Lo: The University of Hong Kong

Nature Communications, 2023, vol. 14, issue 1, 1-15

Abstract: 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 3ʹ-O-methylation in the B-ring. Consistently, a highly-conserved COMT is likely involved in isorhapontigenin (3ʹ-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.

Date: 2023
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DOI: 10.1038/s41467-023-38908-5

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