7WAR
SbSOMT in complex with pinostilbene and nicotinamide adenine dinucleotide(NAD+)
Summary for 7WAR
| Entry DOI | 10.2210/pdb7war/pdb |
| Related | 7VB8 7WAQ 7WAS |
| Descriptor | stilbene O-methyltransferase, 3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxy-phenol, NICOTINAMIDE-ADENINE-DINUCLEOTIDE, ... (9 entities in total) |
| Functional Keywords | pinostilbene, complex, o-methyltransferase, substrate, transferase |
| Biological source | Sorghum bicolor (sorghum) |
| Total number of polymer chains | 2 |
| Total formula weight | 86908.48 |
| Authors | |
| Primary citation | Lui, A.C.W.,Pow, K.C.,Lin, N.,Lam, L.P.Y.,Liu, G.,Godwin, I.D.,Fan, Z.,Khoo, C.J.,Tobimatsu, Y.,Wang, L.,Hao, Q.,Lo, C. Regioselective stilbene O-methylations in Saccharinae grasses. Nat Commun, 14:3462-3462, 2023 Cited by PubMed 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. PubMed: 37308495DOI: 10.1038/s41467-023-38908-5 PDB entries with the same primary citation |
| Experimental method | X-RAY DIFFRACTION (2.101 Å) |
Structure validation
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