Pecio_2023_Phytochemistry_207_113584

Reference

Title : Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block - Pecio_2023_Phytochemistry_207_113584
Author(s) : Pecio L , Alilou M , Kozachok S , Orhan IE , Eren G , Senol Deniz FS , Stuppner H , Oleszek W
Ref : Phytochemistry , 207 :113584 , 2023
Abstract :

The absolute configurations of the known but unusual spiro-flavostilbenoids found in the bark of Yucca schidigera Roezl ex Ortgies, were determined by applying time-dependent density functional theory simulation of electronic circular dichroism spectra. The absolute configurations obtained were as follows: (2S,3R) for yuccaol A, yuccaol D and yuccalide A; (2S,3S) for yuccaol B, yuccaol C and yuccaol E; (2S,3S,2'S,3'S) for gloriosaol A; (2S,3R,2'S,3'R) for gloriosaol C; (2S,3S,2'S,3'R) for gloriosaol D; (2S,3R,2'S,3'S) for gloriosaol E. These findings indicate that the compounds are all biosynthetic derivatives either of (2R)-naringenin and trans-resveratrol or of trans-3,3',5,5'-tetrahydroxy-4'-methoxystilbene. In contrast, gloriosaols are direct derivatives of yuccaols (note that substituting by stilbenoid changes the absolute configuration of C-2 naringenin carbon to 2S). A putative mechanism for their biosynthesis is proposed taking into account key aspects of regio- and stereoselectivity. Yuccaol B and gloriosaol A showed in vitro moderate inhibitory effects against acetyl-/butyrylcholinesterases (AChE/BChE) with IC(50) values of 43/81 and 45/65smicroM respectively. The selectivity index values calculated from the IC(50) values of BChE and AChE were 1.9 and 1.4. Molecular docking simulations showed their interaction with the peripheral anionic site of human AChE and the catalytic site of the human BChE.

PubMedSearch : Pecio_2023_Phytochemistry_207_113584
PubMedID: 36603655

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Citations formats

Pecio L, Alilou M, Kozachok S, Orhan IE, Eren G, Senol Deniz FS, Stuppner H, Oleszek W (2023)
Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block
Phytochemistry 207 :113584

Pecio L, Alilou M, Kozachok S, Orhan IE, Eren G, Senol Deniz FS, Stuppner H, Oleszek W (2023)
Phytochemistry 207 :113584