|WATSON, AMELIA - University Of The Pacific|
|FRANZ, ANDREAS - University Of The Pacific|
Submitted to: Archives for Organic Chemistry (ARKIVOC)
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/26/2018
Publication Date: 5/18/2018
Citation: Watson, A., Wallis, C.M., Franz, A.H. 2018. NMR solution structures and MD-simulation of procyanidin B1, B2, and C1. Archives for Organic Chemistry (ARKIVOC). 2018:279-301.
Interpretive Summary: Procyanidins are compounds that not only protect plants from abiotic stresses, such as drought, and biotic stresses, such as pathogens and insects, but have a variety of health benefits to humans and animals. However, true understanding of how procyanidins provide such benefits can only be understood by examining molecular structures of these compounds. Thus, Nuclear Magnetic Resonance and modeling studies were utilized to derive structures of three procyanidins, B1, B2, and C1. This information can now be utilized in modeling programs to examine interaction with other molecules to show how procyanidins provide benefits to a large variety of organisms.
Technical Abstract: Procyanidins are polyphenols associated with a variety of benefits to the health of both plants and animals. Procyanidins provide increased defense against microbes, act as strong antioxidants, and may decrease the incidence of cancer. Key to understanding how procyanidins function requires understanding of molecular structure in aqueous solution. However, comprehensive studies examining the structures of procyanidins in solution are lacking. Therefore, studies were undertaken using NMR spectroscopy coupled with theoretical calculations and mathematical model fitting to derive solution structures (configuration and conformation) of three common procyanidins: procyanidin B1, B2, and C1. The analysis revealed that the R-/S- naming convention for these compounds may not be as appropriate as using minus (M-)/plus (P-). The (M)-atrop conformation dominated all inter-flavanol linkages in procyanidin B1, B2, and C1. These findings were consistent with existing structural studies, and will further allow future studies examining molecular interactions of procyanidins with different compounds to proceed.