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ZhouEtAl_316_PineTriTetra_Preprint_wSI_20200330gfp.pdf (9.14 MB)
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Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana

preprint
submitted on 31.03.2020 and posted on 21.04.2020 by Bin Zhou, Yvette Alania, Mariana Reis, Rasika Phansalkar, Joo-Won Nam, James McAlpine, Shao-Nong Chen, Ana K. Bedran-Russo, Guido Pauli
Guided by dentin biomechanical bioactivity, this phytochemical study led to the elucidation of an extended set of structurally demanding proanthocyanidins (PACs). Unambiguous structure determination involved detailed spectroscopic and chemical characterization of four A-type dimers (2, 4–6), seven trimers (10–16), and six tetramers (17–22). New outcomes confirm the feasibility of determining the absolute configuration of the catechol monomers in oligomeric PACs by 1D and 2D NMR. Electronic circular dichroism (ECD) as well as phloroglucinolysis followed by MS and chiral phase HPLC analysis generated the necessary chiral reference data.

Funding

R01 DE021040

P41 GM068944

R56DE021040

History

Email Address of Submitting Author

gfp@uic.edu

Institution

University of Illinois at Chicago

Country

United States

ORCID For Submitting Author

0000-0003-1022-4326

Declaration of Conflict of Interest

No conflict of interest.

Licence

Exports