Rare A-Type, Spiro-Type, and Highly Oligomeric Proanthocyanidins from Pinus massoniana

Authors

Bin Zhou, University of Illinois at ChicagoFollow
Yvette Alania, Marquette University
Mariana C. Reis, University of Illinois at Chicago
James McAlpine, University of Illinois at Chicago
Ana K. Bedran-Russo, Marquette UniversityFollow
Guido F. Pauli, University of Illinois at ChicagoFollow
Shao-Nong Chen, University of Illinois at ChicagoFollow

Document Type

Article

Publication Date

7-17-2020

Publisher

American Chemical Society

Source Publication

Organic Letters

Source ISSN

1523-7052

Original Item ID

10.1021/acs.orglett.0c01439

Abstract

An investigation of the dental bioactive proanthocyanidin (PAC) oligomer fractions led to three structurally distinct new PACs (1–3) from pine bark. Pinutwindoublin (1) is the first reported trimer with double A-type interflavanyl linkages (2α→O→5,4α→6 and 2α→O→7,4α→8). Pinuspirotetrin (2) represents the first reported PAC tetramer with a heterodimeric framework consisting of one spiro-type and one A-type dimer. Pinumassohexin (3) was elucidated as a mixed A + B-type hexamer that consists of a peanut-derived tetramer, peanut procyanidin E, and an A-type dimer (5). Compound 3 increased the modulus of elasticity of dentin by an impressive 4.3 times at a concentration of 0.65%.

Comments

Accepted version. Organic Letters, Vol. 22, No. 14 (July 17, 2020): 5304-5308. DOI. © 2020 American Chemical Society. Used with permission.

Recommended Citation

Zhou, Bin; Alania, Yvette; Reis, Mariana C.; McAlpine, James; Bedran-Russo, Ana K.; Pauli, Guido F.; and Chen, Shao-Nong, "Rare A-Type, Spiro-Type, and Highly Oligomeric Proanthocyanidins from Pinus massoniana" (2020). School of Dentistry Faculty Research and Publications. 383.
https://epublications.marquette.edu/dentistry_fac/383