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

24 April 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Isolation of underivatized PACs led to three new, structurally unique PACs (1-3) from pine bark. Pinutwindoublin (1) is the first known trimer with double A-type interflavanyl linkages (2α→O→5,4α→6 and 2α→O→7,4α). Pinuspirotetrin (2) represents the first 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 the tetramer, peanut procyanidin E, and an A-type dimer (5).

Keywords

proanthocyanidins
pinutwindoublin
pinuspirotetrin
pinumassohexin
Pinus massoniana
NMR
structural elucidation
Stereochemistry
Electronic Circular Dichroism Spectroscopy

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