Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthicyanidins from cinnamon

Gen Ichiro Nonaka, Satoshi Morimoto, Itsuo Nishioka

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

A proanthocyanidin trimer, two tetramers, and a pentamer have been isolated in their free phenolic forms from cinnamon, the bark of Cinnamomum zeylanicum (Lauraceae). Partial acid-catalysed degradation of these tannins with phenylmethanethiol, in conjunction with 1H- and 13C-n.m.r. analysis, has unequivocally established their structures as epicatechin-(4β→8, 2β→7)epicatechin-(4α→8)- epicatechin (5); epicatechin-(4β→8)epicatechin-(4β→8, 2β→7)-epicatechin-(4α→8)-epicatechin (6); epicatechin-(4β→6)-epicatechin-(4β→8, 2β→7)- epicatechin-(4α→8)-epicatechin (7); and epicatechin-(4β→8)- epicatechin-(4β→8)epicatechin-(4β-→8, 2β→7)- epicatechin-(4α→8)-epicatechin (8).

Original languageEnglish
Pages (from-to)2139-2145
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1983

Fingerprint

Catechin
Tannins

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{80dd6656f10846a9a520d799bd5478ed,
title = "Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthicyanidins from cinnamon",
abstract = "A proanthocyanidin trimer, two tetramers, and a pentamer have been isolated in their free phenolic forms from cinnamon, the bark of Cinnamomum zeylanicum (Lauraceae). Partial acid-catalysed degradation of these tannins with phenylmethanethiol, in conjunction with 1H- and 13C-n.m.r. analysis, has unequivocally established their structures as epicatechin-(4β→8, 2β→7)epicatechin-(4α→8)- epicatechin (5); epicatechin-(4β→8)epicatechin-(4β→8, 2β→7)-epicatechin-(4α→8)-epicatechin (6); epicatechin-(4β→6)-epicatechin-(4β→8, 2β→7)- epicatechin-(4α→8)-epicatechin (7); and epicatechin-(4β→8)- epicatechin-(4β→8)epicatechin-(4β-→8, 2β→7)- epicatechin-(4α→8)-epicatechin (8).",
author = "Nonaka, {Gen Ichiro} and Satoshi Morimoto and Itsuo Nishioka",
year = "1983",
language = "English",
pages = "2139--2145",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1472-7781",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthicyanidins from cinnamon

AU - Nonaka, Gen Ichiro

AU - Morimoto, Satoshi

AU - Nishioka, Itsuo

PY - 1983

Y1 - 1983

N2 - A proanthocyanidin trimer, two tetramers, and a pentamer have been isolated in their free phenolic forms from cinnamon, the bark of Cinnamomum zeylanicum (Lauraceae). Partial acid-catalysed degradation of these tannins with phenylmethanethiol, in conjunction with 1H- and 13C-n.m.r. analysis, has unequivocally established their structures as epicatechin-(4β→8, 2β→7)epicatechin-(4α→8)- epicatechin (5); epicatechin-(4β→8)epicatechin-(4β→8, 2β→7)-epicatechin-(4α→8)-epicatechin (6); epicatechin-(4β→6)-epicatechin-(4β→8, 2β→7)- epicatechin-(4α→8)-epicatechin (7); and epicatechin-(4β→8)- epicatechin-(4β→8)epicatechin-(4β-→8, 2β→7)- epicatechin-(4α→8)-epicatechin (8).

AB - A proanthocyanidin trimer, two tetramers, and a pentamer have been isolated in their free phenolic forms from cinnamon, the bark of Cinnamomum zeylanicum (Lauraceae). Partial acid-catalysed degradation of these tannins with phenylmethanethiol, in conjunction with 1H- and 13C-n.m.r. analysis, has unequivocally established their structures as epicatechin-(4β→8, 2β→7)epicatechin-(4α→8)- epicatechin (5); epicatechin-(4β→8)epicatechin-(4β→8, 2β→7)-epicatechin-(4α→8)-epicatechin (6); epicatechin-(4β→6)-epicatechin-(4β→8, 2β→7)- epicatechin-(4α→8)-epicatechin (7); and epicatechin-(4β→8)- epicatechin-(4β→8)epicatechin-(4β-→8, 2β→7)- epicatechin-(4α→8)-epicatechin (8).

UR - http://www.scopus.com/inward/record.url?scp=37049097339&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049097339&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:37049097339

SP - 2139

EP - 2145

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1472-7781

ER -