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Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

Erosa-Rejón, Gilda J. ; Yam-Puc, Alejandro ; Peña-Rodríguez, Luis M. and Sterner, Olov LU (2023) In Journal of the Mexican Chemical Society 67(3). p.182-186
Abstract

The trimeric caffeic acid derivative pulcaffeate (1) was isolated from the organic crude extract of the roots of Bourreria pulchra (Boraginaceae). The biosynthesis of 1 appears to involve an intramolecular Diels-Alder reaction between a cyclohexa-1,3-diene intermediate, generated by the oxidation of the aromatic ring of a cinnamic acid unit, and the conjugated double bond of a caffeic acid unit. The structure of the new metabolite was elucidated through a detailed analysis of its1H and13C NMR spectroscopic data. This is the first report of a trimeric metabolite occurring in B. pulchra.

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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Boraginaceae, caffeic acid, cinnamic acid, Diels-Alder reaction, intramolecular cycloaddition
in
Journal of the Mexican Chemical Society
volume
67
issue
3
pages
5 pages
publisher
Mexican Chemical Society
external identifiers
  • scopus:85164410731
ISSN
1870-249X
DOI
10.29356/jmcs.v67i3.1985
language
English
LU publication?
yes
id
f444809d-cc0a-4be8-a55c-9b45c6aa24f7
date added to LUP
2023-09-13 11:17:58
date last changed
2023-09-13 11:44:05
@article{f444809d-cc0a-4be8-a55c-9b45c6aa24f7,
  abstract     = {{<p>The trimeric caffeic acid derivative pulcaffeate (1) was isolated from the organic crude extract of the roots of Bourreria pulchra (Boraginaceae). The biosynthesis of 1 appears to involve an intramolecular Diels-Alder reaction between a cyclohexa-1,3-diene intermediate, generated by the oxidation of the aromatic ring of a cinnamic acid unit, and the conjugated double bond of a caffeic acid unit. The structure of the new metabolite was elucidated through a detailed analysis of its<sup>1</sup>H and<sup>13</sup>C NMR spectroscopic data. This is the first report of a trimeric metabolite occurring in B. pulchra.</p>}},
  author       = {{Erosa-Rejón, Gilda J. and Yam-Puc, Alejandro and Peña-Rodríguez, Luis M. and Sterner, Olov}},
  issn         = {{1870-249X}},
  keywords     = {{Boraginaceae; caffeic acid; cinnamic acid; Diels-Alder reaction; intramolecular cycloaddition}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{182--186}},
  publisher    = {{Mexican Chemical Society}},
  series       = {{Journal of the Mexican Chemical Society}},
  title        = {{Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra}},
  url          = {{http://dx.doi.org/10.29356/jmcs.v67i3.1985}},
  doi          = {{10.29356/jmcs.v67i3.1985}},
  volume       = {{67}},
  year         = {{2023}},
}