Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra
(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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https://lup.lub.lu.se/record/f444809d-cc0a-4be8-a55c-9b45c6aa24f7
- author
- Erosa-Rejón, Gilda J. ; Yam-Puc, Alejandro ; Peña-Rodríguez, Luis M. and Sterner, Olov LU
- organization
- publishing date
- 2023-07
- 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}}, }