Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

Gilda J. Erosa-Rejón; Alejandro Yam-Puc; Luis M. Peña-Rodríguez; Olov Sterner

doi:10.29356/jmcs.v67i3.1985

Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

Gilda J. Erosa-Rejón, Alejandro Yam-Puc, Luis M. Peña-Rodríguez, Olov Sterner

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	182-186
Number of pages	5
Journal	Journal of the Mexican Chemical Society
Volume	67
Issue number	3
DOIs	https://doi.org/10.29356/jmcs.v67i3.1985
Publication status	Published - 2023 Jul

Subject classification (UKÄ)

Organic Chemistry
Analytical Chemistry

Free keywords

Boraginaceae
caffeic acid
cinnamic acid
Diels-Alder reaction
intramolecular cycloaddition

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10.29356/jmcs.v67i3.1985

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title = "Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra",

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 = "Erosa-Rej{\'o}n, {Gilda J.} and Alejandro Yam-Puc and Pe{\~n}a-Rodr{\'i}guez, {Luis M.} and Olov Sterner",

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T1 - Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

AU - Erosa-Rejón, Gilda J.

AU - Yam-Puc, Alejandro

AU - Peña-Rodríguez, Luis M.

AU - Sterner, Olov

PY - 2023/7

Y1 - 2023/7

N2 - 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.

AB - 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.

KW - Boraginaceae

KW - caffeic acid

KW - cinnamic acid

KW - Diels-Alder reaction

KW - intramolecular cycloaddition

U2 - 10.29356/jmcs.v67i3.1985

DO - 10.29356/jmcs.v67i3.1985

M3 - Article

AN - SCOPUS:85164410731

SN - 1870-249X

VL - 67

SP - 182

EP - 186

JO - Journal of the Mexican Chemical Society

JF - Journal of the Mexican Chemical Society

IS - 3

ER -

Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra

Abstract

Subject classification (UKÄ)

Free keywords

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