Eperua oleifera Ducke (Fabaceae) Oilresin Chemical Composition and the Isolation of a Natural Diterpenic Acid Methyl Ester.

IF 2.5 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Chemistry & Biodiversity Pub Date : 2025-09-25 DOI:10.1002/cbdv.202501730

Rayssa Ribeiro, Henrique M G Pereira, Alvicler Magalhães, Fernando Hallwass, Monica C Padilha, Valdir F Veiga-Junior

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引用次数: 0

Abstract

Eperua oleifera Ducke, commonly known as "copaíba-jacaré," produces oilresins traditionally used in folk medicine for wound healing and as antifungal and antibacterial agents, similar to those of Copaifera species. However, its chemical composition remains poorly characterized. This study investigated the oilresin of E. oleifera collected in the Brazilian Amazon region. After derivatization, the sample was analyzed by GC-MS, with data compared to literature, mass spectral libraries, and standards previously isolated. In addition, neutral and acidic fractions were separated using ion-exchange open-column chromatography with silica modified with KOH-impregnated silica as the stationary phase. Twelve diterpenes were identified, including nine carboxylic acids and three alcohols. Hardwickiic acid and copalic acid were the major components, fully characterized by NMR. The most abundant compound in the neutral fraction was isolated and identified by HRMS and NMR as the methyl ester of hardwickiic acid-a compound not previously reported in oilresins. The application of GC-MS enabled the identification of diterpenes based on known fragmentation patterns. In addition, the direct infusion experiment detected a methyl ester that, to our knowledge, has not been previously reported in oilresins.

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油麻科油麻树脂的化学成分及天然二萜酸甲酯的分离。

Eperua oleifera Ducke，俗称“copaíba-jacaré”，生产的油树脂传统上用于民间医学的伤口愈合和抗真菌和抗菌剂，类似于Copaifera物种。然而，其化学成分的特征仍然很差。本研究对采自巴西亚马逊地区的油棕油树脂进行了研究。衍生化后，用GC-MS分析样品，数据与文献、质谱库和先前分离的标准品进行比较。采用离子交换开柱色谱法分离中性馏分和酸性馏分，固定相为浸渍二氧化硅改性二氧化硅。鉴定出12种二萜，包括9种羧酸和3种醇。其主要成分为硬脂酸和钴酸，经核磁共振表征。中性组分中含量最多的化合物经HRMS和NMR分离鉴定为硬脂酸甲酯，这是一种在油性树脂中未见报道的化合物。采用气相色谱-质谱法，可以根据已知的断裂模式对二萜进行鉴定。此外，直接灌注实验检测到一种甲酯，据我们所知，这种甲酯以前没有在油性树脂中报道过。

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来源期刊

Chemistry & Biodiversity 环境科学-化学综合

CiteScore

3.40

自引率

10.30%

发文量

475

审稿时长

2.6 months

期刊介绍： Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level. Since 2017, Chemistry & Biodiversity is published in an online-only format.