Anthocyanidins produced by light and oxygen in heartwood of Peltogyne mexicana

IF 3 2区农林科学 Q1 FORESTRY

Wood Science and Technology Pub Date : 2025-08-19 DOI:10.1007/s00226-025-01686-y

Yusuke Taga, Kosei Yamauchi

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Abstract

Two new types of anthocyanidins, mopanidin (1) and peltogynidin (2) were isolated from the heartwood of Peltogyne mexicana for the first time. The structures of the isolated compounds were determined using NMR and MALDI-TOF MS analysis. These pigment compounds had flavylium moiety and oxymethylene bridge between B and C ring (D ring), and resorcinol moiety as B ring. The result of the monitoring of the oxidation of pigment precursors, it was clarified that 1 and 2 were generated from (+)-mopanol and (+)-peltogynol, respectively. The compounds were considered to be produced by light and oxygen in a different way from common anthocyanidins. Compared to cyanidin, which has similar structure except D ring, 1 and 2 showed an additional absorption around 560–570 nm to show more blueish purple. In addition, they showed more stability than cyanidin in neutral and acidic condition. Considering the result of in silico calculation of their dihedral angles consisting of the AC and B rings, 1 (θ = 174.4º) and 2 (θ = 172.0º) had a nearly planar structure, while cyanidin had a twisted structure (θ = 154.2º). It was suggested that the bulkiness around C-2 due to the nearly planar structure in 1 and 2 contributed to their relatively color stabilities in neutral condition. These findings provide insight into the structural features influencing pigment stability and color change mechanism of P. mexicana.

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墨西哥白杨心材中光和氧产生的花青素

首次从墨西哥Peltogyne心材中分离到两种新的花青素，mopanidin(1)和peltogyynin(2)。通过NMR和MALDI-TOF MS分析确定了分离化合物的结构。这些色素化合物在B环和C环（D环）之间有黄烷部分和氧亚甲基桥，间苯二酚部分为B环。对色素前体氧化的监测结果表明，1和2分别由(+)-mopanol和(+)-peltogynol生成。这些化合物被认为是由光和氧以不同于普通花青素的方式产生的。与除D环外结构相似的花青素相比，1和2在560-570 nm处有额外的吸收，呈现出更蓝的紫色。此外，它们在中性和酸性条件下均表现出比花青素更强的稳定性。结合AC环和B环组成的二面角的计算机计算结果，1 （θ = 174.4º）和2 （θ = 172.0º）具有近平面结构，而花青素具有扭曲结构（θ = 154.2º）。结果表明，由于C-2的近平面结构导致C-2周围的体积较大，这有助于它们在中性条件下相对稳定的颜色。这些发现有助于深入了解墨西哥花色素稳定性的结构特征和颜色变化机制。

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来源期刊

Wood Science and Technology 工程技术-材料科学：纸与木材

CiteScore

5.90

自引率

5.90%

发文量

审稿时长

3 months

期刊介绍： Wood Science and Technology publishes original scientific research results and review papers covering the entire field of wood material science, wood components and wood based products. Subjects are wood biology and wood quality, wood physics and physical technologies, wood chemistry and chemical technologies. Latest advances in areas such as cell wall and wood formation; structural and chemical composition of wood and wood composites and their property relations; physical, mechanical and chemical characterization and relevant methodological developments, and microbiological degradation of wood and wood based products are reported. Topics related to wood technology include machining, gluing, and finishing, composite technology, wood modification, wood mechanics, creep and rheology, and the conversion of wood into pulp and biorefinery products.