Acylated petunidin glycosides in the flowers of Exacum affine (Gentianaceae)

IF 1.4 4区生物学 Q4 CHEMISTRY, MEDICINAL

Phytochemistry Letters Pub Date : 2025-08-06 DOI:10.1016/j.phytol.2025.103021

Fumi Tatsuzawa , Natsu Tanikawa

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Abstract

Four anthocyanins, along with one flavone, caffeoyl-glucose, and secoiridoid glycoside, were isolated from the violet-blue flowers of Exacum affine (Gentianaceae), and their structures were determined using chemical and spectroscopic techniques. Among them, petunidin 3-O-β-glucopyranoside-5-O-[6-O-(trans-caffeoyl)-β-glucopyranoside] is reported for the first time. For petunidin 3-O-β-glucopyranoside-5-O-[6-O-(trans-p-coumaroyl)-β-glucopyranoside], which had previously been identified Yu et al. (2024) via LC-MSⁿ analyses, its exact structure has now been determined. Additionally, petunidin 3,5-di-O-β-glucopyranoside, petunidin 3-O-β-glucopyranoside-5-O-[6-O-(acetyl)-β-glucopyranoside], luteolin 4’-O-(β-glucopyranoside), 1-O-(trans-caffeoyl)-β-glucopyranose, and gentiopicroside were also identified from E. affine flowers. Since the pigment composition was nearly identical between the violet-blue flowers of ‘Royal Dane Blue Deep’ and the purple flowers of ‘Royal Dane Rose Deep,’ except for the amount of luteolin 4’-O-β-glucopyranoside, it was concluded that the bluer coloration of E. affine flowers results from the intermolecular co-pigmentation effect between anthocyanin and flavone.

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仿射龙胆花中乙酰化牵牛花苷的研究

从龙胆科紫蓝色花中分离得到4种花青素、1种黄酮、1种咖啡基葡萄糖和1种环烯醚萜苷，并利用化学和光谱技术对它们的结构进行了测定。其中，petunidin 3-O-β-glucopyranoside-5- o -[6-O-（反式咖啡基）-β-glucopyranoside]为首次报道。Yu et al.（2024）先前通过LC-MSn分析发现了petunidin 3-O-β-glucopyranoside-5- o -[6-O-（反式对香豆醇基）-β-glucopyranoside]，现在已经确定了其确切结构。此外，还从E.仿射花中鉴定出牛牵牛花素3,5-二- o -β-葡萄糖苷、牛牵牛花素3- o -β-葡萄糖苷-5- o -[6-O-（乙酰）-β-葡萄糖苷]、木犀草素4 ' - o -（β-葡萄糖苷）、1-O-（反式咖啡基）-β-葡萄糖苷和龙胆苦苷。由于“皇家丹蓝深”的紫蓝色花与“皇家丹玫瑰深”的紫色花的色素组成几乎相同，除了木犀草素4 ' -O-β-葡萄糖苷的含量外，因此可以得出结论，仿射花的蓝色是由于花青素和黄酮的分子间共色素沉着作用所致。

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来源期刊

Phytochemistry Letters 生物-生化与分子生物学

CiteScore

3.00

自引率

11.80%

发文量

190

审稿时长

34 days

期刊介绍： Phytochemistry Letters invites rapid communications on all aspects of natural product research including: • Structural elucidation of natural products • Analytical evaluation of herbal medicines • Clinical efficacy, safety and pharmacovigilance of herbal medicines • Natural product biosynthesis • Natural product synthesis and chemical modification • Natural product metabolism • Chemical ecology • Biotechnology • Bioassay-guided isolation • Pharmacognosy • Pharmacology of natural products • Metabolomics • Ethnobotany and traditional usage • Genetics of natural products Manuscripts that detail the isolation of just one new compound are not substantial enough to be sent out of review and are out of scope. Furthermore, where pharmacology has been performed on one new compound to increase the amount of novel data, the pharmacology must be substantial and/or related to the medicinal use of the producing organism.