Characterization of Phyllobilins in Hops: Antioxidant and Potentially Bitter Senescence-Related Metabolites.

IF 5.7 1区农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY

Journal of Agricultural and Food Chemistry Pub Date : 2025-07-07 DOI:10.1021/acs.jafc.5c03549

Christian Nadegger,Patricia Frei,Christian A Elvert,Cornelia A Karg,Johanna M Gostner,Jonathan S Lindsey,Christoph R Kreutz,Stefan Schwaiger,Thomas Müller,Simone Moser

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Abstract

Hops is of high relevance to the food sector, and increasingly valued as medicinal plant. Its complex phytochemistry includes phenolic compounds and bitter prenylated polyketides, but phyllobilins─bioactive linear tetrapyrroles from chlorophyll catabolism─remain underexplored. In this work, several dioxobilin-type phylloleucobilins (DPleBs) and phylloxanthobilins (DPxBs) were identified in yellowish leaves of common hops (Humulus lupulus). Isolation from 107 g of leaves yielded 0.24 mg of Hl-DPleB-28 and 0.80 mg of Hl-DPxB-31. Structural elucidation via UV/vis, HR-MS2, and NMR confirmed those as new phyllobilins, featuring an unusual hydroxylation motif, indicating an uncharacterized metabolic pathway. Hl-DPxB constituted about 40% of HPLC peak areas at 420 nm in yellow leaves, suggesting its significant role in the visual senescence of hops. Hl-DPxB-31 possessed high antioxidative activity, comparable to quercetin. A virtual tool predicted over 60% bitterness probability. These findings expand the phytochemical profile of hops and highlight potential for upcycling leaf waste.

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酒花中叶绿磷脂的特性：抗氧化和潜在的苦衰老相关代谢产物。

啤酒花是高度相关的食品部门，并越来越重视作为药用植物。其复杂的植物化学成分包括酚类化合物和苦味烯酰化聚酮，但叶绿磷脂──叶绿素分解代谢产生的具有生物活性的线性四吡啶──仍未被充分发掘。在葎草属植物（Humulus lupulus）的黄黄色叶片中，分离到几种二氧化胆素型叶根绿胆素（DPleBs）和叶根黄胆素（DPxBs）。从107 g叶片中分离得到Hl-DPleB-28 0.24 mg和Hl-DPxB-31 0.80 mg。通过UV/vis， HR-MS2和NMR的结构解析证实了它们是新的叶绿bilins，具有不寻常的羟基化基序，表明未表征的代谢途径。在黄叶420 nm处，Hl-DPxB约占HPLC峰面积的40%，表明其在啤酒花视觉衰老中具有重要作用。Hl-DPxB-31具有与槲皮素相当的抗氧化活性。虚拟工具预测苦味概率超过60%。这些发现扩大了啤酒花的植物化学特征，并强调了升级回收叶片废物的潜力。

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来源期刊

Journal of Agricultural and Food Chemistry 农林科学-农业综合

CiteScore

9.90

自引率

8.20%

发文量

1375

审稿时长

2.3 months

期刊介绍： The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.