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香榧精油的化学成分及关键单萜类化合物的对映体分析

Chemical composition of Torreya grandis essential oils and enantiomeric analysis of key monoterpenes.

作者信息

Yu Jinlong, Yao Boan, Su Fangyao, Liao Zhengmao, Liu Yongguo, Sun Baoguo, Tian Hongyu, Liang Sen

机构信息

Key Laboratory of Geriatric Nutrition and Health, Beijing Technology and Business University, Ministry of Education, Beijing 100048, China; Beijing Key Laboratory of Flavor Chemistry, Beijing 100048, China.

Zhengmao Ecological Agriculture Development Co., Ltd. of Tongshan County, Hubei Province 437600, China.

出版信息

Fitoterapia. 2025 Sep;185:106778. doi: 10.1016/j.fitote.2025.106778. Epub 2025 Jul 31.

DOI:10.1016/j.fitote.2025.106778
PMID:40752795
Abstract

This study chemically characterized three Torreya grandis (T. grandis) essential oil samples provided by Zhengmao Ecological Agriculture Development Co. (Hubei, China), obtained through their standardized steam distillation of: (1) fresh arils, (2) dried arils, and (3) combined leaves/twigs. GC-MS analysis identified 107 terpenoid compounds, with limonene (210.96-328.05 mg/mL) and α-pinene (131.30-237.40 mg/mL) as dominant constituents. Five secondary components (β-pinene, 3-carene, β-myrcene, terpinolene, δ-cadinene) consistently occurred at 10-100 mg/mL. Chiral resolution demonstrated enantiomeric specificity: (-)-α-pinene showed tissue-dependent enrichment (78 % ee in arils vs. 29 % in leaves/twigs), whereas (R)-(+)-limonene maintained near-enantiopurity (∼96 % ee) across all samples. Isolation and optical rotation analysis confirmed (+)-torreyol in leaf/twig oils. Bioactivity assessments revealed concentration-dependent antioxidant capacity (2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging up to 89 % at 100 mg/mL) and selective antibacterial effects, with aril oils exhibiting strong inhibition against Staphylococcus aureus (S. aureus) (30.16 mm zone) but limited activity against Escherichia coli (E. coli), though less potent than BHT (IC 40.73-64.77 mg/mL vs. 94 μg/mL). The distinct enantiomeric patterns and abundant bioactive terpenoids highlight T. grandis essential oils as sustainable, high-value ingredients for flavor/fragrance industries, motivating further research into their biosynthetic regulation and commercial optimization.

摘要

本研究对湖北正茂生态农业发展有限公司提供的三个榧树(Torreya grandis)精油样品进行了化学表征,这些样品通过标准化水蒸气蒸馏法从以下材料中获得:(1)新鲜假种皮、(2)干燥假种皮、(3)叶/枝混合物。气相色谱-质谱联用(GC-MS)分析鉴定出107种萜类化合物,其中柠檬烯(210.96 - 328.05毫克/毫升)和α-蒎烯(131.30 - 237.40毫克/毫升)为主要成分。五种次要成分(β-蒎烯、3-蒈烯、β-月桂烯、萜品油烯、δ-杜松烯)的含量始终在10 - 100毫克/毫升之间。手性拆分显示出对映体特异性:(-)-α-蒎烯表现出组织依赖性富集(假种皮中对映体过量百分比为78%,而叶/枝中为29%),而(R)-(+)-柠檬烯在所有样品中保持接近对映体纯度(约96%对映体过量百分比)。分离和旋光分析证实叶/枝精油中存在(+)-榧树醇。生物活性评估揭示了浓度依赖性抗氧化能力(在100毫克/毫升时,2,2-二苯基-1-苦基肼(DPPH)清除率高达89%)和选择性抗菌作用,假种皮精油对金黄色葡萄球菌(S. aureus)表现出强烈抑制作用(抑菌圈直径为30.16毫米),但对大肠杆菌(E. coli)的活性有限,不过其效力低于丁基羟基甲苯(IC为40.73 - 64.77毫克/毫升,而丁基羟基甲苯为94微克/毫升)。独特的对映体模式和丰富的生物活性萜类化合物突出了榧树精油作为香料/香精行业可持续、高价值成分的特点,这促使人们进一步研究其生物合成调控和商业优化。

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