The essential oil of the condiment species Clinopodium thymifolium (Scop.) Kuntze: new natural products and seasonal variation
The essential oil of the condiment species Clinopodium thymifolium (Scop.) Kuntze: new natural products and seasonal variation
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DOI：
10.1002/jsfa.11583
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发表时间：
2021-10-30
影响因子：
4.1
通讯作者：
Licina, Braho
中科院分区：
文献类型：
--
作者：
Dekic, Milan;Radulovic, Niko;Licina, Braho
风轮菜（Clinopodium thymifolium）是广泛分布于地中海地区的芳香植物物种。它被认为是一种调味品，用于烹饪。作为一种有前途的香料植物，人们正在努力将这种植物作为一种新的作物品种引进，并已在意大利北方成功栽培。结果从一种香料植物C.采用气相色谱和气相色谱/质谱联用技术对麝香草属植物进行了分析。油的化学成分的详细分析的结果表明，胡薄荷酮，胡椒酮，胡椒烯酮和异薄荷酮的统治，以及胡薄荷酮/异薄荷酮的比例与植物的发育阶段的显着变化。此外，对油进行全面的化学分析，结合详细的光谱分析和选定化合物的化学合成，鉴定出两种新的天然产物：甲酸异薄荷酯和2-甲基丁酸新薄荷酯。结论在种群内水平上观察到的化学变异似乎是一种物候变异。从进化的意义上说，胡薄荷酮/异薄荷酮比例的改变表明它们可能在该物种对传粉者的生态适应中发挥作用。在不同的物候阶段，油的化学成分的显著数量变化可能与用于食用目的的植物材料的情况有关。(c)2021化学工业协会。
BACKGROUND Clinopodium thymifolium is an aromatic plant species that is widespread in the Mediterranean region. It has been considered as a condiment and is used in cooking. As a promising spice plant, some efforts are being made to introduce this plant as a new crop species and it has been successfully cultivated in northern Italy. RESULTS Essential oils isolated from the aerial parts of a flavoring species C. thymifolium were analyzed by gas chromatography and gas chromatography/mass spectrometry. The results of a detailed analysis of the chemical composition of the oils showed the domination of pulegone, piperitone, piperitenone and isomenthone, as well as a significant alteration of the pulegone/isomenthone ratio with the developmental stage of the plant. Additionally, a comprehensive chemical analysis of the oils in combination with detailed spectral analyses and chemical synthesis of selected compounds has led to the identification of two new natural products: isomenthyl formate and neomenthyl 2-methylbutanoate. CONCLUSION The observed chemical variability at the intrapopulation level appeared to be a phenological variation. In an evolutionary sense, the alteration of the pulegone/isomenthone ratio suggests their possible role in the ecological adaptation of the species to pollinators. Significant quantitative changes in the chemical composition of the oil at different phenological stages may be relevant in the case of plant material intended for edible purposes. (c) 2021 Society of Chemical Industry.