Comprehensive analysis of chemical and enantiomeric stability of terpenes in Cannabis sativa L. flowers.

IF 3 3区 生物学 Q2 BIOCHEMICAL RESEARCH METHODS Phytochemical Analysis Pub Date : 2024-08-05 DOI:10.1002/pca.3432
Justine Raeber, Bryan Bajor, Michael Poetzsch, Christian Steuer
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Abstract

Objective: Cannabis sativa L. is renowned for its medicinal and recreational uses. With the increasing global legalization of C. sativa L.-based products for medicinal purposes, there is a growing need for well-characterized products. While the stability of cannabinoids such as tetrahydrocannabinol and cannabidiol is well understood, information on the chemical and enantiomeric stability of terpenes remains scarce. This is despite the fact that terpenes are also thought to have pharmacological activity and may contribute to the overall effect of C. sativa L.

Methods: To address these challenges, four analytical methods based on chiral, polar, and apolar gas chromatographic separation combined with either MS or FID detection were developed and validated. These methods successfully separated and quantified a total of 29 terpenes, including 13 enantiomers and 5 diastereomers specific to C. sativa L. Furthermore, terpenes and authentic C. sativa L. flowers and extracts were subjected to UV and heat treatments to observe potential degradation reactions over time.

Results: Each terpene generates a unique pattern of degradation products resulting in a diverse array of oxidation and cyclization products. P-cymene was identified as a major product of terpene aging. Notably, no enantiomeric conversion was detected, suggesting that the formation of (-)-α-pinene in cannabis extracts, for example, originates from other terpenes.

Conclusion: Terpenes have different degradation rates, even though they are structurally similar. In addition, cultivar- and growth-condition-specific enantiomeric ratios were observed in C. sativa L., confirming that enantiomer production is species-specific and has to be considered for therapeutical applications.

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全面分析大麻花中萜烯类化合物的化学稳定性和对映体稳定性。
目的:大麻因其药用和娱乐用途而闻名于世。随着以大麻为基础的药用产品在全球范围内日益合法化,对特性良好的产品的需求与日俱增。四氢大麻酚和大麻二酚等大麻素的稳定性已广为人知,但有关萜类化合物的化学稳定性和对映体稳定性的信息仍然很少。尽管萜烯也被认为具有药理活性,并可能有助于提高大麻的整体效果,但这方面的信息仍然很少:为了应对这些挑战,我们开发并验证了四种基于手性、极性和非极性气相色谱分离并结合 MS 或 FID 检测的分析方法。这些方法成功地分离和定量了 29 种萜烯,包括 13 种对映体和 5 种非对映体。此外,还对萜烯和真正的荠菜花及提取物进行了紫外线和热处理,以观察随着时间的推移可能发生的降解反应:结果:每种萜烯都会产生一种独特的降解产物模式,从而产生一系列不同的氧化和环化产物。经鉴定,对伞花烃是萜烯老化的主要产物。值得注意的是,没有检测到对映体的转化,这表明例如大麻提取物中 (-)-α蒎烯的形成源自其他萜烯:结论:尽管萜烯的结构相似,但它们的降解率却各不相同。此外,在 C. sativa L. 中观察到了与栽培品种和生长条件相关的对映体比率,这证实了对映体的产生具有物种特异性,在治疗应用中必须加以考虑。
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来源期刊
Phytochemical Analysis
Phytochemical Analysis 生物-分析化学
CiteScore
6.00
自引率
6.10%
发文量
88
审稿时长
1.7 months
期刊介绍: Phytochemical Analysis is devoted to the publication of original articles concerning the development, improvement, validation and/or extension of application of analytical methodology in the plant sciences. The spectrum of coverage is broad, encompassing methods and techniques relevant to the detection (including bio-screening), extraction, separation, purification, identification and quantification of compounds in plant biochemistry, plant cellular and molecular biology, plant biotechnology, the food sciences, agriculture and horticulture. The Journal publishes papers describing significant novelty in the analysis of whole plants (including algae), plant cells, tissues and organs, plant-derived extracts and plant products (including those which have been partially or completely refined for use in the food, agrochemical, pharmaceutical and related industries). All forms of physical, chemical, biochemical, spectroscopic, radiometric, electrometric, chromatographic, metabolomic and chemometric investigations of plant products (monomeric species as well as polymeric molecules such as nucleic acids, proteins, lipids and carbohydrates) are included within the remit of the Journal. Papers dealing with novel methods relating to areas such as data handling/ data mining in plant sciences will also be welcomed.
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