目的:大麻以其医药和娱乐用途而闻名。随着基于C.sativaL.的药用产品的全球合法化,对特征良好的产品的需求日益增长。虽然大麻素如四氢大麻酚和大麻二酚的稳定性是众所周知的,有关萜烯的化学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,并且可能有助于C.sativaL.
方法:为了应对这些挑战,基于手性的四种分析方法,极地,开发并验证了非极性气相色谱分离与MS或FID检测的结合。这些方法成功地分离和定量了总共29种萜烯,包括13种对映体和5种非对映体。对萜烯和真正的紫花苜蓿花和提取物进行UV和热处理以观察随时间的潜在降解反应。
结果:每种萜烯都会产生独特的降解产物模式,从而产生多种氧化和环化产物。对异丙基苯被确定为萜烯老化的主要产物。值得注意的是,没有检测到对映体转化,表明大麻提取物中(-)-α-pine烯的形成,例如,源自其他萜烯。
结论:萜烯具有不同的降解率,尽管它们在结构上相似。此外,在苜蓿中观察到品种和生长条件特异性对映体比例,确认对映异构体的产生是物种特异性的,必须考虑用于治疗应用。
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.
CONCLUSIONS: 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.