Cannabicitran: Its unexpected racemic nature and potential origins
Cannabicitran: Its unexpected racemic nature and potential origins
复制标题
大麻素：其意想不到的外消旋性质和潜在起源
DOI：
10.1002/chir.23571
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发表时间：
2023
期刊：
影响因子：
2
通讯作者：
Williamson, R. Thomas
中科院分区：
文献类型：
--
作者：
Wood, Jared S.;Gordon, William H.;Morgan, Jeremy B.;Williamson, R. Thomas
Cannabicitran是一种大麻素，在商业“纯化”大麻二酚（CBD）提取物中含量高达10%。这种天然产物的结构在50多年前首次报道。然而，很少有研究调查cannabicitran或其来源，尽管使用大麻素治疗各种生理条件的兴趣迅速增加。在最近详细的NMR和cannabicitran的计算表征之后，我们的小组发起了ECD和TDDFT研究，旨在明确确定Cannabis sativa提取物中cannabicitran的绝对构型。令我们惊讶的是，我们发现这种天然产物是外消旋的，这引发了人们对其假定的酶促来源的质疑。在此，我们报告了（-）-cannabicitran和（+）-cannabicitran的分离和绝对构型。几种可能的情况下，在工厂和/或提取物加工过程中生产的rachetine进行了讨论。
Cannabicitran is a cannabinoid found in levels up to ~10% in commercial “purified” cannabidiol (CBD) extracts. The structure of this natural product was first reported more than 50 years ago. However, few studies have investigated cannabicitran or its origin despite the rapidly increasing interest in the use of cannabinoids for the treatment of a wide range of physiological conditions. Following on a recent detailed NMR and computational characterization of cannabicitran, our group initiated ECD and TDDFT studies aimed at unequivocally determining the absolute configuration of cannabicitran present inCannabis sativaextracts. To our surprise, we discovered the natural product was racemic, raising questions around its presumed enzymatic origin. Herein, we report the isolation and absolute configuration of (−)‐cannabicitran and (+)‐cannabicitran. Several possible scenarios for production of the racemate in the plant and/or during extract processing are discussed.