A screening program was conducted to find microorganisms that modify the synthetic cannabinoid nabilone. After purification, the products from three cultures were analyzed by spectral methods to determine their chemical structures. An optically active 9S-hydroxy-6aR,10aR-trans cannabinoid was isolated from a culture of an unidentified soil bacterium designated A24007. From Bacillus cereus cultures were isolated a 9S,6'-dihydroxy-6aR,10aR-trans cannabinoid, a 9S-hydroxy-6'-keto-6aR,10aR-trans cannabinoid, a 9-keto-6'-hydroxy-6aS,10aS-trans cannabinoid, and a 6',9-diketo-6aS,10aS-trans cannabinoid. All of these products were optically active, as was a 9S-hydroxy-6aS,10AS-trans cannabinoid also isolated from B. cereus cultures. A series of acidic products were isolated from cultures of Nocardia salmonicolor. All of these products contained a carboxylic acid group at the terminal end of three-position alkyl side chains having varying numbers of carbon atoms. Two of the acidic products contained a 9-keto group, whereas all other carboxylic acid products were 9-hydroxy cannabinoids. The array of products obtained from incubation of nabilone indicates the usefulness of microbial transformations in the preparation of new cannabinoids.

译文

进行了一项筛选程序,以发现修饰合成大麻素纳比酮的微生物。纯化后,通过光谱法分析三种培养物的产物以确定其化学结构。从鉴定为a24007的未鉴定土壤细菌的培养物中分离出光学活性的9s-羟基-6ar,10ar-反式大麻素。从蜡样芽孢杆菌培养物中分离出9S,6 '-dihydroxy-6aR,10ar-反式大麻素,9s-羟基-6'-keto-6aR,10ar-反式大麻素,9-酮-6 '-hydroxy-6aS,10as-反式大麻素和6',9-二酮-6as,10as-反式大麻素。所有这些产品都是光学活性的,从蜡状芽孢杆菌培养物中也分离出9s-羟基-6as,10as-反式大麻素也是如此。从鲑鱼诺卡氏菌培养物中分离出一系列酸性产物。所有这些产物在具有不同碳原子数的三位烷基侧链的末端均包含羧酸基团。其中两个酸性产物含有9-酮基团,而所有其他羧酸产物都是9-羟基大麻素。从纳比酮的孵育中获得的一系列产品表明微生物转化在制备新大麻素中的有用性。

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