Cadinanes are typical plant sesquiterpenes with a broad range of biological functions. We report the isolation of three cadinanes (1-3) from a bacterial endophyte (Streptomyces sp.) of the mangrove plant Bruguiera gymnorrhiza. The structures of two new cadinenens, (+)-11-hydroxy-epicubenol (1) and (+)-12-hydroxy-epicubenol (2) were elucidated by NMR and mass spectrometry. The bacterial product (+)-11-hydroxy-epicubenol was elucidated to be an enantiomer of the plant product pubinernoid C. (+)-12-Hydroxy-epicubenol was established as a diastereomer of the basidiomycete product trichapargin A. In addition, a crystal structure analysis corroborated the structure and configuration of 5,11-epoxy-10-cadinanol (3), a cadinane cycloether initially described as a natural product from liverworth. The discovery of oxygenated cadinanes from a bacterial endophyte may set the basis for the production of cadinanes by bacterial fermentation.

中文翻译：

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来自放线菌红树林内生菌的植物样卡地烷倍半萜

Cadinanes 是典型的植物倍半萜，具有广泛的生物学功能。我们报告了从红树林植物 Bruguiera gemnorrhiza 的细菌内生菌 (Streptomyces sp.) 中分离出三种 cadinanes (1-3)。通过核磁共振和质谱法阐明了两种新的 cadinenens，(+)-11-羟基-epicubenol (1) 和 (+)-12-羟基-epicubenol (2) 的结构。细菌产物 (+)-11-羟基-epicubenol 被阐明为植物产品 pubineroid C 的对映异构体。 (+)-12-羟基-epicubenol 被确定为担子菌产物 trichapargin A 的非对映异构体。晶体结构分析证实了 5,11-epoxy-10-cadinanol (3) 的结构和构型，这是一种最初被描述为来自liverworth 的天然产物的cadinane 环醚。