An unprecedented ergostane with a 6/6/5 tricyclic 13(14?8) abeo-8,14-seco skeleton from Talaromyces adpressus

作者：Zhang, Mi; Li, Qin; Li, Shuangjun; Deng, Yanfang; Yu, Muyuan; Liu, Jinping; Qi, Changxing; Yang, Xiliang^*; Zhu, Hucheng^*; Zhang, Yonghui^*

来源：Bioorganic Chemistry, 2022, 127: 105943.

DOI：10.1016/j.bioorg.2022.105943

• Rearranged steroid
• Talaromyces adpressus
• Dankasterone
• Anti-inflammatory activity
• NF-kappa B pathway

Talasterone A (1), an unprecedented 6/6/5 tricyclic 13(14 -> 8)abeo-8,14-seco-ergostane steroid, together with two known congeners dankasterone B (2) and (14 beta,22E)-9,14-dihydroxyergosta-4,7,22-triene-3,6-dione (3), were characterized from Talaromyces adpressus. The structure of 1 with absolute configuration was elucidated based on NMR spectroscopic data and ECD calculation. Compound 2 belongs to a class of unconventional 13(14 -> 8)abeo-ergostanes, which have been renewed via the 1,2-migration of C-13-C-14 bond to C-8. In addition, compound 1 represents the first example of ergostane with a tricyclic 13(14-+ 8)abeo-8,14-seco-ergostane skeleton. The proposed biosynthetic pathway was established with the support of the coisolation of the known congeners from the producing organism. It is especially noteworthy that compound 1 exhibited potent antiinflammatory activity with an IC50 value of 8.73 +/- 0.66 mu M, inhibiting the NF-kappa B pathway and thus reducing the production of proinflammatory cytokines.

• 单位
  华中科技大学