The biotransformation of patchouli alcohol by Cladosporium cladosporioides afforded 31 products, including 21 new ones (1–3, 5, 6, 8–14, and 17–25). Their structures were determined by extensive spectroscopic data analysis (¹H and ¹³C NMR, HSQC, HMBC, ¹H–¹H COSY, ROESY, and HRESIMS), and the absolute configuration of compounds 1, 2, 8, 9, and 17 was determined by single-crystal X-ray diffraction using Cu Kα radiation. Structurally, compounds 21–24 were patchoulol-type norsesquiterpenoids without Me-12. Among them, a Δ³⁽⁴⁾ double bond existed in compounds 21 and 22; a three-membered ring was formed between C-4, C-5, and C-6 in compound 23; an epoxy moiety appeared between C-3 and C-4 in compound 24. Furthermore, the biotransformation products 9, 10, 12, and 25 showed potent anti-influenza virus activity with EC₅₀ values of 2.11, 7.94, 20.87, and 3.45 μM, respectively.

中文翻译：

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枝孢枝孢菌生物转化广藿香醇及其生物转化产物的抗流感病毒活性

枝孢枝孢菌对广藿香醇进行生物转化，得到31个产物，其中21个新产物（1-3、5、6、8-14、17-25 ）。它们的结构通过广泛的光谱数据分析（ ¹ H 和¹³ C NMR、HSQC、HMBC、¹ H– ¹ H COSY、ROESY 和 HRESIMS）以及化合物1、2、8、9和17的绝对构型确定通过使用 Cu Kα 辐射的单晶 X 射线衍射测定。从结构上看，化合物21-24是不含 Me-12 的广藿香醇型诺倍半萜类化合物。其中，化合物21和22中存在Δ ³⁽⁴⁾双键；化合物23中C-4、C-5、C-6之间形成三元环；化合物24中C-3和C-4之间出现环氧部分。此外，生物转化产物9、10、12和25显示出有效的抗流感病毒活性，EC 50_值分别为2.11、7.94、20.87和3.45μM。