2. Academic Validation
  3. Absolute Configuration of Oxabornyl Polyenes Prugosenes A1-A3 and Structural Revision of Prugosene A2

Absolute Configuration of Oxabornyl Polyenes Prugosenes A1-A3 and Structural Revision of Prugosene A2

  • J Nat Prod. 2024 May 24;87(5):1338-1346. doi: 10.1021/acs.jnatprod.3c01143.
Fu-Long Lin 1 2,  Jia-Ling Gao 1,  Qian Xu 1,  Gao-Qian Wang 1,  Liang-Yan Xiao 1,  Lu Dong 1,  Wei Tang 1,  Jian-Ming Lv 1,  Guo-Dong Chen 1,  Ying Wang 1,  Zhi-Nan Yin 2 3,  Li-Gong Lu 2,  Dan Hu 1,  Hao Gao 1
Affiliations

Affiliations

  • 1 Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou 510632, China.
  • 2 Guangdong Provincial Key Laboratory of Tumor Interventional Diagnosis and Treatment, Zhuhai Institute of Translational Medicine, Zhuhai People's Hospital Affiliated with Jinan University, Jinan University, Zhuhai, 519000, Guangdong China.
  • 3 The Biomedical Translational Research Institute, Faculty of Medical Science, Jinan University, Guangzhou, 510632, China.
PMID: 38447084 DOI: 10.1021/acs.jnatprod.3c01143
Abstract

Oxabornyl polyenes represent a unique group of polyketides characterized by a central polyene core flanked by a conserved oxabornyl moiety and a structurally diverse oxygen heterocyclic ring. They are widely distributed in fungi and possess a variety of biological activities. Due to the significant spatial separation between the two stereogenic ring systems, it is difficult to establish their overall relative configurations. Here, we isolated three oxabornyl polyenes, prugosenes A1-A3 (1-3), from Talaromyces sp. JNU18266-01. Although these compounds were first reported from Penicillium rugulosum, their overall relative and absolute configurations remained unassigned. By employing ozonolysis in combination with ECD calculations, we were able to establish their absolute configurations, and additionally obtained seven new chemical derivatives (4-10). Notably, through NMR data analysis and quantum chemical calculations, we achieved the structural revision of prugosene A2. Furthermore, prugosenes A1-A3 exhibited potent Antiviral activity against the respiratory syncytial virus, with compound 1 displaying an IC50 value of 6.3 μM. Our study thus provides a valuable reference for absolute configuration assignment of oxabornyl polyene compounds.

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