2. Academic Validation
  3. Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum

Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum

  • J Nat Prod. 2016 Jul 22;79(7):1783-90. doi: 10.1021/acs.jnatprod.6b00218.
Haibo Zhou 1,  Liyuan Li 1,  Chongming Wu 2,  Tibor Kurtán 3,  Attila Mándi 3,  Yankai Liu 1,  Qianqun Gu 1,  Tianjiao Zhu 1,  Peng Guo 2,  Dehai Li 1
Affiliations

Affiliations

  • 1 Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
  • 2 Pharmacology and Toxicology Research Center, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing 100193, People's Republic of China.
  • 3 Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
PMID: 27359163 DOI: 10.1021/acs.jnatprod.6b00218
Abstract

Six new pyridone Alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes.

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