4.8 Article

Periconiastone A, an Antibacterial Ergosterol with a Pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane System from Periconia sp. TJ403-rc01

Journal

ORGANIC LETTERS
Volume 21, Issue 20, Pages 8469-8472

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03270

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Funding

  1. Program for Changjiang Scholars of Ministry of Education of the People's Republic of China [T2016088]
  2. National Science Fund for Distinguished Young Scholars [81725021]
  3. Innovative Research Groups of the National Natural Science Foundation of China [81721005]
  4. National Natural Science Foundation of China [21702067, 81573316]

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Periconiastone A (1), an ergosterol with an unprecedented pentacyclo [8.7.0.0(1,5)0(2,14).0(10,15)]heptadecane system, was isolated from Periconia sp. TJ403-rc01. Its structure was assigned by extensive spectroscopic analyses and quantum-chemical C-13 NMR and ECD calculations. A vinylogous alpha-ketol rearrangement and an aldol condensation reaction during biosynthesis were proposed as key steps for the formation of 1. Compound 1 showed antibacterial activity against Gram-positive S. aureus and E. faecalis with MIC values of 4 and 32 mu g/mL, respectively.

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