Caryophyllene sesquiterpenoids with various ring systems from the fungus Pestalotiopsis chamaeropis.

ABSTRACT

Six undescribed caryophyllene sesquiterpenoids named pestalotiopsins O-T, along with eight known analogues, were obtained from the fungus Pestalotiopsis chamaeropis. Their structures and absolute configurations were assigned by NMR spectroscopic analyses, HRESIMS, single-crystal X-ray diffraction, electronic circular dichroism (ECD) calculations, Mo2(OAc)4-induced ECD, and chemical derivatization. Pestalotiopsin P represents the first example of a caryophyllene sesquiterpenoid possessing an oxatricyclo [7.2.2.03.6]tridecane decorated with a rare bridgehead double bond, while pestalotiopsin Q has an oxatricyclic [6.3.1.01,4]dodecane skeleton with an unusual ether bridge between C-1 and C-5. These undescribed caryophyllene sesquiterpenoids were screened for their cytotoxic and anti-inflammatory activities.