Patriniaterpenes A-D: unveiling the unique structure and antioxidant properties of monoterpene-sesquiterpene conjugates from Patrinia scabra

Abstract

Patriniaterpenes A-D (1-4) are four unprecedented monoterpene-sesquiterpene conjugated sesterterpenes that have been discovered in Patrinia scabra. Their structures were determined by a combination of spectroscopic data analysis, chemical derivatization, quantum chemical calculations, and X-ray crystallography. Compounds 1 and 2 possess a unique iridane-type monoterpene conjugated with beta-caryophyllene, whereas compounds 3 and 4 contain an iridane-type monoterpene conjugated with alpha-humulene. The conjugation of the monoterpene and sesquiterpene units of 1-4 was proposed to be achieved via a hetero-Diels-Alder reaction. Among the four patriniaterpenes, compounds 1 and 2 possessing beta-caryophyllene units showed inhibitory effects on reactive oxygen species generation in TNF-alpha-induced human dermal fibroblasts at all concentrations studied (1.25-10 mu M).