A Caryophyllene-Related Sesquiterpene and Two 6,7-Seco-caryophyllenes from Liquid Cultures of Hebeloma longicaudum

Three new caryophyllene-related sesquiterpenes, hebelophyllenes D (1), E (2), and F (3), were isolated from liquid cultures of the ectomycorrhizal fungus Hebeloma longicaudum. Their structures were determined by modern spectroscopic methods. Hebelophyllene D has a tricyclo[5.4.0.02,5]undecane skeleton, while hebelophyllenes E and F are the first naturally occurring 6,7-seco-caryophyllenes.