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

Three new caryophyllene-related sesquiterpenes, hebelophyllenes D (<b>1</b>), E (<b>2</b>), and F (<b>3</b>), were isolated from liquid cultures of the ectomycorrhizal fungus <i>Hebeloma longicaudum</i>. Their structures were determined by modern spectroscopic methods. Hebelophyllene D has a tricyclo[5.4.0.0<sup>2,5</sup>]undecane skeleton, while hebelophyllenes E and F are the first naturally occurring 6,7-seco-caryophyllenes.