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

Abstract

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[5.4.0.0(2,5)]undecane skeleton, while hebelophyllenes E and F are the first naturally occurring 6,7-seco-caryophyllenes.

Endophyte inspired chemical diversity from beta-caryophyllene

“…in cloves) 7-9 and microorganisms [10][11][12][13][14][15] . Due to its strained cyclobutane, macrocyclic moiety and exocyclic olefin, βcaryophyllene acts as a key precursor in nature to form diverse tricyclic sesquiterpenes by transannular rearrangements.…”

Talaromyces wortmannii FS2 emits β-caryphyllene, which promotes plant growth and induces resistance

“…b-Caryophyllene and its analogues are common constituents in essential oils from many herbaceous plants such as Syzygium aromaticum, Cannabis sativa, Rosmarinus oficinalis. Its derivatives have also been reported from several fungal species such as Pestalotiopsis disseminata (Deyrup et al 2006), Wallemia sebi (Frank et al 1999), Poronia punctata (Anderson et al 1988), Naematoloma fasciculare (Shiono et al 2004), Hypoxylon terricola (Edwards et al 1989), Hebeloma longicaudum (Wichlacz et al 1999), Chrysosporium pilosum (Yang et al 2009), Penicillium commune, P. hirsutum, P. allii and P. roqueforti (Larsen and Frisvad 1995). Some of these fungi are endo-or ectomycorrhiza.…”

Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from Pestalotiopsis adusta, an endophytic fungus of Sinopodophyllum hexandrum

“…14 Although b-caryophyllene is widely distributed, its highly oxygenated derivatives are not common. 7 Until now, only a few highly oxygenated caryophyllene-type sesquiterpenes have been reported from terrestrial plant endophyte, including three unprecedented novel compounds cytosporinols A-C. [15][16][17][18][19][20][21][22][23][24] The highly oxygenated caryophyllenetype sesquiterpenes also attracted the interests of synthetic chemists due to their structural characteristics and special bioactivities. 25 In our continuous screening for bioactive natural products from plant endophytes, [26][27][28] we investigated an endophytic fungus Pestalotiopsis adusta collected from the stem bark of wild rare medicinal plant Sinopodophyllum hexandrum (Royle) Ying in Qinling Mountains.…”