Caryophyllenes from a Fungal Culture of Chrysosporium pilosum

Abstract

Four new caryophyllene derivatives, Sch 725432 (1), Sch 601253 (2), Sch 601254 (3), and Sch 725434 (4), were isolated from the fungal fermentation broth of Chrysosporium pilosum by reversed-phase HPLC purification. The structure elucidation of trioxygenated caryophyllenes 1-4 was accomplished on the basis of spectroscopic data interpretation. Sch 725434 (4) possesses a dihydrofuran-3-one ring, forming a tricyclic ring skeleton, which represents an unprecedented ring skeleton for the caryophyllene-type of sesquiterpenes. Compounds 1-4 were evaluated for their antifungal activity.

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.…”

Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

“…20 Therefore, 3 was assigned 1R, 2R, 5S, 6S, 8R, 9S, 10R, 11R, and 12S absolute configuration. Cytosporinols A-C (1-3) are closely related to the known taedolidol, 3 6-epitaedolidol, 3 and punctaporonin C (4), 7-9 all possessing the rare oxatetracyclo[6.3.2.0 1,4 .0 5,13 ]tridecane skeleton, but differ by having different substituents at C-6 (1), C-10 (1-3), and C-11 (3), as well as a tetrasubstituted olefin (1) and a terminal olefin (2). In addition, 1-3 are structurally similar to a synthetic byproduct 5 created in the acid-mediated cyclization of the nonatural enantiomer pestalotiopins, 23,24 but differ in having different configurations for all stereogenic centers and substituents at C-6 and C-11, respectively.…”

“…endophytic to the bark of Pinus taeda; 3 the 6-hydroxpunctaporonins, antibacterial metabolites from a fungicolous Pestalotiopsis disseminata; 4 fuscoatrol A, a cytotoxic agent from a marine-derived Humicola fuscoatra KMM 4629; 5 the punctaporonins (also named as punctatins), antifungal agents from a coprophilous Poronia punctata; [6][7][8][9][10][11] walleminol and walleminone, two cis-fused iso-caryophyllenes from the toxigenic fungus Wallemia sebi; 12 and Sch 725432, 601253, 601254, and 725434, antifungal agents from Chrysosporium pilosum. 13 During an ongoing search for new bioactive natural products from fungi of unique habitats, we initiated chemical studies of the fungi either inhabiting the fruiting body and larvae of Cordyceps sinensis 14 or its surface soil. 15 As an extension, we also studied those species isolated from the soil samples that were collected on the Qinghai-Tibetan plateau at altitudes above 3,200 m, the environment in which Cordyceps sinensis was typically found.…”