Six New Induced Sesquiterpenes from the Cultures of Ascomycete Daldinia concentrica

Abstract

Six new sesquiterpenes having the botryane carbon skeleton (1ϳ6), together with known compounds (7ϳ10) were induced and isolated from the ascomycete Daldinia concentrica (strain S 0318). Structures elucidation was accomplished by NMR spectroscopic and X-ray crystallographic studies.

Botryane, noreudesmane and abietane terpenoids from the ascomycete Hypoxylon rickii

“…None of these genera is regarded to be pathogenic, even though the Xylariaceae have sometimes been reported to cause disease symptoms in stressed and weakened host plants. Interestingly, Qin et al (2008) even reported that they only obtained the botryanes after induction experiments during the fermentation of their Daldinia strain. Further studies should be conducted in order to evaluate the ecological role of botryane sesquiterpenoids in these fungi and their potential as pathogenicity factors during the life cycle of the saprotrophic and endophytic producer organisms.…”

“…Many derivatives are known to have phytotoxic effects and therefore are regarded as pathogenicity factors (Deighton et al, 2001). Meanwhile, similar metabolites were obtained from the genera Hypocrea (an ascospore isolate of a wood-degrading member of the Hypocreaceae; see Yuan et al, 2013), as well as from the xylariaceous genera Geniculosporium (an endophyte, see Krohn et al, 2005) and a strain of an ascospore-derived isolate of Daldinia (Qin et al, 2008). None of these genera is regarded to be pathogenic, even though the Xylariaceae have sometimes been reported to cause disease symptoms in stressed and weakened host plants.…”

New benzene derivatives from cultures of ascomycete Daldinia concentrica

“…Therefore, compound 4 can be identified as (S)-2-hydroxymethyl-3-(1-hydroxypropyl)phenol. 5 . This important information suggested that compound 2 might be a dimer of 4, possessing two completely symmetrical units.…”

“…The initial chemical investigation of the fruiting bodies of D. concentrica reported two new 4:5:4′:5′-tetrahydroxy-1:1′-binaphthyl and dihydroxyperylene quinone in 1958, 2 more than 40 natural products have been so far isolated, including benzene derivatives, 3 azaphilone derivatives, 4 sesquiterpenoids, 5 squalene-type triterpenoids, 6 steroids, 7 cytochalasins, 3d,3e etc. Of these, a substantial number possess significant bioactivities.…”

Non-isoprenoid botryane sesquiterpenoids from basidiomycete Boletus edulis and their cytotoxic activity

“…Botryane sesquiterpenoids possess a non-isopreniod system skeleton, which have been found limited to several fungi such as Botrytis cinerea 1 and Daldinia concentrica 2 . The representative botryane sesquiterpenoids are botrydial 1a and its derivatives, which are characterized from phytopathogenic fungus B. cinerea.…”