Sesquiterpenes and other constituents of Xylaria sp. NC1214, a fungal endophyte of the moss Hypnum sp

Xylaguaianols A−D, isocadinanol A, and 9-hydroxyxylarone, together with several known sesquiterpenes and cytochalasins were encountered in Xylaria sp. NC1214, a fungal endophyte of the moss Hypnum sp. Cytochalasin D showed significant cytotoxicity against five cancer cell lines. Cytochalasins C and...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2015-10, Vol.118, p.102-108
Main Authors: Wei, Han, Xu, Ya-ming, Espinosa-Artiles, Patricia, Liu, Manping X., Luo, Jiang-Guang, U’Ren, Jana M., Elizabeth Arnold, A., Leslie Gunatilaka, A.A.
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Bryophyta - microbiology
Cytochalasins
Cytochalasins - chemistry
Cytochalasins - isolation & purification
Cytochalasins - pharmacology
Drug Screening Assays, Antitumor
Fungal endophyte
Humans
Hypnum sp
Inhibitory Concentration 50
Molecular Conformation
Molecular Structure
Pyrones - chemistry
Pyrones - isolation & purification
Sesquiterpenes
Sesquiterpenes, Guaiane - chemistry
Sesquiterpenes, Guaiane - isolation & purification
Sesquiterpenes, Guaiane - pharmacology
Xylaguaianols
Xylaria sp
Xylariales - chemistry
α-Pyrone
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Summary:Xylaguaianols A−D, isocadinanol A, and 9-hydroxyxylarone, together with several known sesquiterpenes and cytochalasins were encountered in Xylaria sp. NC1214, a fungal endophyte of the moss Hypnum sp. Cytochalasin D showed significant cytotoxicity against five cancer cell lines. Cytochalasins C and Q exhibited moderate, but selective cytotoxicity. [Display omitted] •Isolation and characterization of metabolites from a Xylaria sp. endophytic in a moss.•Structure elucidation of five sesquiterpenes and one α-pyrone by the application of spectroscopic techniques.•Evaluation of cytotoxicity of three cytochalasins against five sentinel tumor cell lines. Oxygenated guaiane-type sesquiterpenes, xylaguaianols A−D (1–4), an iso-cadinane-type sesquiterpene isocadinanol A (5), and an α-pyrone 9-hydroxyxylarone (6), together with five known sesquiterpenes (7–11), and four known cytochalasins (12–15) were isolated from a culture broth of Xylaria sp. NC1214, a fungal endophyte of the moss Hypnum sp. The structures of all compounds were elucidated by the analysis of their spectroscopic data and relative configurations of 1–5 were determined with the help of NMR NOESY experiments. Cytochalasins C (12), D (13), and Q (14) were investigated for their cytotoxic activity against five tumor cell lines. Cytochalasin D showed significant cytotoxicity against all five cell lines, with IC50s ranging from 0.22 to 1.44μM, whereas cytochalasins C and Q exhibited moderate, but selective cytotoxicity.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2015.08.010