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

Han Wei; Ya-ming Xu; Patricia Espinosa-Artiles; Manping X Liu; Jiang-Guang Luo; Jana M U'Ren; A Elizabeth Arnold; A A Leslie Gunatilaka

doi:10.1016/j.phytochem.2015.08.010

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

Phytochemistry. 2015 Oct:118:102-8. doi: 10.1016/j.phytochem.2015.08.010. Epub 2015 Aug 28.

Authors

Han Wei¹, Ya-ming Xu¹, Patricia Espinosa-Artiles¹, Manping X Liu¹, Jiang-Guang Luo², Jana M U'Ren³, A Elizabeth Arnold⁴, A A Leslie Gunatilaka⁵

Affiliations

¹ Southwest Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, The University of Arizona, 250 E. Valencia Road, Tucson, AZ 85706, United States.
² Southwest Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, The University of Arizona, 250 E. Valencia Road, Tucson, AZ 85706, United States; State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China.
³ School of Plant Sciences, College of Agriculture and Life Sciences, The University of Arizona, Tucson, AZ 85721, United States.
⁴ School of Plant Sciences, College of Agriculture and Life Sciences, The University of Arizona, Tucson, AZ 85721, United States; Department of Ecology and Evolutionary Biology, The University of Arizona, Tucson, AZ 85721, United States.
⁵ Southwest Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, The University of Arizona, 250 E. Valencia Road, Tucson, AZ 85706, United States. Electronic address: leslieg1@email.arizona.edu.

Abstract

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 1.44 μM, whereas cytochalasins C and Q exhibited moderate, but selective cytotoxicity.

Keywords: Cytochalasins; Fungal endophyte; Hypnum sp.; Sesquiterpenes; Xylaguaianols; Xylaria sp.; α-Pyrone.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Antineoplastic Agents / pharmacology
Bryophyta / microbiology*
Cytochalasins / chemistry
Cytochalasins / isolation & purification*
Cytochalasins / pharmacology
Drug Screening Assays, Antitumor
Humans
Inhibitory Concentration 50
Molecular Conformation
Molecular Structure
Polycyclic Sesquiterpenes
Pyrones / chemistry
Pyrones / isolation & purification
Sesquiterpenes
Sesquiterpenes, Guaiane / chemistry
Sesquiterpenes, Guaiane / isolation & purification*
Sesquiterpenes, Guaiane / pharmacology
Xylariales / chemistry*

Substances

Antineoplastic Agents
Cytochalasins
Polycyclic Sesquiterpenes
Pyrones
Sesquiterpenes
Sesquiterpenes, Guaiane
cadinane
cytochalasin C

Abstract

Publication types

MeSH terms

Substances

Grants and funding