Heptaketides from Corynespora sp. Inhabiting the Cavern Beard Lichen, Usnea cavernosa: First Report of Metabolites of an Endolichenic Fungus

Two new heptaketides, corynesporol (1) and 1-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1−3 were elucidated from their spectroscopic data. Aeri...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2007-11, Vol.70 (11), p.1700-1705
Main Authors: Paranagama, Priyani A, Wijeratne, E. M. Kithsiri, Burns, Anna M, Marron, Marilyn T, Gunatilaka, Malkanthi K, Arnold, A. Elizabeth, Gunatilaka, A. A. Leslie
Format: Article
Language:English
Subjects:
1-hydroxydehydroherbarin
acetylation
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Applied microbiology
Arizona
Ascomycota - chemistry
Biological and medical sciences
chemical structure
Chemotherapic agents
Corynespora
corynesporol
dehydroherbarin
Drug Screening Assays, Antitumor
Female
Fundamental and applied biological sciences. Psychology
herbarin
Humans
Lecanorales
lichens
Male
Microbiology
Molecular Structure
naphthalene
naphthoquinones
Naphthoquinones - chemistry
Naphthoquinones - isolation & purification
Naphthoquinones - pharmacology
oxidation
peptides
spectral analysis
Usnea
Usnea cavernosa
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Summary:Two new heptaketides, corynesporol (1) and 1-hydroxydehydroherbarin (2), along with herbarin (3) were isolated from an endolichenic fungal strain, Corynespora sp. BA-10763, occurring in the cavern beard lichen Usnea cavernosa. The structures of 1−3 were elucidated from their spectroscopic data. Aerial oxidation of corynesporol (1) yielded herbarin (3). Acetylation of 1 afforded the naphthalene derivative 4, whereas acetylation of 3 gave the corresponding naphthoquinone 6 and dehydroherbarin (5). All compounds were evaluated for their cytotoxicity and ability to inhibit migration of human metastatic breast and prostate cancer cell lines MDA-MB-231 and PC-3M, respectively. Dehydroherbarin (5) inhibited migration of both cell lines at concentrations not toxic to these cell lines. This is the first report of metabolites from an endolichenic fungus.
ISSN:0163-3864
1520-6025
DOI:10.1021/np070466w