Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa: First report of metabolites of an endolichenic fungus

Priyani A. Paranagama, E. M Kithsiri Wijeratne, Anna M. Burns, Marilyn T. Marron, Malkanthi K. Gunatilaka, Anne E Arnold, Leslie Gunatilaka

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1700-1705
Number of pages6
JournalJournal of Natural Products
Volume70
Issue number11
DOIs
StatePublished - Nov 2007

Fingerprint

Usnea
Corynespora
Lichens
Metabolites
Fungi
lichens
cell lines
acetylation
metabolites
Acetylation
fungi
Cells
Cell Line
naphthoquinones
naphthalene
prostatic neoplasms
Naphthoquinones
breast neoplasms
cytotoxicity
Poisons

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa : First report of metabolites of an endolichenic fungus. / Paranagama, Priyani A.; Wijeratne, E. M Kithsiri; Burns, Anna M.; Marron, Marilyn T.; Gunatilaka, Malkanthi K.; Arnold, Anne E; Gunatilaka, Leslie.

In: Journal of Natural Products, Vol. 70, No. 11, 11.2007, p. 1700-1705.

Research output: Contribution to journalArticle

Paranagama, Priyani A. ; Wijeratne, E. M Kithsiri ; Burns, Anna M. ; Marron, Marilyn T. ; Gunatilaka, Malkanthi K. ; Arnold, Anne E ; Gunatilaka, Leslie. / Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa : First report of metabolites of an endolichenic fungus. In: Journal of Natural Products. 2007 ; Vol. 70, No. 11. pp. 1700-1705.
@article{48302046693648a4bc04613b5f430a16,
title = "Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa: First report of metabolites of an endolichenic fungus",
abstract = "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.",
author = "Paranagama, {Priyani A.} and Wijeratne, {E. M Kithsiri} and Burns, {Anna M.} and Marron, {Marilyn T.} and Gunatilaka, {Malkanthi K.} and Arnold, {Anne E} and Leslie Gunatilaka",
year = "2007",
month = "11",
doi = "10.1021/np070466w",
language = "English (US)",
volume = "70",
pages = "1700--1705",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - Heptaketides from Corynespora sp. inhabiting the cavern beard lichen, Usnea cavernosa

T2 - First report of metabolites of an endolichenic fungus

AU - Paranagama, Priyani A.

AU - Wijeratne, E. M Kithsiri

AU - Burns, Anna M.

AU - Marron, Marilyn T.

AU - Gunatilaka, Malkanthi K.

AU - Arnold, Anne E

AU - Gunatilaka, Leslie

PY - 2007/11

Y1 - 2007/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=37249061370&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37249061370&partnerID=8YFLogxK

U2 - 10.1021/np070466w

DO - 10.1021/np070466w

M3 - Article

C2 - 17988097

AN - SCOPUS:37249061370

VL - 70

SP - 1700

EP - 1705

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 11

ER -