Sesquiterpene quinones and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran desert

E. M.Kithsiri Wijeratne; Priyani A. Paranagama; Marilyn T. Marron; Malkanthi K. Gunatilaka; A. Elizabeth Arnold; A. A.Leslie Gunatilaka

doi:10.1021/np070600c

Sesquiterpene quinones and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran desert

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

Research output: Contribution to journal › Article › peer-review

61 Scopus citations

Abstract

Five new metabolites, (+)-(5S,10S)-4′-hydroxymethylcyclozonarone (1), 3-ketotauranin (3), 3α-hydroxytauranin (4), 12-hydroxytauranin (5), and phyllospinarone (6), together with tauranin (2), were isolated from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis. The structures of the new compounds were determined on the basis of their 1D and 2D NMR spectroscopic data and chemical interconversions. All compounds were evaluated for inhibition of cell proliferation in a panel of five cancer cell lines, and only tauranin (2) showed activity. When tested in a flow cytometry-based assay, tauranin induced apoptosis in PC-3M and NIH 3T3 cell lines.

Original language	English (US)
Pages (from-to)	218-222
Number of pages	5
Journal	Journal Of Natural Products
Volume	71
Issue number	2
DOIs	https://doi.org/10.1021/np070600c
State	Published - Feb 2008

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np070600c

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title = "Sesquiterpene quinones and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran desert",

abstract = "Five new metabolites, (+)-(5S,10S)-4′-hydroxymethylcyclozonarone (1), 3-ketotauranin (3), 3α-hydroxytauranin (4), 12-hydroxytauranin (5), and phyllospinarone (6), together with tauranin (2), were isolated from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis. The structures of the new compounds were determined on the basis of their 1D and 2D NMR spectroscopic data and chemical interconversions. All compounds were evaluated for inhibition of cell proliferation in a panel of five cancer cell lines, and only tauranin (2) showed activity. When tested in a flow cytometry-based assay, tauranin induced apoptosis in PC-3M and NIH 3T3 cell lines.",

author = "Wijeratne, {E. M.Kithsiri} and Paranagama, {Priyani A.} and Marron, {Marilyn T.} and Gunatilaka, {Malkanthi K.} and Arnold, {A. Elizabeth} and Gunatilaka, {A. A.Leslie}",

year = "2008",

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doi = "10.1021/np070600c",

language = "English (US)",

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AU - Wijeratne, E. M.Kithsiri

AU - Paranagama, Priyani A.

AU - Marron, Marilyn T.

AU - Gunatilaka, Malkanthi K.

AU - Arnold, A. Elizabeth

AU - Gunatilaka, A. A.Leslie

PY - 2008/2

Y1 - 2008/2

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AB - Five new metabolites, (+)-(5S,10S)-4′-hydroxymethylcyclozonarone (1), 3-ketotauranin (3), 3α-hydroxytauranin (4), 12-hydroxytauranin (5), and phyllospinarone (6), together with tauranin (2), were isolated from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis. The structures of the new compounds were determined on the basis of their 1D and 2D NMR spectroscopic data and chemical interconversions. All compounds were evaluated for inhibition of cell proliferation in a panel of five cancer cell lines, and only tauranin (2) showed activity. When tested in a flow cytometry-based assay, tauranin induced apoptosis in PC-3M and NIH 3T3 cell lines.

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Sesquiterpene quinones and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran desert

Abstract

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