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

84 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

Access to Document

10.1021/np070600c

Cite this

@article{c1269e3e78394c0e9944243573bc5eb7,

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",

month = feb,

doi = "10.1021/np070600c",

language = "English (US)",

volume = "71",

pages = "218--222",

journal = "Journal Of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Sesquiterpene quinones and related metabolites from Phyllosticta spinarum, a fungal strain endophytic in Platycladus orientalis of the Sonoran desert

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

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=40549084959&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=40549084959&partnerID=8YFLogxK

U2 - 10.1021/np070600c

DO - 10.1021/np070600c

M3 - Article

C2 - 18247573

AN - SCOPUS:40549084959

SN - 0163-3864

VL - 71

SP - 218

EP - 222

JO - Journal Of Natural Products

JF - Journal Of Natural Products

IS - 2

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this