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

Abstract

Five new metabolites, (+)-(5 S,10 S)-4'-hydroxymethylcyclozonarone ( 1), 3-ketotauranin ( 3), 3alpha-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.

• Authors: E M Kithsiri Wijeratne, Priyani A Paranagama, Marilyn T Marron, Malkanthi K Gunatilaka, A Elizabeth Arnold, A A Leslie Gunatilaka
• Journal: Journal of natural products (J Nat Prod) Vol. 71 Issue 2 Pg. 218-22 (Feb 2008) ISSN: 0163-3864 [Print] United States
• PMID: 18247573 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Antineoplastic Agents
• Quinones
• Sesquiterpenes
• tauranin

Topics

• Animals
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Apoptosis (drug effects)
• Ascomycota (chemistry)
• Cell Proliferation (drug effects)
• Cupressaceae (microbiology)
• Desert Climate
• Drug Screening Assays, Antitumor
• Humans
• Mice
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Quinones (chemistry, isolation & purification, pharmacology)
• Sesquiterpenes (chemistry, isolation & purification, pharmacology)