Glionitrin B, a cancer invasion inhibitory diketopiperazine produced by microbial coculture.

Abstract

A new diketopiperazine, glionitrin B (1), was produced using a microbial coculture of the fungus Aspergillus fumigatus KMC-901 and the bacterium Sphingomonas sp. KMK-001 that were isolated from acidic coal mine drainage. The structure of 1 was determined to be (3S,10aS)-dithiomethylglionitrin A. This structure was determined by the analyses of extensive NMR data and the circular dichroism spectra of the natural product and a semisynthetic compound derived from glionitrin A. In contrast to glionitrin A (2), glionitrin B (1) is not cytotoxic against the human prostate cancer cell line DU145. However, compound 1 caused suppression of DU145 cell invasion, producing 46% inhibition at 60 μM.

• Authors: Hyun Bong Park, Young-Joo Kim, Jin-Soo Park, Hyun Ok Yang, Kang Ro Lee, Hak Cheol Kwon
• Journal: Journal of natural products (J Nat Prod) Vol. 74 Issue 10 Pg. 2309-12 (Oct 28 2011) ISSN: 1520-6025 [Electronic] United States
• PMID: 21954885 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Diketopiperazines
• glionitrin B

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Aspergillus fumigatus (chemistry)
• Diketopiperazines (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Male
• Molecular Structure
• Prostatic Neoplasms (metabolism)
• Sphingomonas (chemistry)