Varitatin A, a Highly Modified Fatty Acid Amide from Penicillium variabile Cultured with a DNA Methyltransferase Inhibitor

Xueqian He; Zhenzhen Zhang; Yinghan Chen; Qian Che; Tianjiao Zhu; Qianqun Gu; Dehai Li

doi:10.1021/acs.jnatprod.5b00742

Varitatin A, a Highly Modified Fatty Acid Amide from Penicillium variabile Cultured with a DNA Methyltransferase Inhibitor

J Nat Prod. 2015 Nov 25;78(11):2841-5. doi: 10.1021/acs.jnatprod.5b00742. Epub 2015 Nov 12.

Authors

Xueqian He¹, Zhenzhen Zhang¹, Yinghan Chen¹, Qian Che¹, Tianjiao Zhu¹, Qianqun Gu¹, Dehai Li¹

Affiliation

¹ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.

PMID: 26561719
DOI: 10.1021/acs.jnatprod.5b00742

Abstract

A new, highly modified fatty acid amide, varitatin A (1), was isolated from the fungus Penicillium variabile HXQ-H-1 cultivated with the DNA methyltransferase inhibitor 5-azacytidine. The structure including the absolute configuration of 1 was established by analysis of NMR and MS data, together with chemical degradation and Mosher's method based on MPA esters. Compound 1 showed cytotoxicity against HCT-116 cells with an IC50 value of 2.8 μM and also inhibited the effects of protein tyrosine kinases.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azacitidine
DNA / drug effects*
Drug Screening Assays, Antitumor
Fatty Acids, Unsaturated / chemistry
Fatty Acids, Unsaturated / isolation & purification*
Fatty Acids, Unsaturated / pharmacology
HCT116 Cells
Humans
Inhibitory Concentration 50
Methyltransferases / antagonists & inhibitors*
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Penicillium / chemistry*

Substances

Fatty Acids, Unsaturated
varitatin A
DNA
Methyltransferases
Azacitidine