Isolation, structure elucidation, and biological activity of virgineone from Lachnum Wirgineum using the genome-wide Candida albicans fitness test.
A glycosylated tetramic acid, virgineone (1), was isolated from saprotrophic Lachnum virgineum. The antifungal activity of the fermentation extract of L. virgineum was characterized in the Candida albicans fitness test as distinguishable from other natural products tested. Bioassay-guided fractionation yielded 1, a tyrosine-derived tetramic acid with a C-22 oxygenated chain and a beta-mannose. It displayed broad-spectrum antifungal activity against Candida spp. and Aspergillus fumigatus with a MIC of 4 and 16 microg/mL, respectively. Virgineone was also identified in a number of Lachnum strains collected from diverse geographies and habitats.
Ondeyka
John
J
Natural Products Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA.
Harris
Guy
G
Zink
Deborah
D
Basilio
Angela
A
Vicente
Francisca
F
Bills
Gerald
G
Platas
Gonzalo
G
Collado
Javier
J
Gonzáez
Antonio
A
de la Cruz
Mercedes
M
Martin
Jesus
J
Kahn
Jennifer Nielsen
JN
Galuska
Stefan
S
Giacobbe
Robert
R
Abruzzo
George
G
Hickey
Emily
E
Liberator
Paul
P
Jiang
Bo
B
Xu
Deming
D
Roemer
Terry
T
Singh
Sheo B
SB
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001118:Argentina; D001203:Ascomycota / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007668:Kidney / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000935:Antifungal Agents; D006027:Glycosides; D011760:Pyrrolidinones; C535097:virgineone