TY - JOUR
T1 - Formation of Azaphilone Pigments and Monasnicotinic Acid by the Fungus Aspergillus cavernicola
AU - Antipova, Tatiana V.
AU - Zhelifonova, Valentina
AU - Zaitsev, Kirill V.
AU - Zherebker, Alexander
AU - Baskunov, Boris
AU - Oprunenko, Yuri F.
N1 - Funding Information:
Acquiring the NMR spectra was supported in part by the M. V. Lomonosov Moscow State University Program of Development. The high-resolution mass spectrometry study was funded by the Russian Science Foundation grant no. 21-47-04405.
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/6/15
Y1 - 2022/6/15
N2 - Due to the ever-increasing demand for healthy and safe food, much attention has been gained by natural food colorants. This study showed the culture fluid extract of the fungus Aspergillus cavernicola VKM F-906 to contain red pigment and monasnicotinic acid (MNA) in predominant amounts. The structure of the pigment corresponded to cis-cavernamine (red pigment, RP). Two tautomers, NH and OH forms, in rapid equilibrium were present in a solution of RP. The critical factors for RP to form were the presence of NH4+salt and pH 6.3-6.5. In vitro experiments showed that MNA was synthesized from RP as a result of chemical transformations without the participation of enzymes. In this case, the main influence on the reaction rate is exerted by the pH of the medium, which is associated with the keto-enol tautomerism of RP in solution. The culture broth extract and MNA exhibited antifungal activity against Fusarium fungi.
AB - Due to the ever-increasing demand for healthy and safe food, much attention has been gained by natural food colorants. This study showed the culture fluid extract of the fungus Aspergillus cavernicola VKM F-906 to contain red pigment and monasnicotinic acid (MNA) in predominant amounts. The structure of the pigment corresponded to cis-cavernamine (red pigment, RP). Two tautomers, NH and OH forms, in rapid equilibrium were present in a solution of RP. The critical factors for RP to form were the presence of NH4+salt and pH 6.3-6.5. In vitro experiments showed that MNA was synthesized from RP as a result of chemical transformations without the participation of enzymes. In this case, the main influence on the reaction rate is exerted by the pH of the medium, which is associated with the keto-enol tautomerism of RP in solution. The culture broth extract and MNA exhibited antifungal activity against Fusarium fungi.
KW - antifungal activity
KW - Aspergillus cavernicola
KW - azaphilone compounds
KW - cis-cavernamine
KW - fermentation conditions
KW - monasnicotinic acid
UR - http://www.scopus.com/inward/record.url?scp=85131966648&partnerID=8YFLogxK
U2 - 10.1021/acs.jafc.2c01952
DO - 10.1021/acs.jafc.2c01952
M3 - Article
C2 - 35649262
AN - SCOPUS:85131966648
SN - 0021-8561
VL - 70
SP - 7122
EP - 7129
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 23
ER -