Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of Mycena rosea and its Role in the Generation of the Alkaloid Mycenarubinâ
C.
Chembiochem
; 21(11): 1613-1620, 2020 06 02.
Article
en En
| MEDLINE
| ID: mdl-31972067
ABSTRACT
Mycenarubinâ
C, a previously unknown red pyrroloquinoline alkaloid, was isolated from fruiting bodies of the mushroom Mycena rosea and its structure was elucidated mainly by NMR spectroscopy and mass spectrometry. Unlike mycenarubinâ
A, the major pyrroloquinoline alkaloid in fruiting bodies of M.â
rosea, mycenarubinâ
C, contains an eight-membered ring with an additional C1 unit that is hitherto unprecedented for pyrroloquinoline alkaloids known in nature. Incubation of mycenarubinâ
A with an excess of formaldehyde revealed that mycenarubinâ
C was generated nearly quantitatively from mycenarubinâ
A. An investigation into the formaldehyde content of fresh fruiting bodies of M.â
rosea showed the presence of considerable amounts of formaldehyde, with values of 5â
µg per gram of fresh weight in fresh fruiting bodies. Although mycenarubinâ
C did not show bioactivity against selected bacteria and fungi, formaldehyde inhibits the growth of the mycoparasite Spinellus fusiger at concentrations present in fruiting bodies of M.â
rosea. Therefore, formaldehyde might play an ecological role in the chemical defence of M.â
rosea against S.â
fusiger. In turn, S.â
fusiger produces gallic acid-presumably to detoxify formaldehyde by reaction of this aldehyde with amino acids and gallic acid to Mannich adducts.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Pirroles
/
Quinolinas
/
Agaricales
/
Cuerpos Fructíferos de los Hongos
/
Alcaloides
/
Formaldehído
/
Mucorales
Idioma:
En
Revista:
Chembiochem
Asunto de la revista:
BIOQUIMICA
Año:
2020
Tipo del documento:
Article
País de afiliación:
Alemania