TY - JOUR
T1 - Injury-induced biosynthesis of methyl-branched polyene pigments in a white-rotting basidiomycete
AU - Schwenk, Daniel
AU - Nett, Markus
AU - Dahse, Hans Martin
AU - Horn, Uwe
AU - Blanchette, Robert A.
AU - Hoffmeister, Dirk
N1 - Publisher Copyright:
© 2014 The American Chemical Society and American Society of Pharmacognosy.
PY - 2014/12/26
Y1 - 2014/12/26
N2 - A stereaceous basidiomycete was investigated with regard to its capacity to produce yellow pigments after physical injury of the mycelium. Two pigments were isolated from mycelial extracts, and their structures were elucidated by ESIMS and one- and two-dimensional NMR methods. The structures were identified as the previously undescribed polyenes (3Z,5E,7E,9E,11E,13Z,15E,17E)-18-methyl-19-oxoicosa-3,5,7,9,11,13,15,17-octaenoic acid (1) and (3E,5Z,7E,9E,11E,13E,15Z,17E,19E)-20-methyl-21-oxodocosa-3,5,7,9,11,13,15,17,19-nonaenoic acid (2). Stable-isotope feeding with [1-13C]acetate and l-[methyl-13C]methionine demonstrated a polyketide backbone and that the introduction of the sole methyl branch is most likely S-adenosyl-l-methionine-dependent. Dose-dependent inhibition of Drosophila melanogaster larval development was observed with both polyenes in concentrations between 12.5 and 100 μM. GI50 values for 1 and 2 against HUVEC (K-562 cells) were 71.6 and 17.4 μM (15.4 and 1.1 μM), respectively, whereas CC50 values for HeLa cells were virtually identical (44.1 and 45.1 μM).
AB - A stereaceous basidiomycete was investigated with regard to its capacity to produce yellow pigments after physical injury of the mycelium. Two pigments were isolated from mycelial extracts, and their structures were elucidated by ESIMS and one- and two-dimensional NMR methods. The structures were identified as the previously undescribed polyenes (3Z,5E,7E,9E,11E,13Z,15E,17E)-18-methyl-19-oxoicosa-3,5,7,9,11,13,15,17-octaenoic acid (1) and (3E,5Z,7E,9E,11E,13E,15Z,17E,19E)-20-methyl-21-oxodocosa-3,5,7,9,11,13,15,17,19-nonaenoic acid (2). Stable-isotope feeding with [1-13C]acetate and l-[methyl-13C]methionine demonstrated a polyketide backbone and that the introduction of the sole methyl branch is most likely S-adenosyl-l-methionine-dependent. Dose-dependent inhibition of Drosophila melanogaster larval development was observed with both polyenes in concentrations between 12.5 and 100 μM. GI50 values for 1 and 2 against HUVEC (K-562 cells) were 71.6 and 17.4 μM (15.4 and 1.1 μM), respectively, whereas CC50 values for HeLa cells were virtually identical (44.1 and 45.1 μM).
UR - http://www.scopus.com/inward/record.url?scp=84920165876&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84920165876&partnerID=8YFLogxK
U2 - 10.1021/np500552a
DO - 10.1021/np500552a
M3 - Article
C2 - 25420175
AN - SCOPUS:84920165876
SN - 0163-3864
VL - 77
SP - 2658
EP - 2663
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 12
ER -