1'-(2-Phenyl-ethylene)-ditryptophenaline, a new dimeric diketopiperazine from Aspergillus flavus.
A new diketopiperazine dimer, 1'-(2-phenyl-ethylene)-ditryptophenaline [1], was isolated together with ditryptophenaline [2] from the fungus Aspergillus flavus. The structure of 1 was determined by analysis of spectroscopic data. In contrast to the structurally related substance-P antagonist WIN 64821 [3], both 1 and 2 are weak substance-P inhibitors, indicating that stereochemistry at the position of dimerization is an important determinant of biological potency for these molecules.
Barrow
C J
CJ
Natural Products Department, Sterling Winthrop Pharmaceuticals Research Division, Malvern, Pennsylvania 19355.
Sedlock
D M
DM
D001231:Aspergillus flavus / Q000737:chemistry*; D007211:Indoles / Q000302:isolation & purification* / Q000494:pharmacology; D007212:Indolizines / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013329:Structure-Activity Relationship; D013373:Substance P / Q000037:antagonists & inhibitors
D007211:Indoles; D007212:Indolizines; C091079:1'-(2-phenylethylene)ditryptophenaline; D013373:Substance P