Isolation and biosynthesis of aurachin P and 5-nitroresorcinol from Stigmatella erecta.
The isolation of aurachin P (2) from Stigmatella erecta strain Pd e32 is described. Spectroscopic data, in particular NMR data, indicate it is 1'-hydroxyaurachin A with a 1'R,2'S,3'R relative configuration. In addition, a further compound, 5-nitroresorcinol (4a), was isolated and identified as a novel natural product. Feeding of (13)C- and (15)N-labeled precursors indicated this was synthesized solely from glucose and ammonia. To account for the labeling pattern, phloroglucinol (8) is postulated as an intermediate branching off from 3-dehydroquinate (7) in the shikimate pathway.
Höfle
Gerhard
G
Helmholtz Centre for Infection Research (previously GBF, Gesellschaft für Biotechnologische Forschung), Inhoffenstrasse 7, 38124 Braunschweig, Germany. gho@helmholtz-hzi.de
Irschik
Herbert
H
D000641:Ammonia / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000302:isolation & purification*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011801:Quinic Acid / Q000031:analogs & derivatives; D011804:Quinolines / Q000138:chemical synthesis / Q000302:isolation & purification*; D012118:Resorcinols / Q000138:chemical synthesis / Q000302:isolation & purification*; D013237:Stereoisomerism; D020597:Stigmatella / Q000737:chemistry*
C474477:3-dehydroquinic acid; C568005:5-nitroresorcinol; D009574:Nitro Compounds; D011804:Quinolines; D012118:Resorcinols; C568004:aurachin P; D011801:Quinic Acid; D000641:Ammonia; D005947:Glucose