Phenylalanine-independent biosynthesis of 1,3,5,8-tetrahydroxyxanthone. A retrobiosynthetic NMR study with root cultures of Swertia chirata.
Root cultures of Swertia chirata (Gentianaceae) were grown with supplements of [1-13C]glucose, [U-13C6]glucose or [carboxy-13C]shikimic acid. 1,3,5,8-Tetrahydroxyxanthone was isolated and analysed by quantitative NMR analysis. The observed isotopomer distribution shows that 1,3,5,8-tetrahydroxyxanthone is biosynthesized via a polyketide-type pathway. The starter unit, 3-hydroxybenzoyl-CoA, is obtained from an early shikimate pathway intermediate. Phenylalanine, cinnamic acid and benzoic acid were ruled out as intermediates.
Wang
Chang-Zeng
CZ
Biozentrum-Pharmazie, Universität Halle, Halle/Saale, Germany.
Maier
Ulrich H
UH
Keil
Michael
M
Zenk
Meinhart H
MH
Bacher
Adelbert
A
Rohdich
Felix
F
Eisenreich
Wolfgang
W
D000214:Acyl Coenzyme A / Q000378:metabolism; D019817:Benzoic Acid / Q000737:chemistry / Q000378:metabolism; D002247:Carbon Isotopes; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism; D029965:Gentianaceae / Q000378:metabolism*; D005947:Glucose / Q000031:analogs & derivatives / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010649:Phenylalanine / Q000378:metabolism*; D010728:Phosphoenolpyruvate / Q000378:metabolism; D018517:Plant Roots / Q000254:growth & development / Q000378:metabolism; D012765:Shikimic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D013403:Sugar Phosphates / Q000378:metabolism; D014966:Xanthenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D044004:Xanthones
C082323:3-hydroxybenzoyl-coenzyme A; D000214:Acyl Coenzyme A; D002247:Carbon Isotopes; D002934:Cinnamates; D013403:Sugar Phosphates; D014966:Xanthenes; D044004:Xanthones; D012765:Shikimic Acid; D010649:Phenylalanine; C026959:erythrose 4-phosphate; D010728:Phosphoenolpyruvate; D019817:Benzoic Acid; C009689:xanthone; D005947:Glucose