Biogenesis of xanthones in Gentiana lutea

Gupta, Padma; Lewis, John R.

doi:10.1039/j39710000629

Cited by 25 publications

(19 citation statements)

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“…Feeding experiments with intact plants have demonstrated that 2,3¢,4,6-tetrahydroxybenzophenone (THBP; Fig. 1) is involved in xanthone biosynthesis in Gentiana lutea (Gentianaceae) and Garcinia mangostana (Hypericaceae), whereas 2,4¢,4,6-tetrahydroxybenzophenone and 2,3¢,4,4¢,6-pentahydroxybenzophenone were eciently incorporated in Anemarrhena asphodeloides (Liliaceae; Gupta and Lewis 1971;Fujita and Inoue 1981;Bennett et al 1990). Recently, the formation of THBP from one molecule of 3-hydroxybenzoyl-CoA and three molecules of malonylCoA, catalyzed by benzophenone synthase, was detected in cultured cells of Centaurium erythraea ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Regioselective oxidative phenol couplings of 2,3′,4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L.

Peters

Schmidt

Beerhues

1997

Planta

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A crucial step in plant xanthone biosynthesis is the cyclization of an intermediate benzophenone to a xanthone. In cultured cells of Centaurium erythraea RAFN, 2,3¢,4,6-tetrahydroxybenzophenone (THBP) was shown to be intramolecularly coupled to 1,3,5-trihydroxyxanthone, whereas in cell cultures of Hypericum androsaemum L. it was coupled to form the isomeric 1,3,7-trihydroxyxanthone. These regioselective cyclizations that occur ortho and para, respectively, to the 3¢-hydroxy group of the benzophenone depend on cytochrome 450 , as shown by the eectiveness of established 450 inhibitors and blue-light-reversible carbon monoxide inhibition. Furthermore, the reactions absolutely require NADPH and O 2 . The underlying reaction mechanism is probably an oxidative phenol coupling that is catalyzed regioselectively by xanthone synthases. These enzymes are proposed to be cytochrome 450 oxidases. The intramolecular cyclizations of THBP to 1,3,5-and 1,3,7-trihydroxyxanthones catalyzed by the two xanthone synthases represent an important branch point in the plant xanthone biosynthetic pathway.Abbreviations: HMBC = heteronuclear multiple-bond connectivity; HMQC = heteronuclear multiple-quantum coherence; NMR = nuclear magnetic resonance; THBP = 2,3¢,4,6-tetrahydroxybenzophenone

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Section: Introductionmentioning

confidence: 99%

Regioselective oxidative phenol couplings of 2,3′,4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L.

Peters

Schmidt

Beerhues

1997

Planta

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“…Xanthones arise biosynthetically from the shikimate and the acetate-malonate pathways, as shown by feeding experiments (Gupta and Lewis 1971;Fujita andInoue 1977, 1981;Bennett and Lee 1988). In Garcinia mangostana (Hypericaceae), cinnamic acid, benzoic acid, m-hydroxybenzoic acid and malonic acid were found to be efficient precursors of mangostin, indicating that a C6-C1 intermediate and three acetate units form the C13-skeleton (Bennett and Lee 1988).…”

Section: Introductionmentioning

confidence: 99%

Differential accumulation of xanthones in methyl-jasmonate- and yeast-extract-treated cell cultures of Centaurium erythraea and Centaurium littorale

Beerhues¹,

Berger²

1995

Planta

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Cell-suspension cultures of Centaurium erythraea and Centaurium littorale (Gentianaceae) respond to methyl jasmonate and yeast extract with a differential accumulation of xanthones. Methyl jasmonate induced the formation of 1-hydroxy-3,5,6,7-tetramethoxyxanthone, the amount of which increased in both cell cultures around 10 h after addition. A substantial increase in the activity of phenylalanine ammonia-lyase (PAL) was not observed. When challenged with yeast extract the cell cultures accumulated 1,5-dihydroxy-3-methoxyxanthone. This appeared rapidly after addition of yeast extract in C. erythraea but its amount in C. littorale increased only after a lag phase of 25 h. While PAL activity in C. erythraea was strongly suppressed a fourfold increase in its activity was found in C. littorale. Both elicited xanthones accumulated intracellularly. A scheme for xanthone biosynthesis in the two cell cultures is proposed.

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“…Benzophenones are the immediate precursors of xanthones in higher plants, as shown by feeding experiments with differentiated plant organs [1][2][3]. In addition, 2,3',4,6-tetrahydroxybenzophenone was recently found to be converted regioselectively to isomeric xanthones in cell-suspension cultures of Centaurium erythraea and Hypericum androsaemum (Peters, Schmidt and Beerhues, unpublished results).…”

Section: Introductionmentioning

confidence: 99%

Benzophenone synthase from cultured cells of Centaurium erythraea

Beerhues¹

1996

FEBS Letters

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Biogenesis of xanthones in Gentiana lutea

Cited by 25 publications

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Regioselective oxidative phenol couplings of 2,3′,4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L.

Regioselective oxidative phenol couplings of 2,3′,4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L.

Differential accumulation of xanthones in methyl-jasmonate- and yeast-extract-treated cell cultures of Centaurium erythraea and Centaurium littorale

Benzophenone synthase from cultured cells of Centaurium erythraea

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