The biosynthesis of mangostin: the origin of the xanthone skeleton

Bennett, Graham J.; Lee, Hiok-Huang

doi:10.1039/c39880000619

Cited by 33 publications

(29 citation statements)

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Section: Hypothetical Biosynthesis Pathway Of Xanthonesmentioning

confidence: 93%

“…1, compound 7) was identified also in Garcinia mangostana (Hypericaceae) [22]. Cinnamic acid, benzoic acid, m-hydroxybenzoic acid and malonic acid were found to be efficient precursors of this compound [22]. Beerhues and coworkers [21,23] have studied also the biosynthesis of xanthones in H. androsaemum cell suspensions.…”

Section: Hypothetical Biosynthesis Pathway Of Xanthonesmentioning

confidence: 99%

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Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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Calli and suspended cells of Hypericum androsaemum accumulated high levels of 1,3,5,6 and 1,3,6,7 oxygenated xanthones. The major compounds include simple oxygenated xanthones or derivatives with prenyl, pyran or methoxyl groups, four of them being new natural compounds. A hypothetical biosynthetic scheme is proposed based on the isolated compounds and statistical analysis. Xanthone accumulation was influenced greatly by medium factors, namely hormone supplementation. Calli grown with 4.5 mM a-naphtaleneacetic acid (NAA) +2.3 mM kinetin (KIN) had the highest specific xanthone production (1.3% biomass dry weight (DW)), whereas suspended cells grown in similar medium accumulated a lower amount (0.87% DW). Calli displayed a negative linear relationship between total xanthone accumulation and NAA concentration, in the range of 4.5 -22.5 mM. However, in this range the xanthone 1,3,6,7/1,3,5,6 ratio and the biomass production showed a positive linear relationship with NAA concentration. Substitution of 4.5 mM of NAA by the same molar amount of 2,4-dichlorophenoxyacetic acid (2,4-D), in the presence of 2.3 mM of KIN, caused a decrease in xanthone accumulation in calli. The use of N 6 -benzyladenine (BA) instead of KIN reduced xanthone production, independently of the auxin used. This effect was attenuated when both hormones were present.

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Section: Hypothetical Biosynthesis Pathway Of Xanthonesmentioning

confidence: 93%

Section: Hypothetical Biosynthesis Pathway Of Xanthonesmentioning

confidence: 99%

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

et al. 2000

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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%

“…Feeding experiments with intact plants of Garcinia mangostana (Hypericaceae) have shown that m-hydroxybenzoic acid is an efficient precursor of xanthone biosynthesis [3]. This appeared to be also true for xanthone formation in cultured cells of C. erythraea because these accumulate, when treated with a yeast extract, 1,5-dihydroxy-3-methoxyxanthone [6] the 5-hydroxy group of which corresponds to the 3-hydroxy group of m-hydroxybenzoic acid.…”

Section: Introductionmentioning

confidence: 99%

Benzophenone synthase from cultured cells of Centaurium erythraea

Beerhues¹

1996

FEBS Letters

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“…The biosynthetic origin of the hydroxybenzoyl-CoA precursor (11) of xanthones is subject to controversy. Thus, 14 C-labelled phenylalanine (7) was reported to be incorporated into xanthones from Gentiana lutea, albeit with low incorporation rates [10], and label from cinnamic acid and benzoic acid was diverted to the xanthone, mangostin, in Garcinia mangostana [11,12].…”

mentioning

confidence: 99%

Phenylalanine‐independent biosynthesis of 1,3,5,8‐tetrahydroxyxanthone

Wang¹,

Maier²,

Keil

et al. 2003

European Journal of Biochemistry

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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.

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The biosynthesis of mangostin: the origin of the xanthone skeleton

Abstract: Cinnamic, benzoic, and m-hydroxybenzoic acids and benzophenone (1) are efficient precursors to mangostin (3).

Cited by 33 publications

References 1 publication

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Xanthone biosynthesis and accumulation in calli and suspended cells of Hypericum androsaemum

Benzophenone synthase from cultured cells of Centaurium erythraea

Phenylalanine‐independent biosynthesis of 1,3,5,8‐tetrahydroxyxanthone

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