Xanthones in higher plants: Biogenetic proposals and a chemotaxonomic survey

Carpenter, Ian; Locksley, H. D.; Scheinmann, F.

doi:10.1016/s0031-9422(00)88089-9

Cited by 121 publications

(31 citation statements)

References 43 publications

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“…It should be noted that 5 is a fairly common compound in Gentianales and Cornales, but 6 and 7 have much more limited distributions, so far being recorded elsewhere only in a few species of Dipsacaceae (Jensen et al, 1975;Jensen, 1992). XANTHONES ) have a rather restricted occurrence among higher plants, being found almost exclusively in Guttiferae and Gentianaceae (Carpenter et al, 1969;Sultanbava, 1980;Mandal et al, 1992a). Xanthones are sometimes found as the parent polyhydroxylated compounds but more often with a varying degree of substitution at the oxygen atoms.…”

Section: Resultsmentioning

confidence: 99%

Chemotaxonomy and pharmacology of Gentianaceae

Jensen

Schripsema²

2001

Gentianaceae

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Section: Resultsmentioning

confidence: 99%

Chemotaxonomy and pharmacology of Gentianaceae

Jensen

Schripsema²

2001

Gentianaceae

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“…Natural occurrence of 12 xanthones in higher plants and 4 in fungi has been reviewed by Roberts in 1961 and by Dean in 1963 [4,5]. Gottlieb [6] mentioned the isolation of 60 xanthones from higher plants and 7 from fungi, whereas Carpenter et al [7] listed 82 xanthones from higher plants.…”

Section: Introductionmentioning

confidence: 99%

Naturally Occurring Xanthones: Chemistry and Biology

Negi

Bisht

Singh

et al. 2013

Journal of Applied Chemistry

164

120

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Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources of higher plants, fungi, ferns, and lichens. They have gradually risen to great importance because of their medicinal properties. This review focuses on the types, isolation, characterization, biological applications, and biosynthesis of naturally occurring xanthones isolated so far. Different physicochemical and instrumental methods such as liquid-solid and liquid-liquid extraction, TLC, flash chromatography, column chromatography, IR,1H NMR and13C NMR spectroscopy, GLC, HPLC, GC, and LCMS have been widely used for isolation and structural elucidation of xanthones. Hepatoprotective, anticarcinogenic, antileprosy, antimalarial, antioxidant, anticholinergic, mutagenicity, radioprotective, immunomodulatory, antibone resorption, antiparasitic, neuraminidase inhibitory, anticomplement, antibacterial, antifungal, algicidal, anti-HIV, cardioprotective, antitumoral, antidiabetes, antihyperlipidemic, antiatherogenic, anti-inflammatory, antiulcer, antidiabetic, hypolipidemic, analgesic, antiasthmatic, antihistaminic, antiamoebic, diuretic, antidiarrheal, larvicidal, and ovicidal activities have been reported for natural occurring xanthones. To a certain extent, this review provides necessary foundation for further research and development of new medicines.

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“…[11][12][13] Except the two above reported benzophenones 1 and 2, several xanthone and its O-glycosides or C-glycosides with the similar structural characteristics to 1 and 2 have been also isolated from P. tenuifolia, 1,5,8) which supply another evidence to the hypothesis that xanthone is biosynthesized from benzophenone in the plants. 14) In the HMBC spectrum, the proton signal at ϩ in the EI-MS spectrum.…”

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confidence: 89%

Four New Phenones from the Cortexes of Polygala tenuifolia

Jiang

2005

Chem. Pharm. Bull.

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Previous reports described that many saponins, saccharide esters and xanthones had been isolated from Polygala tenuifolia, [1][2][3][4][5][6] whose cortex is used widely in China, Korea and Japan as a tonic, sedative, expectorant and anti-inflammation agent. In the process of our studying the chemical constituents of P. tenuifolia, phenones were also isolated from this plant besides the above mentioned compounds. So in this paper, we describe the isolation and structural identification of four new phenones, tenuiphenones A-D. This is the second report of phenones isolated from the genus of Polygala, besides the former report of benzophenones from P. telephioides. 7) Results and DiscussionThe CHCl 3 and n-BuOH soluble parts of 95% EtOH extract of P. tenuifolia were subjected to silica gel, Sephadex LH-20 column chromatographies and HPLC purification to give compounds 1-6.Compound 1 was obtained as a yellow amorphous powder and its molecular formula was deduced as C 26 ). On acid hydrolysis, 1 afforded glucose and rhamnose, and the GC analyses of their L-cysteine derivatives showed their retention times were identical with those of D-glucose and L-rhamnose, respectively. The 13 C-NMR spectrum (Table 1) displayed 24 carbon signals in total, among which twelve were assigned to the sugar moiety, one for a methoxyl and the remaining eleven were reminiscent of a benzopheonone or a xanthone skeleton. The chemical shift of carbonyl signal (d 194.5) indicated 1 was a benzophenone compound. C-NMR spectrum data of 2 were comprised of six sugar moiety carbon signals (d 75.2, 72.7, 77.8, 69.0, 81.0, 59.9) assigned to be those of the C-glucosyl by comparing with the reported values (d 74.7, 72.1, 77.8, 69.2, 81.1, 60.0), 7,10) and the configuration of the glucosyl residue was deduced to be b from the J value (10.0 Hz) of the anomeric proton. Besides the sugar carbon signals, there were eleven benzophenone skeleton carbon signals in the 13 C-NMR.7) The 1 H-NMR spectrum of 2 showed a ABCX-system aromatic protons at (tenuiphenone A, 1), 3,5-di-C-b b-glucopyranosyl-2,4,6,3-tetrahydroxybenzophenone (tenuiphenone B, 2), 2,4,6-trihydroxyphenyl-(24Z)-triacontene-1-one (tenuiphenone C, 3), 2,4,6-trihydroxyphenyl-(26Z)-dotriacontene-1-one (tenuiphenone D, 4) respectively, on the basis of spectroscopic analyses. The isolation of 1 and 2 supplied an evidence for the hypothesis that xanthone was biosynthesized from benzophenone in the plants.

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Xanthones in higher plants: Biogenetic proposals and a chemotaxonomic survey

Cited by 121 publications

References 43 publications

Chemotaxonomy and pharmacology of Gentianaceae

Chemotaxonomy and pharmacology of Gentianaceae

Naturally Occurring Xanthones: Chemistry and Biology

Four New Phenones from the Cortexes of Polygala tenuifolia

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