Xanthones in cell suspension cultures of Hypericum paturum

Ishiguro, Kyoko; Fukumoto, Hisae; Nakajima, Mariko; Isoi, Koichiro

doi:10.1016/0031-9422(93)85286-z

Cited by 46 publications

(30 citation statements)

References 2 publications

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“…The 1 H spectroscopic properties of the synthetic material closely matched those described for the natural product, 17,18 although the 13 C NMR gave a systematic difference in the chemical shifts of 0.8e1.1 ppm. We assumed that this was due to incorrect calibration of the original spectrum, and indeed when we re-referenced the residual acetone peak, a near perfect match to the reported literature values was observed.…”

Section: Resultsmentioning

confidence: 48%

“…The excess solvent was removed under reduced pressure. The residue was purified by flash chromatography (4:1 light petroleum/ethyl acetate) to give the title compound as a pale yellow solid (1 mg, 64%), mp 318e319 C (lit., 17 To a stirred solution of 5,9,11-trihydroxy-3,3-dimethylpyrano [3,2-a]xanthen-12(3H)-one 3a (2 mg, 0.006 mmol), and anhydrous potassium carbonate (5 mg, 0.037 mmol) in acetone (1 mL) was added dimethyl sulfate (0.002 mL) and the mixture was heated to reflux and stirred for 16 h. The excess of solvents was removed under reduced pressure and the residue was purified by flash chromatography (4:1 light petroleum/ethyl acetate to 2:1 light petroleum/ethyl acetate) to give the title compound as a colorless solid (2 mg, 89%), mp 125e126 C (lit., 16 …”

Section: -Hydroxy-136-tribenzyloxy-9h-xanthen-9-one 11mentioning

confidence: 99%

“…11,12 The cytotoxic xanthone toxyloxanthone B 3a on the other hand is not Garciniaderived being originally isolated from Maclura pomifera and Toxylon pomiferum, 13e16 and subsequently from the Hypericum genus, including Hypericum perforatum (St John's Wort). 17,18 Surprisingly, despite their relative structural simplicity, a-mangostin 1 is the only one of the three compounds to be synthesized. 8 We now report the synthesis of toxyloxanthone 3 that not only constitutes the first synthesis of the natural material, but also, as far as we are aware, illustrates the first use of the aryne-based methodology developed by Larock 19,20 in the synthesis of bioactive natural products.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of toxyloxanthone B

Giallombardo¹,

Nevin²,

Lewis³

et al. 2014

Tetrahedron

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a b s t r a c tA synthesis of the naturally occurring xanthone toxyloxanthone B is described, in which the key step is the regioselective addition of a methyl salicylate to a substituted benzyne, followed by cyclization of the intermediate aryl anion to form the xanthone, the regiochemistry of the aryne addition being confirmed by X-ray crystallography. Subsequent introduction of the pyran ring by [3,3]-rearrangement and deprotection completed the synthesis.

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Section: Resultsmentioning

confidence: 48%

Section: -Hydroxy-136-tribenzyloxy-9h-xanthen-9-one 11mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of toxyloxanthone B

Giallombardo¹,

Nevin²,

Lewis³

et al. 2014

Tetrahedron

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“…The relative stereochemistry of C-28 in 1 and 2 were decided by comparison of the 12,[14][15][16] The stereochemistries at C-27 in 3 and 4, however, had not been discussed so far. Therefore, the C-27 configurations of 3 and 4 were elucidated in the same way as 1 and 2: the The following known compounds were identified by comparison of their spectral data with those in the literature: furohyperforin (5), 12) 33-deoxy-33-hydroperoxyfurohyperforin (6), 17) furohyperforin isomer 2 (7), 12) hyperibone J (8), 10) 8-hydroxyhyperforin 8,1-hemiacetal (9), 17) pyrano [7,28-b]hyperforin (10), 18) calycinoxanthone D (11), 19) 1,3,6-trihydroxy-5-methoxy xanthone (12), 20) 4Ј,5Ј-dihydro-1,6,7-trihydroxy-4Ј,4Ј,5Ј-trimethylfurano(2Ј,3Ј:3,4)xanthone (13), 21) deprenylatedrheediaxanthone (14), 22,23) paxanthone (15), 24) quercetin (16), 25) rutin (17).…”

Section: 4)mentioning

confidence: 99%

Prenylated Phloroglucinol Derivatives from <i>Hypericum perforatum</i> var. <i>angustifolium</i>

et al. 2008

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Hypericum perforatum (St. John's Wort, Clusiaceae) has been used for centuries in the treatment of burns, bruises, swelling, inflammation, and anxiety, as well as bacterial and viral infections. In addition, H. perforatum has become popular herbal medicine quickly in the world for the treatment of mood disorders, since its effectiveness in the therapy for mild to moderate depression with a smaller side effects profile than that of traditional antidepressant medications has been claimed in the United States. Numerous studies have proven the clinical efficacy of H. perforatum in both human and animal behavioral models of depression.1) This medicinal herb produces various types of secondary metabolites, including flavonoids, xanthones, naphthodianthrones, and prenylated phloroglucinols.2) Among others, hyperforin, a main component of H. perforatum being classified as phloroglucinol derivatives, is regarded as a potential leads for new medicinal agents because of its various biological activities (e.g. antibacterial, apoptotic properties, anti-tumor, anti-inflammatory, and anti-depressant). 3,4) We have been studying the chemical constituents of various Hypericum plants for the purpose of the search for biologically active secondary metabolites. We have so far reported anti-HIV agent, biyouyanagin A 5) and xanthones 6,7) from H. chinense, and prenylated benzophenones and xanthones from H. scabrum. 8,9) In continuing this program, we have examined the aerial parts of H. perforatum var. angustifolium. Varieties of H. perforatum with "broad" (var. perforatum) and "narrow" (var. angustifolium) sized leaves have been recognized. 10) H. perforatum var. angustifolium was reported to contain a larger quantity of hypericin, and to have a stronger antimicrobial effect than typical variety, H. perforatum var. perforatum.11) This paper deals with the isolation and characterization of ten prenylated phloroglucinol derivatives, including two new prenylated phloroglucinols named furoadhyperforin isomers A (1) and B (2), together with five xanthones and two flavonoids from this plant material.The methanolic extracts of the air-dried aerial parts of Hypericum perforatum var. angustifolium were successively partitioned between n-hexane, EtOAc, BuOH, and H 2 O. The nhexane, the EtOAc, and the BuOH-soluble fractions were repeatedly subjected to column chromatography, respectively, to afford two new (1, 2) and 15 known (3-17) compounds.Compounds 1 and 2 showed a hydroxyl and a carbonyl absorption bands in their IR spectrum. Their molecular formulae were decided as the same of C 36 H 54 O 5 on the basis of the HR-MS data. The 1 H-and 13 C-NMR spectra of 1 and 2 resembled each other, which indicated the presence of a 2-methylbutanoyl group, three isoprenyl groups, two carbonyl groups, one enol moiety, one oxygenated quaternary carbon, one oxygenated methine, three quaternary carbons, one methine, four methylenes, and three tertiary methyls (Table 1). From these data, 1 and 2 were assumed to be prenylated phloroglucinol derivatives having ...

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“…7 As a continuation of our efforts to purse the active natural products from G. xanthochymus, two new xanthones (1) and (2), together with 12 known xanthones were isolated by repeated column chromatography from the EtOAc fraction of the ethanolic extract of G. xanthochymus gathered in Yunnan province of China. The structures of twelve known compounds 3-14 were elucidated as subelliptenone H (3), 8 ananixanthone (4), 9 pyranojacareubin (5), 10 rheediaxanthone A (6), 11 toxyloxanthone (7), 12 6-deoxyisojacareubin (8), 13 atroviridin (9), 14 6-deoxyjacareubin (10), 15 1-O-methylsymphoxanthone (11), 16 1-O-methylglobuxanthone (12), 17 globuxanthone (13), 18 and garciniaxanthone H (14) 19 by interpreting the NMR spectroscopic data and comparing those data with the published values. In this paper, we reported the isolation and structural elucidation of two new xanthones (1) and (2) using spectroscopic evidence.…”

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confidence: 99%