Xanthones of the Gentianaceae—I

Stout, George H.; Balkenhol, W.J.

doi:10.1016/s0040-4020(01)82816-7

Cited by 51 publications

(27 citation statements)

References 19 publications

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“…These substitutions closely parallel those of other members of the Gentianaceae. Also, the probable presence of glycosides was noted, and this observation coincided with previous reports concerning their presence in the Gentianaceae (10,18).…”

Section: -Mesh F;io Sil a Silicic Acidsupporting

confidence: 91%

“…Carbons 1 and 3 must be occupied by a hydroxyl and a methoxyl function, respectively. Since all positions on ring B were accounted for, only ring 9 AH se arations by column chromatography were carried out by using 100- 10 All test reagents were prepared immediately prior to use.…”

Section: Xanthone VI From Fractionmentioning

confidence: 99%

“…The xanthones obtained from the Gentianaceae are limited to polyoxygenated derivatives, and the variation of substituents is restricted to hydroxyl and/or methoxyl groups (16). There are, however, exceptions to this general rule, as evidenced by the occurrence of mangiferin (a C-glucoside) in Canscora decussata Schult (1) and the presence of certain 0-glucosides isolated from various members of this family (10,17).…”

Section: -Mesh F;io Sil a Silicic Acidmentioning

confidence: 99%

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Phytochemical Investigation of Xanthones of Eustoma grandiflorum (Raf.) Shinners

Sullivan¹,

Stiles²,

Rosler³

1977

Journal of Pharmaceutical Sciences

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Section: -Mesh F;io Sil a Silicic Acidsupporting

confidence: 91%

Section: Xanthone VI From Fractionmentioning

confidence: 99%

Section: -Mesh F;io Sil a Silicic Acidmentioning

confidence: 99%

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Phytochemical Investigation of Xanthones of Eustoma grandiflorum (Raf.) Shinners

Sullivan¹,

Stiles²,

Rosler³

1977

Journal of Pharmaceutical Sciences

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“…& T. in 0.003% yield [2]; from roots of Frasera caroliniensis Walt., in 0.07% yield [3]; and from roots and the aerial part of H. asclepidea (HBK) Don, H. elliptica D. Don, and H. campanulata in yields of 0.10, 0.12, and 0.13%, respectively [4][5][6].…”

mentioning

confidence: 99%

Xanthones from Halenia corniculata. 3. Preparation of Standard 1-Hydroxy-2,3,4,5-tetramethoxyxanthone

et al. 2005

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1-Hydroxy-2,3,4,5-tetramethoxyxanthone, which is used as a standard for quantitative determination of the total content of γ-pyrones, was isolated from the aerial part of Halenia corniculata L. Cornaz., an available raw material in Russia. A method for preparing standard 1-hydroxy-2,3,4,5-tetramethoxyxanthone was developed.We previously proposed a method for quantitative determination of the total content of γ-pyrones in the aerial part of Halenia corniculata L. Cornaz. [1]. The standard sample in this method was 1-hydroxy-2,3,4,5-tetramethoxyxanthone (1), which is the dominant component of the xanthones in the aerial part of H. corniculata. Several methods for preparing 1 are known: from roots and the aerial part of Swertia bimaculata Hf. & T. in 0.003% yield [2]; from roots of Frasera caroliniensis Walt., in 0.07% yield [3]; and from roots and the aerial part of H. asclepidea (HBK) Don, H. elliptica D. Don, and H. campanulata in yields of 0.10, 0.12, and 0.13%, respectively [4-6].Drawbacks of these methods are the unavailability of the raw material, the low yields (0.003-0.13% per mass of absolute dry raw material), and the duration and labor-intensiveness of the process.The goal of the present work was to develop a method for preparing standard 1 from the aerial part of H. corniculata growing in Russia.Several methods for preparing 1 were studied during the course of the work. Method 1 produced 1 in 0.04% yield. Methods 2-4 under the same conditions but using different eluents for column chromatography also isolated 1 in yields of 0.25, 0.12, and 0.04%, respectively. Method 5 involves simultaneous extraction of raw material and hydrolysis by HCl (2%). The resulting product (0.02% yield) was contaminated with oleanolic acid, which interferes with the separation and preparation of 1 as a pure compound.Method 2 gave the highest yield of 1 from the aerial part of H. corniculata and was used to produce three batches of 1. The content of 1 as determined by HPLC was 95.31-96.87% (Fig. 1). The compounds were identified using TLC, melting points, and UV and PMR spectroscopies. The physicochemical properties of the final product were analogous to those of chemically pure 1.

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“…Demethylation of 1-methoxyxanthones, with added methoxy groups in the A and B rings, with aluminum chloride produced 1-hydroxy derivatives (2). However, mixtures resulted with this reagent if the methyl ethers were sensitive to acidic reagents (1).…”

mentioning

confidence: 99%