Chemical Constituents of Gentianaceae IV: New Xanthones of Canscora decussata

Ghosal, Shibnath; Chaudhuri, Ratan K.; Nath, A.

doi:10.1002/jps.2600620128

Cited by 35 publications

(13 citation statements)

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“…Fraction 5 (15 mg) was separated by a low pressure ODS column (15 g) (MeOH/H 2 O, 70 : 30) to yield 1 (91 ± 106 ml, 5 mg), and fraction 8 (25 mg) was purified by HPLC (column A, MeOH/H 2 O, 70 : 30, 1 ml/min, UV 254 nm) to yield 2 (7 mg, t R 11.0 min). [12], 190 ± 192 8C (MeOH)], R f 0.58 and 0.39 (silica gel, solvents A and B, respectively), 0.53 (reversed-phase KC 18 F, solvent C), 1 H-NMR, 13 C-NMR and MS : literature [11], [12].…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…MeOH)], R f 0.65 and 0.41 (silica gel, solvents A and B, respectively), 0.62 (reversedphase KC 18 F, solvent C),13 C-NMR and MS : literature[9],[10].1,3,6-Trihydroxy-5-methoxyxanthone (9): Yellow powder, m. p. 291 ± 292 8C (MeOH) [lit [11],. 290 ± 291 8C (MeOH)], R f 0.65 and 0.41 (silica gel, solvents A and B, respectively), 0.62 (reversedphase KC 18 F, solvent C), 1 H-NMR and MS : literature[11],13 C-NMR (Table 1). 1,6-Dihydroxy-3, 5-dimethoxyxanthone (10): Yellow powder, m. p. 192 ± 193 8C (MeOH) [lit.…”

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confidence: 99%

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Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Tovomita krukovii

et al. 2002

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Assay-guided fractionation of the ethanol extract of Tovomita krukovii resulted in the identification of four new xanthones (1 - 4) and ten known compounds (5 - 14). The structures of compounds 1 - 14 were determined by spectral data to be 3,5-dihydroxy-4-methoxyxanthone (1), 1,3,5,7-tetrahydroxy-8-isoprenylxanthone (2), 1,3,5-trihydroxy-8-isoprenylxanthone (3), 1,5,7-trihydroxy-8-isoprenylxanthone (4), 1,3,7-trihydroxy-2-isoprenylxanthone (5), 1,5-dihydroxyxanthone (6), 1,6-dihydroxy-5-methoxyxanthone (7), 1,3,5-trihydroxyxanthone (8), 1,3,6-trihydroxy-5-methoxyxanthone (9), 1,6-dihydroxy-3,5-dimethoxyxanthone (10), 1,3,7-trihydroxyxanthone (11), 3-geranyl-2,4,6-trihydroxybenzophenone (12), betulinic acid (13), and 3,4-dihydroxybenzoic acid (14). Compounds 2, 3, 12 and 13 showed inhibitory effects against Candida albicans secreted aspartic proteases (SAP) with IC50 values of 15 microg/ml, 25 microg/ml, 40 microg/ml, and 6.5 microg/ml, respectively, while the other compounds were inactive. In addition, compound 12 showed activity against C. albicans, C. neoformans, S. aureus and methicillin resistant S. aureus (MRS).

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Section: Extraction and Isolationmentioning

confidence: 99%

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confidence: 99%

Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Tovomita krukovii

et al. 2002

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“…[16] Those were identified as β-amyrin (melting point [m.p. ], mixed m.p., co-thin layer chromatography [tlc], [α] D , infrared [IR], m.p., and mixed m.p.…”

Section: Phytochemical Profilementioning

confidence: 99%

“…[17] The identity of these xanthones was established by chemical reactions and spectral (ultraviolet [UV], IR, nuclear magnetic resonance [NMR], and MS) evidence. They also discussed phylogenetic significance of the co-occurrence of these and other polyoxygenated xanthones in the plant.…”

Section: Phytochemical Profilementioning

confidence: 99%

Phytopharmacologic aspects of Canscora decussata Roem and Schult

Sethiya¹,

Patel²,

Mishra³

2010

Phcog Rev

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Nature is an inexhaustible source of secondary metabolites–different types of alkaloids, terpenoids, phenolics, and other classes of organic compounds. In the process of isolation, purification and determination of the structures of lead, with their biological effectiveness, every type of experimental tool and strategy, known too and developed over the years by various practitioners. The present review is an attempt to compile information on various aspects of Canscora decussata, “Shankhpushpi” of Indian traditional system of medicine. The phytoconstituents, such as phenolic compounds, xanthones, and triterpenoids were isolated from different parts of the plant. The plant possesses immunomodulatory, analgesic, anticonvulsant, antitubercular, antiinflammatory, spermicidal, central nervous system–depressive, and cardiostimulant properties. Clinical trials of marketed formulation showed very encouraging results.

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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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Chemical Constituents of Gentianaceae IV: New Xanthones of Canscora decussata

Cited by 35 publications

References 5 publications

Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Tovomita krukovii

Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Tovomita krukovii

Phytopharmacologic aspects of Canscora decussata Roem and Schult

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

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