A flavone glycoside from Andrographis alata

Damu, Amooru G.; Jayaprakasam, B.; Rao, Karumanchi V.; Gunasekar, Duvvuru

doi:10.1016/s0031-9422(98)00342-2

Cited by 31 publications

(15 citation statements)

References 10 publications

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“…The signal at d 1.98 (3H, s), which, in conjunction with two carbon resonances at d 170.2 and 20.6 in its 13 C NMR spectrum indicated the presence of an acetyl moiety in 1. Acid hydrolysis of 1 afforded D-glucose and an aglycone, echioidinin [10]. The glucose residue in 1 was found to be linked to C-2 0 as the anomeric proton at d 5.16 was correlated to C-2 0 (d 155.3) in the HMBC spectrum, further supported by a strong NOE correlation between H-1 00 (d 5.16) and H-3 0 (d 7.32) in its NOESY spectrum.…”

Section: Resultsmentioning

confidence: 99%

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A new acylated flavone glycoside fromColebrookea oppositifolia

Reddy

Gunasekar

2009

Journal of Asian Natural Products Research

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A new acylated flavone glycoside, echioidinin 2'-O-beta-D-(2''-O-acetyl)glucopyranoside (1) along with the three known flavonoids, 5,6,7,8,5'-pentamethoxy-3',4'-methylenedioxyflavone (2), 5,2',6'-trihydroxy-7-methoxyflavone (3), and kaempferol 7,4'-dimethyl ether 3-O-beta-D-glucopyranoside (4), were isolated from the roots of Colebrookea oppositifolia. The structure of compound 1 was elucidated by extensive spectral and chemical studies.

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Section: Resultsmentioning

confidence: 99%

“…The extract was concentrated and the residue on crystallization from MeOH gave yellow needles of echioidinin (4 mg), mp 263 -2658C, identified by direct comparison of its spectral data with the literature values [10]. The sugar in the aqueous layer was identified as D-glucose by co-PC (BAW, 4:1:5).…”

Section: Acid Hydrolysis Ofmentioning

confidence: 99%

A new acylated flavone glycoside fromColebrookea oppositifolia

Reddy

Gunasekar

2009

Journal of Asian Natural Products Research

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“…The three-dimensional structure of irinotecan was constructed in the Molecular Operating Environment. The interaction of irinotecan in the binding domain cavity of MRP4 was analyzed from a ligand-interaction study of the Molecular Operating Environment (21)(22)(23).…”

Section: Mice and Cell Lines-mrp4mentioning

confidence: 99%

Compartmentalized Accumulation of cAMP near Complexes of Multidrug Resistance Protein 4 (MRP4) and Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Contributes to Drug-induced Diarrhea

Moon

Zhang

Ren³

et al. 2015

Journal of Biological Chemistry

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Background: Diarrhea is an adverse side effect associated with many therapeutics. Results: Irinotecan induced hyperactive cystic fibrosis transmembrane conductance regulator (CFTR) function by inhibiting multidrug resistance protein 4 (MRP4) and formation of MRP4-CFTR macromolecular complexes. Conclusion: MRP4-CFTR-containing macromolecular complexes play an important role in drug-induced diarrhea. Significance: These studies help define molecular mechanisms of drug-induced diarrhea.

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Results and DiscussionCompound 3, obtained as yellow crystals, mp 210-211°C, showed the pseudomolecular ion at m/z 301.0714 in its positive high resolution chemical ionization mass spectrometry (HR-CI-MS) corresponding to the molecular formula C 16 H 12 O 6 . This was corroborated by decoupled 13 C-NMR spectrum which showed signals for all the sixteen carbons of the molecule.

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confidence: 99%

“…1) As part of our continuing investigation on the flavonoid constituents of Andrographis species, [2][3][4][5][6] we have examined the whole plant of A. elongata, a plant hitherto not investigated for its chemical constituents and report here the isolation and structure elucidation of two new 2Ј-oxygenated flavones (3, 5), in addition to three known flavones (1, 2, 4).…”

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Two New 2'-Oxygenated Flavones from Andrographis elongata.

Jayakrishna

Harikishore

Rao

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Andrographis elongata T. And (Acanthaceae) is an herbaceous plant distributed throughout the Western Ghats of South India.1) As part of our continuing investigation on the flavonoid constituents of Andrographis species, [2][3][4][5][6] we have examined the whole plant of A. elongata, a plant hitherto not investigated for its chemical constituents and report here the isolation and structure elucidation of two new 2Ј-oxygenated flavones (3, 5), in addition to three known flavones (1, 2, 4). Results and DiscussionCompound 3, obtained as yellow crystals, mp 210-211°C, showed the pseudomolecular ion at m/z 301.0714 in its positive high resolution chemical ionization mass spectrometry (HR-CI-MS) corresponding to the molecular formula C 16 H 12 O 6 . This was corroborated by decoupled 13 C-NMR spectrum which showed signals for all the sixteen carbons of the molecule. The UV absorption maxima of 3 in MeOH (258, 303 nm) and a bathochromic shift of 62 nm with AlCl 3 / HCl suggested that it is a 5-hydroxyflavone.The 1 H-NMR spectrum of 3 showed the presence of a methoxyl (d 3.83), a chelated hydroxyl (d 12.88), two nonchelated hydroxyls (d 9.88, 2H) and a singlet at d 6.26 assigned to H-3. A set of meta coupled doublets (Jϭ2.2 Hz) resonating at d 6.38 and 6.61 were ascribed to H-6 and H-8 protons, respectively. From heteronuclear multiple bond connectivity (HMBC) and rotating frame Overhauser enhancement spectroscopy (ROESY) studies the methoxyl group at d 3.83 was placed at C-7 as the methoxyl protons showed correlation with C-7 at 165.1 ppm in its HMBC spectrum ( Fig. 1) and two strong nuclear Overhauser effects (NOEs) were observed between methoxyl protons at C-7 and H-6 (d 6.38) and H-8 (d 6.61) protons (Fig. 1). The presence of AB 2 type aromatic proton signals of ring B at d 7.10 (1H, t, Jϭ8.2 Hz) and 6.40 (2H, d, Jϭ8.2 Hz) were typical of 4Ј, and 3Ј and 5Ј protons of 2Ј,6Ј-dihydroxy (or methoxy) flavones.7-9) The presence of 2Ј,6Ј-dioxygenation in 3 was also supported by the chemical shift values of the B-ring carbons which were very similar to those observed for the B-ring carbons of 2Ј,6Ј-dihydroxyflavones. 9,10) The electron impact-mass spectra (EI-MS) of compound 3 exhibited the molecular ion as the base peak at m/z 300, with the diagnostic peaks of retro-Diels-Alder cleavage of ring C at m/z 167 and 134 supporting the presence of a hydroxyl and a methoxyl in ring A, and two hydroxyls in ring B. From HMBC correlations the two non-chelated hydroxyls were located at C-2Ј and C-6Ј positions as both these hydroxyl bearing carbons at 156.6 ppm showed cross peaks with H-3Ј and H-5Ј (d 6.40), and H-4Ј (d 7.10) protons (Fig. 1). Thus the structure of compound 3 was elucidated as 5,2Ј,6Ј-trihydroxy-7-methoxyflavone.Compound 5, obtained as yellow amorphous powder showed [MϩH] ϩ peak at m/z 607.1807 in its HR-FAB-MS corresponding to the molecular formula C 32 H 30 O 12 , and was corroborated by 13 C-NMR spectrum which showed signals for all the 32 carbons of the molecule. The UV spectrum exhibited absorption maxima at 2...

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A flavone glycoside from Andrographis alata

Cited by 31 publications

References 10 publications

A new acylated flavone glycoside fromColebrookea oppositifolia

A new acylated flavone glycoside fromColebrookea oppositifolia

Compartmentalized Accumulation of cAMP near Complexes of Multidrug Resistance Protein 4 (MRP4) and Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Contributes to Drug-induced Diarrhea

Two New 2'-Oxygenated Flavones from Andrographis elongata.

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