Guibourtacacidin: a new Leuco-anthocyanidin from Rhodesian copalwood; (Guibourtia coleosperma)
- Authors: De Bruyn, Guustaaf Cornelis
- Date: 1962
- Subjects: Phanerogams , Angiosperms , Flavonoids , Anthocyanidins
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4459 , http://hdl.handle.net/10962/d1011043
- Description: A new leuco-anthocyanidin, (+)-7,4'dihydroxyflavan- 3:4-diol has been isolated from the heartwood of Guibourtia coleosperma. The heartwood extractives were fractionated by enrichment procedures involving fractional precipitation and Craig partitioning, to give a high RF (subscript) low molecular weight fraction containing the above leuco -anthocyanidin. This was further fractionated by "preparative" paper chromatography . The leuco-anthocyanidin was amorphous and present in low proportion (0.004%) in the wood. On boiling with alcoholic hydrochloric acid the compound gave an anthocyanidin which was identified as 3,7,4'-trihydroxyflavylium chloride. The degradation products formed by alkali fusion, on a micro-scale, were resorcinol and ♭-resorcylic acid, and also p (underscore)-hydroxybenzoic acid. This indicated resorcinol and phenol A and B nuclei respectively. The formation of amorphous dimethyl ether and tetra-acetoxy derivatives indicated two phenolic and two alcoholic hydroxyl groups. The above indicates that the compound was 7,4'-dihydroxyflavan- 3:4- diol and a molecular weight estimation showed it to be monomeric. Comparison of the infrared absorption spectra of the natural dimethyl ether with synthetic (±) dimethoxyflavan- 3:4-diol, to which a tentative 2:3- trans- 3:4-cis conformation had been assigned (Phatak and Kulkarni 94), showed close identity. Crystalline (±)-7, 4 '-dihydroxyflavan- 3:4 - diol was synthesised by catalytic hydrogenation over platinum oxide of the corresponoing (±) -7,4'-dihydroxyflavanonol. The flavanonol was synthesised by sodium hyposulphite reduction of the 7,4 ' -dihydroxyflavonol. The infrared absorption spectra of the natural and synthetic diols were similar but not identical. Chromatographic evidence showed the apparent identity of the synthetic and natural flavan- 3:4- diols, and two possible configurations were assigned for the natural flavan-3:4-diol. The new leuco-anthocyanidin was observed to form an O(underscore)-ethyl ether derivative on manipulation in ethanol. A monomeric leuco- fisetinidin from the heartwood was identified, by two dimensional paper chromatography, as (+) - mollisacacidin. The condensed tannins found also in the heartwood of G.(underscore)- coleosperma appear to be polymeric forms of leuco - fisetinidin and leuco - guibourtinidin. These polymeric tannins form a large proportion of the heartwood extractives and furnish high yields of fisetinidin and guibourtinidin chlorides on boiling with alcoholic hydrochloric acid. Examination of some other members of the Guibourtia spp . by paper chromatography showed that only G (underscore). coleosperma contained the new leuco - anthocyanidin as well as a leuco - fisetinidin. G. (underscore) tessmannii and G. (underscore) demeusii heartwoods contained only leuco-fisetinidin and the related polymers and a close chemical relationship to G.(underscore) coleosperma is thus apparent. G.(underscore) arnoldiana on the other hand is not chemically interrelated with the above members since it appeared to contain only leuco - cyanidin. (±) - 7,4 ' -Dihydroxyflavan- 4-ol was synthesised by hydrogenation of the corresponding flavanone over platinum oxide. Observations were made regarding its reddenig and ease of condensation.
- Full Text:
- Date Issued: 1962
- Authors: De Bruyn, Guustaaf Cornelis
- Date: 1962
- Subjects: Phanerogams , Angiosperms , Flavonoids , Anthocyanidins
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4459 , http://hdl.handle.net/10962/d1011043
- Description: A new leuco-anthocyanidin, (+)-7,4'dihydroxyflavan- 3:4-diol has been isolated from the heartwood of Guibourtia coleosperma. The heartwood extractives were fractionated by enrichment procedures involving fractional precipitation and Craig partitioning, to give a high RF (subscript) low molecular weight fraction containing the above leuco -anthocyanidin. This was further fractionated by "preparative" paper chromatography . The leuco-anthocyanidin was amorphous and present in low proportion (0.004%) in the wood. On boiling with alcoholic hydrochloric acid the compound gave an anthocyanidin which was identified as 3,7,4'-trihydroxyflavylium chloride. The degradation products formed by alkali fusion, on a micro-scale, were resorcinol and ♭-resorcylic acid, and also p (underscore)-hydroxybenzoic acid. This indicated resorcinol and phenol A and B nuclei respectively. The formation of amorphous dimethyl ether and tetra-acetoxy derivatives indicated two phenolic and two alcoholic hydroxyl groups. The above indicates that the compound was 7,4'-dihydroxyflavan- 3:4- diol and a molecular weight estimation showed it to be monomeric. Comparison of the infrared absorption spectra of the natural dimethyl ether with synthetic (±) dimethoxyflavan- 3:4-diol, to which a tentative 2:3- trans- 3:4-cis conformation had been assigned (Phatak and Kulkarni 94), showed close identity. Crystalline (±)-7, 4 '-dihydroxyflavan- 3:4 - diol was synthesised by catalytic hydrogenation over platinum oxide of the corresponoing (±) -7,4'-dihydroxyflavanonol. The flavanonol was synthesised by sodium hyposulphite reduction of the 7,4 ' -dihydroxyflavonol. The infrared absorption spectra of the natural and synthetic diols were similar but not identical. Chromatographic evidence showed the apparent identity of the synthetic and natural flavan- 3:4- diols, and two possible configurations were assigned for the natural flavan-3:4-diol. The new leuco-anthocyanidin was observed to form an O(underscore)-ethyl ether derivative on manipulation in ethanol. A monomeric leuco- fisetinidin from the heartwood was identified, by two dimensional paper chromatography, as (+) - mollisacacidin. The condensed tannins found also in the heartwood of G.(underscore)- coleosperma appear to be polymeric forms of leuco - fisetinidin and leuco - guibourtinidin. These polymeric tannins form a large proportion of the heartwood extractives and furnish high yields of fisetinidin and guibourtinidin chlorides on boiling with alcoholic hydrochloric acid. Examination of some other members of the Guibourtia spp . by paper chromatography showed that only G (underscore). coleosperma contained the new leuco - anthocyanidin as well as a leuco - fisetinidin. G. (underscore) tessmannii and G. (underscore) demeusii heartwoods contained only leuco-fisetinidin and the related polymers and a close chemical relationship to G.(underscore) coleosperma is thus apparent. G.(underscore) arnoldiana on the other hand is not chemically interrelated with the above members since it appeared to contain only leuco - cyanidin. (±) - 7,4 ' -Dihydroxyflavan- 4-ol was synthesised by hydrogenation of the corresponding flavanone over platinum oxide. Observations were made regarding its reddenig and ease of condensation.
- Full Text:
- Date Issued: 1962
A study of electrospun nanofibers and diatomaceous earth materials for the extraction of alkaloids, flavonoids and aromatic amines in various matrices
- Mothibedi, Kediemetse (Kedimetse)
- Authors: Mothibedi, Kediemetse (Kedimetse)
- Date: 2013 , 2013-04-07
- Subjects: Nanofibers , Electrospinning , Sorbents , Extraction (Chemistry) , Alkaloids , Flavonoids , Amines , Matrices , Goldenseal , Ginkgo , Dyes and dyeing -- Chemistry
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4288 , http://hdl.handle.net/10962/d1003052 , Nanofibers , Electrospinning , Sorbents , Extraction (Chemistry) , Alkaloids , Flavonoids , Amines , Matrices , Goldenseal , Ginkgo , Dyes and dyeing -- Chemistry
- Description: The thesis explored the use of different sorbent materials in solid phase extraction method development. The methods included the use of the polymeric Agilent Bond Elut Plexa solid phase extraction and electrospun polymer-silica composite sorbents for clean-up and preconcentration. Sample clean-up for alkaloids (hydrastine and berberine) in goldenseal, Hydrastis canadensis and flavonoids (quercetin, kaempferol and isorhamnetin) in Ginkgo biloba was achieved using Bond Elut Plexa SPE sorbent. Clean-up of flavonoids in Ginkgo biloba was also achieved using electrospun polymer-silica composite (polystyrene-silica, polyacrylonitrile-silica and nylon 6-silica) sorbents. All analysis of flavonoids and alkaloids was carried out using an Agilent 1200 Series HPLC coupled with a diode array detector. Good peak separation was achieved in less than 6 min employing an Agilent ZORBAX Eclipse Plus C18 column (4.6 x 75 mm, 3.5 μm) at 35⁰C. The mobile phases employed were 0.1% phosphoric acid/methanol gradient and 0.5% phosphoric acid/methanol (40:60) for alkaloids and flavonoids respectively. The calibration curves exhibited linearity up to 120 μg mL⁻¹ with correlation coefficients of more than 0.9980. The recoveries ranged from 73-109% with relative standard deviation of less than 5% for all analytes. Agilent Chem Elut supported liquid extraction was employed for the development of a sample preparation method for the determination of 24 banned aromatic amines from azo dyes in textile following the EU standard method EN 14362-1:2003 (E) and the Chinese standard method GB/T 17592-2006. The supported liquid extraction was effective in the extraction of the aromatic amines from textile (cotton, wool and polyester/cotton [80%:20%]). Most of the recoveries obtained were conforming to the minimum requirements set in the EN 14362-1:2003 (E) standard method and the relative standard deviations were less than 15%. Good peak separation was obtained within 70 min run time using the Agilent Zorbax SB-Phenyl column (4.6 mm x 250 mm, 5-micron) or the Agilent DB-35 MS (J & W) (30 m x 0.25 mm, 0.25 μm film thickness. It was demonstrated that the polymeric Agilent Bond Elut Plexa, electrospun nanofibers and diatomaceous earth were effective in extraction of alkaloids, flavonoids and aromatic amines in different matrices. The developed methods were simple, rapid and reproducible.
- Full Text:
- Date Issued: 2013
- Authors: Mothibedi, Kediemetse (Kedimetse)
- Date: 2013 , 2013-04-07
- Subjects: Nanofibers , Electrospinning , Sorbents , Extraction (Chemistry) , Alkaloids , Flavonoids , Amines , Matrices , Goldenseal , Ginkgo , Dyes and dyeing -- Chemistry
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4288 , http://hdl.handle.net/10962/d1003052 , Nanofibers , Electrospinning , Sorbents , Extraction (Chemistry) , Alkaloids , Flavonoids , Amines , Matrices , Goldenseal , Ginkgo , Dyes and dyeing -- Chemistry
- Description: The thesis explored the use of different sorbent materials in solid phase extraction method development. The methods included the use of the polymeric Agilent Bond Elut Plexa solid phase extraction and electrospun polymer-silica composite sorbents for clean-up and preconcentration. Sample clean-up for alkaloids (hydrastine and berberine) in goldenseal, Hydrastis canadensis and flavonoids (quercetin, kaempferol and isorhamnetin) in Ginkgo biloba was achieved using Bond Elut Plexa SPE sorbent. Clean-up of flavonoids in Ginkgo biloba was also achieved using electrospun polymer-silica composite (polystyrene-silica, polyacrylonitrile-silica and nylon 6-silica) sorbents. All analysis of flavonoids and alkaloids was carried out using an Agilent 1200 Series HPLC coupled with a diode array detector. Good peak separation was achieved in less than 6 min employing an Agilent ZORBAX Eclipse Plus C18 column (4.6 x 75 mm, 3.5 μm) at 35⁰C. The mobile phases employed were 0.1% phosphoric acid/methanol gradient and 0.5% phosphoric acid/methanol (40:60) for alkaloids and flavonoids respectively. The calibration curves exhibited linearity up to 120 μg mL⁻¹ with correlation coefficients of more than 0.9980. The recoveries ranged from 73-109% with relative standard deviation of less than 5% for all analytes. Agilent Chem Elut supported liquid extraction was employed for the development of a sample preparation method for the determination of 24 banned aromatic amines from azo dyes in textile following the EU standard method EN 14362-1:2003 (E) and the Chinese standard method GB/T 17592-2006. The supported liquid extraction was effective in the extraction of the aromatic amines from textile (cotton, wool and polyester/cotton [80%:20%]). Most of the recoveries obtained were conforming to the minimum requirements set in the EN 14362-1:2003 (E) standard method and the relative standard deviations were less than 15%. Good peak separation was obtained within 70 min run time using the Agilent Zorbax SB-Phenyl column (4.6 mm x 250 mm, 5-micron) or the Agilent DB-35 MS (J & W) (30 m x 0.25 mm, 0.25 μm film thickness. It was demonstrated that the polymeric Agilent Bond Elut Plexa, electrospun nanofibers and diatomaceous earth were effective in extraction of alkaloids, flavonoids and aromatic amines in different matrices. The developed methods were simple, rapid and reproducible.
- Full Text:
- Date Issued: 2013
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