Wood, chloroform extract

FIGURE 3.33 (a) Total-ion chromatogram of a chloroform extract of a wood sliver from a telephone pole for determination of pentachlorphenol (b) expanded view of chromatogram ranging from 20 to 25 min. Peak at retention time of 20.14 min was determined to be pentachlorphenol. Conditions 30-m x 0.25-mm-i.d. DB-5 column with 0.25-u.m film. Column conditions 40°C at 8°C/min to 250°C after 1 min isothermal hold splitless injection of 1 aL (1 min delay time). 

The natural ryanoids are conveniently isolated from ryania by wet chloroform extraction and rotary chromatography on silica gel with chloroform/methanol/ aqueous methylamine followed by reverse phase HPLC with aqueous methanol (2,7,8). Ryanodine 0 and dehydroryanodine 0 are the major ryanoids, each making up 480-700 ppm (w/w) relative to the stem-wood, with seven other ryanoids contributing 10-64 ppm (w/w) each (8). 

Urban (116), found that completely methylated cellulose was soluble in chloroform, whereas methylated lignin was insoluble in this solvent. Therefore, he reacted the wood with dimethyl sulfate until methylation was complete. On extraction of this wood with chloroform, both the methyl lignin and methylcellulose were dissolved without being separated. 

Extraction Procedure from Powdery Stem Wood. A 0.1 g sample of R. speciosa ground powdery wood was weighed in a 40 mb screw-capped tube, and 10 mb of chloroform was added. Tubes were placed in an ultrasonic bath for 15 min at a temperature of 60 °C and then centrifuged for 5 min at 4500 rpm. A 1 mb aliquot was removed, and organic solvent was dried under a nitrogen stream, taken up with 1 mb of mobile phase (water/methanol, 75 25, v/v), and filtered with a 0.45 pm PTFE membrane filter. The resulting solution was analyzed by HPbC. 

Wood etal. (1988) developed the reversed-phase high-performance liquid chromatographic (HPLC) method for piperine determination in black pepper and its oleoresins. ft employs bonded C18 stationary phase (ODS-2) and acetonitrile-aqueous acetic acid mobile phase with UV detection. As the spectropho-tometric method which invariably yields higher results because of the contributions from other alkaloids such as piperyline and piperettine, the HPLC method relates more to piperine. Utilizing the UV absorption property of piperine, spectrophotometric estimation methods were developed by different groups using solvents such as benzene, ethanol, ethylene dichloride, acetone, ethyl acetate, chloroform and cyclohexane. Sowbhagya et al. (1990) proved that extractability with acetone was very efficient. 

The purification procedure can be modified by omitting the last addition of chloroform (Lundquist and Kirk 1980). This results in a somewhat less efficient removal of carbohydrates but separation of the organic layer is easier. The precipitation in ether included in the preferred method removes residual extractives and other contaminants but also causes losses of ether-soluble lignin constituents. Purification procedures involving gel permeation chromatography (Kirk and Lundquist 1970, Bardet et al. 1985) should be considered when there is an interest in retaining the latter type of materials. Ether solubles from a preparation of spruce MWL have been examined (Lundquist et al. 1977). Hydrophilic constituents of dioxane-water extracts from milled spruce wood have recently been investigated (Lundquist et al. 1990). 

Prior to bromination, small sticks of wood (1.5 mm radial 1.5 mm tangential 5 mm longitudinal) are extracted overnight with benzene-ethanol (2 1, v/v) in a Soxhlet extractor. The extracted sample is dehydrated sequentially with ethanol and water mixtures with increasing ethanol concentration up to 100%, and finally with chloroform. The sample is brominated at room temperature in a nonaqueous system with a solution of bromine in chloroform (0.3 ml in 20 ml). The bromine solution is slowly dropped into a 125-ml Erlenmeyer flask that contains 70 ml of chloroform and 1 g of wood sticks with stirring. After stirring for 30 min, the brominated wood sticks are washed several times with an excess of chloroform at room temperature to remove unreacted bromine and then with ethanol. 

Off. Prep.—Extractum Cannabis, U.S. (Br.) Fluidextractum Cannabis, U.S. Tinctura Cannabis (from Extract), Br. Collodium Salicylici Composita (from Fluidextract), A. E Mistura Chlorali et Potassii Bromidi Composita (from Extract), N.F. Mistura Chloroform) et Morphinae Composita (from Tincture), N.F. Source Wood 1926... 

Ryania. A genus of tropical American shrubs and trees belonging to the Flacourtiaceae family. The wood of various species is insecticidal. Oround stem wood of Ryanie speciosa Vahl., Flacourtiaceae is employed in the commercial insecticide formulations Ryanex, Ryanicide (formerly). See Polkers et al., U.S. pat. 2,400,295 (1946 to Merck Co.) Pepper, Carruth, J. Econ, Entomol 38, 59 (1945) Heal, Agr. Chem. 4, 37 (May. 1949). Insecticidal components such as ryanodine, g.v., are extractable by water, chloroform, or methanol. Toxicity data Kuna, Heal, J. Pharmacol Exp. Then 93, 407 (1948). 

In order to compare synthetic ifflaiamine with the natural alkaloid, Chamberlain and Grundon (198, 199) reexamined a crude alkaloid extract derived from the wood of Flindersia ifflaiana and obtained two isomeric alkaloids. Ifflaiamine (264) mp 122-125° [a]D-6.2° in methanol and -9.15° in chloroform picrate, mp 189-192° had properties different from those reported earlier (Volume IX). The second alkaloid (mp 53-54° picrate, mp 188-191°) was shown to be the 1,2-dimethylallyl derivative 267 by comparison with the synthetic racemate (mp 106-108° picrate, mp 186-190°). The alkaloid was levorotatory, but too little was available to obtain an accurate value of the specific rotation. 

Mr 240.26, yellow needles, mp. 206-208 °C, soluble in alcohol, chloroform, or fats. C. is the main component of a mixture of various an-thrones and anthranols known as chrysarobinum obtained by benzene extraction from araroba or goa powder (yellow-brown powder from cavities in the heart-wood of the 20-30 m high tree Andira araroba, Fabaceae, endemic to Brazil and for long cultivated in India) which, after dying on wool, gives a dark violet color. C. is also isolated from Cassia and Rumex species and from Ferreirea spectabilis (Fabaceae) it is also formed by Penicillium islandicum. 

In an attempt to produce CMF under milder reaction conditions, Gao et al. described an aqueous-organic biphasic reaction system where a combination of concentrated HCI (37%) and H3PO4 (85%) were used in the aqueous phase with chloroform as the extracting solvent at only 45°C [125]. CMF was obtained in 47% isolated yield from fructose, although glucose and cellulose gave poor yields of CMF, 7.3% and 7.8%, respectively. Surprisingly, CMF yields up to 31% were obtained when cellulosic feedstocks (e.g., eucalyptus wood) were used. 

Wood (1985) suggested that chloroform might be a more effective extractant. However, chloroform has the disadvantage of forming hydrochloric acid upon storage, and hence its use will lead to the production of phaeophytins and phaeophorbides during the extraction procedure. While this may not seriously affect total analyses, it will surely be noted in HPLC analysis. Thus, if chloroform is to be employed as the extractant, frequent solvent clean-up becomes necessary. 

The more polar flavonoids occur in the alcohol-soluble fraction of the wood, whereas lipophilic flavonoids, if present, appear in the chloroform or ether extract. Flavonoids may crystallize directly from such extracts, but are more usually obtainable in pure form after some suitable chromatographic separation. They are then characterized by standard spectroscopic procedures (14, 15) and, where appropriate, by comparison with authentic markers. Some wood flavonoids are labile in solution, undergoing oxidation or polymerisation during handling. It is possible during the processes of extraction and purification that interconversions of one type to another (e.g. of dihydroflavonol to flavonol) may occur. Care must therefore be exercised in flavonoid analyses of wood tissues to avoid artifact production in this way. Also, some structural analyses have not been entirely unambiguous examples will be mentioned in later sections where is has not proved possible to re-isolate and confirm the presence of a particular wood flavonoid. 

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