Lignans of western red cedar (Thujaplicata Donn). IX. Plicatinaphthalene

1969 ◽  
Vol 47 (23) ◽  
pp. 4495-4498 ◽  
Author(s):  
Harold MacLean ◽  
B. F. MacDonald

The last of nine lignans detectable by thin-layer chromatography in the hot-water soluble extractives of western red cedar (Thujaplicata Donn) heartwood has been determined as 6-hydroxy-2(hydroxy-methyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthalene 2) by spectrometric methods, by degradation studies of derivatives, and by preparation of its trimethyl ether derivative 3 from dehydroanhydropicropodophyllin by opening of the methylenedioxy group with boron trichloride.

1969 ◽  
Vol 47 (3) ◽  
pp. 457-460 ◽  
Author(s):  
Harold MacLean ◽  
B. F. MacDonald

The isolation and structure of a new lignan, 1,6-dihydroxy-2-(hydroxymethyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthol, 2), in which the 4-aryltetrahydronaphthalene structure of plicatin (1) has been aromatized to a 4-arylnaphthol nucleus are described. Proof of structure of the parent compound and its tetramethyl, tetraacetyl, and tetraethyl derivatives is presented both by analytical and spectral techniques, in addition to the synthesis of the tetramethyl derivative starting from podophyllotoxin.


1966 ◽  
Vol 44 (13) ◽  
pp. 1541-1545 ◽  
Author(s):  
Harold MacLean ◽  
Koji Murakami

In addition to the already known plicatic acid and plicatin, five new lignans have been separated by thin-layer and column chromatography from the hot-water extractive of western red cedar (Thujaplicata Donn) heartwood, and two chemical structures have been identified. These are 2-(4″-hydroxy-3″,5″-dimethoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (thujaplicatin methyl ether) (I) and 2-(3″,4″-dihydroxy-5″-methoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (thujaplicatin) (II). The former is the first known example of a lignan containing a guaiacyl and a syringyl nucleus and the first example of a syringyl-group lignan isolated from a conifer. Proof of structure by synthesis, degradation, analysis, and various spectra is presented. The other components which apparently belong to this lignan series are still being investigated.


Eisei kagaku ◽  
1967 ◽  
Vol 12 (6) ◽  
pp. 384-385
Author(s):  
Fukujiro Fujikawa ◽  
Kunio Hirai ◽  
Misuzu Tachibana ◽  
Utaka Otani

Author(s):  
Nondita Prasad ◽  
Balbir Singh ◽  
Diksha Puri

  Objective: Justicia gendarussa Burm. (family Acanthaceae) commonly known as nilinirgundi, is found in Southern India possesses multifarious biological activities due to large range of phytoconstituents. The present study is designed to evaluate the various pharmacognostic parameters of the leaves of J. gendarussa, found in Dehradun district of Uttarakhand for its authentication.Methods: Fresh leaves were taken for the morphological and microscopical (histology and powder) evaluation. Physicochemical parameters (ash values, extractives values, florescence analysis, microbial contamination, and loss on drying) were also performed. Phytochemical screening and thin-layer chromatographic fingerprinting of extracts were also performed to check the presence of various phytoconstituents.Results: The microscopy of the leaves evinced the presence of anisocytic stomata, cuboidal calcium oxalate crystals, cystoliths, multicellular covering trichomes, starch grains and oil globules. The quantitative estimation of total ash, acid insoluble, and water soluble ash values were 13.8%, 1.2%, and 4.5% w/w, respectively. The alcohol soluble and water soluble extractives were estimated as 11.45% and 15.67% w/w, respectively. Foreign organic matter and loss on drying values obtained were 0.23% and 11.2% w/w. Phytochemical screening of petroleum ether, chloroform, methanol and aqueous extracts ascertained the presence of alkaloids, phenolic compounds, saponins, tannins, carbohydrates, flavonoids, glycosides, steroids and triterpenoids. The thin-layer chromatography (TLC) profiling of different extracts revealed the presence of potential compounds which can be further isolated with the help of high-performance liquid chromatography or high-performance TLC.Conclusion: The results of this study provide suitable standards for the authentication of this plant. In the present study, there are certain variations observed from the evaluations done on the same species by other research groups. The probable reason suggested for such disparity is due to the environmental and geographical differences in the locations of the plant collected.


Author(s):  
Neelutpal Gogoi ◽  
Biman Bhuyan ◽  
Trinayan Deka

Objectives: In this study, systematic pharmacognostic study and preliminary phytochemical screening of the bark of Cascabela thevetia L. were carried out. Methods: The selected plant part was collected, processed and stored in an airtight container. From the bark different pharmacognostic studies like macroscopic and microscopic evaluation, physicochemical parameters, fluorescence analysis were done. Powdered bark was successively extracted by petroleum ether, chloroform, ethyl acetate, and methanol using a Soxhlet apparatus and finally macerated with the hydro-alcoholic solvent system (30:70). The preliminary phytochemical analysis and thin layer chromatography of the extracts were done to find the nature and number of the different phytoconstituents present. Results: Transverse microscopy reveals the presence of crystal oxalate, cork cell, starch granules, vascular bundle, phloem fiber, parenchyma cells, and collenchyma cells. Powder microscopy also showed the presence of cork cell, fiber and calcium oxalate crystal. Results obtained in different physicochemical analysis like total ash, acid insoluble ash, water soluble ash, alcohol-soluble extractive, water-soluble extractive, and moisture content were 8.67%, 0.83%, 5.33%, 4.53%, 12.27%, and 7.83% respectively. Phytochemical analysis showed the presence of alkaloid, flavonoid, triterpenoid, phytosterol, tannin, saponin, anthraquinone, carbohydrate and fatty acid in the different extracts. TLC (Thin Layer Chromatography) study revealed 4 spots in petroleum ether, chloroform, ethyl acetate, and methanol extracts and 3 spots in the Hydro-alcoholic extract with different solvent systems. Conclusion: The results obtained from the study will provide a reliable basis for identification, purity, and quality of the plant.


1967 ◽  
Vol 45 (7) ◽  
pp. 739-740 ◽  
Author(s):  
Harold MacLean ◽  
B. F. MacDonald

The structure of a seventh lignan from the hot-water extractive of western red cedar, which was partially separated in a previous paper, has been determined as 2,3-dihydroxy-2-(3″,4″-dihydroxy-5″-methoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (I). This lignan is the fifth member of the thujaplicatin series and is trivially named dihydroxythujaplicatin. Methylation, ethylation, and degradation studies provide proof of structure by comparison with known compounds.


2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Beata Polak ◽  
Emilia Pajurek

AbstractThe separation of some water- and fat-soluble vitamins via micellar systems of reversed-phase high-performance thin-layer chromatography (HPTLC) and pressurized planar electrochromatography (PPEC) was subjected to research. Hence, the influence of the mobile phase composition (surfactant and acetonitrile concentration, eluent buffer pH) on the migration distances and zone separation of some vitamins (thiamine, riboflavin, niacin, pyridoxine, cyanocobalamin, folic acid, ergocalciferol and α-tocopherol) was investigated. Our results indicated that the applied technique has an impact on the solute order. Comparing the system capacity of HPLC and PPEC (measured as height of the theoretical plate) for the mobile phase systems with and without surfactant shows differences, especially for fat-soluble vitamin. The variances and reproducibilities (% RDS) values of the vitamin are less in PPEC than in TLC. Moreover, the migration distances of water-soluble vitamins are longer than fat-soluble ones. Overall, eluent consisting of 50% acetonitrile, 18.75 mM SDS, the buffer of pH 6.99 via the PPEC technique was most appropriate for determining the investigated vitamins in the artificial mixture and the two commercially available vitamin combinations.


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