THE STRUCTURES OF TWO NEW ALKALOIDS: CHASMACONITINE AND CHASMANTHININE

1964 ◽  
Vol 42 (1) ◽  
pp. 154-159 ◽  
Author(s):  
O. Achmatowicz Jr ◽  
Léo Marion
Keyword(s):  
Benzoic Acid ◽  
Cinnamic Acid

A re-examination of the root of Aconitumchasmanthum Stapf has shown that it contains several alkaloids. Of these, besides indaconitine, the presence of which had been reported long ago, four new alkaloids have been isolated: base A (C26H43O6N), base B (C25H41O6N), chasmaconitine (C34H47O9N), and chasmanthinine (C36H49O9N). Chasmaconitine gives rise to bikhaconine on hydrolysis, and has been shown by conversion to delphinine to be N-ethyl-N-desmethyl-delphinine. Chasmanthinine is also hydrolyzable to bikhaconine. Whereas in chasmaconitine bikhaconine is esterified with acetic and benzoic acid, in chasmanthinine it is esterified with acetic and trans-cinnamic acid. The complete structures and absolute configurations of both bases are derived.

Antioxidant Activity and Phenolic Compound Profile of Pistachio Skins (Pistacia vera L., Cultivars Kallehghuchi and Ohadi)

2020 ◽  
Vol In Press (In Press) ◽  
Author(s):  
Shima Azadedel ◽  
Parichehr Hanachi ◽  
Azra Saboora
Keyword(s):  
Antioxidant Activity ◽  
Phenolic Compounds ◽  
Benzoic Acid ◽  
Gallic Acid ◽  
Cinnamic Acid ◽  
High Mass ◽  
Total Phenolic ◽  
Pistacia Vera ◽  
Native Plant ◽  
Pharmaceutical Industries

Background: Pistachio, with the scientific name Pistacia vera L., a native plant in Asia, is a member of the Anacardiaceae family. Pistachio nuts and skins are known as a rich source of phenolic compounds with antioxidant, anti-inflammatory, and antimicrobial properties. Objectives: In the current study, the industrial production of phenolic compounds with antioxidant activity was investigated because of the high mass production of pistachio skin in Iran. Methods: The extraction of two pistachio cultivars, namely Kalleghuchi and Ohadi were carried out by using two methods (maceration and ultrasonic extraction) and four solvents (acetone 70%, ethanol 50%, methanol 50%, and water). Antioxidant properties of pistachio skins were determined by three methods (Folin-Ciocalteau colorimetric method, DPPH assay, TLC/DPPH analysis). Results: The results showed that the highest content of total phenolic compounds were measured by ultrasonic and maceration methods related to Ohadi and Kallehghuchi in acetone solvents 17.4 ± 0.04 and 17.26 ± 0.1 mg/g DW, respectively. The highest antioxidant activity was measured by ultrasonic and maceration methods related to Ohadi in acetone and water solvents IC50 = 0.057 ± 0.001 and 0.059 ± 0.002 µg/ml, respectively. By TLC/DPPH analysis, gallic acid, 4-hydroxy-3, 5-dimethoxy benzoic acid, tannic acid, and some unidentified compounds were determined. By HPLC analysis, gallic acid, coumaric acid, cinnamic acid, 4-hydroxy-cinnamic acid, and 4-hydroxy benzoic acid were determined. Conclusions: In conclusion, this study clarifies some special biochemical characteristics of pistachio skins. Therefore, according to the results of the study, pistachio skins could be successfully used in the food and pharmaceutical industries.

Exhaustive C-methylation of carboxylic acids by trimethylaluminium: A new route to t-butyl compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1665 ◽  
Author(s):  
A Meisters ◽  
T Mole
Keyword(s):  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Carboxylic Acids ◽  
Cinnamic Acid ◽  
Benzoic Acids ◽  
Naphthoic Acid ◽  
Triphenylacetic Acid

Carboxylic acids are exhaustively C-methylated to t-butyl compounds by excess trimethylaluminium at c. 120�. Benzoic acid for example, gives t-butylbenzene. Similarly methylated are o-fluoro-, o-bromo-, and m-chloro-benzoic acids, 5-chloro-3-phenylsalicylic acid, 1-naphthoic acid, palmitic, oleic and undec-10-enoic acids. Adamantane-1-carboxylic acid gives mostly l-isopropenyladaman- tane, along with some 1-t-butyladamantane. Cinnamic acid gives mainly the allylically rearranged 2-methyl-4-phenylpent-2-ene. Triphenylacetic acid behaves atypically; 1,1,1-triphenylpropan-2-one and 3,3,3-triphenylpropyne result.

scholarly journals An attempt to determine the resistance of poplars to infection by Chondroplea populea (Sacc. Kłęb.) = Dothichiza populea Sacc. et Briard) on the basis of the composition of epiphytic bacterial microflora

2015 ◽  
Vol 44 (2) ◽  
pp. 165-188 ◽  
Author(s):  
K. Danilewicz
Keyword(s):  
Carbon Source ◽  
Benzoic Acid ◽  
Aromatic Compound ◽  
Cinnamic Acid ◽  
Resistant Variety ◽  
Epiphytic Bacteria ◽  
Gentisic Acid ◽  
Lignin Model ◽  
Resistance To Infection ◽  
Poplar Cuttings

Epiphytic bacteria isolated from the bark of shoot nodes of two year poplar cuttings hydrolyse chitin whereas those isolated from the internodes do not show this property. The epiphytic microflora of the sensitive variety P. 'Robusta' embraces coryneform bacteria and <i>Pseudomonas</i> which can as a carbon source utilize o-OH benzoic acid, gentisic acid or trans-cinnamic acid in 10<sup>-2</sup>M concentration. The resistant variety P. 'NE-42' is featured by Pseudomonas capable of catabolizing only genetisic acid in 10<sup>-2</sup>M con-centration. The ability of the bacteria to grow media containing either water extracts from the bark or phenolic acids (lignin model precursors) is correlated which the aromatic compound composition of the bark and resistance to infection by fungi.

scholarly journals Antimicrobial Phenolic Compounds from Anabasis Aphylla L

2009 ◽  
Vol 4 (3) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Hua Du ◽  
Ye Wang ◽  
Xiaojiang Hao ◽  
Chun Li ◽  
Youliang Peng ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Phenolic Compounds ◽  
Benzoic Acid ◽  
Cinnamic Acid ◽  
Antimicrobial Agents ◽  
Inhibitory Concentration ◽  
Control Plant ◽  
Acid Methyl Ester ◽  
Spectrometric Analysis ◽  
Bacterium Bacillus

Bioassay-guided fractionation of an ethyl acetate extract from the aerial parts of Anabasis aphylla, a Chenopodiaceous species widely distributed in the northwest of China, led to the isolation of six phenolic compounds, which were identified by means of spectrometric analysis as 1-(2-hydroxy-4,6-dimethoxyphenyl)-ethanone (1), 3,4-dihydroxy cinnamic acid tetracosyl ester (2), 4-hydroxy-3-methoxy benzoic acid (3), 2-hydroxy benzoic acid (4), 3,4-dihydroxy cinnamic acid methyl ester (5) and 4-hydroxy benzoic acid pentadecane ester (6). These compounds were further screened for their minimum inhibitory concentration (MIC) and median inhibitory concentration (IC50) by use of the microdilution-MTT assay for antimicrobial activity against one Gram-positive bacterium ( Bacillus subtilis), three Gram-negative bacteria ( Agrobacterium tumefaciens, Pseudomonas lachrymans, and Xanthomonas vesicatoria), and one yeast ( Candida albicans). Apart from compound 6, which had no activity against any of the tested microorganisms, the other compounds showed selective inhibitory activity. This is the first report on the antimicrobial activity of the phenolic compounds isolated from A. aphylla. The obtained results provide promising baseline information for the potential use of the extract and some isolated compounds from this plant as antimicrobial agents to control plant and animal diseases.

Biosynthesis of phenolic acids in tomato plants infected with Agrobacterium tumefaciens

1974 ◽  
Vol 52 (9) ◽  
pp. 2041-2047 ◽  
Author(s):  
Kailash C. Chadha ◽  
Stewart A. Brown
Keyword(s):  
Agrobacterium Tumefaciens ◽  
Benzoic Acid ◽  
Phenolic Acids ◽  
Cinnamic Acid ◽  
Acid Metabolism ◽  
Oxidation Products ◽  
Causative Organism ◽  
Coumaric Acid ◽  
Tomato Plants ◽  
Qualitative And Quantitative

Tomato plants 21 days old were inoculated with Agrobacterium tumefaciens, the causative organism of crown gall, and 72 h later [3-14C]cinnamic or [carboxyl-14C]benzoic acid was administered by wick-feeding to these and to uninfected control plants. After a further 48 h both groups were examined for incorporation of label into phenolic acids. The pattern of incorporation into bound phenolic acids of the controls was in accord with biosynthetic pathways previously demonstrated in normal plants, but qualitative and quantitative divergence from this pattern was observed in the bound phenolic acids of the infected plants. The data suggest interference by the pathogen with β-oxidation of at least two phenylpropanoid acids of the lignification pathway. In infected plants, lowered incorporation of 14C from cinnamic acid into phenylpropanoid acids of the lignification pathway and their β-oxidation products was accompanied by the appearance of labelled o-coumaric acid, consistent with some diversion of cinnamic acid metabolism toward ortho-hydroxylation. Incorporation of 14C from benzoic acid into gentisic and especially salicylic acid of infected plants was much lower than in the controls.

scholarly journals Antioxidant Activity, Total Phenolics and Taxol Contents Response of Hazel (Corylus avellana L.) Cells to Benzoic Acid and Cinnamic Acid

2012 ◽  
Vol 40 (1) ◽  
pp. 69 ◽  
Author(s):  
Ebrahim BEMANI ◽  
Faezeh GHANATI ◽  
Laleh YOUSEFZADEH BOROUJENI ◽  
Faezeh KHATAMI
Keyword(s):  
Antioxidant Activity ◽  
Benzoic Acid ◽  
Cancer Cells ◽  
Cinnamic Acid ◽  
Human Cancer ◽  
Corylus Avellana ◽  
Cell Extract ◽  
Phenolic Contents ◽  
Human Cancer Cells ◽  
Corylus Avellana L

Hazel (Corylus avellana L.) plant has been recently introduced as a plant with the ability to produce Taxol. In the present research effects of different concentrations of benzoic acid and cinnamic acid on the phenolic compounds, Taxol content, and antioxidant activity of extracts of suspension-cultured hazel cells were investigated. The cells were treated with different concentrations of benzoic acid (0, 0.5, and 1 mM) and cinnamic acid (0, 0.15, 0.3 and 0.6 mM) on day 7 of subculture and were harvested on day 14. Benzoic acid in higher concentrations increased Taxol (4 fold of the control) and antioxidant activity of the cell extract. Cinnamic acid supply did not bring remarkable increase in Taxol content but increased phenolic contents and antioxidant activity of hazel cells extract. Interestingly, the extract of hazel cells showed more cytotoxicity for human cancer cells than pure Taxol. Further investigations may suggest the extract of cinnamic- and benzoic acid- fed hazel cells for treatment of cancer cells.

PREPARATION OF CAFFEIC AND DIHYDROCAFFEIC ACIDS BY METHODS SUITABLE FOR INTRODUCTION OF C14 INTO THE β-POSITION

1959 ◽  
Vol 37 (12) ◽  
pp. 1431-1438 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Acetic Acid ◽  
Benzoic Acid ◽  
Caffeic Acid ◽  
Malonic Acid ◽  
Cinnamic Acid ◽  
Catalytic Hydrogenation ◽  
Benzoyl Chloride ◽  
Protocatechuic Acid ◽  
Barium Carbonate ◽  
Hydrogen Bromide

3,4-(Dibenzyloxy)-benzoyl chloride (m.p. 95°) was prepared from the corresponding acid, and reduced to 3,4-(dibenzyloxy)-benzaldehyde (m.p. 86°) by Rosenmund's method. The over-all yield of this aldehyde was 52%, based on the barium carbonate used for preparation of the acid. The aldehyde was debenzylated by hydrogen bromide in acetic acid, and the protocatechualdehyde thus obtained was condensed with malonic acid, to give caffeic acid. Condensation of 3,4-(dibenzyloxy)-benzaldehyde with malonic acid gave 3,4–(dibenzyloxy)-cinnamic acid (m.p. 206–208°) which was converted to dihydrocaffeic acid by catalytic hydrogenation. The over-all yields of caffeic and dihydrocaffeic acids were 36% and 39%, respectively, based on barium carbonate. Protocatechuic acid was readily obtained by hydrogenolysis of 3,4-(dibenzyloxy)-benzoic acid; the yield was 70% based on carbonate.

Sign in / Sign up

Export Citation Format

Share Document