Chemical composition of Capparis spinosa fruit

Abstract

The known compounds cappariloside A and stachydrin, an adenosine nucleoside, and for the first time from plants of the Capparidaceae family the known compounds hypoxanthine and uracil were isolated from Capparis spinosa (Capparidaceae) fruit.Capparis spinosa (Capparidaceae) is widely distributed throughout the whole world. Information on alkaloids, flavonoids, and glycosides [1][2][3][4][5] in addition to lipids and carbohydrates [6] from this plant has been published.Herein we report a study of alkaloids from fruit of C. spinosa growing in Xinjiang Autonomy Region of China. The alcohol extract of ground and defatted ripe fruit of C. spinosa produced total extracted substances containing also water-soluble alkaloids of the betaine type. The lipophilic components were removed by washing the acidic solution of extracted substances with ether. The total alkaloids were obtained by treatment of the acidic solution with conc. ammonia to adjust the pH to 9 and extraction with n-butanol (fraction A). The dried alkaloidal fraction A was chromatographed over a silica-gel column with elution by CHCl 3 , CHCl 3 :CH 3 OH, and CH 3 OH. Work up with CH 3 OH of the CHCl 3 :CH 3 OH (12:1) fractions isolated amorphous hypoxanthine (1) and uracil (2) [7,8], which were identified using PMR and 13 C NMR spectral data and authentic samples (spectral properties are given in Experimental).Crystalline 3, mp 228-229°C, was isolated from CHCl 3 :CH 3 OH (10:1) fractions. The UV spectrum of 3 had absorption maxima at 206.4 and 259.6 nm. The IR spectrum had absorption bands for active H at 3425, 3370 (NH 2 ), 3320, and 3143 (OH) cm −1 ; lactone ring (tetrahydrofuran), 1680; ether, 1100 and 1030; and tri-and disubstituted aromatic rings, 1600, 1577, 870, 822, 795, and 765. The mass spectrum of 3 gave a peak for the molecular ion with m/z 267 and fragments with m/z 148 and 119 produced by cleavage of the tetrahydrofuran ring. Peaks for ions with m/z 134 and 133 corresponded to fragments formed by cleavage of the C-N bond between the main part of the molecule and the tetrahydrofuran ring. NMR data ( 1 H and 13 C) are given in Experimental.The spectral data (UV, IR, mass, NMR) were reminiscent of those of adenosine (3) [9]. However, the lack of an authentic sample prohibited reliable identification of 3 as adenosine. As a result, a single-crystal x-ray structure analysis (XSA) of 3 showed that the isolated base was in fact the known nucleoside adenosine (C 10 H 13 N 5 O 4 ), which is constructed from D-ribose and a purine base in which the N-9 atom of the purine base adenine is bonded to C-1 of D-ribose [10][11][12][13]. Adenosine

Pharmacological Effects of Capparis spinosa L.

“…The remarkable feature of glucosinolates in plants is their ability to give rise to a host of secondary metabolites, primarily because of myrosinase enzyme activity. The liberated compounds include small molecular weight biologically active compounds such as butyl and isopropyl isothiocyanates ( 31–32 , (Afsharypuor et al ., )) and indole‐3 acetonitrile glycosides ( 33 , 34 , (Çaliş et al ., ; Fu et al ., )) all of which have been isolated from C . spinosa (Fig.…”

“…In fact, this compound can be regarded as a novel amino acid as it contains a carbon skeleton that carries both amino and carboxylic acid groups. Another modified amino acid or alkaloid is ( 2 ) which has been isolated from fruits (Fu et al ., ). The fruits of C .…”

“…The isolation of nucleotide bases including uracil, hypoxanthine and adenosine from the fruit has also been described by Fu et al . () A number of authors have also examined the composition of the seed oil of C . spinosa and the major constituents were established to be oleic (27%) and linoleic (31%) acids followed by palmitic and a rare lipid, vaccenic acid (Matthäus and Özcan, ; Argentieri et al ., ).…”

Characterization of volatile components from ethyl acetate extract of Stixis suaveolens (Roxb.) by comprehensive two‐dimensional gas chromatography hyphenated with a time‐of‐flight mass spectrometer

“…[13] Fruits of C. spinosa were also shown to contain stachydrin, hypoxanthine and uracil. [14] Biological activities of some identified substances are also reported such as: Phytol (93) for anti-nociceptive and antioxidant activities. [15,16] Besides, other compounds with lower concentration shows also bioactivities such as indole (18) (antibacterial, anti-carnogenic), [17] vacxvbnillin (27) (antiviral, cancer-preventive), [18] trans-cinnamic acid (28) (anti-mutagenic), and myristic acid (66) (antibacterial, antifungal).…”

Capparis spinosa L. in A Systematic Review: A Xerophilous Species of Multi Values and Promising Potentialities for Agrosystems under the Threat of Global Warming

“…Aquaeous ethanolic fruit extracts contained flavonoids equivalent to rutin, phenolic compounds, tocopherol, carotenoid and vitamin C (Huseini et al, 2013 ). In addition to the known capparilloside A and stachydrine, an adenosine nucleoside, hypoxanthine and uracil were isolated from C. spinosa (Capparidaceae) fruits in China (Fu et al, 2007 ).…”