Novel lipid constituents identified in seeds of Nigella sativa (Linn)

Abstract

Lipídeos inéditos foram isolados de matéria insaponificável extraída de sementes de Nigella sativa Linn, usando-se n-hexano. O dienoato e os dois monoésteres inéditos foram identificados por técnicas espectrométricas, incluindo IV, RMN de 1 H e 13 C, espectrometria de massas, e análise química. O dienoato (1) foi identificado como metilnonadeca-15, 17-dienoato e os dois monoésteres foram identificados como pentil hexadec-12-enoato (2) e pentil pentadec-11-enoato (3). Ácido linoleico, ácido oléico, b-sitosterol e stigmasterol foram identificados como parte das estruturas dos lipídeos. Todos os compostos mostraram atividade moderada contra Staphylococcus aureus e baixa atividade contra shigella spp e Klebsiella pneumoniae.Novel lipids were isolated from the unsaponifiable matter extracted from seeds of Nigella sativa Linn by using n-hexane. The new dienoate and two monoesters were the new lipids identified by spectral (IR, 1 H-and 13 C-NMR spectra, mass spectrum, elemental analysis) and chemical analysis. The dienoate (1) was identified as methylnonadeca-15,17-dienoate and two monoesters were identified as pentyl hexadec-12-enoate (2) and pentyl pentadec-11-enoate (3). Linoleic acid, oleic acid, b-sitosterol and stigmasterol were identified as part of the lipid structures. All compounds exhibited moderate activity against Staphylococcus aureus and poor activity against shigella spp, and Klebsiella pneumoniae.Keywords: Nigella sativa, seeds, Ranunculaceae, aliphatic esters IntroductionNigella sativa Linn., a plant belonging to the family Ranunculaceae, grows as a small herb and is cultivated throughout India and other tropical regions of the world. 1,2 It is commonly known as black cumin seed and kalaungi in Hindi in India. The seed contains alkaloids nigellidine, 3 nigellimine and nigellicine, 4,5 tannin, steroids a-spinasterol, 6 campesterol, cholesterol, stigmasta-7-en3b-ol, stigmasterol and b-sitosterol, flavonoids of trigillin quercetin-3-glucoside, saponin and nigellone. 7,.8 Recent pharmacological investigations of the seed extract revealed that a wide spectrum of biological activities including anti-inflammatory, antidiabetic, analgesic, antibacterial, antifungal, anti-helmintic, 9 bronchodilatory, 10 hypertensive and immunoprotecting activities. 11 The seeds are believed to have carminative, diuretic, lactogoge, stimulatory and diaphoretic properties and are used in the treatment of bronchial asthma and eczema. [12][13][14][15] The hexane and benzene extracts of its seeds were exhibited 67% and 40% post-coital anti-implantation activity at the dose level of 500 mg kg -1 per day, respectively. 16 The present study reports the isolation and structural elucidation of three new lipids (Figure 1) isolated from seeds of Nigella sativa Linn. Linoleic acid, oleic acid, b-sitosterol and stigmasterol were identified as part of the structures of the new lipids. Results and DiscussionThe novel natural compounds were identified mainly by their 1D ( 1 H and 13 C NMR), 2D ( 1 H-1 H COSY), DEPT and mass spectrometry analy...

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“…From this point we can say NS possess a good antioxidant comparable with standard antioxidant (vitamin E) in agree with (Mehta et al ,2008). The antioxidant activity of our both herbals attributed for total phenolic content, this justify and support the behavior of both herbals for stopping LDL oxidation specially NS, NS phenolic content was found in this study higher than SL (p<0.01), while vitamin E possess high phenolic content than both NS and SL (p<0.01).…”

A review on therapeutic potential of Nigella sativa: A miracle herb

“…Saturated fatty acids (palmitic, stearic acid) amount to about 30% or less. α-sitosterol is a major sterol, which accounts for 44% and 54% of the total sterols in Tunisian and Iranian varieties of black seed oils respectively, followed by stigmasterol (6.57-20.92% of total sterols) [15][16][17] .…”

“…The positive inhibition may be attributed to the two important active ingredients of N. sativa, TQ and melanin [25] . Different crude extracts of N. sativa were tested for antimicrobial effectiveness against different bacterial isolates which comprised of 16 gram negative and 6 gram positive representatives. These isolates showed multiple resistances against antibiotics, specially the gram negative ones.…”

Comparison of Two Regimens of Nigella sativa Extract for Treatment of Subclinical Mastitis Caused by Staphylococcus aureus

“…(Ranunculaceae), commonly known as black seed or black cumin, is used in herbal medicine all over the world for the treatment and prevention of a number of diseases and conditions that include asthma, diarrhoea and dyslipidaemia (Hawari and Al-Dabbas, 2008). Nigella (Nigella sativa L.) is an annual herbaceous plant belonging to the Ranunculaceae family growing in countries bordering the Mediterranean Sea and is cultivated throughout India and other tropical regions of the world (Mehta et al, 2008;Saganuwan, 2009;Cheikh-Rouhou et al, 2007). A number of reports have been published on the action of N. sativa extracts or its oil on the different bacterial isolated (Al-Haj et al, 2010;Hawari and Al-Dabbas, 2008).…”