International E-publication: Publish Projects, Dissertation, Theses, Books, Souvenir, Conference Proceeding with ISBN.  International E-Bulletin: Information/News regarding: Academics and Research

A comprehensive review on secondary metabolites of Nigella sativa L (Seeds)

    ,

Author Affiliations

  • 1School of Studies in Chemistry and Biochemistry, Vikram University, Ujjain 456010, MP, India
  • 2School of Studies in Chemistry and Biochemistry, Vikram University, Ujjain 456010, MP, India

Res.J.chem.sci., Volume 7, Issue (12), Pages 16-29, December,18 (2017)

Abstract

Nigella sativa L. synthesizes and accumulates a variety of biological active secondary metabolites. Due to various substances isolated and identified the claim made in traditional medicinal system. Seeds are generally called kalongi (Ranunculacae) is an annual flowering plant, originate from S. W. Asia. Seeds and NSO showed as a folk medicine for a prehistoric usage in all systems of medicines and are used as food also. This comprehensive account provides a botanical distribution of plant, chemical constituents and pharmacological potential are reviewed and summarized the information focusing on its wide spectrum biological and medicinal properties including anti-tumor, antipyretic, analgesic, antinematode, antihypertensive, antidiabetic, antiulcerogenic and anti- bacterial as well as dietary nutritive supplements and also focused on synthesis and properties of nanopaticles due to secondary metabolites show reducing and stabilizing activity.

References

  1. Sezik E., Yesilad E., Honda G., Takaishi Y., Takoda Y. and Tanaka T. (2001)., Traditional medicine in turkey folk medicine in Central Anatolia., J. Ethnopharmacol., 75(2), 95-115.
  2. Satyavati G.V. and Gupta A.K. (1987)., Medicinal Plants of India., 2, 337-340.
  3. Khan M.A. and Afzal M. (2016)., Chemical composition of Nigella sativa Linn: Part 2 Recent advances., Inflammopharmacol, 24(2-3), 67-79.
  4. Khan M.A., Chen H.C., Tania M. and Zhang D. (2011)., Anticancer activities of Nigella sativa (black cumin)., Afr. J. Tradit. Complement Altern. Med., 8(5 Suppl), 226-232.
  5. Farooq T.J. and Abdulrahman M.A. (2011)., The effects of Nigella sativa oil administration on some physiological and histological values of reproductive aspects of rats., Iraqi J. Vet. Med., 35(2), 53.
  6. Prakash S. (1972)., Wealth of India., CSIR New Delhi, 3 PID.
  7. Adams R.P. (1995)., Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy., Carol Stream IL, Allured Publishing Co.
  8. Chen H.S., Han G.Y., Liu M.Z. and Liang H.Q. (1991)., A new alkaloids and its artificial derivative with an indazole ring from Nigella glandulifera., Chinese Chemical Letters, 2, 787-88.
  9. Tian Z., Liu Y.M., Chen S.B., Yang Y.S., Xiao P.G., Wang L. and Wu E. (2006)., Cytotoxicity of two triterpenenoids from Nigella glandulifera., Molecule, 11(9), 693-99.
  10. Lebreton P. and Cles M. (1986)., Flavonoids, Marqueurs Systematiques chez les Renonculacees., Plantes Medicinales et Phytotherapie, 20, 275-86.
  11. Merfort I., Wray V., Barakat H.H., Hussen S.A.M., Nawwar M.A.M. and Willuhn G. (1997)., Flavonol triglycosides from seeds of Nigella sativa., Phytochemistry, 46(2), 359-363.
  12. Fico G., Braca A., Tome F. and Morelli I. (2001)., A new phenolic compound from Nigella damascene seeds., Fitoterapia, 72(4), 462-463.
  13. Hao H.F., Ren L.J. and Chen Y.M. (1996)., Studies on the chemical constituents of seeds from Nigella Glandulifera., Acta Pharmaceutica Sinica, 31(9), 689-694.
  14. Rahman A., Malik S., Hassan S., Choudhary M.I., Ni C.Z. and Clardy J. (1995)., Nigellidine: A new indazole alkaloid from the seeds of Nigella sativa., Tetrahedr. Lett., 36(12), 1993-96.
  15. Sohail M., Ahmed S., Choudhary M.I. and Ur-Rahman H. (1985)., Nigellimine-N-oxide: A new isoquinoline alkaloid from the seeds of Nigella sativa., Heterocycles, 23(4), 953-955.
  16. Rahman A., Malik S. and Zaman K. (1992)., Nigellimine: A new isoquinoline alkaloid from the seeds of Nigella sativa., J. Nat. Prod., 55(5), 676-78.
  17. Rahman A., Malik S., Cun-Heng H. and Clardy J. (1985)., Isolation and structure determination of Nigellicine, a novel alkaloid from the seeds of Nigella sativa., Tetrahedr. Lett., 26(23), 2759-62.
  18. Morikawa T., Xu F., Kashima Y., Matsuda H., Ninomiya K. and Yoshikawa M. (2004)., Novel dolabellane-typediterpene alkaloids with lipid metabolism promoting activities from the seeds of Nigella sativa., Organic Lett., 6(6), 869-872.
  19. Yessuf A.M. (2015)., Phytochemical Extraction and Screening of Bio Active Compounds from Black Cumin (Nigella Sativa) Seeds Extract., American Journal of Life Sciences, 3(5), 358-364.
  20. Salama R.B. (1973)., Sterols in the seeds oil of Nigella sativa., Planta Medica, 24(4), 375-77.
  21. Mehta B.K., Pandit V. and Gupta M. (2009)., New Principles from seeds of Nigella sativa., Natural Product Research, 22(2), 138-48.
  22. Mehta B.K., Gupta M. and Verma M. (2006)., Steroids and aliphatic esters from the seeds of Nigella sativa., Ind.J. Chem., 45B(6), 1567-1571.
  23. Mehta B.K., Verma M. and Gupta M. (2008)., Novel lipid constituents identified in seeds of Nigella sativa., J. Braz. Chem. Soc., 19(3), 458-462.
  24. Menounds P., Staphylakis K. and Gegiou D. (1986)., The sterols of Nigella sativa seeds oil., Phytochemistry, 25(3), 761-763.
  25. Mehta B.K., Mehta P. and Gupta M. (2009)., A new naturally acetylated triterpene saponin from Nigella sativa., Carbohydr. Res., 344(1), 149-51.
  26. Ansari A.A., Hassan L., Kene L., Rahman A. and Wehler T. (1998)., Structural studies on a saponin isolated from Nigella sativa., Phytochemistry, 27(12), 3977-3979.
  27. Taskin M.K., Caliskan O.A., Hassan A., Hassan A.G., Khan I.A. and Bedir E. (2005)., Triterpene saponin from Nigella sativa L., Turk J. Chem., 29(5), 561-69.
  28. Nickavara B., Mojab F., Javidnia K. and Amoli M.A.R. (2003)., Chemical Composition of the Fixed and Volatile Oils of Nigella sativa L. from Iran., Z. Naturforsch., 58C, 629-31.
  29. Singh N., Verma M., Mehta D. and Mehta B.K. (2005)., Two new lipid constituents of Nigella sativa (seeds)., Ind. J. Chem., 44B(8), 1742-1744.
  30. Mehta B.K., Sharma U., Pandit V., Agrawal S., Joshi N. and Gupta M. (2008)., Isolation and characterization of new compounds from seeds of Nigella sativa., Med. Chem. Res., 17, 462-473.
  31. Joshi B.S., Singh K.L. and Roy R. (2001)., Structure of a new isobenzofuranone derivative from Nigella Sativa., Magn. Reso. Chem., 39(12), 771-72.
  32. Gupta M. and Mehta B.K. (2016)., A rapid and pollutionless microwave assisted efficient extraction from seeds of Nigella sativa., Natural Products: An Indian Journal of Chemistry, 12(2), 62-67.
  33. Scheunert A. and Theile E. (1952)., Vitamin C content in green plants with special references to the content of dihydro ascorbic acid., Pharmazie, 7(12), 776-780.
  34. Mahfouz M. and El-Dakhakhny M. (1960)., The isolation of a crystalline active principle from Nigella sativa L. seeds., Journal of Pharmaceutical Sciences of the United Arab Republic, 19.
  35. Hassib A. (1998)., Sudan, Extraction of melanin from Nigella sativa L., Khartoum, Patent No. 451(1998).
  36. El-Oeid A., Hassib A., Ponten F. and Westermark B. (2006)., Effect of herbal melanin on IL-8: A ossible role of Toll-like receptor4 (TLR4)., Biochem. Biophy. Res. Commun., 344, 1200-1206.
  37. Prota G. (1988)., Progress in the chemistry of melanins and related metabolites., Medical Research Review, 8(4), 525-556.
  38. Pezzella A., d, An integrated approach to the structure of Sepia melanin. Evidence for a high proportion of degraded 5, 6-dihydroxyindole-2-carboxylic acid units in the pigment backbone., Tetrahedron, 53(24), 8281-8286.
  39. Kaskoos R.A. (2011)., Fatty acid composition of black cumin oil from Iraq., Research Journal of Medicinal Plant, 5(1), 85-89.
  40. Sekine S., Kubo K., Tadokoro T. and Saito M. (2007)., Effect of docosahexaenoic acid Ingestion on temporal change in urinary excretion of mercapturic acid in ODS rats., J. Clin. Biochem. Nutr., 41, 184-190.
  41. Song J.H., Fujimoto K. and Miyazawa T. (2000)., Polyunsaturated (n-3) fatty acids susceptible to peroxidation are increased in plasma and tissue lipids of rats fed docosahexaenoic acid-containing oils., J. Nutr., 130(12), 3028-3033.
  42. El-Dakhakhny M., Madi N.J., Lembert L. and Ammon H. P.T. (2002)., Nigella sativa oil, nigellone and derived thymoquinone inhibit synthesis of 5-lipoxygenase products in polymorphonuclear leukocytes from rats., J. Ethnopharmacol, 81(2), 161-164.
  43. Houghton P.J., Zarka R., Heras B. and Hoult J.R.S. (1995)., Fixed oil of Nigella sativa and derived thymoquinone inhibit eicosanoid generation in leukocytes and membrane lipid peroxidation., Planta Medica, 61(1), 33-36.
  44. Ahmed O.G. and El-Mottaleb N.A. (2013)., Renal function and arterial blood pressure Alterations after exposure to acetaminophen with a potential role of Nigella sativa oil in adult male rats., J. Physiol. Biochem., 69(1), 1-13.
  45. Al-Ghamdi M.S. (2001)., The anti-inflammatory, analgesic and antipyretic activity of Nigella sativa., J. Ethnopharmacol., 76, 45-48.
  46. Dwarampudi L.P., Palaniswamy D., Nithyanantham M. and Raghu P.S. (2012)., Antipsoriatic activity And cytotoxicity of ethanolic extract of Nigella sativa seeds., Pharmacogn. Mag., 8(32), 268-272.
  47. El-Mezayen R., El-Gazzar M., Nicolls M.R., Marecki J.C., Dreskin S.C. and Nomiyama H. (2006)., Effect of thymoquinone on cyclooxygenase expression and prostaglandin production in a mouse model of allergic airway inflammation., Immunol. Lett., 106(1), 72-81.
  48. Muralidharan C.V., Kim J.J., Abuawad A., Naeem M., Cui H. and Mousa S. (2016)., Thymoquinone Modulates Blood Coagulation in Vitro via Its Effects on Inflammatory and Coagulation Pathways., Int. J. Mol. Sci., 17, 474.
  49. EI-Dakhakhny M., Barakat M., AbdEl-Halim M. and Aly S.M. (2000)., Effects of Nigella sativa oil on gastric secretion and ethanol induced ulcer in rats., J. Ethnopharmacol., 72(1), 299-304.
  50. Rajkapoor B., Anandan R. and Jayakar B. (2002)., Antiulcer effect of Niigella sativa Linn against gastric ulcers in rats., Current Science., 82(2), 177-179.
  51. Daba M.H. and Abdel-Rahman M.S. (1998)., Hepatoprotective activity of thymoquinone in isolated rat Hepatocytes., Toxicology Letters, 95(1), 23-29.
  52. Lei X., Lv X., Liu M., Yang Z., Ji M. and Guo X. (2012)., Thymoquinone inhibits growth and augments 5-fluorouracil-induced apoptosis in gastric cancer cells both in vitro and in vivo., Biochem. Biophys. Res. Commun., 417(2), 864-868.
  53. Parvardeh S., Fatehi M. and Hosseinzadeh H. (2003)., Antimicrobial effect of thymoquinone: The major component of Nigella sativa seeds in mice., Faslnamah-I Giyahan-I Daruyi (Parsian), 742(5), 43-50.
  54. Hosseinzadeh H. and Parvardeh S. (2004)., Anticonvulsant effects of thymoquinone, the major constituent of Nigella sativa seeds in mice., Phytomedicine, 11(1), 56-64.
  55. Parverdeh S. and Fatehi M. (2003)., Effect of thymoqunone and Nigella sativa seeds oil on Lipid peroxidation level during global cerebral ischemia-reperfusion injury in rat hippocampus., Pharmaceutical Biology (Taylor and Francies, Netherland), 41(8), 616-621.
  56. Islam S.K., Nazrul B.P., Ahsan T., Huque S. and Ahsan S. (2004)., Immunosupressive and Cytotoxic properties of Nigella sativa., Phytother. Res., 18(5), 395-398.
  57. Majdalawieh A.F. and Fayyad M.W. (2016)., Recent advances on the anti-cancer properties of Nigella sativa, a widely used food additive., J. Ayurveda. Integr. Med., 7(3), 173-180.
  58. Salomi M.J., Nair S.C. and Panikkar K.R. (1991)., Inhibitory effects of Nigella sativa and saffron on chemical carcinogenesis in mice., Nutrition Cancer., 16, 67-72.
  59. Samarakoon S.R., Thabrew I., Galhena P.B., De Silva D. and Tennekoon K.H. (2010)., A comparison of the cytotoxic potential of standardized aqueous and ethanolic extracts of a polyherbal mixture comprised of Nigella sativa (seeds), Hemidesmus indicus (roots) and Smilax glabra (rhizome)., Pharmacognosy Res., 2(6), 335-342.
  60. Chakravarti N. (1993)., Inhibition of histamine release from mast cells by nigellone., Annual Allergy, 70(3), 237-242.
  61. Shoieb A.M., Elgayyar M., Dudrick P.S., Bell J.L. and Patrica K. (2003)., In vitro inhibition of growth and induction of apoptosis in cancer cell lines by thymoquinone., Int. J. Oncol., 22(1), 107-113.
  62. Asfour W., Almadi S. and Haffar L. (2013)., Ethanolic extract of Nigella sativa seeds lacks the hemopreventive efficacy in the post initiation phase of DMH-induced colon cancer in a rat model., Pharmacology & Pharmacy, 4, 222-230.
  63. Majdalawieh A.F., Hmaidan R. and Carr R.I. (2010)., Nigella sativa modulates splenocyte proliferation, Th1/Th2 cytokine profile, macrophage function and NK anti-tumor activity., J. Ethnopharmacol., 131(2), 268-275.
  64. Taha R.A.M. (2004)., Egyptian, Spasmolytic and calcium antagonist activities of thymoquinone., J. Biomed. Sci., 16, 152-167.
  65. El Tahir K.E.H., Al-Ajmi M.F. and Al Bakairi A.M. (2003)., Some cardiovascular effects of the Dethymoquinonated Nigella sativa volatile oil and its major components α-pinene and p- cymene in rats., Saudi Pharmaceutical J., 11(3), 104-110.
  66. Morikawa T., Xu F., Kashima Y., Matsuda H. and Yoshikawa M. (2004)., Nigellamines A3, A4, A5 and C, new dolabellane-type diterpene alkaloids, with lipid metabolism-promoting activities from the Egyptian medicinal food black cumin., Chemical Pharmaceutical Bullatin, 52(4), 494-97.
  67. Zaher K.S., Ahmed W.M. and Zerizer S.N. (2008)., Observations on the biological effects of black cumin seed (Nigella sativa) and green tea (Camellia sinensis)., Global Veterinaria, 2(4), 198-204.
  68. Toma C.C., Olah N.K., Vlase L., Mogoșan C. and Mocan A. (2015)., Comparative Studies on Polyphenolic Composition, Antioxidant and Diuretic Effects of Nigella sativa L. (Black Cumin) and Nigella damascena L. (Lady-in-a-Mist) Seeds., Molecules, 20, 9560-9574.
  69. Salem M.L. and Hossain M.S. (2000)., Protective effect of black seed oil from Nigella sativa against murine cytomegalovirus infection., Int. J. Immunopharmacol., 22 (9), 729-740.
  70. Goga A., Hasić S., Bećirović S. and Ćavar S. (2012)., Phenolic Compounds and Antioxidant Activity of Extracts of Nigella sativa L., Bulletin of the Chemists and Technologists of osnia and Herzegovina., 39, 15-19.
  71. Salman M.T., Khan R.A. and Shukla I. (2005)., Antimicrobial activity of Nigella sativa oil Against Staphylococcus aureus obtained from clinical specimens., In: 38th Annual Conference of Indian Pharmacological Society, Chennai, India, 28-30 Dec.
  72. Ahmed S., Rahman S.R. and Gomes D.J. (2004)., Prevalence of multi drug resistant bacteria in diabetic wound infection population, Bangladesh., J. Med. Sci., 10, 49-52.
  73. Bakht H.B.M., Gomes D.J. and Huq F. (2000)., Emergence of multi-drug resistant group B streptococci infections of hospitalized neonates B., J. Med. Sci., 6, 9-12.
  74. Rafati S., Niakan M. and Naseri M. (2014)., Anti-microbial effect of Nigella sativa seed against staphylococcal Skin infection., Med. J. Islam. Repub. Iran., 28, 42.
  75. Khan M.A., Ashfaq M.K., Zuberi H.S. and Zuberi A.H. (2003)., The in vivo antifungal activity of the aqueous extract from Nigella sativa seed., Phytother. Res., 17, 183-186.
  76. Alqorashi A., Akhtar N. and Aljabre S. (2007)., The effect of thymoquinone and B on the growth of Aspergillus Niger., Sci. J. King Faisal Univ., 8(1), 137-145.
  77. Aljabre S.H.M., Randhawa M.A., Akhtar A., Alakloby O. M., Alqurashi A.M. and Aldossary A. (2005)., Antidermatophyte activity of ether extract of Nigella sativa and its active principle, thymoquinone., J. Ethnopharmacol., 101, 116-119.
  78. Aljabre S.H.M. (2005)., In vitro antifungal activity of thymoqyuinone against Scopulariopsis brevicaulis., Arab J. Pharm. Sci., 3, 27-33.
  79. Al-Shebani W.H. and Al-Tahan F.J. (2009)., Anti-inflammatory effect of watery suspension of Nigella sativa Linn(seeds) in mice., Iraqi Journal of Vaterinary Science. 23, suppl. II, 245-248. Proceeding of the 5th Scientific conference, College of Veterinary medicine, University of Mosul
  80. Al-Naqeep G., Al-Zubairi A.S., Ismail M., Amom Z.H. and Esa N. (2011)., Antiatherogenic potential of Nigella sativa seeds and oil in diet-induced hypercholesterolemia in rabbits., Evid. Based Complement Alternat. Med., ID 213628.
  81. Crede H.H.R. (2004)., Pharmaceutical composition containing black cumin oil, flax oil and borago oil, (S. Africa). PCI., Int. Appl., WO2004012753 A1.
  82. Aljabre S.H.M., Alakloby O.M. and Randhawa M.A. (2015)., Dermatological effects of Nigella sativa., Journal of dermatology & dermatologic surgery, 19(2), 92-98.
  83. Kumar P.M., Vinmathi V., Gautam P., Wilson A.H. and Jacob S.J.P. (2015)., Green Synthesis of Silver Nanorods Using Aqueous Seed Extract of Nigella Sativa and Study of its Antidiabetic Activity., Australian Journal of Basic and Applied Sciences, 9(10), 295-298.
  84. Amooaghaie R., Saeri M.R. and Azizi M. (2015)., Synthesis, Characterization and Biocompatibility of silver nano-particles synthesized from Nigella sativa leaf extract in comparison with chemical silver nanoparticles., Ecotoxicology and Environmental Safety, 120, 400-408.
  85. Fragoon A.L., Zhu J. and Zhao J. (2012)., Biosynthesis of Controllable Size and Shape Gold Nanoparticles by Black Seed (Nigella Sativa) Extract., J. Nanosci. Nanotech., 12(3), 2337-2345.
  86. Sangeetha J., Sandhya J. and Philip J. (2014)., Biosynthesis and Functionalization of Silver Nanoparticles Using Nigella sativa, Dioscorea alata and Ferula asafetida., Science of Advanced Materials, 6(8), 1681-1690.
  87. Ravindran J., Nair H.B., Sung B., Prasad S., Tekmal R.R. and Aggarwal B.B. (2010)., Thymoquinone Poly (lactide-co-glycolide) Nanoparticles Exhibit Enhanced Anti-proliferative, Anti-inflammatory and Chemosensitization Potential. Biochem., Pharmacol., 79(11), 1640-1647.
  88. Manju S., Malaikozhundan B., Chen J.C. and Vaseeharan B. (2014)., Essential Oil of Nigella Sativa Based Synthesis of Silver Nanoparticles and Its Effect on Pathogenic Vibrio Harveyi and Vibrio Parahaemolyticus isolated from Aquatic Environments., J. Fish. Soc. Taiwan, 41(2), 123-134.