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The ethnobotany, phytochemistry, and biological properties of Nigella damascena - A review
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- 1. * & Department of Biological, Chemical and Pharmaceutical Sciences and Technologies (STEBICEF), University of Palermo, Palermo, Italy
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Badalamenti, Natale, Modica, Aurora, Bazan, Giuseppe, Marino, Pasquale, Bruno, Maurizio (2022): The ethnobotany, phytochemistry, and biological properties of Nigella damascena - A review. Phytochemistry (113165) 198: 1-16, DOI: 10.1016/j.phytochem.2022.113165, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113165
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References
- Agradi, E., Fico, G., Cillo, F., Francisci, C., Tom`e, F., 2001. Estrogenic activity of phenolic compounds from Nigella damascena evaluated using a recombinant yeast screen. Planta Med 67, 553-555. https://doi.org/10.1055/s-2001-16485.
- Ahmad, M.F., Ahmad, F.A., Ashraf, S.A., Saad, H.H., Wahab, S., Khan, M.I., Ali, M., Mohan, S., Hakeem, K.R., Athar, M.T., 2021. An updated knowledge of Black seed (Nigella sativa Linn.): review of phytochemical constituents and pharmacological properties. J. Herb. Med. 25, 100404. https://doi.org/10.1016/j. hermed.2020.100404.
- Alaeddin, A., Gulsel, K., 1990. The fatty acids of Nigella damascena L. seed oil. Acta Pharm. Turc. 32, 41-43.
- Aleo, N., Amato, F., Aleo, M., 2011. Le piante tossiche della flora trapanese (Sicilia). Quad. Bot. Amb. Appl. 22, 31-49.
- Alu' datt, M.H., Rababah, T., Alhamad, N.M., Gammoh, S., Ereifej, K., Alodat, M., Hussein, N.M., Kubow, S., Torley, P.J., 2016. Antioxidant and antihypertensive properties of phenolic-protein complexes in extracted protein fractions from Nigella damascena and Nigella arvensis. Food Hydrocolloids 56, 84-92. https://doi.org/ 10.1016/j.foodhyd.2015.12.008.
- Badalamenti, N., Rosselli, S., Zito, P., Bruno, M., 2021a. Phytochemical profile and insecticidal activity of Drimia pancration (Asparagaceae) against adults of Stegobium paniceum (Anobiidae). Nat. Prod. Res. 35, 4468-4478. https://doi.org/10.1080/ 14786419.2020.1729154.
- Badalamenti, N., Ilardi, V., Rosselli, S., Bruno, M., 2021b. The ethnobotany, phytochemistry and biological properties of genus Ferulago - a review. J. Ethnopharmacol. 274, 114050. https://doi.org/10.1016/j.jep.2021.114050.
- Ballero, M., Frescu, I., 1993. Le piante di uso officinale nella Barbagia di Seui (Sardegna Centrale). Fitoterapia 64, 141-150.
- Bazan, G., Marino, P., Guarino, R., Domina, G., Schicchi, R., 2015. Bioclimatology and vegetation series in Sicily: a geostatistical approach. Ann. Bot. Fenn. 52, 1-18. https://doi.org/10.5735/085.052.0202.
- Bekemeier, H., Leuschner, G., Shmollack, W., 1967. Antipyretische, antioedematose ¨und analgetische wirkung von damascenin im vergleich mit acetylsalicyls¨aure und phenylbutazon. Arch. Int. Pharmacodyn. Ther. 168, 199-211.
- Bekemeier, Heinz, Leuschner, G., Schmollack, W., 1968. Antipyretic, antiinflammatory, and analgetic effect of damascenine. In: Dumbovich, B from Conf. Hung. Ther. Invest. Pharmacol., 4th. Soc. Pharmacol. Hung., pp. 449-451
- Bernal, W., Lee, W.M., Wendon, J., Stolze Larsen, F., Williams, R., 2015. Acute liver failure: a curable disease by 2024? J. Hepatol. 62, S112-S120. https://doi.org/ 10.1016/j.jhep.2014.12.016.
- Birari, R.B., Bhutani, K.K., 2007. Pancreatic lipase inhibitors from natural sources: unexplored potential. Drug Discov. Today 12, 879-889. https://doi.org/10.1016/j. drudis.2007.07.024.
- Borschberg, H.J., 1975. Ph.D. Thesis, Eidenossischen Technischen Hochschule. ETH) Zurich. No. 5578.
- Bouguezza, Y., Noureddine, B., Mustapha, T., Amara, S., Bachra, K., 2013. Acute and sub-chronic toxicity study of Nigella damascena methanolic seed extract in mice. Int. J. Pharm. Bio Sci. 4, 413-419.
- Bouguezza, Y., Khettal, B., Tir, L., Boudrioua, S., 2015. Damascenine induced hepatotoxicity and nephrotoxicity in mice and in vitro assessed human erythrocyte toxicity. Interdiscipl. Toxicol. 8, 118-124. https://doi.org/10.1515/intox-2015- 0018.
- Braca, A., Autore, G., De Simone, F., Marzocco, S., Morelli, I., Venturella, F., De Tommasi, N., 2004. Cytotoxic saponins from Schfflera rotundifolia. Planta Med 70, 960-966. https://doi.org/10.1055/s-2004-832623.
- Brullo, S., Giusso del Galdo, G., Guarino, R., Minissale, P., 2007. A survey of the weedy communities of Sicily. Ann. Bot 7, 127-161. https://doi.org/10.4462/annbotrm- 9091.
- Cabrita, L., Froystein, N.A., Andersen, O.A., 2000. Anthocyanin trisaccharides in blue berries of Vaccinium padifolium. Food Chem 69, 33-36. https://doi.org/10.1016/ S0308-8146(99)00230-7.
- Cai, X.H., Wang, Y.Y., Zhao, P.J., Li, Y., Luo, X.D., 2010. Dolabellane diterpenoids from Aglaia odorata. Phytochemistry 71, 1020-1024. https://doi.org/10.1016/j. phytochem.2010.03.005.
- Camlica, M., Yaldiz, G., 2019. Effect of cultural condition on seed growth and content of essential oil of two populations and one cultivar of genus Nigella. Ann. Phytomed. 8, 56-62. https://doi.org/10.21276/ap.2019.8.1.6.
- Cao, X.W., Wang, F.J., Liew, O.W., Y, Z., Zhao, J., 2020. Analysis of triterpenoid saponins reveals insights into structural features associated with potent protein drug enhancement effects. Mol. Pharm. 17, 683-694. https://doi.org/10.1021/acs. molpharmaceut.9b01158.
- Celenk, V.U., Sarikahya, N.B., Kirmizigul, S., 2020. Isolation and structural studies on saponins from three Cephalaria species from Anatolia. Chem. Nat. Compd. 56, 180-182. https://doi.org/10.1007/s10600-020-02980-w.
- Chen, S., Li, M., Jiang, W., Zheng, H., Qi, L.W., Jiang, S., 2020. The role of Neu1 in the protective effect of dipsacoside B on acetaminophen-induced liver injury. Ann. Transl. Med. 8, 823. https://doi.org/10.21037/atm-19-3850.
- Choi, J.S., Woo, W.S., 1987. Triterpene glycosides from the roots of Patrinia scabiosifolia. Planta Med 52, 62-65. https://doi.org/10.1055/s-2006-962622.
- Dagli, M., Sarikahya, N.B., Nalbantsoy, A., Suheyla Kirmizigul, S., 2019. Comparative phytochemical screening and cytotoxic efficacy of endemic Cephalaria tuteliana. Nat. Prod. Commun. 14 (10), 1-5. https://doi.org/10.1177/1934578X19862647.
- Daukˇsas, E., Venskutonis, P.R., Sivik, B., 2002. Comparison of oil from Nigella damascena seed recovered by pressing, conventional solvent extraction and carbon dioxide extraction. Food Chem. Toxicol. 67, 1021-1024. https://doi.org/10.1111/j.1365- 2621.2002.tb09447.x.
- Demasi, S., Caser, M., Lonati, M., Cioni, P.L., Pistelli, L., Najar, B., Scariot, V., 2018. Latitude and altitude influence secondary metabolite production in peripheral apine populations of the Mediterranean species Lavandula angustifolia Mill. Front. Plant Sci. 9, 983. https://doi.org/10.3389/fpls.2018.00983.
- Doepke, W., Fritsch, G., 1970. The alkaloid content of Nigella damascena. Pharmazie 25, 69-70.
- Dunham, N.R., Peper, S.T., Downing, C.D., Kendall, R.J., 2017. Aflatoxin contamination in corn sold for wildlife feed in Texas. Ecotoxicology 26, 516-520. https://doi.org/ 10.1007/s10646-017-1782-7.
- D' Agostino, G., Giambra, B., Palla, F., Bruno, M., Badalamenti, N., 2021. The application of the essential oils of Thymus vulgaris L. and Crithmum maritimum L. as biocidal on two Tholu bommalu indian leather puppets. Plants 10, 1508. https://doi.org/ 10.3390/plants10081508.
- Edris, A.E., 2009. Anti-cancer properties of Nigella spp. essential oils and their major constituents, thymoquinone and β -elemene. Curr. Clin. Pharmacol. 4, 43-46. https://doi.org/10.2174/157488409787236137.
- Ewins, A.J., 1912. Constitution and synthesis of damascenine, the alkaloid of Nigella damascena. J. Chem. Soc., Perkin Trans. 101, 544-552. https://doi.org/10.1039/ CT9120100544.
- Fang, Y., Kang, Y., Zou, H., Cheng, X., Xie, T., Shia, L., Hang, Z., 2018. β -elemene attenuates macrophage activation and proinflammatory factor production via crosstalk with Wnt/β -catenin signaling pathway. Fitoterapia 124, 92-102. https:// doi.org/10.1016/j.fitote.2017.10.015.
- Farag, M.A., El-Kersh, D.M., Rasheed, D.M., Heiss, A.G., 2017. Volatiles distribution in Nigella species (black cumin seeds) and in response to roasting as analyzed via solidphase microextraction (SPME) coupled to chemometrics. Ind. Crop. Prod. 108, 564-571. https://doi.org/10.1016/j.indcrop.2017.07.011.
- Fico, G., Braca, A., Tome, F., Morelli, I., 2000. Phenolic derivatives from Nigella damascena seeds. Pharm. Biol. 38, 371-373. https://doi.org/10.1076/ phbi.38.5.371.5967.
- Fico, G., Braca, A., Tome, F., Morelli, I., 2001. A new phenolic compound from Nigella damascena seeds. Fitoterapia 72, 462-463. https://doi.org/10.1016/S0367- 326X (01)00276-3.
- Fico, G., Bader, A., Flamini, G., Cioni, P.L., Morelli, I., 2003. Essential oil of Nigella damascena L. (Ranunculaceae) seeds. J. Essent. Oil Res. 15, 57-58. https://doi.org/ 10.1080/10412905.2003.9712267.
- Fico, G., Panizzi, L., Flamini, G., Braca, A., Morelli, I., Tom`e, F., Cioni, P.L., 2004. Biological screening of Nigella damascena for antimicrobial and molluscicidal activities. Phytother Res 18, 468-470. https://doi.org/10.1002/ptr.1454.
- Gagliano Candela, R., Lazzara, G., Piacente, S., Bruno, M., Cavallaro, G., Badalamenti, N., 2021. Conversion of organic dyes into pigments: extraction of flavonoids from blackberries (Rubus ulmifolius) and stabilization. Molecules 26, 6278. https://doi. org/10.3390/molecules26206278.
- Gao, J.B., Zhang, X.J., Zhang, R.H., Zhu, L.L., Pu, D.B., Li, X.L., Li, H.L., Xu, M., Xiao, W. L., 2018. In vitro human dihydroorotate dehydrogenase inhibitory, anti-inflammatory and cytotoxic activities of alkaloids from the seeds of Nigella glandulifera. Planta Med 84, 1013-1021. https://doi.org/10.1055/a-0598-4866.
- GBIF, 2021. Nigella damascena L. In GBIF backbone taxonomy [accessed via GBIF.org on 2021-12-08]. https://doi.org/10.15468/39omei.
- Geraci, A., Polizzano, V., Schicchi, R., 2018. Ethnobotanical uses of wild taxa as galactagogues in Sicily (Italy). Acta Soc. Bot. Pol. 87, 1-18. https://doi.org/ 10.5586/asbp.3580.
- Giacca, A., Xiao, C., Oprescu, A.I., Carpentier, A.C., Lewis, G.F., 2011. Lipid-induced pancreatic β -cell dysfunction: focus on in vivo studies. Am. J. Physiol. Endocrinol. Metab. 300, E255-E262. https://doi.org/10.1152/ajpendo.00416.2010.
- Heiss, A.G., Oeggl, K., 2005. The oldest evidence of Nigella damascena L. (Ranunculaceae) and its possible introduction to central Europe. Veg. Hist. Archaeobotany 14, 562-570. https://doi.org/10.1007/s00334-005-0060-4.
- Kirmizibekmez, H., Kan, Y., Aydin, A., Yesilada, E., 2021. Protective effect of Nigella sativa and Nigella damascena fixed oils against aflatoxin induced mutagenicity in the classical and modified Ames test. Chem. Biodivers. 18, e2000936 https://doi.org/ 10.1002/cbdv.202000936.
- Higuchi, R., Kawasaki, T., 1976. Pericarp saponins of Akebia quinata Decne. I. Glycosides of hederagenin and oleanolic acids. Chem. Pharm. Bull. 24, 1021-1032. https://doi. org/10.1248/cpb.24.1021.
- Huxley, A., Griffiths, M., Levy, M., 1992. The New RHS Dictionary of Gardening. Macmillan Press, London.
- Hwang, D.I., Won, K.J., Kim, D.Y., Kim, H.B., Li, Y., Lee, H.M., 2019. Chemical composition of Patrinia scabiosifolia flower absolute and its migratory and proliferative activities in human keratinocytes. Chem. Biodivers. 16, e1900252 https://doi.org/10.1002/cbdv.201900252.
- Ilardi, V., Badalamenti, N., Bruno, M., 2020. Chemical composition of the essential oil from different vegetative parts of Foeniculum vulgare subsp. piperitum (Ucria) Coutinho (Umbelliferae) growing wild in Sicily. Nat. Prod. Res. Article (in press).
- Ireland, C., Faulkner, D.J., Finer, J., Clardy, J., 1976. A novel diterpene from Dollabella californica. J. Am. Chem. Soc. 98, 4664-4665. https://doi.org/10.1021/ ja00431a063.
- Jabbour, F., Du Pasquier, P.E., Chazalviel, L., Le Guilloux, M., Conde e Silva, N., Deveaux, Y., Manicacci, D., Galipot, P., Heiss, A.G., Damerval, C., 2021. Evolution of the distribution area of the Mediterranean Nigella damascena and a likely multiple molecular origin of its perianth dimorphism. Flora 274, 151735. https://doi.org/ 10.1016/j.flora.2020.151735.
- Jari´c, S., Mitrovi´c, M., Karadˇzic ´, B., Kosti´c, O., Djurjevi´c, L., Pavlovi´c, M., Pavlovic ´, P., 2014. Plant resources used in Serbian medieval medicine. Ethnobotany and Ethnomedicine. Genet. Resour. Crop Evol. 61, 1359-1379. https://doi.org/10.1007/ s10722-014-0118-1.
- Jenny, L., Borschberg, H.J., 1995. Synthesis of the dolabellane diterpene hydrocarbon (±)-δ- araneosene. Helv. Chim. Acta 78, 715-731. https://doi.org/10.1002/ hlca.19950780318.
- Kawai, H., Kuroyanagi, M., Umehara, K., Akira Ueno, A., Satake, M., 1988. Studies on the saponins of Lonicera japonica Thunb. Chem. Pharm. Bull. 36, 4769-4775. https:// doi.org/10.1248/cpb.36.476.
- Kien, C.L., 2009. Dietary interventions for metabolic syndrome: role of modifying dietary fats. Curr. Diabetes Rep. 9, 43-50. https://doi.org/10.1007/s11892-009-0009-6.
- Kokdil ¨, G., Yilmaz, H., 2005. Analysis of the fixed oils of the genus Nigella L. (Ranunculaceae) in Turkey. Biochem. Systemat. Ecol. 33, 1203-1209. https://doi. org/10.1016/j.bse.2005.07.013.
- Kokdil ¨, G., Delialioglu, N., Ozbilgin ¨, B., Emekdas, G., 2005. Antilisterial activity of Ballota species growing in Turkey: antibacterial activity screening of Nigella L. species growing in Turkey. Ank. Univ. Eczacilik Fak. Derg. 34, 183-190.
- Kokoska, L., Havlik, J., Valterova, I., Nepovim, A., Rada, V., Vanek, T., 2005. Chemical composition of the essential oil of Nigella orientalis L. seeds. Flavour Fragrance J. 20, 419-420. https://doi.org/10.1002/ffj.1449.
- Landa, P., Marsik, P., Vanek, T., Rada, V., Kokoska, L., 2006. In vitro anti-microbial activity of extracts from the callus cultures of some Nigella species. Biologia 61, 285-288.
- Landa, P., Marsik, P., Havlik, J., Kloucek, P., Vanek, T., Kokoska, L., 2009. Evaluation of antimicrobial and anti-inflammatory activities of seed extracts from six Nigella species. J. Med. Food 12, 408-415. https://doi.org/10.1089/jmf.2007.0600.
- Larson, A.M., 2007. Acetaminophen hepatotoxicity. Clin. Liver Dis. 11, 525-548. https://doi.org/10.1016/j.cld.2007.06.006.
- Leete, E., Marion, L., Spenser, I.D., 1955. The biogenesis of alkaloids. XIV. Biosynthesis of damascenine and trigonelline Can. J. Chem. 33, 405-410. https://doi.org/10.1139/ v55-048.
- Lehmann, H., Schwenen, L., 1988. Nigellic acid - an endogenous abscisic acid metabolite from Vicia faba leaves. Phytochemistry 27, 677-678. https://doi.org/10.1016/0031- 9422(88)84073-1.
- Leporatti, M.L., Ghedira, K., 2009. Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia. J. Ethnobiol. Ethnomed 5, 31. https://doi. org/10.1186/1746-4269-5-31.
- Li, X., Wang, G., Zhao, J., Ding, H., Cunnigham, C., Chen, F., Flynn, D.C., Reed, E., Li, Q. Q., 2005. Antiproliferative effect of β -elemene in chemoresistant ovarian carcinoma cells is mediated through arrest of the cell cycle at the G2-M phase. Cell. Mol. Life Sci. 62, 894-904. https://doi.org/10.1007/s00018-005-5027-1.
- Li, G.Q., Zhang, Y.B., Guan, H.S., 2008. A new isoxazol from Glehnia littoralis. Fitoterapia 79, 238-239. https://doi.org/10.1016/j.fitote.2008.01.002.
- Li, Y., Kong, D., Fu, Y., Sussman, M.R., Wu, H., 2020. The effect of developmental and environmental factors on secondary metabolites in medicinal plants. Plant Physiol. Biochem. 148, 80-89. https://doi.org/10.1016/j.plaphy.2020.01.006.
- Liu, J., Zhang, J., Wang, F., Zou, Y.F., Chen, X.F., 2013a. Isolation and characterization of new minor triterpenoid saponins from the buds of Lonicera macranthoides. Carbohydr. Res. 370, 76-81. https://doi.org/10.1016/j.carres.2013.01.019.
- Liu, Y.M., Sun, L., Liu, Q.H., Lu, S.R., Chen, B.Q., 2013b. Dolabellane-type diterpene alkaloids from Nigella glandulifera. Biochem. Systemat. Ecol. 49, 43-46. https://doi. org/10.1016/j.bse.2013.03.003.
- Malhotra, S.K., 2004. In: Peter, K.V. (Ed.), "Nigella" in Handbook of Herbs and Spices, vol. 2. Woodhead Publishing, Cambridge, UK, pp. 206-207.
- Margout, D., Kelly, M.T., Meunier, S., Auinger, D., Pelissier, Y., Larroque, M., 2013. Morphological, microscopic and chemical comparison between Nigella sativa L. cv (black cumin) and Nigella damascena L. cv. J. Food Agric. Environ. 11, 165-171.
- Matthaus, B., Ozcan ¨, M.M., 2011. Fatty acids, tocopherol, and sterol contents of some Nigella species seed oil. Czech J. Food Sci. 29, 145-150. https://doi.org/10.17221/ 206/2008-cjfs.
- McGill, M.R., Sharpe, M.R., Williams, C.D., Taha, M., Curry, S.C., Jaeschke, H., 2012. The mechanism underlying acetaminophen-induced hepatotoxicity in humans and mice involves mitochondrial damage and nuclear DNA fragmentation. J. Clin. Invest. 122, 1574-1583. https://doi.org/10.1172/JCI59755.
- Mohamed, K.M., Ohtani, K., Kasai, R., Yamadi, K., 1994. Dolabellane diterpene glucosides from Chrozophora obliqua. Phytochemistry 37, 495-500. https://doi.org/ 10.1016/0031-9422(94)85086-0.
- Mohamed, K.M., Ohtani, K., Kasai, R., Yamasaki, K., 1995. 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry 39, 151-161. https://doi.org/10.1016/0031-9422(94)00917-I.
- Monschein, M., Jaindl, K., Buzimki´c, S., Bucar, F., 2015. Content of phenolic compounds in wild populations of Epilobium angustifolium growing at different altitudes. Pharm. Biol. 53, 1576-1582. https://doi.org/10.3109/13880209.2014.993039.
- Moore, B.D., Andrew, R.L., Kulheim, C., Foley, W.J., 2014. Explaining intraspecific diversity in plant secondary metabolites in an ecological context. New Phytol 201, 733-750. https://doi.org/10.1111/nph.12526.
- Moretti, A., D' Antuono, L.F., Elementi, S., 2004. Essential oils of Nigella sativa L. and Nigella damascena L. seed. J. Essent. Oil Res. 16, 182-183. https://doi.org/10.1080/ 10412905.2004.9698690.
- Morikawa, T., Xu, F., Kashima, Y., Matsuda, H., Ninomiya, K., Yoshikawa, M., 2004a. Novel dolabellane-type diterpene alkaloids with lipid metabolism promoting activities from the seeds of Nigella sativa. Org. Lett. 6, 869-872. https://doi.org/ 10.1021/ol036239c.
- Morikawa, T., Xu, F., Ninomiya, K., Matsuda, H., Yoshikawa, M., 2004b. Nigellamines A3, A4, A5, and C, new dolabellane-type diterpene alkaloids, with lipid metabolism-promoting activities from the Egyptian medicinal food black cumin. Chem. Pharm. Bull. 52, 494-497. https://doi.org/10.1248/cpb.52.494.
- Morikawa, T., Ninomiya, K., Xu, F., Okumura, N., Matsuda, H., Muraoka, O., Hayakawa, T., Yoshikawa, M., 2013. Acylated dolabellane-type diterpenes from Nigella sativa seeds with triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells. Phytochem. Lett. 6, 198-204. https://doi.org/10.1016/j. phytol.2013.01.004.
- Mukhamedziev, M.M., Alimbaeva, P.K., Gorovits, T.T., Abubakirov, N.K., 1971. Structure of dipsacoside B - A triterpene glycoside from Dipsacus azureus. Chem. Nat. Compd. 7, 145-149. https://doi.org/10.1007/BF00568685.
- Mupunga, I., Izaaks, C.D., Shai, L.J., Katerere, D.R., 2016. Aflatoxin biomarkers in hair may facilitate long-term exposure studies. J. Appl. Toxicol. 37, 395-399. https://doi. org/10.1002/jat.3422.
- Mutschler, E., 1965. Chemistry and pharmacology of the alkaloids damascenine and arecoline. IV. Comparative pharmacologic studies of derivatives of damascenine and arecoline. Arzneim. Forsch. 15, 1421-1428.
- Nakamura, M.T., Nara, T.Y., 2004. Structure, function, and dietary regulation of delta 6, delta 5, and delta 9 desaturases. Annu. Rev. Nutr. 24, 345-376. https://doi.org/ 10.1146/annurev.nutr.24.121803.063211.
- Ogawa, K., Nakamura, S., Asada, Y., Yamashita, M., Matsuda, H., 2017. Oxazonigelladine and dolabellane-type diterpene constituents from Nigella damascena seeds. Tetrahedron 73, 7054-7060. https://doi.org/10.1016/j.tet.2017.10.061 Sci-31.
- Ogawa, K., Nakamura, S., Hosokawa, K., Ishimaru, H., Saito, N., Ryu, K., Fujimuro, M., Nakashima, S., Matsuda, H., 2018. New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1. J. Nat. Med. 72, 439-447. https://doi.org/10.1007/s11418-017-1166-6.
- Ooi, E.M., Watts, G.F., Ng, T.W., Barrett, P.H., 2015. Effect of dietary fatty acids on human lipoprotein metabolism: a comprehensive update. Nutrients 7, 4416-4425 https://dx.doi.org/10.3390%2Fnu7064416.
- Pasi, S., Aligiannis, N., Pratsinis, H., Skaltsounis, A.L., Chinou, I.B., 2009. Biologically active triterpenoids from Cephalaria ambrosioides. Planta Med 75, 163-167. https:// doi.org/10.1055/s-0028-1088391.
- Pendes, A., Delaude, C., 1994. Structure elucidation of an acetylated saponin of Blighia welwitschii by NMR spectroscopy. Carbohydr. Res. 263, 79-88. https://doi.org/ 10.1016/0008-6215(94)00160-x.
- Pignatti, S., Guarino, R., La Rosa, M., 2017. Flora d' Italia, second ed., vol. 1. Edagricole, Edizioni Agricole di New Business Media, Bologna, p. 798.
- Pommerehne, H., 1899. On damascenin, a component of the seeds of Nigella damascena L. Archiv. der Pharmazie (Weinheim, Germany) 237, 475-480. https://doi.org/ 10.1002/ardp.18992370610.
- Pommerehne, H., 1900. The damascenine, a component of the seeds of Nigella damascena L. Archiv. der Pharmazie (Weinheim, Germany) 238, 531-555.
- Pommerehne, H., 1901. On the damascenine, a component of the seeds of Nigella damascena L. Arch. Pharm. (Weinheim, Ger.) 239, 34-39.
- Rchid, H., Nmila, R., Bessiere, J.M., Sauvaire, Y., Chokairi, M., 2004. Volatile components of Nigella damascena L. and Nigella sativa L. seeds. J. Essent. Oil Res. 16, 585-587. https://doi.org/10.1080/10412905.2004.9698804.
- Rodriguez, A.D., Gonz`alez, E., Ramirez, C., 1998. The structural chemistry, reactivity, and total synthesis of dolabellane diterpenes. Tetrahedron 54, 11683-11729. https://doi.org/10.1016/S0040-4020(98)83033-0.
- Saito, S., Sumita, S., Tamura, N., Nagamura, Y., Nishida, K., Itao, M., Ishiguro, I., 1990. Saponins from the leaves of Aralia elata seem. (Araliaceae). Chem. Pharm. Bull. 38, 411-414. https://doi.org/10.1248/cpb.53.696.
- Salehi, B., Quispe, C., Imran, M., Ul-Haq, I., Zivkovi ˇ´c, J., Abu-Reidah, I.M., Sen, S., Taheri, Y., Acharya, K., Azadi, H., del Mar Contreras, M., Segura-Carretero, A., Mnayer, D., Sethi, G., Martorell, M., Razis, A.F.A., Sunusi, U., Kamal1, R.M., Suleria, H.A.R., Sharifi-Rad, J., 2021. Nigella plants - traditional uses, bioactive phytoconstituents, preclinical and clinical studies. Front. Pharmacol. 12, 625386. https://doi.org/10.3389/fphar.2021.625386.
- Sampaio, B.L., Edrada-Ebel, R., Da Costa, F.B., 2016. Effect of the environment on the secondary metabolic profile of Tithonia diversifolia: a model for environmental metabolomics of plants. Sci. Rep. 6, 29265.
- Schmitz, G., Ecker, J., 2008. The opposing effects of n-3 and n-6 fatty acids. Prog. Lipid Res. 47, 147-155. https://doi.org/10.1016/j.plipres.2007.12.004.
- Shanaida, M., 2019. Carboxilic acids of Nigella sativa and N. damascen a seeds. Ukr. Biopharm. J. 3, 71-76. https://doi.org/10.24959/ubphj.19.229.
- Sieniawska, E., Sawicki, R., Golus, J., Swatko-Ossor, M., Ginalska, G., Skalicka- Wozniak, K., 2018. Nigella damascena L. essential oil-a valuable source of β -elemene for antimicrobial testing. Molecules 23, 256/1-256/11. https://doi.org/10.3390/ molecules23020256.
- Sieniawska, E., Michel, P., Mroczek, T., Granica, S., Skalicka-Wo´zniak, K., 2019. Nigella damascena L. essential oil and its main constituents, damascenine and β -elemene modulate inflammatory response of human neutrophils ex vivo. Food Chem. Toxicol. 125, 161-169. https://doi.org/10.1016/j.fct.2018.12.057.
- Suhas, S.J., Ashish, K.S., Gaurav, S., 2016. Inhibitory studies of some selected plant products as methicillin resistant Staphylococcus aureus (MRSA). World J. Pharm. Pharmaceut. Sci. 5, 598-606. https://doi.org/10.20959/wjpps201610-7711.
- Sytar, O., 2015. Phenolic acids in the inflorescences of different varieties of buckwheat and their antioxidant activity. J. King Saud Univ. Sci. 27, 136-142. https://doi.org/ 10.1016/j.jksus.2014.07.001.
- Tanikawa, N., Homma, K., Tatsuzawa, F., 2019. Flavonoids of the rose-pink, blue, and white flowers of Nigella damascena L. (Ranunculaceae). Sci. Hortic. 257, 108609. https://doi.org/10.1016/j.scienta.2019.108609.
- Tao, L., Zhou, L., Zheng, L., Yao, M., 2006. Elemene displays anti-cancer ability on laryngeal cancer cells in vitro and in vivo. Cancer Chemother. Pharmacol. 58, 24-34. https://doi.org/10.1007/s00280-005-0137-x.
- Telci, I., Sahin-Yaglioglu, A., Eser, F., Aksit, H., Demirtas, I., Tekin, S., 2014. Comparison of seed oil composition of Nigella sativa L. and N. damascene L. during seed maturation stages. J. Am. Oil Chem. Soc. 91, 1723-1729. https://doi.org/10.1007/ s11746-014-2513-3.
- The World Flora online. http://www.worldfloraonline.org/. (Accessed 12 January 2021).
- Toki, K., Saito, N., Nogami, A., Tatsuzawa, F., Shigihara, A., Honda, T., 2009. Flavonoid glycosides isolated from the blue flowers of Nigella damascena. Heterocycles 78, 2287-2294. https://doi.org/10.3987/COM-09-11719.
- Toma, C.C., Olah, N.K., Vlase, L., Mogosan, C., 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. https://doi.org/10.3390/molecules20069560.
- Tutin, T.G., 1972. Nigella L. In: Tutin, T.G., Heywood, V.H., Burges, N.A., Moore, D.M., Valentine, D.H., Walters, S.M., Webb, D.A. (Eds.), Flora Europaea. Edits. University Press, Cambridge, pp. 209-210.
- Ugurlu ˘Aydin, Z., Donmez ¨, A., 2019. Numerical analyses of seed morphology and its taxonomic significance in the tribe Nigelleae (Ranunculaceae). Nord. J. Bot. 37, 121. https://doi.org/10.1111/njb.02323.
- Ulusu, F., Sahin, A., 2021. Investigation on the effects of different concentrations of some fertilizers on yield, quality and essential and fixed oil composition of Nigella damascene. Rom. Biotechnol. Lett. 26, 2722-2735. https://doi.org/10.25083/rbl/ 26.3/2722.2735.
- Vioque, J., Pastor, J., Vioque, E., 1994. Estudio de la composicion ´en ´acidos grasos del aceite de las semillas en algunas plantas silvestres espatnolas. Consejo Superior de Investigaciones Cientificas 45, 161-163 https://doi.org/10.3989%2Fgya.1994.v45. i3.988.
- Vishin, M.L., Mothes, K., Engelbrecht, L., Schroter ¨, H.-B., 1960. Biosynthesis of damascenine in Nigella damascena L. Nature 188, 61-62. https://doi.org/10.1038/ 188061a0.
- Vokou, D., Katradi, K., Kokkini, S., 1993. Ethnobotanical survey of Zagori (Epirus, Greece), a renowned centre of folk medicine in the past. J. Ethnopharmacol. 39, 187-196. https://doi.org/10.1016/0378-8741(93)90035-4.
- Wajs, A., Bonikowski, R., Kalemba, D., 2009. Different isolation methods for determination of composition of volatiles from Nigella damascena L. seeds. Nat. Prod. Commun. 4, 1577-1580. https://doi.org/10.1177/1934578x0900401125.
- Wallis, J.G., Watts, J.L., Browse, J., 2002. Polyunsaturated fatty acid synthesis: what will they think of next? Trends Biochem. Sci. 27, 467. https://doi.org/10.1016/s0968- 0004(02)02168-0.
- Wang, G., Li, X., Huang, F., Zhao, J., Ding, H., Cunnigham, C., Coad, J.E., Flynn, D.C., Reed, E., Li, Q.Q., 2005. Antitumor effect of β -elemene in non-small-cell lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death. Cell. Mol. Life Sci. 62, 881-893. https://doi.org/10.1007/s00018-005-5017-3.
- Wu, W., Liu, K., Tang, X., 1999. Preliminary study on the antitumor immuno-protective mechanism of β -elemene. Zhonghua Zhongliu Zazhi 21, 405-408.
- Xu, K., Zhan Shu, Z., Xu, Q.M., Liu, Y.L., Li, X.R., Wang, Y.L., Yang, S.L., 2013. Cytotoxic activity of Pulsatilla chinensis saponins and their structure - activity relationship. J. Asian Nat. Prod. Res. 15, 680-686. https://doi.org/10.1080/ 10286020.2013.790901.
- Yang, L., Wen, K.S., Ruan, X., Zhao, Y.X., Wei, F., Wang, Q., 2018. Response of plant secondary metabolites to environmental factors. Molecules 23, 762. https://doi.org/ 10.3390/molecules23040762.
- Ye, W.C., Zhang, Q.W., Zhao, S.X., Che, C.T., 2001. Four new oleanane saponins from Anemone anhuiensis. Chem. Pharm. Bull. 49, 632-634. https://doi.org/10.1248/ cpb.49.632.
- Yoshimitsu, H., Nishida, M., Okawa, M., Nohara, T., 2007. Four new triterpene glycosides from Nigella damascena. Chem. Pharm. Bull. 55, 488-491. https://doi. org/10.1248/cpb.55.488.
- Zhang, L.T., Wang, X.L., Wang, T., Zhang, J.S., Huang, Z.Q., Shen, T., Lou, H.X., Ren, D. M., Wang, X.N., 2020. Dolabellane and clerodane diterpenoids from the twigs and leaves of Casearia kurzii. J. Nat. Prod. 83 (10), 2817-2830. https://doi.org/10.1021/ acs.jnatprod.9b00427.
- Zhao, J., Li, Q.Q., Zou, B., Wang, G., Li, X., Kim, J.E., Cuff, C.F., Huang, L., Reed, E., Gardner, K., 2007. In vitro combination characterization of the new anticancer plant drug β -elemene with taxanes against human lung carcinoma. Int. J. Oncol. 31, 241-252. https://doi.org/10.3892/ijo.31.2.241.
- Zheng, Q., Koike, k., Han, L.H., Okuda, H., Nikaido, T., 2004. New biologically active triterpenoid saponins from Scabiosa tschiliensis. J. Nat. Prod. 67, 604-613. https:// doi.org/10.1021/np0304722.
- Zhou, Y., Shen, K., Hou, S., Qiu, M., Luo, Z., 2003. Experimental study on apoptosis induced by elemene in glioma cells. Ai Zheng 22, 959-963.