Indian Journal of Traditional Knowledge Vol 18(1), January 2019, pp 140-143

Sisymbrium irio L.: A Herb used in the Unani system of medicine for broad spectrum therapeutical applications

Temesgen Hailu%, Rajinder K. Gupta#, & Archna Rani*,+ Department of Applied Chemistry Delhi Technological University, Shahbad Daulatpur, Main Bawana Road, Delhi 110042, India E-mail: [email protected]; #[email protected]; %[email protected]

Received 03 October 2018; revised 11 December 2018

Medicinal herbal plants constitute effective sources of natural products consumed as phytomedicines and the products obtained from medicinal plants have been playing a significant role in drug discovery efforts for treatment of animals and human diseases. Sisymbrium irio is one of the class of Cruciferae family used in Unani medicine. The plant is known for its value in traditional medicine. The various parts of Sisymbrium irio such as, flowers, leaves, stem, seeds and aerial parts contains different types of phytochemicals such as tannin, alkaloids, flavonoids, saponins, glycosides, carbohydrates, phenolics, amino acids, proteins, steroids, fatty acids that are responsible for pharmacological actions such as antimicrobial, antifungal, anticancer, antiinflammatory, antidepressant, rheumatoid, antipyretic, analgesic, detoxify liver and spleen, bronchoprotective role, voice disorders, cytotoxic, phytotoxic, diuretic, expectorant, febrifuge, boils, pimples, cough, hepatoprotective and stomachic treatments. The different solvent extracts of the plant parts such as leaves, stem, seeds and flowers exhibited a higher antioxidants activity which could be attributed to its higher contents of phenolics and flavonoids constituents. This preexisting knowledge necessitates a qualitative screening of the plant with scientific approach to identify natural template for safer drug discovery and designing.

Keywords: Cruciferae, Phytochemicals, Phytomedicine, Sisymbrium irio, Unani medicines IPC Code: Int. Cl.18 A61K 36/31, A61K 36/00, A61K 39/00, A01N 43/40, A61K 36/00

Drugs derived from plants have great interest due to Cruciferae, called Khubah (Arabic); Asalio, diverse applications in Unani medicine. The Khubkalan, khubkhala (Hindi); Khakasi, Khakshi medicinal herbal plant materials are the basis for (Persian); Khubakalan (Urdu) and London Rocket/Rocket synthetic drugs, modern medicines, pharmaceuticals, Mustard (common names) and is found in different food supplements, and folk medicines1. The discovery parts of the world3. In the traditional medicine this of new drugs is attained through natural compounds plant has a significant role for treatment of coughs, and their products, followed by other synthetic drugs. upper body mobbing, rheumatism, purification of This situation run in the direction of improved liver, irritation, decrease inflammation and injuries4. international quest for natural medicine, leading to the In 2003, Guil et al., reported that Sisymbrium irio is phytochemical investigation of plants in diverse used to treat inflammation, rheumatism, antipyretic, ecological environments for their various medicinal analgesic, antimicrobial and antioxidant potential and properties2. These medicinal herbal plant materials are food supplements5. The seeds of plant are widely used used to treat different types of human and animal for treatments of voice disorders6, as an expectorant, diseases because they contain different types of febrifuge7, treating inflammation & rheumatoid8, secondary metabolites or pharmacologically bioactive reduces fever, painkilling, antibacterial & antifungal components belonging to different classes of activities9. The 70% ethanolic extract of the plant was compounds such as tannins, saponin, flavonoids, subjected to qualitative phytochemical analysis and alkaloids, phenolic substances, glycosides, steroids the results showed the existence of various types and terpenoids. These bioactive secondary of pharmacological active components such as metabolites play different role, in the human body and nitrogen containing compounds, phenolic compounds, also protects the plants from predators. The medicinal saponins, gums, mucilage, tannins, oils, saturated and herbal plant Sisymbrium irio belong to the family unsaturated fatty acids, glycosides, proteins, amino 10 —————— acids, carbohydrates, phytosterols and flavonoids . *Corresponding author This report focuses on the details of phytochemistry HAILU et al.: SISYMBRIUM IRIO L.: HERB USED FOR BROAD SPECTRUM THERAPEUTICAL APPLICATIONS 141

and broad-spectrum pharmaceutical applications of found in various parts of Sisymbrium irio plant and are various parts of Sisymbrium irio. mentioned in the Table 1.

Phytochemistry Pharmaceutical applications of Sisymbrium irio The plants synthesize secondary metabolites to The plant Sisymbrium irio is used for the treatment protect themselves, nevertheless, the study also shows of different types of diseases such as inflammatory that they have significant roles for protection and conditions and rheumatism21, expectorant, febrifuge prevention of the different kinds of livestock and and for treatment of voice disorders22, chest human diseases. These plant metabolites have congestion, rheumatism, detoxify liver and spleen, anticancer activity, antimicrobial activity, scavenges reduces swelling and clean wounds23, antipyretic, free radicals, act as hormone, stimulates enzymatic analgesic, antimicrobial and antioxidant potential24. activity & various therapeutic uses11. Numerous The seeds of London rocket are used for the treatment phytochemicals are identified from various parts of of inflammatory conditions, boils, pimples, cough, Sisymbrium irio these are: derivatives of terpenes12, cholera and non-specific fever. Crude extracts of the saponins, tannins, sterols, triterpenes13, flavonoids14, seeds were tested for antipyretic, analgesic and alkaloids15, glycosides, stigmasterol’s, sitosterols16, 17 antimicrobial effects. The ethanolic extract exhibited and glucosinolates18, 19. The study conducted on the significant antipyretic and analgesic effects as aerial part of the plant showed the oils obtained from well25. It also exhibited marked antibacterial action Sisymbrium irio comprised of two esters & seven against both gram-positive and gram-negative acids (38.80%), eleven sulfur and eleven nitrogen organisms and was found to be non toxic in acute containing compounds (36.41%), fifteen terpenes studies9. The polarity-based extract of the Sisymbrium derivatives (8.19%), five aromatic compounds (3.53%), irio was active to inhibit the growth of major disease- six aliphatic hydrocarbons (6.29%), four fatty alcohols causing bacterial strains26. The n-hexane extract of (2.49%) and three additional chemicals compounds plant leaves inhibited the growth of microbial strains (1.17%)12. Another study on phytochemical such as Klebsiella pneumoniae and Staphylococcus investigation of the different parts (leaves, stem, epidermidis27. The ethyl acetate extract of the flowers and roots) of Sisymbrium irio showed the leaves was active against the gram-negative bacteria presence of flavonoids, triterpenoids, steroids, tannins, such as Escherichia coli, Klebsiella pneumonia and carbohydrates, saponins and alkaloids at different Pseudomonas aeruginosa, whereas the plant seed levels in different extracts of plant organs and the demonstrated greater inhibitory effect against absence of cardiac glycosides and anthraquinones13. Pseudomonas aeruginosa and Staphylococcus The different types of bioactive secondary metabolites epidermidis27. Sisymbrium irio aqueous extract Table 1 — Compounds isolated from Sisymbrium irio Phytochemicals Part of the plant Flavonoids (apigenin, apigenin-7-galactoside, apigenin-7-O-β-D-glucoside, luteolin-7-O-glucoside, Aerial part14 apigenin-7-di-glucoside, apigenin-7-O-(6ʹʹ acetyl) glucoside, apigenin-7-O-gluco(6ʹʹ,1ʹʹʹ)rhamnoside, apigenin-7-O-gluco(6ʹʹ,1ʹʹʹ) rhamnoside, apigenin-7-O-gluco(6ʹʹ, 1ʹʹʹ) rhamnoside-5- methoxide, Kaemp- ferol,kaempferol-3-O-xylosoid-7-galactoside Alkaloid (nicotine) Aerial parts15 β-sitosterol, stigmasterol and β-sitosterol-glucoside Aerial parts16 β-sitosterol, β-sitosterol-D-glucoside, isorhamnetin & quercetin Aerial & Seeds parts17 Glucosinolates Aerial parts18, 19 Terpenoids, dioctyl adipate, N-(n-propyl) acetamide, isopropyl isothiocyanate, Aerial parts12 isobutyl isothiocyanate, 3,7,11,15-tetramethyl-2-hexadecen-1-ol, cis-8,11,14- eicosatrienoic acid, heptacosane, palmitic acid, n-butyl isothiocyanate, di- methoxy acetophenone aliphatic hydrocarbons & aromatic compounds Sitosteryl-6ʹ-O-undecanoate-β-D-glucoside, (Z)-8, 11, 12-trihydroxyoctadec-9-enoic acid, 1,2-dipalmitoyl- Aerial parts20 3-O-α-6ʹʹʹ-sulfoquinovosyl glycerol, crotanoyl cosmosiin, tetracosanoic acid, β-sitosterol, ursolic acid, indole-3-carboxaldehyde, indole-3-carboxylic acid, -sitosterol-D-glucoside, apigenin, naringenin-4ʹ-O- glucopyranoside, -adenosine and apigenin-7-O--glucoside 142 INDIAN J TRADIT KNOWLE, JANUARY 2019

was active against all tested pathogenic microbes such membrane or renewal of injured liver cells, this may be as Staphylococcus aureus, Enterococcus faecium, due to the existence of bioactive flavonoids15. In the Acinetobacter baumanii, Pseudomonas aeruginosa, Mediterranean region Sisymbrium irio leaves are Escherichia coli ATCC 25922, Enterobactercloace, consumed as food and used as folk medicine for Staphylococcus aureus ATCC 29213, and infections of the throat and chest14. This plant is used in Klebsiellapneumoniae28. The plant has numerous Unani system of medicine for various therapeutic uses therapeutic uses for the treatment of acute diseases, and recommended for the prevention of dengue fever. chronic, ribs bottleneck, to decrease pain in the joints due to the presence of bioactive components. and muscles pain, inflammation, treat the liver and the irritation, injuries, painkilling, reduce fever& Conclusion and Recommendation antibioticuses29. The ethanolic extracts of Sisymbrium From this review, it is certain that various irio seeds shows phytotoxic, cytotoxic and phytochemicals are present in different parts of insecticidal activities30. The ethanolic extracts Sisymbrium irio plant, which need further of the seeds of this plant showed antiinflammatory phytochemical and biological investigation to develop activity, antidepressant, swim stress immobility and into useful therapeutic uses and for the development bronchoprotective role31. Secondary metabolites such of novel drug molecules. as isothiocyanates and nitriles, which are found in Acknowledgements Sisymbrium irio have wide applications against Temesgen Hailu would like to thank the Ministry different kinds of the microbial diseases32. The study of Education, Ethiopia for the financial support and shows the uses of Sisymbrium irio for the Dire Dawa University for the study leave. treatment/inhibition of cancers and development of 33 safer and more effective therapeutic agents . The Conflict of interest statement activity may be attributed to the presence of The author(s) declare(s) that here is no conflict of β-sitosterol, as in vivo study showed β-sitosterol had a benefits concerning the publication of this paper. significant rolein the diets of mice & rats fed with colon carcinogens that reduced the proliferative References variations of the cancer growth34. β-sitosterol had 1 Ncube N, Afolayan A & Okoh A, Assessment techniques of an distracted the structure of cancer cell membranes & timicrobial properties of natural compound of plant origin: current methods and future trends, International Journal of altered the signalling pathways that regulate cancer Current Microbiology Applied Science, 3 (5) (2014) 362-376. 35 growth & apoptosis . The Sisymbrium irio extracts 2 Kumara S, Sudipta K, Lokesh P, Neeki A, Rashmi P showed hepatoprotective effects against CCl4 induced et al, Phytochemical screening and in vitro antimicrobial hepatotoxicity in albino rats36. The hepatotoxic activity of Bougainvillea spectabilis flower extracts, properties of the CCl was mainly due to the presence Int. J. Phytomed, 4 (2012) 375–379. 4 3 Khoshoo T, Biosystematics of Sisymbrium irio Complex XII: of intermediate reactive metabolite, trichloromethyl Distributional Pattern, Caryologia: International Journal of 37 radical . Trichlor omethyl radical bound covalently Cytology, Cytosystematics and Cytogenetics, 19(2) (1966) to the macromolecules & encouraged peroxidative 143-150, DOI: 10.1080/00087114.1966.10796212. deprivation of membrane phospholipids of 4 Lev F, Sisymbrium irio medicinal substances in Jerusalem from early times to the present day Archaeo press, (Oxford, endoplasmic reticulum rich in polyunsaturated fatty UK), 2003, 62. acids, that leads to unnecessary build-up of 5 Guil J, Guerrero J, Gimenez M & Tarija M, Nutritional 38 phospholipids in tissues such as liver . composition of wild edible Cruciferae species, J. Food Histopathological study revealed that post treatment Biochem, 23 (3) (1998) 283. with Sisymbrium irio clearly exhibited the significant 6 Meyer B, Ferrigni N, Putnam J, Jacobsen L, Nichols D et al, 36 Brine Shrimp: A convenient general bioassay for active plant protection of liver cells . The effectiveness of constituents, Planta Medica, 45 (1982) 31-34. antihepatotoxicity of drug mayrely on its capacity in 7 Ghazanfar S, Handbook of Arabian medicinal plants, CRC decreasing the harmful effect/mending the usual Press, Boca Raton, Ann Arbor, London, Tokyo, 1994, 587. hepatic functioning impaired by a hepatotoxin36. 8 BolusL, Medicinal plant of North Africa, Reference Sisymbrium irio extracts have powerful reducing Publications, Inc: Chemical constituents of Sisymbrium irio L., from Jordan, Nat Prod Res. 24(5) (1983) 448-56. ability of carbon tetrachloride action to raise the 9 Vohora S, Nagvi S & Kumar H, Antipyretic analgesic and levels of the enzyme in testing groups, this shows antimicrobial studies on Sisymbrium irio L., Planta Med, 38 the defense of structural integrity of hepatocyte (1980) 255. HAILU et al.: SISYMBRIUM IRIO L.: HERB USED FOR BROAD SPECTRUM THERAPEUTICAL APPLICATIONS 143

10 Trease G & Evans W, Pharmacognosy 15th edition, English 26 Shabnam B, Ziaur R, Khalid R & Naveed I, Biological Language Book, Society Baillere Tindall, Oxford University screening of polarity-based extracts of leaves and seeds of Press, 17 (2002) 417-547. Sisymbrium irio L., Pak. J. Bot., 47 (2015) 301-305. 11 Doss A & Anand S, Preliminary Phytochemical Screening 27 Gamal M, Saad A & Mohammed H, Antimicrobial Activities of Asteracantha longifolia & Pergularia daemia, World and Cytotoxicity of Sisymbrium irio L., extract against Applied Sciences Journal, 18 (2) (2012) 233-235. ISSN 1818 Multi-Drug Resistant Bacteria (MDRB) & Candida albicans. - 4952. © IDOSI Publications DOI: 10.5829/ idosi. Wasj. 18. Int. J. Curr. Microbiol. App. Sci, 6(4) (2017) 1-13. 02.1136. 28 Clinton B & Avinoam D, Bedouin Plant Utilization in Sinai 12 Al-Qudah M & Abu Z, Chemical composition of essential and the Negev Economic Botany, New York Botanical oils from aerial parts of Sisymbrium irio from Jordan, Garden Press, 35(2) (1981) 145-162. E-Journal of Chemistry, 7 (2010) 6 –10. 29 Sumaira Sh, Sirajud D, Rehmanullah & Zahir M, 13 Hany E, Yousef M, & Fahad A, Phytochemical Analysis and in Pharmacognostic standardization and pharmacological study Vitro Antioxidant Properties of Sisymbrium irio L., Growing in of Sisymbrium irio L., American Journal of Research Saudi Arabia, Research Journal of Pharmaceutical, biological Communication, 1 (7) (2013) 241-253. & Chemical Sciences, 8(3) (2017) 2533. 30 Singh RK, Acute toxicity, antiinflammatory and bronchial s 14 Al-Jaber N, Phytochemical and biological studies of mooth muscles investigation of Sisymbrium irio L., seeds in Sisymbrium irio L., Growing in Saudi Arabia, Journal of experimental animal models, International Journal of Saudi Chemical Society, 15 (2011) 345–350. Research Studies in Biosciences, 1, (2015) 48-53. 15 Dania F, Ibrahim S & Ashour H, Investigation of the Main 31 Singh RK, Studies on ethanolic extract of Sisymbrium irio L, Alkaloid of London Rocket (Sisymbrium irio L) as a Wild Seeds on in vitro rat mast cells, International Journal of Medicinal Plant Grown in Iraq, Int. J. Pharm. Sci. Rev. Res, Development Research, 6 (7)(2016) 8336-8338. 56, (2016) 279-281. 32 Conrad A, Biehler D, Nobis T, Richter H, Engels Ietal, 16 Shaza M, Ali A, Perwez A, Ebtesam S, Mai et al, Isolation, Broad spectrum antibacterial activity of a mixture of biological evaluation and validated HPTLC-quantification isothiocyanates from nasturtium (Tropaeolimajoris herba) & "of the marker constituent of the edible Saudi plant horseradish (Armoraciae rusticanae radix), Drug Res, Sisymbrium irio L., Saudi Pharmaceutical Journal, 25 (Stuttgart), 63 (2013) 65–68. (2017) 750–759. 33 Yukes J & Michael J, Dominican Medicinal Plants: A Guide 17 Kahan M, Kalim S & Kahan M, Chemical constituents of the for Health Care Providers. Dominican Medicinal Plants: A aerial parts of Sisymbrium irio L., Journal of the Indian Guide for Health Care Providers, New York: New York Chemical Society, 68 (1991) 532. Botanical Garden, 2010. 18 Cole R, Low Molecular Weight Sulphur Containing Natural 34 Awad A, Downie A, Fink C & Kim U, Dietary phytosterols i Products, Phytochemistry, 15 (1976) 759. nhibits the growth & metastasis of MDA-MB-231 human bre 19 Griftiths D, Deighton N & Nicholas A, Identification of ast cancer cells grown in SCID mice,Anticancer Res, 20 glucosinolate on the leaf surface of plants from the (2000) 821–824. Cruciferae and other closely related species, Phytochemistry, 35 Von H, Fink C & Awad A, Beta-sitosterol activates 57 (2001) 693–700. the sphingomyelin cycle and induces apoptosis in LNCaP 20 Mahmoud A & Musa H, Chemical constituents of human prostate cancer cells, Nutr. Cancer, 32 (1998) 8–12. Sisymbrium irio L., from Jordan, Natural Product Research, 36 Dania F, Kassim H, Sura F & Ashour H, Hepatoprotective 5 (2010) 448–456. Effects of London Rocket (Sisymbrium irio L) Extract 21 Care E, Plant Taxonomy Prentice Hall, Inc., Englewood against CCl4 induced Hepatotoxicity in Albino Rats, Int. J. Cliffs, NJ, 1955, 321. Pharm. Sci. Rev. Res., 46(1) (2017) 8-12 22 Schulz O, Cruciferae, In: Engler, A, Prantl, K. (Eds.), Die 37 Lesiuk S, Czechowska G, Zimmer S, Slomka M, Madro A Naturlichen Pflanzenfamilien, Wilhelm Engelmann, et al, Catalase, superoxide dismutase and glutathione Leipzig, 2 (1936) 227–658. peroxidase activities in various rat tissues after Prevention of 23 Rollins R, The Cruciferae of continental North America: CCl4-induced hepatotoxicity albino rats, Int. J. Toxicol., 19 Systematics of the mustard family from Arctic to Panama. (1999) 429-441. Stanford University Press, Stanford, California, 1993, 97. 38 Srivastava S, Chen N & Holtzman J, The in vitro NADPH- 24 Wagner L, Herbst D, Sohmer S & Yevonn W, Manual of the dependent inhibition by CCl4 of the ATP-dependent calcium flowering plants of Hawaii, 1990, 1853. uptake of hepatic microsomes from male rats. Studies on the 25 Al-Mujalli A, Fouda T & Hussein H, Effects of London mechanism of inactivation of the hepatic microsomal rocket (Sisymbrium irio) on goats’ health: Clinical and calcium pump by the CCl3 radical, J. Biol. Chem, 265 (1990) laboratory studies. Bulg. J. Vet. Med., 1 (2013) 48−52. 8392-8399.