sign in sign up
<<
Home , Farfugium, Farfugium japonicum, Tussilago

Australian Journal of Basic and Applied Sciences, 5(12): 1787-1791, 2011 ISSN 1991-8178

Pyrethrum, Coltsfoot and Dandelion: Important Medicinal from Family

Shahram Sharafzadeh

Department of Agriculture, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran

Abstract: Medicinal plants synthesize substances that are useful to the maintenance of health in humans and animals. Asteraceae (Compositae) is one of the largest families contains very useful pharmaceutical genera such as chrysanthemum, and . Pyrethrum is under cultivation around the world and is known for its insecticidal activity. Coltsfoot is a perennial . The extracts of coltsfoot exhibit antioxidant and antimicrobial activity. Dandelion is almost stemless and a perennial herb. This plant is a good indicator of environmental pollution. Dandelion has shown anti-inflammatory activity and the aqueous extract seems to have anti-tumour activity. The objective of this study was review of researches regarding to these plants and their secondary metabolites.

Key words: Chrysanthemum cinerariaefolium, Tussilago farfara, Taraxacum officinale, secondary metabolites, compositae.

INTRODUCTION

Medicinal and aromatic plants use by 80% of global population for their medicinal therapeutic effects as reported by WHO (2008). Many of these plants synthesize substances that are useful to the maintenance of health in humans and other animals. These include aromatic substances, most of which are phenols or their oxygen-substituted derivatives such as tannins. Others contain alkaloids, glycosides, saponins, and many secondary metabolites (Naguib, 2011). Asteraceae (Compositae) is one of the largest families of vascular plants represented by 22750 and over 1528 genera all over the world (Bremer, 1994). This family contains very useful pharmaceutical genera such as chrysanthemum, Tussilago and Taraxacum (Hadaruga, et al., 2009). The objective of this study was review of researches regarding the pyrethrum, coltsfoot and dandelion and their secondary metabolites.

Pyrethrum: Pyrethrum, Chrysanthemum cinerariaefolium, is under cultivation around the world with Kenya production for about 83% of the present world production (Bhat, et al., 1985). Its flowers yield an important insecticide, i.e. the pyrethrins. The pyrethrin content has been an important character for breeders (Pandita, et al., 1989). Pyrethrum is a perennial temperate plant and has white flowers with yellow center. This plant needs a rainfall of 1000-1200 mm and a well drained fertile soil. Vernalization is essential for flower initiation in this plant (Dessalgne, et al., 2011). An important group of compounds isolated from pyrethrum flowers known as Pyrethroids. These compounds include Cinerin I (5.1%), Cinerin II (5.3%), Jasmolin I (2.5%), Jasmolin II (2.4%), Pyrethrin I (19.9%) and Pyrethrin II (15.3%) (Essig and Zhao, 2001). They are extracted as an oil or dry powder shortly after the flower blooms. Approximately 94% of the total yield of the Pyrethrin is concentrated in the of the flower (Casida and Quistad, 1995). There are several sesquiterpene lactones in pyrethrum such as Chrysanolide, β-Cyclopyrethrosin, Chrysanin, Dihydro-β-cyclopyrethrosin and Taraxasterol (Doskotch, et al., 1971). Pyrethrosin, (11R)-11, 13-Dihydrotatridin-A, (11R)-11,13-Dihydrotatridin-B, (11R)-6-O-β-D-Glucosyl- 11,13-dihydrotatridin-B, Tatridin-A and Tatridin-B, are another sesquiterpene lactones (Sashida, et al., 1983; Galal, 2001). Researchers identified flavonoid compounds such as Apigenin-4-glucuronide, Apigenin-7 galacturonic acid methyl ester, Apigenin-7-glucuronic acid, Jaceidin and Luteolin (Rao, et al., 1973; Sashida, et al., 1983). Arachidic, Behenic ,Heneicosanoic ,Heptadecanoic, Heptacosanoic ,Hexacosanoic Linoleic, Linolenic, Lignoceric, Myristic, Nonadecanoic, Nonacosanoic, Oleic, Octacosanoic, Palmitic, Pentadecanoic, Pentacosanoic, Stearic, Tricosanoic and Triacontanoic are fatty acids identified in pyrethrum (Head, 1968). Saggar, et al., (1997) isolated essential oils of pyrethrum and identified (E)-β-Farnesene, Germacrene D, Isocaryophyllene, Spathulenol, trans-Chrysanthemumic acid, α-Copaene, β-Cubebene, δ-Cadinene and δ- Nerolidol as constituents of oil.

Corresponding Author: Shahram Sharafzadeh; Department of Agriculture, Firoozabad Branch, Islamic Azad University, Firoozabad, Iran. E-mail: [email protected]; Tel: +98-9177158317. 1787 Aust. J. Basic & Appl. Sci., 5(12): 1787-1791, 2011

Pyrethrum is known for its insecticidal activity (Casida, 1980; Moorman and Nguyen, 1997). About 200,000 kg of pyrethrins are used as an insecticide each year (Crosby, 1995). Carpenter, et al., (1950) showed the toxicity of pyrethrins and allethrin to rats, rabbits and dogs. They reported the oral LD50 of Pyrethrum oleoresin at 820 mg/kg on male and female Sherman strain white rats, whereas the LD50 of the purified 20% pyrethrins extract was 1870 mg/kg. This shows greater toxicity of the unpurified oleoresin. Pyrethrins are generally effective insecticides that display low toxicity to mammals and breakdown quickly under environmental conditions such as sunlight (Chen and Casida, 1969). Some by-products such as pyrethrum marc (pymarc), a product of pyrethrum is known to have a relatively high nutrient concentration. researchers show that wastes products such as pymarc may offer an alternative and effective material for supply of plant nutrients on a long term basis on mineralisation, which can increase nutrients, particularly P in P deficient soils (Nyongesa, et al., 2009).

Coltsfoot: Coltsfoot, Tussilago farfara, is a perennial weed in the temperate zone and can spread into cultivated fields from which is the major cause of its weediness (Wild, et al., 2003). This is widely spread in Korea, , North Africa, Siberia, and . Its flower buds are known as an important folk medicine used in the treatment of cough and wheezing (Bensky, et al., 2004). Pyrrolizidine alkaloids, a class of hepatotoxic and tumorigenic compounds, have been detected in herbal plants. A number of -containing plants have been used as vegetables in Japan, including Tussilago farfara, japonicus, japonicum, and Symphytum officinale (Hirono, et al., 1983; Fu, et al., 2002). The tumorigenic substances in T. farfara are and senkirkine (Roeder, 2000). The root and leaves of coltsfoot has medicinal benefits in chronic bronchitis, asthma, influenza, chest complaints and inflammations. The leaves are smoked like tobacco, as a domestic remedy for asthma (Ergen Akcin, 2007; Qureshi, et al., 2007). Coltsfoot also contains triterpenes like friedelane, bauerane, lanostane, lupane, ursane and oleanane (Ehrman, et al., 2007). The extracts of coltsfoot exhibit antioxidant effect, antimicrobial activity, and inhibitory effects on NO synthesis in LPS-activated macrophages and diacylglycerol acyltransferase activity (Ryu, et al., 1999; Kokoska, et al., 2002; Cho, et al., 2005). Its extracts contain valuable antioxidant active components, which might be helpful in preventing or slowing the progress of various oxidative stresses (Dobravalskyte, et al., 2011). Hadaruga, et al., (2009) revealed biocompounds in leaf of this plant as alpha-Bisabolol oxid B (2.76%), alpha-Bisabolol (20.65%), Camazulene (7.18%), Bisabolol-oxid A (0.91%) and in root as alpha-Bisabolol (14.23%) and Camazulene (3.17%). Five oplopane-type sesquiterpenoids, 7β-senecioyloxyoplopa-3(14)Z,8(10)-dien-2-one (1), 7β- angeloyloxyoplopa-3(14)Z,8(10)-dien-2-one (2), 7β-(4-methylsenecioyloxy)oplopa-3(14)E,8(10)-dien-2-one (3), 1α-angeloyloxy-7β-(4-methylsenecioyloxy)oplopa-3(14)Z,8(10)-dien-2-one (4) and 1 α,7 β -di(4 methylsenecioyloxy)oplopa-3(14)Z,8(10)-dien-2-one (5), were isolated from the flower buds of coltsfoot (Yaoita, et al., 1999). An investigation showed bisabolane-type sesquiterpenoids, (3R,4R,6S)-3,4-epoxybisabola-7(14),10-dien-2- one and (1R,3R,4R,5S,6S)-1-acetoxy-8-angeloyloxy-3,4-epoxy-5-hydroxybisabola-7(14),10-dien-2-one, and a new oplopane-type sesquiterpenoid, 14(R)-hydroxy-7β -isovaleroyloxyoplop-8(10)-en-2-one, in coltsfoot flower bud (Yaoita, et al., 2001). Tussilagone, isolated from the flower of T. farfara, is a sesquiterpenoid that is known to exert a variety of pharmacological activities such as anti-inflammatory activities in murine macrophages by inducing heme oxygenase-1 (HO-1) expression (Hwangbo, et al., 2009). Wu, et al., 2008. reported some active substances of T. farfara from previous works: some triterpenoids such as arnidiol, faradiol, bauerenol, isobauerenol and some common flavonoids, quercetin, kaempferol and their glycosides. They found Chromones from the flower buds of T. farfara.

Dandelion: Dandelion, Taraxacum officinale, is almost stemless and perennial herb. The stems are 1–2.5 cm in length. The leaves form a basal, radial rosette. The capitulum is composed of up to 250 ligulate, perfect, yellow florets (Holm, et al., 1997). Dandelion has been used for medicinal purposes including to improve liver function, lower cholesterol, lower blood pressure (Mattern, 1994), decrease body weight in obese patients, treat gall bladder ailments (Dalby, 1999) and as a diuretic (Racz-Kotilla, et al., 1974). Dandelion contains terpenoid and sterol bitter principles (principally taraxacin and taraxacerin), in the roots, leaves, and flowers. Other compounds include betaamyrin, taraxasterol, and taraxerol and free sterols (sitosterin, stigmasterin, and phytosterin). It contains large amounts of polysaccharides (primarily fructosans and inulin),

1788 Aust. J. Basic & Appl. Sci., 5(12): 1787-1791, 2011 smaller amounts of pectin, resin, and mucilage, and various flavonoids (Rutherford, 1972; Cordatos, 1992). Leaves also contain appreciable amounts of furan fatty acids (Hannemann, et al., 1989). Dandelion has feed value, with low amounts of essential oils and tannin that might affect quality or palatability (Falkowski, et al., 1990). It is a rich source of vitamins and minerals, including beta carotene, nonprovitamin A carotenoids, xanthophylls, chlorophyll, vitamins C and D, many of the B-complex vitamins, choline, iron, silicon, magnesium, sodium, potassium, zinc, manganese, copper, and phosphorous. (Cordatos, 1992; Popescu, et al., 2010). This plant is a good indicator of environmental pollution and is often used as a biomonitor because the leaves and roots accumulate metals, including As, Br, Cd, Co, Cu, Cr, Hg, Mn, Pb, Sb, Se and Zn (Kuleff and Djingova, 1984; Djingova, et al., 1986; Simon, et al., 1996). of dandelion can be a potential source of photoallergic contact dermatitis (Lovell and Rowan, 1991; Mark, et al., 1999). Dandelion has shown anti-inflammatory activity in animal studies (Mascolo, 1987; Jeon, et al., 2008) and the aqueous extract seems to have anti-tumour activity (Nevall, et al., 1996). This plant use in therapy for hepatitis and the drug also has diuretic and choleretic actions (Bradley, 1992; Bisset, 1994). It is used to treat a variety of diseases including cancer (Sigstedt, et al., 2008). The drug Taraxaci radix cum herba contains: sesquiterpenlactones, triterpenes, phytosterols, carbohydrates, phenolic acids and flavonoids (Bradley, 1992; Bissett, 1994; Newall, et al., 1996; Williams, et al., 1996). Results of the comparative quantitative chemical analysis in different parts of plant revealed that total hydroxycinnamic acid derivatives and flavonoids had the highest values in leaves and flowers (Popescu, et al., 2010). Sengul, et al., (2009) indicated antioxidant activity (43.05%) and total phenolic content (15.50 mgGAE/g DW) in this plant.

REFERENCES

Bensky, D., S. Clavey, E. Stoger and A. Gamble, 2004. Chinese . In: Niemeier, G., Ed., Materia Medica. 3rd ed., Seattle: Eastland Press., pp: 442. Bhat, B.K., R.C. Menary and P.N. Pandita, 1985. Population improvement in Pyrethrum (Chrysanthemum cinerariaefolium Vis.). Euphytica, 34: 613-617. Bisset, N.G., 1994. Herbal Drugs and Phytopharmaceuticals CRC Press. Boca Raton, Ann Arbor, London, Tokyo. Bradley, P.R., 1992. British Herbal Medicine Association, Bournemouth, British Herbal Compendium 1. Bremer, K., 1994. Asteraceae: Cladistic and Classification. Timber press, Portland. Carpenter, C.P., C.S. Weil, U.C. Pozzani and Jr.H.C. Symthe, 1950. Comparative acute and subacute toxicities of allethrin and pyrethrin. Arch. Indian Hyg. Occup. Med., 2: 420-432. Casida, J.E. and G.B. Quistad, 1995. Pyrethrum; a benefit to human welfare. In “Pyrethrum flowers; Production, Chemistry, Toxicology, and uses”. Casida J.E. and G.B. Quistad (eds.). Oxford University Press. New York, NY. pp 345-350. Casida, J.E., 1980. Pyrethrum Flowers and Pyrethroid Insecticides. Environmental Health Perspectives, 34: 189-202. Chen, Y.-L. and J.E. Casida, 1969. Photodecomposition of pyrethrin I, allethrin, phthalthrin, and dimethrin. J. Agr. Food Chem., 17: 208-215. Cho, J.S., H.M. Kim, J.H. Ryu, Y.S. Jeong, Y.S. Lee and C.B. Jin, 2005. Neuroprotective and antioxidant effects of the ethyl acetate fraction prepared from Tussilago farfara L. Biol. Pharm. Bull., 28: 455-460. Cordatos, E., 1992. Taraxacum officinale. In: Murray, M. and J. Pizzorno, eds. A Textbook of Natural Medicine. Seattle: Bastyr University Press. Crosby, D.G., 1995. Environmental fate of pyrethrins. In “Pyrethrum flowers; Production, Chemistry, Toxicology, and uses”. Casida J.E. and G.B. Quistad (eds.). Oxford University Press. New York, NY. pp: 194- 213. Dalby, R., 1999. The delightful dandelion. Am. Bee J., 139(4): 300-301. Dessalgne, F.H., S.A. Mekonnen and B.A. Indris, 2011. Variability of pyrethrum (Chrysanthemum cinerariaefolium) clones for chemical traits grown at Bekoja and Meraro of south eastern Ethiopia. Int. J. Med. Arom. Plants, 1(2): 166-174. Djingova, R., I. Kuleff, I. Penev and B. Sansoni, 1986. Bromine, copper, manganese and lead content of the leaves of Taraxacum officinale (dandelion). Sci. Total Environ., 50: 197-208. Dobravalskyte, D., T. Talou, P.R. Venskutonis, 2011. Activity of natural antioxidants extracted from greater calamint, sweet cicely and coltsfoot cultivated in Lithuania and in France. Retrieved from: http://llufb.llu.lv/conference/foodbalt/2011/FOODBALT-Proceedings-2011-73-78.pdf.

1789 Aust. J. Basic & Appl. Sci., 5(12): 1787-1791, 2011

Doskotch, R.W., F.S. El-feraly and C.D. Hufford, 1971. Sesquiterpene lactones from Pyrethrum flowers. Can. J. Chem., 49: 2103-2110. Ehrman, T.M., D.J. Barlow and P.J. Hylands, 2007. Virtual Screening of Chinese Herbs with Random Forest. J. Chem. Inform. Model., 47(2): 264-278. Ergen Akcin, O., 2007. Morphological and Anatomical Characteristics of Cichorium intybus L., Tragopogon latifolius Boiss. and Tussilago farfara L. (Asteraceae). Int. J. Natu. Engin. Sci., 1(3): 81-85. Essig, K. and Z. Zhao, 2001. Method development and validation of a high performance liquid chromatographic method for Pyrethrum extract. J. Chromatogr. Sci., 39: 473-480. Falkowski, M., I. Kukulka and S. Kozlowski, 1990. Biological properties and fodder value of dandelion. Pages 208–211 in Gaborcik, N., V. Krajcovik and M. Zimkova, eds. Soil-grassland-animal relationships: Proceedings of the 13th General Meeting of the European Grassland Federation, 1990. Banska Bystrica, Czechoslovakia. 2. Fu, P.P., Y.-Ch. Yang, Q. Xia, M.W. Chou, et al., 2002. Pyrrolizidine Alkaloids - Tumorigenic Components in Chinese Herbal Medicines and Dietary Supplements. Journal of Food and Drug Analysis, 10(4): 198-211. Galal, A.M., 2001. Microbial transformation of pyrethrosin. J. Nat. Prod., 64: 1098-1099. Hadaruga, N.G., D.I. Hadaruga, C. Tatu, A. Gruia et al., 2009. Multivariate analysis (PCA) in Compositae biocompounds class. J. Agroaliment. Proc. Technol., 15(2): 201-210. Hannemann, K., V. Puchta, E. Simon, et al., 1989. The common occurrence of furan fatty acids in plants. Lipids, 24:296-298. Head, S.W., 1968. Fatty acid composition of extract from Pyrethrum flowers (Chrysanthemum cinerariaefolium). J. Agric. Food Chem., 16: 762-765. Hirono, I., I. Ueno, S. Aiso, T. Yamaji and M. Haga, 1983. Carcinogenic activity of and cannabifolius. Cancer Lett., 20: 191-198. Holm, L., J. Doll, E. Holm, J. Pancho and J. Herberger, 1997. World Weeds: natural histories and distribution. John Wiley and Sons, New York, NY., pp: 1129. Hwangbo, Ch., H.S. Lee, J. Park, J. Choe and J.H. Lee, 2009. The anti-inflammatory effect of tussilagone, from Tussilago farfara, is mediated by the induction of heme oxygenase-1 in murine macrophages. Int. Immunopharmacol., 9: 1578-1584. Jeon, H.J., H.J. Kang, H.J. Jung, Y.S. Kang, et al., 2008. Anti-inflammatory activity of Taraxacum officinale, J. Ethnopharmacol., 115(1): 82-88. Kokoska, L., Z. Polesny, V. Rada, A. Nepovim and T. Vanek, 2002. Screening of some Siberian medicinal plants for antimicrobial activity. J. Ethnopharmacol., 82:51-53. Kuleff, I. and R. Djingova, 1984. The dandelion (Taraxacum officinale) - a monitor for environmental pollution? Water Air Soil Pollut., 21: 77-85. Lovell, C.R., M. Rowan, 1991. Dandelion dermatitis. Contact Dermatitis, 25: 185-188. Mark, K.A., R.R. Brancaccio, N.A. Soter and D.E. Cohen, 1999. Allergic contact and photoallergic contact dermatitis to plant and pesticide allergens. Arch. Dermatol., 135: 67-70. Mascolo, N., G. Autore, F. Capasso, A. Menhini and M.P. Fasulo, 1987. Biological screening of Italian medicinal plants for anti-inflammatory activity. Phytother. Res., 1: 28-31. Mattern, V., 1994. Don’t weed ‘em, eat ‘em. Organic Gard., 41: 70-74. Moorman, R., and K. Nguyen, 1997. Identification and quantitation of the six active compounds in a pyrethrin standard. J. Assoc. Off. Anal. Chem., 65: 921-926. Naguib, N.Y.M., 2011. Organic vs chemical fertilization of medicinal plants: a concise review of researches. Adv. Environ. Biol., 5(2): 394-400. Newall, C.A., S.A. Anderson and J.D. Phillipson, 1996. Herbal Medicines. The Pharmaceutical Press, London. Nyongesa, H.W., R.K. Obura, B.K. Kitur, J.P. Ouma and L.N. Nakhone, 2009. Effect of organic and inorganic nutrient sources on maize yield and yield components in Nandi district, Rift Valley Province, Kenya. African Crop Science Conference Proceedings, 9: 55-61. Pandita, P.N., B.K. Bhat and M.K. Bhan, 1989. Selection indices in Pyrethrum (Chrysanthemum cinerariaefolium Vis.). Pesticides, 23(1): 27-28. Popescu, M.-L., M. Dinu, D.D. Ursache, 2010. Contributions to the pharmacognostical and phytobiological study on Taraxacum officinale (L.) Weber. Farmacia, 58(5): 646-653. Qureshi, R.A., M.A. Ghufran, S.A. Gilani, K. Sultana and M. Ashraf, 2007. Ethnobotanical studies of selected medicinal plants of Sudhan Gali and Ganga Chotti Hills, district Bagh, Azad Kashmir. Pak. J. Bot., 39(7): 2275-2283. Racz-Kotilla, E., G. Racz and A. Solomon, 1974. The action of Taraxacum officinale extracts on the body weight and diuresis of laboratory animals. Planta Med., 26: 212-217.

1790 Aust. J. Basic & Appl. Sci., 5(12): 1787-1791, 2011

Rao, P.R., T.R. Seshadri and P. Sharma, 1973. Polyphenolic constituents of Pyrethrum flowers (Chrysanthemum cinerariaefolium). Curr. Sci., 42: 811-812. Roeder, E., 2000. Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie., 55: 711-726. Rutherford, P.P. and A.C. Deacon, 1972. β-Fructofurasonidase from roots of dandelion (Taraxacum officinale Weber). Biochem. J., 126: 569-573. Ryu, J.H., Y.S. Jeong and D.H. Sohn, 1999. A new bisabolene epoxide from Tussilago farfara, and inhibition of nitric oxide synthesis in LPS-activated macrophages. J. Nat. Prod., 62: 1437-1438. Saggar, P., W.N. Wamicha, S.C. Chhabra and P. Ndalut, 1997. Isolation, identification and bioassay of repellent factors in the essential oil of Pyrethrum for grain protection against Sitophilus zeamais (Molts.). Pyrethrum Post, 19: 126-131. Sashida, Y., H. Nakata, H. Shimomura and M. Kagaya, 1983. Sesquiterpene lactones from Pyrethrum flowers. Phytochemistry, 22: 1219-1222. Sengul, M., H. Yildiz, N. Gungor, B. Cetin, Z. Eser and S. Ercisli, 2009. Total phenolic content, antioxidant and antimicrobial activities of some medicinal plants. Pak. J. Pharm. Sci., 22(1): 102-106. Sigstedt, S.C., C.J. Hooten, M.C. Callewaert, A.R. Jenkins, et al., 2008. Evaluation of aqueous extracts of Taraxacum officinale on growth and invasion of breast and prostate cancer cells. Int. J. Oncol., 32(5): 1085- 1090. Simon, L., H.W. Martin and D.C. Adriano, 1996. Chicory (Cichorium intybus L.) and dandelion (Taraxacum officinale Web.) as phytoindicators of cadmium contamination. Water Air Soil Pollut., 91: 351-362. Wild, J.-D., E. Mayer and G. Gottsberger, 2003. Pollination and reproduction of Tussilago farfara (Asteraceae). Bot. Jahrb. Syst., 124: 273-285. Williams, Ch.A., F. Goldstone and J. Greenham, 1996. Flavonoids and cinnamic acids and coumarins from different tissues and medicinal preparations of Taraxacum officinale. Phytochemistry, 42: 121-127. World Health Organization (WHO), 2008. "Traditional medicine" Fact sheet number: 134 (December) ".http://www.who.int/mediacentre/factsheets/fs134/en/. Wu, D., M. Zhang, C.F. Zhang, Z.T. Wang, 2008. Chromones from the flower buds of Tussilago farfara. Biochem. Syst. Ecol., 36: 219-222. Yaoita, Y., H. Kamazawa, and M. Kikuchi, 1999. Structures of New Oplopane-Type Sesquiterpenoids from the Flower Buds of Tussilago farfara L. Chem. Pharm. Bull., 47(5): 705-707. Yaoita, Y., N. Suzuki and M. Kikuchi, 2001. Structures of New Sesquiterpenoids from Farfarae Flos. Chem. Pharm. Bull., 49(5): 645-648.

1791