Tanacetum vulgare L.

Chamaemelum tanacetum (Vis.) E.H.L. Krause, Chrysanthemum asiaticum Vorosch., Chrysanthemum boreale (DC.) B. Fedtsch. (illeg.), Chrysanthemum vulgare (L.) Bernh. (illeg.), Chrysanthemum vulgare var. boreale (Fisch. ex DC.) Makino ex Makino & Nemoto, Dendranthema lavandulifolium var. tomentellum (Hand.-Mazz.) Y. Ling & C. Shih, Pyrethrum vulgare (L.) Boiss., Tanacetum boreale Fisch. ex DC., Tanacetum crispum Steud., Tanacetum umbellatum Gilib. (inval.), Tanacetum vulgare subsp. boreale (Fisch. ex DC.) Á. Löve & D. Löve, Tanacetum vulgare subsp. boreale (Fisch. ex DC.) Kuvaev, Tanacetum vulgare var. boreale (Fisch. ex DC.) Trautv. & C.A. Mey., Tanacetum vulgare var. crispum DC.

Asteraceae

Bachelors buttons, Bitter Buttons, Common Tansy, Cow Bitter, Garden Tansy, Ginger Plant, Gold Leaf Tansy, Golden Buttons, Hindheel, Mugwort, Parsley Fern, Scented Fern, Stinking Willie, Tansy, Yellow Buttons

Tanacetum vulgare is of Eurasian origin, but was widely introduced globally and to North America where it became invasive in some areas (Wolf et al. 2012).

Tansy is a cool climate species. In its native and nonnative range, it occurs from near sea level to 1,600 m elevation in woodlands, meadows, rangeland, prairies, alpine grassland, montane steppe, marshes, mires, disturbed sites, gardens, pastures, railroads, roadsides, irrigation ditches, stream banks, river banks and lake shores. It is adaptable to a wide range of soil types. It can be found in dry soils, nutrient-poor soils and loamy and sandy soils to heavy, wet or moist soils but thrives in nutrient-rich, moist, well-drained soils. It occurs in sites with full sun to partial shade.

The young leaves and flowers are edible (Fernald et al. 1958; MacNicol 1967; Larkcom 1980; Facciola 1990; Harris 1995). Young aromatic leaves finely chopped are used in salads, puddings, cakes, biscuits, fritters, fish dishes, etc. Leaf juice has been used to flavour omelettes known as tansies. Crushed tansy leaves have been used to flavour whiskey. Tansy cheese is made by steeping the herb and pouring the extract into milk before curdling. The plant is also used as a flavouring substitute for nutmeg and cinnamon. Leaves and flowering tops are brewed into a bitter lemon-flavoured tea. Flowers have unique flavour eaten and are used for garnishing.

A robust, herbaceous perennial with erect, distally branched stems reaching 50–150 cm high (Plates 1 and 2). Leaves alternate, basal cauline, petiolate or sessile, lamina oval to elliptic in outline, 5–25 cm by 2–10 cm wide, pinnately lobed with 4–10 pairs of primary elliptic–lanceolate lobes and dentate margins, surfaces sparsely hairy or glabrous, gland dotted (Plates 1 and 2). Flowering heads, axillary and terminal (Plate 5), numerous in corymbiform pattern, each head compact, oblate, flat topped, yellow, with more than 100 individual florets. Involucre 5–10 mm across, receptacle convex to conic (Plates 3 and 4). Ray florets disciform, outer ones pistillate, corolla 3–4 lobes, yellow. Disc florets with 2–3 mm yellow corolla. Achene 1–2 mm, 4–5-angled or ribbed, gland-dotted with crown-toothed pappus.

Sesquiterpene lactones tanacetin, β-hydroxyarbusculin A and reynosin were isolated from T. vulgare by Samek et al. (1973). Yunusov et al. (1979) isolated the following sesquiterpene lactones from the dried aerial parts: chrysanin, tamarin, tanachin and tavulin. Tanavulgarol, an oxygenated sesquiterpene, was isolated from T. vulgare (Chandra et al. 1987b). Two germacranolides and an n-decyl glucoside were isolated from the aerial parts (Chandra et al. 1987a). Four flavonoids were isolated from tansy flowers: tilianin, acacetin, cosmosiin and apigenin (Kurkina et al. 2011) besides luteolin, cinaroside, eupatilin, jaceidin and jaceoside reported earlier by the main author Kurkina. The flavonoids 6-hydroxyluteolin 6,3′-dimethyl ether (jaceosidin) and quercetagetin 3,6,3′-trimethyl ether (jaceidin) had been reported from the flowers of T. vulgare (Ivancheva et al. 1998). The following flavonoids were detected in T. vulgare leaves: flavones (scutellarein-6-methyl ether (hispidulin), scutellarein-6-4′-dimethyl ether (pectolinarigenin), luteolin, 6-hydroxyluteolin 6-methyl ether (nepetin), 6-hydroxyluteolin 6,3′-dimethyl ether (jaceosidin)) and flavonols (quercetagetin-3- methyl ether, quercetagetin 3,6-dimethoxy ether (axillarin), quercetagetin 3,6,3′-trimethyl ether (jaceidin)) (Ivancheva et al. 1998).

Some wild tansy plants were found to produce 80–90 % β-thujone, whereas others gave the normal content (70–85 %) of α–isothujone throughout the growing season (Von Rudloff and Underhill 1965). Significant variations in the content of the minor components were found to occur only in very young plants, when appreciable amounts of ϵ-, γ- and δ-cadinene and an unidentified labile (possibly C₅) alcohol were detected.

Three tansy chemotypes were identified from tansy specimens growing in the province of Eastern Flanders (Belgium): the β-thujone, trans-chrysanthenyl acetate and camphor/β-thujone types (De Pooter et al. 1989). The essential oil content of Hungarian samples of Tanacetum vulgare varied from 0.02 to 0.66 % and exhibited a heterogeneous distribution of chemotypes (Tétényi et al. 1975). Twenty-six different chemotypes were found. Individuals and populations containing artemisia ketone and umbellulone as their main components were the most frequent. The following compounds were indentified in the essential oils of five Tanacetum vulgare genotypes: artemisia alcohol, γ-campholenol, davanone, lyratol, lyratyl acetate and 4-thujen-2α-yl acetate (Héthelyi et al. 1981). The essential oil from clone 409 of Tanacetum vulgare from Hungary was found to contain trans-chrysanthenyl acetate (75 %) and trans-chrysanthenol (5–10 %) (Neszmélyi et al. 1992).

The strained tricyclic sesquiterpene ketones vulgarone A and longipin-2-en-1-one (vulgarone B) were isolated as constituents of Chrysanthemum vulgare essential oil (Uchio et al. 1976, 1977; Uchio 1978). Vulgarone B was transformed into vulgarone A via a sigmatropic shift in the laboratory by irradiation with UV light. The essential oil of tansy from Eastern Kazakhstan was found to contain > 50 components out of which 39 were identified (Dembitskii et al. 1984). The oil contained a substantial amount of α-thujone (19 %), artemisia ketone and L-camphor (12 %), while δ-terpinenol-4, (-)-borneol, bornyl acetate, neryl acetate, α-terpineol, carvone, achillenol (santolina alcohol), camphor, b-thujone, nerol geraniol, filipendulol (epichrysanthenol) and thymol were present in small amounts. The terpene hydrocarbon fraction included α-pinene (1.0 %), achillene (1.5 %), camphene (1.5 %), β-pinene, sabinene, β-myrcene, limonene, β-phellandrene, 1.8-cineole (3.0 %), γ-terpinene, p-cymene and terpinolene. Sesquiterpene hydrocarbons were present in an amount of 1.1 %. Among them were ylangene, longicyclene, γ-elemene, p-gurgunene, β-elemene, β-caryophyllene, β-selinene, δ-cadinene, γ-cadinene, ar-curcumene, 8-cadinene, calamenene and calacorene. The plant belonged to the thujone chemotype. Tansy genotypes in Finland were distributed among eight ‘well-defined’ main groups: sabinene, thujone, umbellulone, camphor, bornyl acetate, alpha-pinene, 1,8-cineole and germacrene D (Holopainen et al. 1987). The sesquiterpene germacrene D was identified for the first time in the present study in the essential oil of tansy. Most of these ‘well-defined chemotypes’ were again divided into subgroups A and B. In addition to the ‘well-defined chemotypes’, a number of ‘mixed chemotypes’ were also detected in the crossings. Those chemotypes accounted for 20 % of the whole crossing material tested.

Essential oil from aerial parts of T. vulgare plant from ‘Tierra del Fuego’ (Argentina) afforded β-thujone (91.65 %) as the major constituent (Gallino 1988), thus indicating that the plant belonged to the thujone chemotype. Some minor components included sabine, 1,8-cineol, α-thujone, germacrene D, terpinen-4-ol, γ-terpinene, p-cymene, pinocarvone, sabinol, eugenol and unidentified sesquiterpene alcohol. Traces of α-pinene, β-pinene, α-terpinene, α-terpineol, terpinolene, limonene, unidentified sesquiterpene hydrocarbon, myrtenol, myrcene, umbellulone and carvacrol were also found. Major constituents T. vulgare essential oils included camphor, isopinocamphone, trans-chrysanthenyl acetate, sabinene, bornyl acetate and germacrene D (Hendriks et al. 1989). Tansy leaf oil in Holland was found to contain bicyclogermacrene trace, bornyl acetate 0.9 %, camphene 1.40 %, camphor 9.4 %, β- caryophyllene 0.7 %, 1,8-cineole 0.4 %, p-cymene 0.4 %, germacrene D 6.50 %, α-pinene 0.3 %, β-pinene trace, sabinene 3.9 %, sabinene hydrate 0.4 %, terpinene-4-ol 0.4 %, α-terpinene 0.3 %, γ-terpinene 0.3 %, α-thujone 0.9 % and β-thujone 67.9 % (Hendriks et al. 1990).

An investigation of 14 samples of Tansy occurring in the northeastern part of the Netherlands revealed the presence of an artemisia ketone, a chrysanthenol/chrysanthenyl acetate, a lyratol/lyratyl acetate and a β-thujone chemotype (Hendriks et al. 1990). The essential oils of the flower heads contained a higher percentage of the main constituent than the oil obtained from the leaves. Vulgarone A and B were detected in five samples; however, vulgarone A was only found in the leaf oils. Cis-longipinane-2, 7-dione, a component of Bulgarian Tansy, could be detected only in two samples. Examination of the essential oils and extract of tansy plant occurring in the Chicoutimi area (Quebec) revealed several chemotypes (Collin et al. 1993). Half of the plants belong to a camphor-1,8-cineole-borneol (concentration > 52 %) mixed chemotype. The β-thujone chemotype (> 60 %) was also present in six samples. Four specimens of a chrysanthenone type (> 50 %) were also observed. Finally, one sample showed a high concentration of dihydrocarvone (> 60 %). A commercial sample produced in the vicinity of Quebec City belonged mainly to the β-thujone chemotype. A small population of T. vulgare was found to comprise three pure chemotypes based on the sesquiterpene lactones: only germacranolides, only eudesmanolides and no sesquiterpene lactones (Todorova and Ognyanov 1999). Mixed chemotypes were not identified because probably these pure chemotypes were unable to produce hybrids. Of the 20 constituents identified in the essential oil from the aerial parts of Tanacetum vulgare from India, six were monoterpene hydrocarbons (3.9 %), 10 oxygenated monoterpenes (81.9 %), one sesquiterpene hydrocarbon (1.7 %), two phenolic compounds (3.0 %) and a long-chain hydrocarbon (1.5 %) (Charles et al. 1999). The oil belongs to the thujone (66.8 %) chemotype. (+)-10 Hydroxy-3-thujone was characterized from the oil. Tansy genotypes in Finland were distributed among eight ‘well-defined’ main groups: sabinene, thujone, umbellulone, camphor, bornyl acetate, α-pinene, 1,8-cineole and germacrene D (Holopainen et al. 1987). The sesquiterpene germacrene D was identified for the first time in the present study in the essential oil of tansy. Most of these ‘well-defined chemotypes’ were again divided into subgroups A and B. In addition to the ‘well-defined chemotypes’, a number of ‘mixed chemotypes’ were also detected in the crossings. Those chemotypes accounted for 20 % of the whole crossing material tested.

A total of 55 volatile compounds were detected, and 53 were identified in the air-dried flower heads of 20 Finnish tansy genotypes (Keskitalo et al. 2001). Fifteen genotypes were well defined and five were mixed chemotypes. The most frequently encountered monoterpene was camphor with or without several satellite compounds such as camphene, 1,8-cineole, pinocamphone, chrysanthenyl acetate, bornyl acetate and isobornyl acetate. In 13 genotypes, camphor concentration exceeded 18.5 %, and in seven genotypes, camphor was less than 7.2 %. Other chemotypes rich in trans thujone, artemisia ketone, 1,8-cineole or davadone D were also identified. Davadone-D and a mixed chemotype, containing tricyclene and myrcene, were identified from a Finnish tansy for the first time. Geographically, most chemotypes containing camphor originated from Central Finland, whereas chemotypes without camphor such as artemisia ketone, davadone D and myrcene–tricyclene originated from South or Southwest Finland. The group comprising the highest concentration of camphor chemotypes had the tallest shoots. The groups with chemotypes containing davadone-D or artemisia ketone, which originated from Southwest Finland, produced the most number of flower heads, had the tallest corymb and were last to flower. Also, the group consisting from chemotypes with a high concentration of camphor and originated from South Finland exhibited late flowering.

Forty-one constituents were identified in the essential oils from inflorescences and leaves of tansy grown in Vilnius district (Lithuania), and the oils were distributed among four chemotypes (Mockute and Judzentiene 2004). The major constituents of the camphor chemotype (10 samples) were camphor (22.3–41.4 %) and 1,8-cineole (10.6–26.4 %); the α-thujone chemotype (six samples) was found to be dominated by α-thujone (25.7–71.5 %) and 1,8-cineole (11.3–22.3 %); the major constituents of the 1,8-cineole-chemotype (three samples) was dominated by 1,8-cineole (24.5–32.7 %) and camphor (8.3–23.8 %); and the artemisia ketone chemotype (one sample of inflorescences) predominantly featured artemisia ketone (30.5 %) and camphor (23.0 %). The oil from inflorescences of the above chemotypes contained higher amounts of the first major component and oxygenated monoterpenes (mean 83.6 %) than the leaf oils (mean 73.7 %). An opposite correlation was noticed for mono- and sesquiterpene hydrocarbons and oxygenated sesquiterpenes. The yield of essential oils of tansy plants from 40 different locations in North, Mid- and South Norway ranged between 0.35 and 1.90 % (v/w) (average: 0.81 %); the most abundant thujone plants were especially rich in essential oil volatiles (0.95 %) (Rohloff et al. 2004). Seven chemotypes could be identified as follows: (A) α-thujone (two individuals), (B) β-thujone (22), (C) camphor (six), (D) chrysanthenyl acetate/chrysanthenol (three), (E) chrysanthenone (two), (F) artemisia ketone/artemisia alcohol (three) and (G) 1,8-cineole (two). The thujone chemotype was dominated by β-thujone (81 %) associated with α-thujone, but tansy plants rich in α-thujone were also detected (61 %). Tansy genotypes in Norway could be grouped into the following chemotypes: the mixed chemotypes Steinvikholmen (thujone–camphor), Alvdal (thujone–camphor–borneol), Goldsticks (thujone–camphor–chrysanthenyl type) and Brumunddal (thujone–camphor–1,8-cineole-bornyl acetate/borneol-α-terpineol) and the distinct chemotype Richters, with average concentrations of (E)-chrysanthenyl acetate > 40 % in both leaf and flower essential oil (Dragland et al. 2005). The essential oil of Tanacetum vulgare leaves from Perú was characterized by a high amount of ß-thujone (87.83 %), and belonged to the thujone chemotype (De La Cruz et al. 2008).

Altitude, geographical, temperature gradient, as well as soil-climate conditions were found to impact on the essential oil composition of T. vulgare (Vaverková et al. 2006). In the lowest-lying locality with a relatively large sunshine, the content of β-thujone in the essential oil was the highest, whereas in the regions lying towards the north, the content of the essential oil was decreased and the content of camphor was increased. In the northernmost region of Slovakia, an increased number of chemovars of the camphor–cineole type was observed. The following compounds were identified in T. vulgare essential oil in Slovakia: α-pinene, camphene, sabinene, β-pinene, myrcene, 1,8-cineole, artemisia ketone, β-thujone, camphor, borneol, umbellulone, D-carvone, chrysantenyl acetate, bornyl acetate, thymol, germacrene and carvacrol (Mikulášová and Vaverková 2009).

Ninety-four components were detected in the essential oils from aerial parts and capitula of Tanacetum vulgare subsp. siculum (Formisano et al. 2009) Alpha-thujone, β-thujone and 1,8-cineole were the main constituents. Based on the chemical profile, this Tanacetum species was assigned to the thujone chemotype. Five known sesquiterpene lactones with the eudesmane skeleton, douglanin, ludovicin B, ludovicin A, 1α-hydroxy-1-deoxoarglanine and 11,13-dehydrosantonin, were isolated from the flowers of a subspecies of T. vulgare in Sicily (Rosselli et al. 2012). This T. vulgare species can be assigned to the eudesmanolide chemotype.

The water-soluble pectin complex from tansy flowers was found to consist of four different polysaccharide fractions (Yakovlev and Sysoeva 1983). Polysaccharide I contained 64 % of d-galacturonic acid and the neutral monosaccharides (PC, GLC), galactose, glucose, arabinose, xylose and rhamnose in a quantitative ratio of 5:3:3:1:4. Polysaccharide II contained 20 % of galacturonic acid and the neutral monosaccharides (PC, GLC) galactose, glucose, arabinose, xylose and rhamnose in a quantitative ratio of 10:8:3:1:2. Polysaccharide (III) contained 30 % of a uronic acid and the neutral monosaccharides galactose, glucose, arabinose, xylose and rhamnose in a quantitative ratio of 9:5:2:1:4. Polysaccharide (IV) contained 18 % of uronic acid and the neutral monosaccharides galactose, glucose, arabinose, xylose and rhamnose in a quantitative ratio of 8:7:2:1:1.

Tanacetan TVF, isolated from floccules of tansy, was found to be a branched pectic polysaccharide with backbone of linear α-1,4-d-galacturonan (Polle et al. 2002). The ramified regions appeared to be rhamnogalacturonan-I with core of α-1,2-l-rhamno-α-1,4-d-galacturonan. The side sugar chains were attached by 1,4-linkages to the l-rhamnopyranose residues of the core and consist of single residues of β-galactopyranose and β-1,4-galactopyranan with branching points of 4,6-substituted β-d-galactopyranose residues. In addition, the branching regions contained the side chains of a branched α-1,5-arabinofuranan bearing 2,5-and 3,5-substituted α-l-arabinofuranose residues as the branching points. Some side chains of rhamnogalacturonan appeared to represent arabinogalactan, containing the branched sugar chains of α-1,5-arabinofuranan attached to the linear chains of β-1,4-galactopyranan by 1,3- and 1,6-linkages. The residues of α-l-arabinofuranose appeared to occupy the terminal positions of the arabinogalactan side chains. Four acidic polysaccharide fractions (designated T-I to T-IV) were isolated and purified from Tansy florets (Xie et al. 2007). The average M _r of fractions T-I through T-IV was estimated to be 326, 151, 64 and 9 kDa, respectively. Tansy polysaccharides consisted primarily of galacturonic acid, galactose, arabinose and rhamnose. Fractions T-II through T-IV contained an arabinogalactan type II structure.