Hieracium / Havikskruid / Pilosella off. / Muizenoor

In grazige bermen en op andere grazige plekken vallen de oranje tot rood gekleurde hoofdjes van Oranje havikskruid, Hieracium aurantiacum, direct op. Deze planten uit de Composietenfamilie zijn sterk behaard, maar hebben geen donzig zilverwitte beharing aan de onderzijde van de bladeren. Aan de bloeistengel zitten de hoofdjes zeer dicht bij elkaar; pas wanneer er meerdere hoofdjes in bloei staan vormt zich een schermvormige bloeiwijze.

Havikskruiden kunnen ook ongeslachtelijke tot bevruchting komen. We noemen dat een apomictische voortplanting. In het vruchtbeginsel wordt dan alleen DNA afkomstig van dezelfde plant bij elkaar gevoegd. Het zal duidelijk zijn dat in dit geval de dochterplant volstrekt het zelfde genoom heeft als de moederplant. Het is een natuurlijke vorm van kloneren.

Alleen de Hieracium pilosella wordt medicinaal gebruikt.

Biological activity of new flavonoid from Hieracium pilosella L.

Monika Gawrońska-Grzywacz, Tadeusz Krzaczek, Renata Nowak, Renata Los, Anna Malm, Małgorzata Cyranka, Wojciech Rzeski

Hieracium pilosella L. (Asteraceae) is a well-known plant used in ethno-medicine as its inflorescences are particularly rich in beneficial polyphenolics. This research aimed to elucidate the structure of a new flavone glycoside isolated from the inflorescences of Hieracium pilosella and evaluate its antioxidant, antimicrobial and antiproliferative activities. The chromatographic methods were successfully applied to isolate the new flavonoid. Its structure was determined by subsequent UV, NMR and MS experiments and identified as isoetin 4′-O-β-D-glucopyranoside. Free radical scavenging capacity was examined by measuring the scavenging activity of the new isoetin derivative on 2,2-diphenyl-1-picrylhydrazyl (DPPH). The compound was also screened for spectrum of antimicrobial activity using the agar well diffusion method. Minimum inhibitory concentration (MIC) for Pseudomonas aeruginosa ATCC 9027 was performed by the micro-dilution broth method. The antiproliferative effect of tested glycoside was assessed in two human tumor cell lines derived from lung (A549) and colon (HT-29) carcinoma and cell proliferation was determined by means of MTT method. The tested compound showed high antiradical activity, reducing the DPPH? with EC50 7.9 μM (3.7 µg/ml) and exhibited narrow antimicrobial spectrum among tested microorganisms. The compound was active against Pseudomonas aeruginosa ATCC 9027 (MIC 125 μg/ml) which is prone to causing infections that are difficult to treat due to it developing extremely rapid antibiotic resistance. In the antiproliferative studies, cell proliferation of the colon (HT-29) carcinoma cell line was significantly decreased after exposure to the compound. The results indicate that isoetin 4′-O-β-D-glucopyranoside possesses antioxidant capacity and very promising antibacterial activity and could have uses as an effective antipseudomonal agent as well a antiproliferative agent.

Hieracium pilosella herba (Fam. Asteraceae) is a component part of the French and the British Herbal

Pharmacopoeia. The following monographs exists:

- Piloselle published in the French Pharmacopoeia (Fr.Ph. 1996): Whole plant or fragmented plant of Hieracium pilosella L. Content: minimum 2.5 per cent of ortho-dihydroxycinnamic derivatives, expressed as chlorogenic acid (C16H18O9; MT 354.3) (dried drug)

- Pilosella (BHP): Pilosella consists of the dried plant of Pilosella officinarum C.H. & F.W. Schultz (Fam. Compositae), a stoloniferous, scapigerous herb up to 30cm in height, indigenous to the British Isles, Europe and Western Asia. Pilosella consists largely of leaf and contains the coumarin umbelliferone present predominantly as the 7-glucoside, the flavone luteolin and its 7-glucoside and other flavonoids, caffeic acid and chlorogenic acid.

The plant is small, 10-30cm long. Widely polymorphic, where the stump emits creeping stolons. The flowering stem is lonely, erect, hairy and it ends in a white capitule where the involucre is covered by glandular dark hair. The leaves are lanceolate, about 3cm long, greyish above with scattered slender

hairs and whitish underneath due to the dense covering of branched hairs. Flowers solitary, pale yellow, composite, about 2-3cm diameter, outer flowers often reddish underneath. The fruit is cylindrical and has simple, brittle tuft of hair (Paris, 1971). Taste, bitter, slightly aromatic; odour, faint (Wren, 1998).

Synonyms: Mouse-ear; mouse-ear Hawkweed

Constituents: (Bézanger-Beauquesne et al., 1980 ; Bruneton, 1998; Fournier, 1948; Garnier et al., 1961 ; Gruenwald, 2007; Paris and Moyse, 1971 ; Stanojevic et al., 2009; Van Hellemont, 1986; Wren, 1998)

Hydroxycoumarins: umbelliferone (mainly as 7-glucoside; about 0.60% of the dry plant material), skimmine

Flavonoids: luteolin, luteolin-7-glucoside, apigenin-7-O-glucoside (about 0.25% of the dry plant material), isoetin 4’-O-β-D-glucopyranoside (Gawrońska-Grzywacz et al., 2011)


Triterpenoids: alpha- and beta-amyrin, taraxerol, taraxasterol and fern-7-en-3-beta-ol (GawronskaGrzywacz and Krzaczek, 2007)

Organic acids: caffeic acid, chlorogenic acid (about 20% of the dry plant material)

Ascorbic acid

According to Stanojevic et al., 2009, the content of total phenolic compounds is about 240 mg gallic acid equivalents/g of dry extract, while total flavonoids content is close to 80 mg equivalents rutin/g of dry extract.

Le Livre des Plantes Médicinales et Vénénouses de France (Fournier, 1948) describes the

following plant properties: diuretic and in consequence aperitif and depurative, astringent, vulnerary,

Assessment report on Hieracium pilosella L., herba

EMA/HMPC/680373/2013 Page 6/14

and bactericide. It also includes the reference from Laemmer (1922) as a strong uropoietic, with an

increase in chlorure and urea elimination and it is also reporting the internal use of preparations from

this specie since Early Middle Ages and Modern ages.

The Resources Médicinales de la Flore FranÇaise (Garnier et al., 1961) includes Hieracium

pilosella activity as a dechlorurant and azoturic diuretic. It is also used for influenza (grippe), to

increase diuresis, to relieve Malta and swaying fevers, as an infusion. Also used in combination with

other herbs for rheumatism, gout and urinary lithiasis.

The reference in the Précis de Matière Médicale (Paris and Moyse, 1971) for Hieracium pilosella

includes its strong diuretic activity; the whole plant is used as an infusion or decoction. It is useful

against brucelloses.

The British Herbal Pharmacopoeia (1979) listed several therapeutic actions for Pilosella herba:

Spasmolytic, Expectorant, Anticatarrhal, Diuretic, Sialagogue, Topically vulnerary. The following

indications are included: bronchitis, bronchitic asthma, whooping cough, heamoptysis, oedema.

Topically applied for herniae and fractures as lotion or compress. Specific indications are: whooping

cough, pulmonary affections with excessive sputum, doreness and haemoptysia.

The Avis aux fabricants concernant les demandes d’autorisation de mise sur le marché de

spécialités pharmaceutiques a base de plantes (Ministry of Health and Family, France, 1986)

includes the therapeutic indication « traditionally used to promote water elimination » for Pilosella; this

is the same indication included in the Précis de Phytothérapie by Leclerc (1994) for the aerial

parts from H. pilosella.

The monograph in the Potter’s New Cyclopaedia of Botanical Drugs and Preparations (Wren,

1988) listed the following medicinal uses: expectorant, diuretic, spasmolytic, sialagoge, vulnerary. It

is used mainly for whooping cough, bronchitis and asthma as an infusion, and for wounds as a

compress. An extract shows weak antifungal activity.

The a as a diuretic

The monograph included in the PDR for Herbal Medicines (2007) describes the internal use of aerial

part of Mouse Ear in the treatment of asthma, bronchitis, coughs and whooping cough, and externally

in the treatment of wounds. The plant has shown to have diuretic, spasmolytic and diaphoretic effects.

Also the reference by Bishop et Davy (1994) cited the use of the specie against respiratory

infections in the British Isles.