Ajuga reptans / Zenegroen

Kruipend zenegroen is een inheems laagblijvend en bodembedekkend plantje, die vaak in tuinen wordt aangeplant, soms onder vorm van de soort, maar vaker als de roodbladige cultivar 'Atropurpurea'.  Ook roze kweekvormen zijn bekend.

h 7,5 cm br 60cm - soms woekerend - winterhard -  wintergroen
Blad : Rozetten van glanzende, spatelvormige bladeren. Ajuga reptans heeft groen blad.
Bloei : Lichtblauwe lipbloemen. april / juni.
Bloemen vormen een nectarbron voor insecten.
Vormt uitlopers.

Ajuga decumbens / Ajuga reptans (Latein) / Günsel (Deutsch)

Verwendete Teile
  • herba (Kraut)
  • Harpagid u. a. Iridoidglykoside
  • Ajugalactone u. a. Ecdysteroide
  • Diterpene
  • adstringierend
  • abführend
  • mild analgetisch
  • Wundheilung

Chem Pharm Bull (Tokyo). 2011;59(8):1065-8. Four new iridoid glucosides from Ajuga reptans.
Ono M1, Furusawa C, Ozono T, Oda K, Yasuda S, Okawa M, Kinjo J, Ikeda T, Miyashita H, Yoshimitsu H, Nohara T.
Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid glycoside exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and H₂O₂ scavenging activities.

Phytochemistry. 1996 May;42(1):199-203. Triacylated anthocyanins from Ajuga reptans flowers and cell cultures.
Terahara N1, Callebaut A, Ohba R, Nagata T, Ohnishi-Kameyama M, Suzuki M.
Four anthocyanins were isolated from Ajuga reptans flowers and one from the cell cultures. By FAB mass spectrometry measurements, the structures of these pigments were determined as delphinidin and cyanidin glucosides acylated with two cinnamic acids, while three of them were also malonylated. A delphinidin-based pigment in the crude extract from cell cultures was identical to the major flower pigment as shown by HPLC co-chromatography. Moreover, by application of 1H and 13C NMR consisting of DQF-COSY, NOESY, ROESY, 2D-HOHAHA, HSQC and HMBC methods, the structures of two new anthocyanins were identified as delphinidin and cyanidin 3-O-(2-O-(6-O-(E)-p-coumaryl-beta-D-glucopyranosyl)-(6-O-(E)-p- coumaryl)-beta-D-glucopyranosyl)-5-O-(6-O-malonyl-beta-D-glucopyranoside ). The deacylated anthocyanins were confirmed as delphinidin and cyanidin 3-sophoroside-5-glucosides.

J Nat Prod. 1992 Aug;55(8):1145-8. Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans.
Breschi MC1, Martinotti E, Catalano S, Flamini G, Morelli I, Pagni AM.
The traditional therapeutic indications for the use of Ajuga reptans (Labiatae) have been investigated. The H2O-soluble part of a crude and partially purified MeOH extract and two isolated iridoids (8-O-acetylharpagide and harpagide), were tested for a biological activity on isolated smooth muscle preparations from guinea pig.

C-29 ecdysteroids from Ajuga reptans var. reptans.
Ványolós A, Simon A, Tóth G, Polgár L, Kele Z, Ilku A, Mátyus P, Báthori M
Department of Pharmacognosy, University of Szeged, Eotvos utca 6, H-6720 Szeged, Hungary.
Journal of Natural Products [2009, 72(5):929-932]
Investigation of the ecdysteroid constituents of the herb Ajuga reptans var. reptans resulted in the isolation of three new ecdysteroids, named reptanslactone A (2), reptanslactone B (3), and sendreisterone (5), and the known 24-dehydroprecyasterone (1) and breviflorasterone (4). The structures of compounds 1-5 were determined by spectroscopic methods including one- and two-dimensional NMR measurements.

Antinociceptive effect of some extracts from Ajuga chamaecistus Ging. ssp. tomentella (Boiss.) Rech. f. aerial parts
Mahnaz Khanavi12, Araz Mohammad Davoodipoor1, Seyede Nargess Sadati2*, Mohammad Reza Shams Ardekani12 and Mohammad Sharifzadeh3
The genus Ajuga is used for the treatment of joint pain, gout, and jaundice in traditional Iranian medicine (TIM). Ajuga chamaecistus ssp. tomentella is an exclusive subspecies of Ajuga chamaecistus in the flora of Iran. The aim of this study was to evaluate antinociceptive properties of some extracts from aerial parts of A. chamaecistus ssp. tomentella.

Antinociceptive activities of total water and 80% methanol extracts, hexane, diethyl ether and n-butanolic partition fractions of the methanolic extract were analyzed using the formalin test in mice. Indomethacin (10 mg/kg) and normal saline were employed as positive and negative controls, respectively.

Oral administration of all extracts (200, 400 and 600 mg/kg) 30 min before formalin injection had no effect against the acute phase (0–5 min after formalin injection) of the formalin-induced licking time, but hexane fraction (200 mg/kg) caused a significant effect (p < 0.001) on the chronic phase (15–60 min after formalin injection). Total water and diethyl ether extracts at a dose of 400 mg/kg showed a very significant analgesic activity on the chronic phase (p < 0.001 and p < 0.01, respectively).

The results of this study suggest that the extracts of A. chamaecistus ssp. tomentella have an analgesic property that supports traditional use of Ajuga genus for joint pain and other inflammatory diseases.

Five species of genus Ajuga (Lamiaceae) are found in the flora of Iran in which Ajuga chamaecistus has been contained several endemic subspecies including A. chamaecistus ssp. tomentella[1]. Some species which belong to this annual and perennial genus are used as the medicinal plant in the traditional medicine of several countries mostly in Africa, Asia, and China as for wound healing; anthelmintic, antifungal, antifebrile, antitumor, antimicrobial, and diuretic agent, and for the treatment of hypertension, hyperglycemia, joint pain, etc. [2-4]. Ajuga chamaepitys (L.) Schreb. which grows in the Middle East and Asia has been used in the treatment of rheumatism, gout, dropsy, jaundice, and sclerosis. A. decombens Thunb. that originally grows in East Asia is used for analgesia, inflammation, fever, and joint pain [5]. Moreover in Iranian traditional medicine, the genus Ajuga (Kamaphytus) has been used for treatment of joint pain, gout, and jaundice [6].

Also, several biological studies have been performed on many species of this genus which have confirmed their ethno pharmacological properties such as hypoglycemic [7], anti-inflammatory [8], anabolic, analgesic, anti-arthritis, antipyretic, hepatoprotective, antibacterial, antifungal, antioxidant, cardiotonic [5], and antimalarial [9] properties and their application in the treatment of joint diseases [10].
As well, many phytochemical studies on Ajuga species have been performed which have led to the isolation of phytoecdysteroids [11,12], neo- clerodanediterpenoids [13], phenylethyl glycosides [3], withanolides [2], iridoids and flavonoids [14], and essential oils [15].
Prior to this study, we have isolated 10 compounds; 20-hydroxyecdysone, cyasterone, ajugalactone, makisterone A, and 24-dehydroprecyasterone (phytoecdysteroids), 8-acetylharpagide (iridoid), cis- and trans-melilotoside, lavandulifolioside, leonoside B, and martynoside (phenylethanoid glycosides), from diethyl ether and n-butanolic fractions of Ajuga chamaecistus ssp. tomentella. Cytotoxicity evaluation of some fractions of this plant showed the cytotoxicity of hexane fraction against normal and cancer cell lines. Most of the isolated compounds were inactive in the cytotoxicity assay [16,17].
The aim of this study was to evaluate antinociceptive effects of oral administration of total water and 80% methanolic extracts and partition fractions of hexane, diethyl ether and n- butanol obtained from methanolic extract of aerial parts of Ajuga chamaecistus ssp. tomentella in an attempt to validate the traditional use of the plants belonging to genus Ajuga.

Ajuga turkestanica

Turkesterone een ecdysteroïde uit Ajuga turkestanica is geen anabool steroid, maar als je oude Russische dierstudies mag geloven heeft turkesterone meer anabole werking dan methandienone, de actieve stof in Dianabol. Turkesterone is een bestanddeel van Ajuga turkestanica, een aan munt verwante plant die groeit in Klein-Azië.
Om die reden bestuderen Amerikaanse bewegingswetenschappers, die op zoek zijn naar behandelmethoden voor ouderdomsspierzwakte of sarcopenia, het effect van Ajuga turkestanica op oude muizen. Hun studie verscheen in het weinig bekende wetenschappelijke tijdschrift European Review for Medical and Pharmacological Sciences.
De Amerikanen gaven hun proefdieren gedurende 4 weken elke dag Ajuga turkestanica-extract door hun voer. Het humane equivalent van de dosis was, als je uitgaat van een iemand van 80 kg, 400 mg extract per dag. Dat extract bestond voor 40 procent uit ecdysteroïden. 

De ongewone anabole werking van Ajuga turkestanica
Toen de onderzoekers na die periode spiercellen uit de triceps van de muizen bestudeerden, hadden de ecdysteroïden de Notch-receptor geactiveerd. [Figuur hierboven] Als stoffen via de Notch-receptor stamcellen aanschakelen, dan ontwikkelen ze zich tot nieuwe spiercellen.
De onderzoekers ontdekten dat Ajuga turkestanica ook via de Wnt-pathway voor spiergroei leek te zorgen.
Onderzoekers vermoeden dat sarcopenia het gevolg is van het uitdoven door de Notch- en Wnt-pathways. "It is possible that the phytoecdysteroid-induced alterations in Notch and Wnt signaling will better prepare aged skeletal muscle for repair following exposure to muscle injury", concluderen de Amerikanen.

Eur Rev Med Pharmacol Sci. 2014;18(17):2584-92.

There are three Bugles in the British flora - the common creeping from (Ajuga reptans), the erect Bugle (A. pyramidalis), a rare Highland species, and the Yellow Bugle or Ground Pine (A. Chamaepitys), which likewise has its reputation as a curative herb."
The whole herb is used medicinally, and it is gathered in May and early June, when the leaves are at their best, then dried. 

Medicinal Action and Uses
Ajuga is bitter, astringent and aromatic.
The roots have been considered more astringent than the rest of the plant. 
1 OZ. of the dried herb to 1 pint of boiling water - given frequently, allays haemorrhages and is also employed in coughs and spitting of blood in incipient consumption. In some biliary disorders, a wineglassful of the infusion is suggested.
It has also been considered good for the bad effects of excessive drinking. Green (Universal Herbal, 1832) gives as his opinion that '...they do not, like many other plants of the same value, produce costiveness, but rather operate as gentle laxatives.' He states that a decoction of the herb has been employed for quinsy on the Continent. 

Culpepper had a great opinion of the value of the Bugle and says:
'if the virtues of it make you fall in love with it (as they will if you be wise) keep a syrup of it to take inwardly, and an ointment and plaster of it to use outwardly, always by you.
The decoction of the leaves and flowers in wine dissolveth the congealed blood in those that are bruised inwardly by a fall or otherwise and is very effectual for any inward wounds, thrusts or stabs in the body or bowels; ... It is wonderful in curing all ulcers and sores, gangrenes and fistulas, if the leaves, bruised and applied or their juice be used to wash and bathe the place and the same made into lotion and some honey and gum added, cureth the worse sores.
Being also taken inwardly or outwardly applied, it helpeth those that have broken any bone or have any member out of joint.'

Dualistic Properties of Cosmetic Formulations Based on Phenylpropanoids from Ajuga reptans
Author(s)   Silvia Vertuani, Paola Ziosi, Roberto Dal Toso, Chiara Beatrice Vicentini, Stefano Manfredini

Our continued interest in the research and development of cosmetic active ingredients deriving from natural sources led us to investigate the potential of a purified extract of Ajuga reptans, a plant belonging to the family Labiatae and known for its traditional use in skin healing. The extracts deriving from a biotechnology platform are composed by meristematic cell culture, developed in the frame of a NTFP (non-timber forest product) project, and characterized by high content in phenylpropanoid, of which teupolioside represents the majority component. The latter is a phenylpropanoid glucoside, structurally correlated echinacoside and known in the literature for the antioxidant properties. This study was conducted with the purpose of evaluating the applicability of the Ajuga reptans extract within different cosmetic formulations. In particular, Photochemiluminescence (PCL) was used to proof the antioxidant capacity of cosmetic formulations containing the product, in relation to the change of the title of teupolioside. Furthermore, UVA and UVB filtering properties were also investigated. The results of the study showed relevantly antioxidant capacity of the finished formulation against superoxide anion, which is the main reactive oxygen species responsible for skin aging and significant synergic capacities to filter UV radiation

S. Vertuani, P. Ziosi, R. Toso, C. Vicentini and S. Manfredini, "Dualistic Properties of Cosmetic Formulations Based on Phenylpropanoids from Ajuga reptans," Journal of Cosmetics, Dermatological Sciences and Applications, Vol. 3 No. 3B, 2013, pp. 64-72. doi: 10.4236/jcdsa.2013.33A2014.

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