Bugle-weed - Ajuga reptans

Family: Lamiaceae (Mint family) ^[E-flora]

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"Ajuga reptans is an evergreen Perennial growing to 0.3 m (1ft) by 0.6 m (2ft in) at a slow rate.
It is hardy to zone (UK) 6 and is not frost tender. It is in leaf 12-Jan It is in flower from May to July, and the seeds ripen from Jul to September. The flowers are hermaphrodite (have both male and female organs) and are pollinated by Bees, lepidoptera, self.The plant is self-fertile.
It is noted for attracting wildlife.
Suitable for: light (sandy), medium (loamy) and heavy (clay) soils. Suitable pH: acid, neutral and basic (alkaline) soils. It can grow in full shade (deep woodland) semi-shade (light woodland) or no shade. It prefers dry moist or wet soil and can tolerate drought." ^[PFAF]

Habitat / Range
"Mesic to dry waste places in the lowland and montane zones; rare in the lower Fraser Valley; introduced from Europe." ^{[IFBC-E-flora]}

Hazards

"The plant is said to be a narcotic hallucinogen that is known to have caused fatalities(274)." ^[PFAF] "No health hazards or side effects are known in conjunction with the proper administration of designated therapeutic dosages." ^[PDR]

"in the last decades, the use of these species in folk medicine has drastically diminished because of their presumed toxicity. This is mainly associated to a particular class of natural compounds known as neo-clerodane diterpenoids (Firenzuoli et al., 2002), whose presence in Ajuga species is well reported (Camps et al., 1987)." ^(frezza2018)

Conversely, the total absence of neoclerodane diterpenoids which are, in turn, chemotaxonomic markers at the species and genus level and are very toxic compounds, provides a phytochemical rationale for the possible ongoing use of this particular sample in the ethnopharmacological field. For this, due to the high variability in the biosynthesis of these metabolites, the necessity of an accurate phytochemical analysis of the raw materials for botanical employments is extremely required." ^(frezza2018)

Edible Uses

• Young Shoots - Raw⁷. ^[PFAF] Edible - leaf and young stem - taste is poor ^{[ARA 12.1]}
  

Medicinal Uses

"Bugle has a long history of use as a wound herb and, although little used today, it is still considered very useful in arresting haemorrhages and is also used in the treatment of coughs and spitting of blood in incipient consumption^4,254,268." ^[PFAF]

"Ajuga reptans L. is aplant used in the traditional medicine of many countries from the centre and, especially, the eastern part of Europe. The extracts obtained from bugle (Ajuga reptans L.) are used due to the content of polyphenols of the flavonoidic and polyphenolcarboxylic acids type (due to its antioxidant, vascular and antimicrobial qualities), as well as of iridoids (antiinflamatory and wound healing) as antidiarrhoeaic, antileucoreic, hepatoprotecting and vulnerar. Unlike bugle, blue bugleweed, Ajuga genevensis L., is used only in our country as a substitute of the medicinal species, as, due to the fact that it is not very demanding as to the pedoclimatic conditions, it is largely outspread in the wild flora." ^{(Ghita et al.,2011)}

Whole Plant

"Aromatic, astringent and bitter^4,7,9. The plant is usually applied externally⁷. It is also commonly used fresh in ointments and medicated oils²³⁸." ^[PFAF] "Unproven Uses: Internally, Bugle is used as an astringent for inflammation of the mouth and larynx. It is also used for gallbladder and stomach disorders. Externally, the plant is used for the treatment of wounds." ^[PDR]

Harvesting: "The whole herb, gathered in May and early June, when the leaves are at their best, and dried." "The roots have by some authorities been considered more astringent than the rest of the plant."^{(ModHerb-Online)} "It is harvested as it comes into flower in late spring and dried for later use^4,7." ^[PFAF] "The medicinal parts are the aerial parts collected during the flowering season and dried" ^[PDR]
Effect: "In its action, it rather resembles digitalis, lowering the pulse and lessening its frequency, it allays irritation and cough, and equalizes the circulation and has been termed 'one of the mildest and best narcotics in the world.' It has also been considered good for the bad effects of excessive drinking."^{(ModHerb-Online)}
Homeopathic: "A homeopathic remedy is made from the whole plant.⁷ It is widely used in various preparations against throat irritations and especially in the treatment of mouth ulcers[7]." ^[PFAF]
Antihemorrhagic: "In herbal treatment, an infusion of this plant is still considered very useful in arresting haemorrhages and is employed in coughs and spitting of blood in incipient consumption and also in some biliary disorders, a wineglassful of the infusion - made from 1 OZ. of the dried herb to 1 pint of boiling water - being given frequently."^{[ModHerb-Onlne]}
Laxative: "Green (Universal Herbal, 1832) gives as his opinion that 'the leaves may be advantageously used in fluxes and disorders of that kind as 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."^{[ModHerb-Onlne]}
"Mode of Administration: Bugle is used topically, in alcoholic extracts, as a water infusion and in teas."^[PDR]

Historical Usage

"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; and is an especial help in wound drinks and for those that are liver-grown, as they call it. 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. An ointment made with the leaves of Bugle, Scabious and Sanicle bruised and boiled in hog's lard until the herbs be dry and then strained into a pot for such occasions as shall require, it is so efficacious for all sorts of hurts in the body that none should be without it." ^{(ModHerb-Online)}

"There is one British record, from Sussex,¹³⁵ of the ostensibly folk use of Ajuga reptans for wounds, a purpose for which it was anciently valued on account of its considerable astringency. Two Irish records add support to that. In the early nineteenth century, country people in Londonderry are said to have applied the juice to bruises as those were at the stage of turning black.¹³⁶ And in Sligo—if, as seems likely, glas-na-coille was a mishearing of glasnair choille (the name in Irish)—it supplied till much later a cure for whitlows reckoned infallible.¹³⁷" ^[MPFT]

"A. reptans has a long tradition of use in the folk medicine of several countries of the world (Israili and Lyoussi, 2009). This is due to the fact that this species is well known to possess many important pharmacological properties (Chiej, 1984) which are due to the several classes of natural compounds that have been identified in the plant (Israili and Lyoussi, 2009; Glyad, 2002; Manguro et al., 2006). Actually, this regards the entire Ajuga L. genus whose species are known to possess antihypertensive, antidiabetic, diuretic, antibacterial, antifungal, antimalarial, antimicrobial, anti-inflammatory, antitumor, antioxidant, insecticide and laxative effects (Frezza et al., 2017)." ^(frezza2018)

Pharmacology

Antioxidant & Antibacterial

Ajuga genevensis L. and A. reptans L.

"This research was designed to investigate the phytochemical profile (e.g. iridoids, polyphenolic compounds, phytosterols), as well as the biological potential (antioxidant, antibacterial, antifungal, anti-inflammatory properties) of two selected Ajuga species collected from different regions of Romanian spontaneous flora. The main compounds identified in A. reptans aerial parts extracts were 8-O-acetylharpagide, isoquercitrin and β-sitosterol, whilst in A. genevensis were 8-O-acetylharpagide, luteolin and campesterol. The extracts were screened for their antioxidant potential using different methods (DPPH, TEAC, EPR) and the results showed a good activity, in accordance with the polyphenol content (18–26 mg GAE/g dw). The antifungal activity on the tested strains was good. The determination of few parameters linked with the inflammatory mechanism allowed the assessment of in vivo anti-inflammatory potential. Ajuga reptans and A. genevensis ethanol extracts had anti-inflammatory activity through lowering the oxidative stress, phagocytosis, PMN and total leukocytes. The best anti-oxidative and anti-inflammatory activity was observed for the Ajuga reptans 100 mg dw/mL extract when compared with diclofenac, thus the dose could be correlated with the pharmacological effect. These findings provide substantial evidence that both selected Ajuga species have the potential to be valued as sources of phytochemicals in effective anti-inflammatory herbal preparations." ^{(Toiu et al.,2019)}

"Ajuga genevensis L. (blue bugle, blue bugleweed or Geneva bugleweed) is a pubescent plant widespread in many countries of Europe. “Suliman” is the Romanian name of the species and traditionally is used for sedative, antihemorrhagic and anti-inflammatory effects, as well as for its wound-healing and epithelization capacity in topic remedies [22]. Also, the plant is used for its remarkable property to precipitate the proteins from digestive tract, in treatment of diarrhoeal diseases." ^{(Toiu et al.,2019)}

"Methanol and ethanol have been proven as effective solvents for extraction of phenolic compounds. As they have quite similar polarity, the bioactive compounds extracted in these solvents are very similar, therefore the detected differences between the methanol and ethanol extracts were only quantitatively ones. The main reason for this concept was that usually, the methanol extract is obtained for the purpose of phytochemical analysis, in laboratory, thus a rapid and simple extraction method is useful for the characterization of vegetal products (30 min at 60 ◦C), whereas the extract used in phytotherapy is generally the ethanol one, obtained by maceration at room temperature (7 days by maceration). Taking this into account, we intended to compare the results obtained by the two methods in order to evaluate if the theoretical method (with methanol) will extract the same compounds and in similar concentration and if those results could be extrapolated into practice, to ensure a more practical approach of our study." ^{(Toiu et al.,2019)}

"The phytochemical evaluation of the six samples collected in different harvesting time and locations showed that the aerial parts of A. genevensis and A. reptans harvested in April from Cluj County contain the highest number of polyphenolic compounds and iridoids, respectively." ^{(Toiu et al.,2019)}

"In the present research, only A. reptans 100 mg dw/mL extract proved to have important anti-inflammatory effects by reducing NO synthesis and it was comparable with that induced by diclofenac. Because the effects on NOx were not always correlated with the in vitro antioxidant tests, it may be presumed that the antioxidant activity was not significantly involved." ^{(Toiu et al.,2019)}

"The most abundant compounds identified in the aerial parts of Ajuga reptans were isoquercitrin β-sitosterol and 8-O-acetylharpagide. The presence of these active substances may be associated with assessed biological activities. Using various methods, the antioxidant effect of Ajuga reptans and Ajuga genevensis extracts was evaluated and good antiradical capacities were evidenced, depending firstly on the nature of the extraction solvent and secondly on the different harvesting time and place. The antimicrobial assays revealed that Ajuga reptans petroleum ether extract presented potent activity against A. niger and C. albicans. The exhibited antifungal effects might be due to the presence of phytochemicals, primarily to 8-O-acetylharpagide, the main iridoid glycoside. By monitoring some inflammation parameters, it was possible to determine the in vivo anti-inflammatory activity and a probable mechanism of action could be suggested with the help of these findings. The Ajuga reptans 100 mg dw/mL extract displays important anti-inflammatory effects by reducing NO synthesis and it was comparable with those determined by diclofenac. The results indicate variations between the Ajuga species extracts, therefore, the necessity of selecting not only the proper solvent but also the appropriate harvesting time of plant material, to extract the highest possible amounts of phytochemicals. The anti-inflammatory effect of Ajuga reptans and A. genevensis ethanol extracts was observed by decreasing the oxidative stress, phagocytosis, PMN and total leukocytes. The Ajuga reptans 25 mg dw/mL and 100 mg dw/mL extracts presented higher anti-oxidant and anti-inflammatory activities, comparable with diclofenac. These findings support the usage of Ajuga reptans and Ajuga genevensis as anti-inflammatory agents in ethnobotanical medicine. Also, the results indicate that both selected Ajuga species have the potential to be valued as an important source of bioactive compounds in new herbal preparations with anti-inflammatory activity. Further in vivo experiments are recommended in order to develop effective and safe medicine-based phytopharmaceuticals." ^{(Toiu et al.,2019)}

Antibacterial

"All extracts showed comparable activities against four bacterial strains: Escherichia coli, Listeria monocytogenes, Pseudomonas aeruginosa and Salmonella typhimurium. Ajuga genevensis and A. reptans ethanol extracts exerted the best antimicrobial activity against S. aureus with MIC = 0.78 mg/mL, MBC = 1.56 mg/mL for both species. Escherichia coli, Salmonella typhimurium and Listeria monocytogenes were the less susceptible strains for methanol extracts obtained from both species, with a MBC value of 12.5 mg/mL." ^{(Toiu et al.,2019)}

Antifungal

"The best susceptibility to the Ajuga reptans petroleum ether extract was shown by Candida albicans (0.006 mg/mL and 0.012 mg/mL for minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC). From the same Ajuga species, following highest sensitivity was shown to chloroform and ethanol extracts, with MFC = 0.025 mg/mL and MIC = 0.012 mg/mL, respectively and the most resistant strains against ethanol extract of Ajuga genevensis being Penicillium fumiculosum and Aspergillus niger (MFC 0.2 mg/mL). In their article, Kawamura and Ohara, (2005) stated that high level of iridoids contained within the plant extracts might be linked to the antifungal activity of these extracts. All extracts of aerial parts from Ajuga species showed high concentrations of iridoid glycosides, mainly 8-O-acetylharpagide." ^{(Toiu et al.,2019)}

Phytochemicals

"The plant contains digitalis-like substances (these are commonly found in Digitalis species and are used in treating heart complaints) and is thought to possess heart tonic properties²⁶⁸." ^[PFAF]

Insecticide: "The effects of crude methanolic extracts of Ajuga remota and A. reptans (Labiatae) were tested in the laboratory against the developing stages of Aedes aegypti, A. togoi and Culex quinquefasciatus. The extracts caused severe inhibition of development when young fourth instar larvae were exposed until adult emergence. The rate of mortality was correlated with extract's concentrations and the duration of exposure. The different mosquito species showed almost the same sensitivity to an extract of A. remota. Extracts of A. reptans (LC(90)-values from 98 to 128 ppm when tested against A. togoi) were more efficient than those of A. remota (LC(90)-values from 384 to 700 ppm). Among the different plant parts, effectiveness of the derived extracts was roots over leaves over shoots over flowers. Treatment of developing stages caused a reduced quality of the emerged female adults. The results point out that the ecdysteroid regulation of the mosquitoes is influenced by the effective compounds of the extracts" ^{(Marcard et al.,1986)}

"The highest level of hydroxylated polyenoic fatty acids was found in Ajuga reptans (101.1 Ug/g dry mass)." ^(kuhn1989)

Cultivation

• Groundcover
  • "A good ground-cover for a position in semi-shade²⁰⁰, forming a carpet and rooting as it spreads²⁰⁸. Fairly fast growing but it does not always smother out weeds and can become bare at the centre if not growing in good conditions¹⁹⁷." ^[PFAF]
  • Ajuga is rabbit resistant ^{[ARA 16.3]}

Propagation
"Seed - sow spring or autumn in a cold frame. The seed usually germinates in 3 - 4 weeks at 10^oC³³, though it can be erratic²³⁸. Prick out the seedlings when they are large enough to handle and plant them out in the summer^K. Division of runners at almost any time of year. Very easy, the divisions can be planted straight out into their permanent positions if required." ^[PFAF]

Arbuscular mycorrhizal

"The arbuscular mycorrhizal (AM) fungi colonizing plants at a woodland site in North Yorkshire (UK) have been characterized from the roots of five plant species (Rubus fruticosus agg. L., Epilobium angustifolium L., Acer pseudoplatanus L., Ajuga reptans L. and Glechoma hederacea L.), and identified using small-subunit rRNA (SSUrRNA) gene amplification and sequencing." ^{(helgason2002)}

"Archaeospora trappei and Glomus sp. UY1225 had variable effects on the host plants, conferring a range of P uptake and growth benefits on Lysimachia nummularia and T. scorodonia, increasing P uptake whilst not affecting biomass in Ajuga reptans and Glechoma hederacea, and failing to form mycorrhizas with A. pseudoplatanus." ^{(helgason2002)}

"Scutellospora dipurpurescens was the only fungus to increase Ajuga biomass, although it did not increase plant P content significantly and plants colonized by it fell on the same concentration trajectory as the controls (Fig. 4b). In contrast, plants colonized by the other three fungi all had elevated tissue P con- centration and total P content, but showed no growth response." ^{(helgason2002)}

"The data in Table 1 suggest that the AM families are not distributed homogeneously among the five host-plant species. Scutellospora was not found in Acer, Ajuga or Glechoma; Glomus was rare or absent from Rubus and Epilobium; and Acaulospora was only found twice (10%) in Acer despite being the most frequently sequenced genus." ^{(helgason2002)}

"Three of the four fungi used were from our trap- culture programme. Glomus sp. UY1225 has occurred in several trap-culture attempts, and has been found in many plant species in Pretty Wood including Ajuga (from whose roots it was originally isolated),...." ^{(helgason2002)}

"On this basis, there were four main types of plant response to fungi (Table 2; Fig. 4): (a) roots uncolonized and no growth response: NUEP as in control plants (e.g. Glechoma with S. dipurpurescens) (b) roots uncolonized, NUE_P reduced (i.e. higher tissue P concentration), seen in Acer with all fungi except G. hoi (c) roots colonized, growth stimulated, but NUE_P reduced and P concentration increased; this occurred in Acer with G. hoi, in Lysimachia with all fungi except possibly S. dipurpurescens, and in Teucrium with all fungi except possibly A. trappei (d) roots colonized, P content increased with no change in biomass, resulting in high tissue P concen- tration and low NUE_P. This pattern occurs in Glechoma and Ajuga with all fungi except S. dipurpurescens." ^{(helgason2002)}

"Pattern (d) occurred only in those plants with a stoloniferous growth habit (Glechoma and Ajuga)." ^{(helgason2002)}

Uses of Other Ajuga Sp.

"More than one hundred species and fifty varieties and subspecies of Ajugu plants are unevenly distributed over the world [ 11. While in America there are recorded only three newly introduced species, and two endemic species in Australia, these Labiatae are especially abundant in China, Korea and Japan and also widespread in Europe." ^(camps1993)

"They have been used in folk medicine in various cultures and several interesting medicinal properties, such as antifebrile, anthelmintic, hypoglycaemic and vulnerary effects have been attributed to them. Traditionally, in China some Ajuga plants have been used to treat inflammation (2)." ^(camps1993)

Ecdysteroids (Arthropod steroid hormones)

"Ajugarins I-III were the first insect antifeedants, isolated by I. Kubo and coworkers ⁴, from Ajuga remota. At a later stage, the same authors isolated from the same plant two other related structures, ajugarins IV and V, and also clerodin ^9-11." ^(camps1993)

"The main structural characteristics are the but-13-en-15,16-olide ring and oxygen substituents at particular sites of the decalin system. ... these patterns are important to elicit antifeedant activity." ^(camps1993)

"The antifeedant activities of ajugarins I-III were investigated by the host-plant leaf disk method [12] using Zea mays (maize) for the monophagous Spodoptera exempta and Ricinus communis for the polyphagous S. littoralis. Activity levels of 100 ppm against S. exempta and 300 ppm against S. littoralis were found. The other two ajugarins exhibited no antifeedant activities, and only moderate insecticidal and growth inhibitory activities were reported for ajugarin IV against different insects." ^(camps1993)

"Also from A. reptans we isolated two minor components (with the yields from dry plant indicated) ajugarep tansone A (8 ppm) and ajugareptansone B (6 ppm) with neo-clerodane structures closely related to ajugarins." ^(camps1993)

"We also studied Ajuga iva collected in Beer-Sheva (Israel) and isolated four new neo-clerodanes named ivains I-IV (300,10,40 and 60 ppm yield from dry plant, respectively)." ^(camps1993)

"Although the insect antifeedant activity of these series of compounds is presumed from their structural similitudes with ajugarins, only the activities of ajugacumbins A-C are mentioned in the literature [33]. In the host- plant leaf disk method using Boehmeria nivea with larvae of Pureda vesta Fabricius, the lowest effective concentration for antifeedant activity was 50 ppm for ajugacumbin A and 200 ppm for the other two compounds." ^(camps1993)

"When we investigated the total content and relative composition of phytoecdysteroids in different parts of normally grown or in oitro micropropagated A. reptans plants ⁶⁸, that content was extremely low ( ~/- 60 ppm/dry wt) in leaves of these micropro- pagated plants, whereas that of the corresponding roots was the highest detected in our experiments ( ~/- 4000 ppm/dry wt). The relative composition was very variable in the different materials analysed, the major components being ajugalactone (45-57%) in leaves of wild plants and 29-norcyasterone (51%) in roots of micropropagated plants, respectively." ^(camps1993)

"From all the data obtained of our in vivo and in vitro experiments, we conclude that ecdysteroid production is related to organised macrostructures in the plant and occurs in the roots. The contents in the different materials studied seem to indicate a relationship between growth and ecdysteroid production." ^(camps1993)

"As far as the biosynthesis of phytoecdysteroids in A. reptans is concerned, two major biosynthetic pathways appear to be operating, side chain dealkylation and 5-hydroxylation,..." ^(camps1993)

Effects of Ecdysteroids

"... there may be a wide varia- tion in the susceptibility of different insects to these compounds. Insects possess diverse abilities to absorb, detoxify and efficiently eliminate phytoecdysteroids, ...." ^(camps1993)

"...it has been shown that phytoecdysteroids exhibited different activities in vertebrates ³. Among them, it is worth mentioning: the stimulation of protein, an anabolic activity in murine liver ⁷¹. the suppression of the hyperglycaemia induced by either glucagon or alloxan in diabetic mice ⁷², the inhibition of the development of hypercholesterolaemia and hyperlipidaemia produced by Triton WR-1339 in rats and antiatherosclerotic action in rabbits ⁷³, the increase of bile acids and bilirubin levels and decrease of cholesterol content in the bile secretion of normal rats or rats with induced toxic hepatitis ⁷⁴, the normalization of the respiratory chain and the terminal pathway of electron transport in hepatocytes of rats with induced hepatitis ⁷⁵ and the potentiation of the effects of insulin ⁷⁶." ^(camps1993)

Ecdysteroid Production

"Cell cultures of different species of Ajuga have been obtained. Synthesis of 20E and turkesterone was established in both callus and suspension cultures of A. turkestanica, the 20E concentration in the cells being several times higher than that in the roots and leaves of the plants, whereas the turkesterone concentration was somewhat lower than in the intact plant (Lev et al., 1990). A number of studies has been carried out on sterile culture and A. reptans shoots and roots cultivated separately (Tomás et al., 1992, 1993; Camps and Coll, 1993). The plants cloned in vitro retained the ecdysteroid composition inherent to both intact wild plants and glasshouse plants. Ajugalactone and cyasterone (C₂₉-ecdysteroids), 29-norsengosterone and 29-norcyasterone (C₂₈-ecdysteroids) and 20E (C₂₇-ecdysteroid)(20-hydroxyecdysone) were found. PolB was not found in plants in vitro, but was detected in intact plants. The ecdysteroid content in the roots of the plants in vitro amounted to 0.4% of the dry weight and was 1.5–2.5 times higher than that in intact plant roots. The ratio of C₂₈/C₂₉-phytoecdysteroids in intact and in in vitro cloned plants was substantially different. A. reptans roots were established to be the site of ecdysteroid biosynthesis." ^{(Dinan et al.,2009)}

"All of the A. reptans hairy root clones were shown to synthesize 20E, norcyasterone, cyasterone and isocyasterone, which are characteristic ecdysteroids of intact plant roots. The component ratio was also similar to that in intact plant roots, with 20E prevailing. There was a positive correlation between the ecdysteroid content and the clone growth-rate. Selection resulted in the isolation of the rapidly growing Ar-4 clone, where the 20E concentration amounted to 0.14% of the dry weight. When growing the Ar-4 clone in an Airlift-type fermenter for 45 days, the weight of the culture increased 230-fold, and the 20E content was as much as 0.12% of dry weight. Regenerated plants cultivated from high-producing hairy root clones of A. reptans var. atropurpurea were shown to have higher ecdysteroid accumulation than untransformed regenerants (Tanaka and Matsumoto, 1993). The transformed plants had root/total plant weight ratios of 68–75%, compared to 50% for normal regenerant plants, the ecdysteroid content being as high as in the parent clones. Thus, the possibility of obtaining microclonal reproduction of modified plants with an increased ability to produce ecdysteroids was demonstrated, with the associated possibility of creating phytophagous insect-resistant plants." ^{(Dinan et al.,2009)}

"The presence of ecdysteroids was not detected in A. reptans callus cultures by Tomás et al. (1992). However, trace amounts of 20E were detected in A. reptans callus and suspension cultures by Mboma et al. (1986)." ^{(Dinan et al.,2009)}

"Genetically modified rhizogenic culture of A. reptans var. atropurpurea also proved to be a boon for ecdysteroid biosynthesis research...." ^{(Dinan et al.,2009)}

"A. reptans plants are characterized by a low ecdysteroid content. However, in contrast to Rh. carthamoides callus cultures which are incapable of synthesizing significant amounts of ecdysteroids, strains of A. reptans cultures were obtained which surpassed both plants cultivated in vitro and wild plants in their ecdysteroid content. The content of 20E was found to increase significantly during long-term (for 9 years) cultivation of S. coronata and A. reptans callus cultures. This is likely to be a result of cell differentiation over time. Thus, ecdysteroid-producing cell cultures were shown to retain their biosynthetic abilities to different extents. In young callus cultures with high or moderate ecdysteroid content (S. coronata and Rh. carthamoides), a decrease in ecdysteroid synthesis occurs. After being introduced into culture, species with low ecdysteroid content, such as A. reptans match, or even surpass, intact plants as far as ecdysteroid accumulation is concerned. Moreover, ecdysteroid accumulation dynamics in cell cultures of phylogenetically distant spe- cies is similar in spite of the difference in morphological features." ^{(Dinan et al.,2009)}

Pytochemicals in Genus

"In the flora of Romania [18] there are mentioned 8 species and 2 hybrids of Ajuga, out of which A. reptans L. is known as a medicinal plant for its bitter-astringent principles, a reason according to which it has recently been offered more attention, along with its close kin – A. genevensis L." ^{(Hemcinschi et al.,2009)}

"The flourishing aerial parts of Ajuga reptans L. and Ajuga genevensis L. from the Lamiaceae family, common in orchards, hay fields and pastures, known under the name of bugle and blue bugleweed respectively are characterized by the content of tanins and iridoids, due to which, in folk medicine, both species are used, in the forms of infusions and tinctures, as antidiarrhoeaic, antileucoreic, vulnerar and hepatoprotecting remedies [1, 2]." ^{(Hemcinschi et al.,2009)}

"Both species contain iridoids (harpagid, 8-O-acetilharpagid, ajugol), antocianosides, tanins, polyphenolcarboxilic acids (rozmarinic acid, caffeic acid), flavonoids [3], volatile oils, rezins, ozes, and also diterpens with a neo-clerodan skeleton, generically called ajugavensins [4, 5]." ^{(Hemcinschi et al.,2009)}

"As the iridoidic compounds of the harpagoside/harpagide type are extremely interesting for therapeutics due to the anti-inflammatory and pain killing actions, the only used vegetal product in the present being the secondary tubers of Harpagophytum procumbens originating from South Africa (indicated in the treatment of the chronic forms of inflammatory rheumatism, and also in chronic gastro-intestinal inflammatory affections), the identification of a possible European source of such active principles would be an interesting challenge." ^{(Hemcinschi et al.,2009)}

"The TLC analysis for the absolute methanol extracts indicated the fact that in case of Ajuga reptans there are 3 major iridoid components while in case of Ajuga genevensis there are only two (Fig. 18, Pl. IV); likewise, from the quantitative point of view the iridoids seem to be better represented in bugle compared to blue bugleweed." ^{(Hemcinschi et al.,2009)}

"If, as we may notice, aucubin is absent from both species (as also shown by literature),...." ^{(Hemcinschi et al.,2009)}

"In case of the iridoids (Fig. 20, Pl. IV), the quantitative differences in the same species, Ajuga reptans L., are, as can be seen, extreme: the Tg. Neamt 1 population has an iridoid content of over 1.5g, while population 2, harvested in the same restricted perimeter, not greater than 200 m², contain by 2 and a half times less non-volatile monoterpens; the Guranda population with over 2% proved to be the richest. For Ajuga genevensis L., the intraspecific differences are much smaller, fact also seen by comparing the 4 Mascateni populations (Fig. 21, Pl. V)." ^{(Hemcinschi et al.,2009)}

"On the other hand, if we compare the flavonoid, polyphenolcarboxilic acid and iridoid contents determined in Ajuga reptans L. and Ajuga genevensis L. individuals prelevated from the same place (Baisa), where we assume the existence of the same pedoclimatic offer, the discriminating factor being, for sure, the genetic heredity, we get the image in Fig. 22, Pl. V." ^{(Hemcinschi et al.,2009)}

"As we see, the flavonoids are found in the Baisa populations of the two mentioned Ajuga species, in the smallest quantity, followed by the polyphenolcarboxilic acids, and the highest concentration is that of the iridoids." ^{(Hemcinschi et al.,2009)}

"If the flavonoids are quantitatively close for the two species, the content of the polyphenolcarboxilic acids is much raised at Ajuga reptans L. compared to A. genevensis, and the iridoids present almost equal values." ^{(Hemcinschi et al.,2009)}

"The results of our researches showed intra and inter-specific variations of certain anatomical and chemical characters in the investigated Ajuga species.
The histo-anatomical differences refer especially to the vegetative organs, being represented by the frequency and localization of the hairs (non-glandular and glandular), the development and lignification degrees of the mechanical tissues (periphloemic sclerenchymatous fibre cordons, libriform fibres from the secondary xylem), the ratio secondary phloem/secondary xylem, the number of xylem cells per surface unit, the endoderm and stele type in the root (polyarch in the adventitious roots formed on the rhizome and diarch or triarch in their branching), the thickness of the limb and the number of palisadic cell layers.
For the populations belonging of the investigated Ajuga species there is a certain intra- and inter-specific chemical variation, referring especially to the values registered for iridoids.
Nevertheless, to establish the clear interdependence regarding the quantitative variations of the active principles, one should achieve some multiannual studies (with a constant harvesting of the individuals in the same locations) with the simultaneous monitoring of both the climatic conditions of each year and the composition of the soil. We consider that if future researches will establish that, especially for Ajuga reptans L, the total iridoidic is in its greatest part constituted of derivates of the harpagid type, it would be possible that the species furnish convenient raw material to obtain some preparations useful to the part of the population with LOHAS orientation (Life of Health and Sustainability)." ^{(Hemcinschi et al.,2009)}

Activities of genus & Phytochemicals contained within it

Ajuga decumbens Thunb.

"Ajuga decumbens Thunb is a member of Labiatae family and widespread in China, Korea and Japan. This plant possesses diverse pharmacological activities, such as anti-inflammatory, antitumor, antibacterial, antiviral, cytotoxic, as well as insecticidal activities. Several compounds have been isolated from A. decumbens, which display a wide spectrum of biological and pharmacological activities." ^{(Ni et al.,2015)}

"The genus Ajuga is widely spread throughout the temperate regions of Europe, Asia, Australia, North America, and Africa [1,2]; this group contains many medicinal plants such as A. decumbens Thunb., A. bracteosa Wall. ex Benth, A. forrestii Diels, A. nipponensis Makino, A. ciliata, etc. Studies have shown that Ajuga spp. are widely used for the treatment of hypertension, hyperglycemia, pneumonia, acute and chronic pharyngitis [3-6]. Additionally, Ajuga has been used in Iranian traditional medicine for the treatment of joint pain, gout, and jaundice [7]. All plants of A. decumbens have been utilized as a kind of folk medicine for a long time in China and Japan owing to their antibacterial, anti- inflammatory, antitumor and antiviral activities [8- 11]. Many compounds whose structures have been characterized were isolated from A. decumbens. Diterpenes and iridoid glycosides are the main bioactive compounds for the treatment of chronic pelvic inflammation and hysteromyoma [12,13]. It is urgent to understand the structure-activity relationships between the chemical constituents and biological activities of this plant with regard to its enormous social and economic implications. The primary objective of this review is to comprehensively report the various biological properties of A. decumbens as well as its main chemical constituents." ^{(Ni et al.,2015)}

Misc uses of other species

• Ajuga bracteosa - "The leaf paste is used orally against constipation" ^{(Ahmed et al.,2013)}
• Ajuga macrosperma - Wall. ex Benth. "Whole plant pounded up and applied directly to a sore gum, tooth, or cheek." (Anderson,1986)
• Ajuga genevensis & Ajuga reptans - Internal as tea - Respiratory tract ^{(Vogl et al.,2013)}
• Ajuga chamaepitys subsp. tridactylites (Ging. ex Benth.) P.H. Davis - Jaundice, Joints pain, Gout (25) ^{(Naghibi,2005)}

"Aerial parts of a group of 50 plant species of south-eastern Spain, belonging to different botanical families, were harvested in 1995 and 1996. From each sample three extracts were obtained using organic solvents of increasing polarity. Activity was tested in bioassays using the stored grain pest Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). Larval growth inhibition was significantly induced when extracts were incorporated into the diet at 0.05%. The most active plants were: Anabasis hispanica, Senecio lopezii, Bellardia trixago and Asphodelus fistulosus. However, only with Ajuga iva was 70% mortality obtained." ^{(pascual-villalobos1998)}

"Ajuga iva (Labiatae) gave the best results because 70 – 100% of mortality in larvae was produced when the extracts were incorporated into the diet...." ^{(pascual-villalobos1998)}

Ajuga bracteosa

Ajuga bracteosa Wall. ex. Benth - Whole plant - Internal colic, pimples, jaundice, hypertension and sore throat ^{(Hamayun,2006)}

Ajuga bracteosa Wallich ex Benth.; "Ethnomedicinal uses: Water extract of fresh leaves is generally administered orally with sugar to children against gastric problems. Luke warm leaf extract is also given against malarial fever and jaundice. Leaf juice is used to cure the mouth ulcers." ^{(Kumar et al.,2009)}

"Ajubractins A–E (855–856, 795–797) and 15-epi-lupulin B (821) were isolated from a dichloromethane extract of Ajuga bracteosa.301 Among them, 795–797 and 821 showed moderately high antifeedant activities (FR ¼ 0.14–0.15). Data analysis from the behavioral responses of S. littoralis exposed to the clerodane diterpenoids hativenes A–C (827–829), from Ajuga pseudoiva, showed that the all of the compounds tested had strong anti- feedant activity at 100, 10, and 1 mg l, which began to dissipate at 0.1 mg l.317 Comparison of the antifeedant index at the latter two concentrations also indicated that a change in the relative conguration of carbons C-12 and C-15 did not modify the activity considerably. 14,15-Dehydroajugareptansin (859), from Ajuga reptans, had signicant activity against sixth stadium larvae of Spodoptera littoralis.207 Overall, these data, compared to those of other clerodanes isolated from Ajuga and Salvia species, helped to clarify different authors' suggestions and conclusions, which related the antifeedant activity of cler- odanes to the presence of a perhydrofuranofuran moiety, a trans decalin ring system bearing an epoxide, and acetate groups." ^{(li et al.,2016)}

Ajuga remota Benth.

Phytochemicals

"Cyasterone (29) and ecdysterone (30), recently isolated (Anonymous, 1981) from the leaves and roots of the east African medicinal plant Ajuga remota Benth. (Labiatae), were fed to larvae of the fall armyworm, Spodoptera frugiperda (J. E. Smith), and the pink bollworm, Pectinophora gossypiella (Saunders). The larvae grew as many as 3 head coverings or cuticles without shedding any old ones. Their mouths became buried so deeply inside the coverings that the larvae were physically unable to eat and starved to death." ^{(Martin Jacobson,1982)}

"Ajugarins I, II, and III (38-40), obtained from the leaves of Ajuga remota Benth., are active feeding deterrents for Spodoptera exempta, S. littoralis (Boisduval), and the lo- cust Schistocerca gregaria Forskal (Kubo and Nakanishi, 1979; Trivedi et al., 1979)." ^{(Martin Jacobson,1982)}

Ectomycorrhiza

Ajuga genevensis, Ajuga pyramidalis and Ajuga reptans - positive for Arbuscular Mycorrhiza ^(wang2006)

References

1. Ahmed et al.,2013 - Ahmed, Ejaz, et al. "Ethnobotanical appraisal and medicinal use of plants in Patriata, New Murree, evidence from Pakistan." Journal of Ethnobiology and Ethnomedicine 9.1 (2013): 13.
   
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6. Duke2 - https://phytochem.nal.usda.gov/phytochem/plants/show/73?et=, Accessed Aug 7, 2019
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8. (Ghita et al.,2011) Ghita, G., et al. "Contributions to the phytochemical study of some samples of Ajuga reptans L. and Ajuga genevensis L." Bulletin of the Transilvania University of Brasov. Series VI: Medical Sciences (2011): 7-14.
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11. (Hemcinschi et al.,2009) Hemcinschi, Anca, et al. "Comparative histo-anatomy and chemical composition of two Ajuga species from the romanian flora." Analele Stiintifice Ale Universitatii" Al. I. Cuza" Din Iasi 55.2 (2009): 33.
12. (Kumar et al.,2009) Kumar, Mahesh, Yash Paul, and V. K. Anand. "An ethnobotanical study of medicinal plants used by the locals in Kishtwar, Jammu and Kashmir, India." Ethnobotanical leaflets 2009.10 (2009): 5.
13. (kuhn1989) Kühn, Hartmut, et al. "Occurrence of free and esterified lipoxygenase products in leaves of Glechoma hederacea L. and other Labiatae." European Journal of Biochemistry 186.1‐2 (1989): 155-162.
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16. Marcard et al.,1986 - Marcard, M., C. P. W. Zebitz, and H. Schmutterer. "The effect of crude methanolic extracts of Ajuga spp. on postembryonic development of different mosquito species." Zeitschrift fuer Angewandte Entomologie (Germany, FR) (1986).
17. ModHerb-Online - Bugle, Common, Botanical.com, A Modern Herbal, Mrs. M. Grieve, http://botanical.com/botanical/mgmh/b/buglec82.html, Accessed Dec 7, 2013
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24. (Toiu et al.,2019) Toiu, Anca, et al. "Comparative phytochemical profile, antioxidant, antimicrobial and in vivo anti-inflammatory activity of different extracts of traditionally used Romanian Ajuga genevensis L. and A. reptans L.(Lamiaceae)." Molecules 24.8 (2019): 1597.
25. (Vogl et al.,2013) Vogl, Sylvia, et al. "Ethnopharmacological in vitro studies on Austria's folk medicine—An unexplored lore in vitro anti-inflammatory activities of 71 Austrian traditional herbal drugs." Journal of ethnopharmacology 149.3 (2013): 750-771.
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27. (wang2006) Wang, B. Q. I. U., and Y-L. Qiu. "Phylogenetic distribution and evolution of mycorrhizas in land plants." Mycorrhiza 16.5 (2006): 299-363.

Journals of Interest

• Movahhedin N, Zengin G, Bahadori MB, Sarikurkcu C, Bahadori S, Dinparast L. 2016. Ajuga chamaecistus subsp. scoparia (Boiss.) Rech.f.: A new source of phytochemicals for antidiabetic, skin-care, and neu- roprotective uses. Ind Crops Prod. 94:89–96.
• MALAKOV P., PAPANOV G. Y., DE LA TORRE M. C., RODRÍGUEZ B.,1991 - Neo-clerodane diterpenoids from Ajuga genevensis., Phytochemistry; 30(12): 4083-4085.
• A. Venditti, C. Frezza, F. Maggi, G. Lupidi, M. Bramucci, L. Quassinti, C. Giuliani, K. Cianfaglione, F. Papa, M. Serafini, A. Bianco, ‘Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): Two new harpagide derivatives and an unusual iridoid glycosides pattern’, Fitoterapia 2016, 113, 35-43.
• Takasaki M, Tokuda H, Nishino H, Konoshima T. Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens. J Nat Prod 1999; 62: 972–975.
• Hailu, W.; Engidawork, E. Evaluation of the diuretic activity of the aqueous and 80% methanol extracts of Ajuga remota Benth (Lamiaceae) leaves in mice. BMC Complement. Altern. Med. 2014, 14, 135.

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