Ajuga reptans extract (Ajuga reptans)

Description
Ajuga reptans extract is obtained from the perennial herb Ajuga reptans, belonging to the Lamiaceae family. The extract represents a concentrated and stable form of the plant’s bioactive constituents, including phenolic compounds, iridoids, and flavonoids. Due to its phytochemical profile, it is used as a functional ingredient in cosmetic formulations, dietary supplements, and selected technical applications, where botanical actives are required in a standardized form.

Botanical identification

Description of the extract

Key constituents

Indicative nutritional values per 100 g of extract

Average estimated values. The extract is not used as a food ingredient but as a functional component. Typical usage levels range from tens to hundreds of milligrams.

Nutritional profile note

From a nutritional perspective, extract of Ajuga reptans is not intended to provide energy or macronutrient intake.
Its relevance is functional, linked to the concentration of bioactive compounds (iridoids, flavonoids, and tannins) compared with the fresh plant.

Medical applications (traditional and scientific interest)

Note: medical applications are traditional or experimental and do not replace pharmacological treatments.

Cosmetic applications

Main INCI functions:

• Skin conditioning

• Soothing

• Astringent

• Protecting

Industrial applications

Safety and usage considerations

INCI name / Technical name:

• INCI: Ajuga Reptans Extract

• Technical name: Ajuga reptans extract

CAS number:
90082-42-1

EC number:
290-256-5

Formula
Not uniquely definable.
The extract is a complex mixture of plant-derived secondary metabolites, mainly including:

• iridoids

• flavonoids

• phenylpropanoids

• tannins

Name breakdown and function of the components

• Ajuga: botanical genus of the source plant

• reptans: botanical species, identifying the creeping habit of the plant

• extract: concentrated form obtained by removing the extraction solvent, providing improved stability, ease of handling, and consistent dosing

The phytochemical components contribute to the functional, protective, and antioxidant-related properties of the extract.

Description of the production process and raw materials used
The production process typically includes:

• Harvesting and selection of the aerial parts of Ajuga reptans

• Controlled drying to preserve active constituents

• Extraction using suitable solvents (water, ethanol, or hydroalcoholic mixtures)

• Filtration and concentration of the liquid extract

• Final drying (spray drying or vacuum drying) to obtain a free-flowing powder

Main raw materials:

• Ajuga reptans dried plant material

• Extraction solvents (water, ethanol)

• Optional technological carriers used during drying

Appearance, color, odor, and solubility

• Appearance: fine powder

• Color: light brown to dark brown

• Odor: characteristic, herbal

• Solubility: partially soluble in water; soluble in hydroalcoholic mixtures

Environmental impact
Ajuga reptans extract is considered to have a low environmental impact, as it is derived from a renewable botanical source. When produced using responsible agricultural practices and controlled extraction processes, it does not pose significant environmental hazards. The extract is not classified as environmentally dangerous; however, compliance with good manufacturing practices and appropriate waste management remains essential to minimize environmental footprint.

Studies

Ajuga reptans has been studied in the medical field for about fifteen years, mostly on guinea pigs, and scientific publications are not numerous.

We start from 1992 with an Italian study which found vasoconstrictor characteristics (1), then a 1996 study which discovered four anthocyanins (flavonoid family) in flowers (2) confirmed by a subsequent work by the same authors in 2001 (3), then a 2004 study finding out the effectiveness of Ajuga against mosquito-like insects (4) and another 2009 publication on the discovery of new steroids from the seedling (5). For those who would like to delve deeper, I suggest these two recent studies (6).

References__________________________________________________________________________

(1) Breschi, M. C., Martinotti, E., Catalano, S., Flamini, G., Morelli, I., & Pagni, A. M. (1992). Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans. Journal of natural products, 55(8), 1145-1148.

Abstract. The traditional therapeutic indications for the use of Ajuga reptans (Labiatae) have been investigated. The H20-soluble part of a crude and partially purified MeOH extract and two isolated iridoids (8-Q-acetylharpagide and harpagide), were tested for a biological activity on isolated smooth muscle preparations from guinea pig.

 (2) Terahara N, Callebaut A, Ohba R, Nagata T, Ohnishi-Kameyama M, Suzuki M. Triacylated anthocyanins from Ajuga reptans flowers and cell cultures. Phytochemistry. 1996 May;42(1):199-203. doi: 10.1016/0031-9422(95)00838-1. 

Abstract. 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.

(3) Terahara N, Callebaut A, Ohba R, Nagata T, Ohnishi-Kameyama M, Suzuki M. Acylated anthocyanidin 3-sophoroside-5-glucosides from Ajuga reptans flowers and the corresponding cell cultures. Phytochemistry. 2001 Oct;58(3):493-500. doi: 10.1016/s0031-9422(01)00172-8. 

Abstract. Four anthocyanins from Ajuga reptans flowers and its cell cultures were isolated, and a fifth was also characterized by HPLC-mass spectrometry. By means of chemical and spectroscopic analyses, their structures were identified as delphinidin 3-(p-coumaroyl-feruloyl)sophoroside-5-malonylglucoside, delphinidin 3-(diferuloyl)sophoroside-5-malonylglucoside, and cyanidin 3-(di-p-coumaroyl)sophoroside-5-glucoside, respectively. The other two were tentatively identified as delphinidin 3-(diferuloyl)sophoroside-5-glucoside and cyanidin 3-(feruloyl-p-coumaroyl)sophoroside-5-malonylglucoside. In neutral aqueous solution, the crude extract from A. reptans flower cell cultures and the major anthocyanin cyanidin 3-(di-p-coumaroyl)sophoroside-5-malonylglucoside were more stable than cyanidin 3-glucoside, and also prevented more efficiently peroxidation than did the latter. A. reptans flower cell culture anthocyanins may have a potential as natural colorants for food utilities or other purposes.

(4) Fekete G, Polgár lL, Báthori M, Col J, Darvas B. Per os efficacy of Ajuga extracts against sucking insects. Pest Manag Sci. 2004 Nov;60(11):1099-104. doi: 10.1002/ps.928. PMID: 15532684.

(5) Ványolós A, Simon A, Tóth G, Polgár L, Kele Z, Ilku A, Mátyus P, Báthori M. C-29 ecdysteroids from Ajuga reptans var. reptans. J Nat Prod. 2009 May 22;72(5):929-32. doi: 10.1021/np800708g. 

Abstract. 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.

(6) Fujimoto Y, Maeda I, Ohyama K, Hikiba J, Kataoka H. Biosynthesis of 20-hydroxyecdysone in plants: 3β-hydroxy-5β-cholestan-6-one as an intermediate immediately after cholesterol in Ajuga hairy roots. Phytochemistry. 2015 Mar;111:59-64. doi: 10.1016/j.phytochem.2014.12.019. Epub 2015 Jan 12. PMID: 25593010.

Findling S, Zanger K, Krueger S, Lohaus G. Subcellular distribution of raffinose oligosaccharides and other metabolites in summer and winter leaves of Ajuga reptans (Lamiaceae). Planta. 2015 Jan;241(1):229-41. doi: 10.1007/s00425-014-2183-2. 

Abstract. In Ajuga reptans, raffinose oligosaccharides accumulated during winter. Stachyose, verbascose, and higher RFO oligomers were exclusively found in the vacuole whereas one-fourth of raffinose was localized in the stroma. The evergreen labiate Ajuga reptans L. can grow at low temperature. The carbohydrate metabolism changes during the cold phase, e.g., raffinose family oligosaccharides (RFOs) accumulate. Additionally, A. reptans translocates RFOs in the phloem. In the present study, subcellular concentrations of metabolites were studied in summer and winter leaves of A. reptans to gain further insight into regulatory instances involved in the cold acclimation process and into the function of RFOs. Subcellular metabolite concentrations were determined by non-aqueous fractionation. Volumes of the subcellular compartments of summer and winter leaves were analyzed by morphometric measurements. The metabolite content varied strongly between summer and winter leaves. Soluble metabolites increased up to tenfold during winter whereas the starch content was decreased. In winter leaves, the subcellular distribution showed a shift of carbohydrates from cytoplasm to vacuole and chloroplast. Despite this, the metabolite concentration was higher in all compartments in winter leaves compared to summer leaves because of the much higher total metabolite content in winter leaves. The different oligosaccharides did show different compartmentations. Stachyose, verbascose, and higher RFO oligomers were almost exclusively found in the vacuole whereas one-fourth of raffinose was localized in the stroma. Apparently, the subcellular distribution of the RFOs differs because they fulfill different functions in plant metabolism during winter. Raffinose might function in protecting chloroplast membranes during freezing, whereas higher RFO oligomers may exert protective effects on vacuolar membranes. In addition, the high content of RFOs in winter leaves may also result from reduced consumption of assimilates