St. John's Wort Eco extract is produced from the flowery caps of Hypericum perforatum L, coming from organic crops.
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1 St. John s Wort Eco BOTANY Hypericum perforatum L, common name St. John's Wort. This is a perennial plant, mildly aromatic, member of the Clusiaceae (Gutiferaceae) family, which grows 30-60cm tall. Stems are highly branched, glabrous, with black glands along 2 longitudinal ridges. Leaves are opposite, elliptic-oblong to linear, 3.cm long, dotted with numerous, tiny translucent secretor glands (perforatum), edges of the lower surfaces lined with black glandular hairs. Flowers are regular, clustered in corymbs at the tips of the stem, with five golden-yellow petals also dotted with black secretor hairs along the margins. Stamens are triadelphous, golden yellow. Three carpels, with red styles. St. John's Wort Eco extract is produced from the flowery caps of Hypericum perforatum L, coming from organic crops. CHEMISTRY Flavonoids 4-%. Mainly hyperoside, rutin, quercetin, quercitrin, isoquercitrin and bioflavonoids such as amentoflavone (derivative of biapigenin). V 01-03/
2 Phloroglucinols 0,2-4%. In this group, hyperforin and adhyperforin are found. Anthraquinones (naphtodianthrones) %, mainly hypericin and pseudohypericin (ratio 1:2) and a mixture of their biosynthetic precursors: protohypericin and protopseudohypericin, which can be transformed into cyclic compounds by the action of light. Hypericin is a pigment, which gives red colour to the oil and blackish colour to the dots on the leaves and petals of this plant. -R Hypericin Pseudohypericin H OH Fig. 1. Structure of hypericin and pseudohypericin Other active principles Catechins ( (+)-catechin, (-)-epicatechin), catechin tannins, chlorogenic acid and caffeic acids. TRADITIONAL USES This plant has been already mentioned in the old herbal medicine treatises by Dioscorides, Galeno and Plinius. Different versions exist about the origin of the genus name; according to the most accepted one, it comes from the Greek words hyper (above) and eikon (image) in reference to the sacred use of the plant to ward off evil. St. John s Wort has been used in the popular medicine for many years as a cure for wounds, urinary infections and disorders affecting the nervous system. Other therapeutic effects are: digestive (ulcer relief), regulation of the menstrual cycle, diuretic, tension-lowering, antipyretic, anti-diarrhoea, antihaemorrhoids. V 01-03/
3 COSMETIC PROPERTIES Anti-inflammatory activity Several studies reported the anti-inflammatory activity of flavonoids. As St. John s Wort contains flavonoids, an extract was fractionated to obtain fractions rich in flavonoids. They were evaluated and showed that the richest fraction in flavonoids is the one that had more anti-inflammatory activity. Therefore, the anti-inflammatory properties of St. John s Wort were proved. Abdel-Salam, O.M.E. (0) evaluated the anti-inflammatory effects of Hypericum perforatum administered systemically as well as orally. When administered systemically, (0-300 mg/kg subcutaneous) H. perforatum produced a dose-dependent significant inhibition of the edematogenic response to subplantar injections of carrageenan. The hydroalcoholic extracts of Calendula officinalis, Hypericum perforatum, Plantago lanceolata and Glycyrrhiza glabra have been found to exert antiinflammatory effects. Herold A. et al. (03) studied their possible action mechanism by studying their antioxidant potential. In particular, they investigated the ability of these plants to modulate the respiratory burst of human activated neutrophils, as an indicator of their antioxidant capacity. The results evidenced significant antioxidant capacity for the hydroalcoholic extracts of H. perforatum and C. officinalis. Using reactive oxygen species (ROS)- generating systems H. perforatum and C. officinalis showed strong ROS scavenging capacity, with H. perforatum extract exhibiting the highest scavenging activity. These results confirmed the anti-inflammatory effects of H. perforatum and C. officinalis. Kumar V. et al. (01) studied the anti-inflammatory activity of a standardized 0% aqueous ethanolic extract of H. perforatum. Their results evidenced anti-inflammatory activity for this extract. Additionally, the extract strengthened the anti-inflammatory activity of indomethacin. Because of the above explained reasons, St. John s Wort is highly recommendable to formulate cosmetic products for sensitive or irritated skins. V 01-03/
4 Anti-bacterial activity Water extract of H. perforatum was found to have anti-bacterial effects against Gram (+) bacteria, especially against methicillin-resistant strains of Staphylococcus aureus, with MIC between 1.3 and 2. mg herb/ml (Reichling J. et al. (01). A petrolether extract of the aerial parts of H. perforatum L. was reported to be active against Gram (+) bacteria. Hyperforin was the antimicrobial principle, showing high efficacy against methicillin-resistant strains of Staphylococcus aureus with MIC=1.0 μg/ml. A butanol fraction of this plant showed anti- Helicobacter pylori activity with MIC ranging between 1.6 and 31.2 μg/ml (Reichling J. et al., 01). In a study using chloroform and methanol extracts of 34 Hypericum species, 33 of them inhibited methicillin-multiresistant Staphylococcus aureus, most of them showing inhibition area diameters >mm for chloroform extracts and > 7mm for methanol extracts (Gibbons S. et al., 02). Thus, St. John s Wort is highly recommendable to formulate cosmetic products with purifying antiseptic activity. Finally, we would like to mention that the publication Plants preparations used as ingredients of cosmetic products (Council of Europe Publishing, 1994) includes a monograph on the glycolic and oily extracts of St. John s Wort flowery caps, where the following cosmetic effects are attributed to them: Astringent, products to be applied before and after sun, calming. Maximum recommended concentration is % of the glycolic as well as the oily extract, when included in astringent and calming products, bath products, cracked-skin care preparations and baby-oil. To formulate before- and after-sun products, the maximum recommended concentration is %. Other possible effects are granulation-promoting agent (stimulates wound healing) and antiirritant. * No clear-cut data can be found in the literature about the photo-toxic potential of St. John s Wort extract and oil (Int J Toxicol, 01; Schempp C.M. et al., 00). V 01-03/
5 BIBLIOGRAPHIC EFFICACY STUDY Hypericum perforatum has been traditionally used to externally treat inflammation, wounds and skin diseases. The study conducted by Kimberly D.P. Hammer et al. (07) showed its anti-inflammatory activity, just as any of its components, such as, flavonoids. 1. Experimental method Different extracts (process, solvent) of St. John s Wort were made, using plant material of different origins. The objective was to find what extracts offered a higher anti-inflammatory activity and see if there was a relationship with the component in the plant. The composition of the extracts was analysed by LC-MS-UV, to detect characteristic compounds in Hypericum perforatum: rutin, quercetin, hyperoside, quercitrin, isoquercitrin, amentoflavone, hypericin, pseudohypericin, chlorogenic acid and hyperforin. To study the anti-inflammatory activity of St. John s Wort, macrophage crops were used, and an inflammatory response was induced by lipopolysaccharide (LPS). This anti-inflammatory response starts in the cell with an activation of phospholipase A2, which attacks the lipid membrane producing arachidonic acid. This arachidonic acid can follow two metabolic pathways to result in inflammation mediators: 1-Cyclooxigenase enzyme (COX): determines the production of prostaglandins (PG), prostacyclins and thromboxanes. 1. Lipoxygenase enzyme: leads to the leukotriene production. PGE 2 is the most important prostaglandin in the inflammatory process as it produces vasodilation and pain, and increases vascular permeability together with other factors. In this study, PGE 2 production was activated by using LPS. Therefore, the ability of St.John s Wort extracts and compounds to block the cyclooxygenase pathway and reduce PGE 2 production was evaluated. 2. Results The quantification of actives in the different ethanolic extracts showed chlorogenic acid (-28µM) as one of the most important. Amongst flavonoids, the highest concentration was for rutin (8-1µM), then hyperoside (3-7µM), isoquercitrin (0,4-2µM), amentoflavone (0,2-2µM), quercitin (0,2-1µM) and quercitrin (0,1-0,3µM). Hyperforin was also found in the extracts (-70µM). Pseudohypericin (0,2-1µM) and hypericin (0,04-0,2µM) were also found. V 01-03/
6 Regarding the anti-inflammatory activity, all the extracts of St.John s Wort showed a significant reduction in PGE 2 production, amongst 43 and 93%. Many of St. John s Wort actives showed anti-inflammatory activity, mainly flavonoids. From these flavonoids, all of them except rutin, showed a significant reduction in PGE 2 levels, higher than 0% at - µm concentration. Hyperforin also showed activity but at higher concentrations: µm. Chlorogenic acid and hypericin didn t show this anti-inflammatory effect (table 1). Constituent Hyperforin Quercetin Quercitrin Isoquercitrin Rutin Hyperoside Amentoflavone Concentration (µm) % reduction in LPS-induced PGE Chlorogenic acid 1,,,, 40 0 Table 1. Anti-inflammatory activity of constituents of St. John s Wort extract 3. Conclusions This study confirms the anti-inflammatory activity of St. John s Wort and that it is due to the combined action of its components, especially by the effect of flavonoids. St. John s Wort Eco extract is, having demonstrated anti-inflammatory activity, suitable for treating sensitive skin, as it soothes its irritation. V 01-03/
7 COSMETIC APPLICATIONS Action Active Cosmetic application Anti-inflammatory Flavonoids Anti-irritant Anti-bacterial Hyperforin Purifying Antiseptic RECOMMENDED DOSE The recommended dose is between 0.% and.0%. BIBLIOGRAPHY Abdel-Salam, O.M.E. Antiinflamatory, Antinociceptive, and Gastric Effects of Hypericum perforatum in Rats. The Scientific World Journal, 0; : Alonso, J. Tratado de Fitofármacos y Nutracéuticos. Barcelona: Corpus, 04, p: (633.8 ALO). Birt et al. Hypericum in infection: identification of anti-viral and anti-inflammatory constituents. Pharmaceutical Biology. 09, 47(8): Buendía Sánchez E. el hipericón en el tratamiento de la depresión. Revista de Fitoterapia, 00; 1 (1): (ref. 4467). Bombardelli E, Morazzoni P. Hypericum perforatum. Fitoterapia, 199; 66 (1): (ref. 61). Council of Europe. Plants preparations used as ingredients of cosmetic products. Strasbourg Cedex: Council of Europe Publishing, 1994; p: (61*8 PAT). ESCOP. (ed). Monographs (Second Edition). Exeter (UK), 03; p: (633.8(031)ENC). Gambhir SS, Goel RK, Das Gupta G. Anti-inflammatory & anti-ulcerogenic activity of amentoflavone. Indian J Med Res, 1987; 8: Gibbons S, Ohlendorf B, Johnsen I. The genus Hypericum a valuable resource of anti-staphylococcal leadsd. Fitoterapia 02; 73: (ref. 428). Hammer K. et al. inhibition of prostaglandin E2 production by anti-inflammatory Hypericum perforatum extracts and constituents in RAW264.7 mouse macrophage cells. Journal of Agricutural and Food Chemistry. 07, (18): V 01-03/
8 Herold A, Cremer L, Calugaru A, Tamas V, Ionescu F, Manea S, Szegli G. Antioxidant properties of some hydroalcoholic plant extracts with antiinflammatory activity. Roum Arch Microbiol Immunol, 03; 62 (3-4): Kumar V, Singh PN, Bhattacharya SK. Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L. Indian J Exp Biol, 01; 39 (4): Lavagna SM, SecciD, Chimenti P, Bonsignore L, Ottaviani A, Bizzarri B. Efficacy of Hypericum and Calendula oils in the epithelial reconstruction of surgical wounds in childbirth with caesarean section. Farmaco, 01; 6 (-7): Reichling J, Weseler A, Saller R. A Current Review of the Antimicrobial Activity of Hypericum perforatum L. Pharmacopsychiatry, 01; 34: Schempp CM, Lüdtke R, Winghofer B, Simon JC. Effect of topical application of Hypericum perforatum extract (St. John s wort) on skin sensitivity to solar simulated radation. Photodermatol Photoimmunol Photomed, 00; 16 (3): Final Report on the Safety Assessment of Hypericum Perforatum Extract and Hypericum Perforatum Oil. Int J Toxicol, 01; (2; Suppl. 2): Web sites: [consultado en marzo de 06]. V 01-03/
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