Lipo-amino acid cholesteryl derivatives promote recovery

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1 j. Soc. Cosmet. Chem., 47, (November/December 1996) Lipo-amino acid cholesteryl derivatives promote recovery effect for damaged skin HIROJI ISHII, NAOKO MIKAMI, and KAZUTAMI SAKAMOTO, Ajinomoto Central Research Laboratories, Tokyo, Japan. Accepted for publication January 15, Synopsis The ability of cholesteryl derivatives to promote the recovery effect in skin damaged by sodium lauryl sulfate was investigated. Among cholesteryl derivatives, acylglutamic acid cholesteryl ester (AGCE) was shown to be effective, either by itself or as a substitute for ceramide (type III). Recovery was evaluated in vivo on human skin using dermal scores, water-holding capacity (conductance), and transepidermal water loss (TEWL). When substituted for ceramide in an artificial stratum corneum lipid model, AGCE also formed a lameliar structure. INTRODUCTION It is well known that the softness of the skin is related to its water content (1). Skin damage caused by external stimulation or irritation results in the destruction of the barrier function of the stratum corneum, which in turn reduces the water-holding capacity and water content of the skin (2,3). Skin characterized by a pathological stratum corneum, such as senile xerotic skin, also has a much lower water content than that of healthy skin (4). This marked decrease in the water-holding capacity of damaged skin is often accompanied by a selective loss of intercellular lipids in the stratum corneum (5). Thus, the use of intercellular lipids as emollients is increasing in recognition as a means of maintaining the softness and flexibility of skin. Stratum corneum lipids consist mainly of ceramides, cholesteryl esters, cholesterol, and fatty acids (6). Ceramides are reported to be the main components of the stratum corneum lipids, and to play an important role in promoting the water-holding capacity of skin by forming a lameliar structure that acts as a moisture evaporation barrier (5,7). Cholesterol and cholesteryl derivatives are also thought to be effective components in these lipid bilayers for retaining water and promoting the recovery of water-holding capacity in damaged skin (7). For example, it has been reported that stratum corneum lacking cholesterol and cholesteryl derivatives exhibits a decrease in its water content and high rates of skin disease (8). Although ceramides are recognized as the key com- 351

2 352 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS ponents in stratum comeurn lipids, they are difficult to incorporate into cosmetic products due to their poor solubility and high cost as raw materials. Acylglutamic acid cholesteryl esters (AGCEs) are cholesteryl derivatives synthesized from cholesterol and lipo-amino acid (lauroyl glutamic acid); they have a cholesterol group and exhibit a structural resemblance to ceramide. Therefore, the present study investigated the possibility of using cholesteryl derivatives including AGCEs as an alternative to ceramides. AGCEs and other cholesteryl derivatives were examined with respecto their ability to promote the recovery effect in skin damage induced by sodium lauryl sulfate (SLS). Recovery was evaluated in damaged skin using dermal scores, water-holding capacity (conductance), and transepidermal water loss (TEWL). The utility of these measures has already been demonstrated with subjective clinical assessment of the skin surface (9,10), the skin surface hygrometer (11), and the evaporimeter (12,13), respectively. Since AGCE is hypothesized to play a role similar to ceramide in the stratum corneum, we examined whether AGCE would be incorporated into the lameliar structure and thereby exert a water-holding capacity. In order to clarify this point, we composed an artificial stratum corneum lipid model containing either ceramide (Model A) or AGCE (Model B) and examined the formation and arrangement of the resulting lameliar structure. The efficacy of models A and B in promoting the recovery of damaged skin was then verified in order to assess the possibility of using AGCE as a substitute for ceramide. EXPERIMENTAL MATERIALS SLS was obtained from Nikko Chemicals Company, Tokyo, Japan. Cholesteryl hydroxy stearate was obtained from Nisshin Oil Mills, Ltd., Tokyo, Japan. AGCEs were products of Ajinomoto Co., Inc., Tokyo, Japan. AGCE-202 is a mixed ester of cholesteryl/ octyldodecylauroyl glutamate. AGCE-301 is a mixed ester of cholesteryl/behenyl/ octyldodecylauroyl glutamate. Phosphatidyl ethanol amine, cholesterol sulfate, and ceramide (type III) were obtained from Sigma Chemical Co., St. Louis, MO. Petrolatum, pristane (2,6,10,14-tetramethyl pentadecane), squalene, myristic acid, oleic acid, palmitic acid, stearic acid, linoleic acid, and cholesterol were obtained from Junsei Chemical Co., Ltd., Tokyo, Japan. Triolein was obtained from Tokyo Chemical Industries Co., Ltd., Tokyo, Japan. All materials were used without further purification. SUBJECTS Eight healthy male volunteers ranging in age from 24 to 29 years served as subjects. METHOD Induction of skin damage by 1% sodium lauryl sulfate (14,15) Skin damage was induced by applying of sodium lauryl sulfate (SLS)(1.0 wt % solution in deionized water) to the volar side of the forearm in a closed patch for 24 hours, using occlusive aluminum chambers (Finn-Chamber, Epitest, Helsinki, Finland)

3 LIPO-AMINO ACID CHOLESTERYL DERIVATIVES 353 held in place by plastic tape (Tegaderm, 3M, Minnesota, USA). Prior to application of 1% SLS, the site was washed with a mild detergent (Minon Body Shampoo, Yamanouchi Pharmaceuticals Co., Ltd., Tokyo, Japan). Derreal scoring and application of samples. After 24-hour occlusive patch removal and rinsing with water, TEWL and conductance were measured and each area was graded according to dermal scores. After induction of skin damage (after day 0), 2pl/cm 2 of cholesteryl derivatives were applied three times per day after the instrumental measurements and dermal scores gradings. The dermal scores were as follows: 0: No visible skin reaction 1: Barely perceptibl erythema 2: Mild erythema 3: Well-defined erythema 4: Erythema and edema 5: Erythema and edema with vesiculation Experimental days were designated as follows: Day -1: dermal scores prior to induction of skin damage Day 0: dermal scores 30 minutes after patch removal Day 1: dermal scores 24 hours after induction of skin damage Day 2: dermal scores 48 hours after induction of skin damage Day 3: dermal scores 72 hours after induction of skin damage Conductance measurements and TEWL. The water-holding capacity of the stratum corneum was measured quantitatively using a skin surface hygrometer (11) (model Skicon 200, IBS Inc., Hamamatsu, Japan), which reads the conductance (ps) of the skin. Conductance was measured five times at the same site, and the values were averaged to obtain individual values. TEWL was measured quantitatively with an evaporimeter (EP-1, ServoMed, Stockholm, Sweden). This instrument measures the vapor pressure gradient and is described in detail by Nilsson (13). The probe was held in place for each measurement until a stable TEWL value was established (approximately 30 seconds). TEWL values were then measured every 10 seconds for 50 seconds and were averaged to obtain individual values. APPLICATION OF CHOLESTERYL TEST MATERIALS ON DAMAGED SKIN (CHOLESTERYL DERIVATIVES AND ARTIFICIAL STRATUM CORNEUM LIPID MODELS)(11) 2pl/cm 2 of samples were applied to each patch site. Each sample was applied on the damaged skin daily for three days. Differences in measured values between samples were tested for significance using a Student t-test for paired samples. PREPARATION OF STRATUM CORNEUM LIPID The compositions of stratum corneum lipid model A (including ceramide) and model B (AGCE-301) are listed in Table I, based on Elias' analysis of the mammalian stratum comeurn (16). Models were prepared according to the method described by Friberg and

4 354 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Table Composition of Model A and Model B Model A Model B wt.% Ceramide (type III) AGCE Squalene Squalene 7 Triolein Triolein 25 Cholesterol sulfate Cholesterol sulfate 2 Cholesterol Cholesterol 14 Phosphatidyl ethanolamine Phosphatidyl ethanolamine 5 Pristane Pristane 4 Free acids* Free acids* 25 I Total 100 * Constitution of free acids (wt%): oleic acid, 35; palmitic acid, 36; myristic acid, 15; stearic acid, 10; linoleic acid, 4. 4 t mean_+s.e. ' [ ' I ' I ' I ' days after application --' & '" []m blank AGCE-301 AGCE-202 Petrolatum - Cholesteryl Hydroxystearate Figure 1. Dermal scores following application of cholesteryl derivatives.

5 LIPO-AMINO ACID CHOLESTERYL DERIVATIVES 355 Osborne (17). Fatty acids were first mixed and partially (41%) neutralized by the addition of an aqueous NaOH solution. Total water content in each model was adjusted to 25 wt. %. CHARACTERIZATION OF THE STRATUM CORNEUM LIPID In order to form a lamellar structure, models with deionized water were heated to about 80øC and allowed to cool to room temperature (25øC). This heating and cooling process was repeated several times, and the resulting structure was observed using a polarizing microscope and small-angle x-ray diffractometry (Cu-Kot radiation). RESULTS RECOVERY EFFECT OF CHOLESTERYL DERIVATIVES FOR DAMAGED SKIN After a 24-hour closed patch with 1 wt % SLS, the volar side of the forearm showed 40 30' 20' O 10' o o mean_+s.e. O I I I ' I ' I days after application = blank,i, AGCE-301 ß *, AGCE-202 [] Petrolatum - Cholesteryl Hydroxystearate Figure 2. Water-holding capacity following application of cholesteryl derivatives.

6 356 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS 15 E LM mean_s.e. 0 ' I ' I ' I ' I ' I ' days after application = blank ' AGCE-301 ß *' AGCE-202 []-- Petrolatum - Cholesteryl Hydroxystearate Figure 3. TEWL recovery following application of cholesteryl derivatives. well-defined erythema with an average dermal score of 3 (Figure 1). Application of petrolatum produced significant recovery compared to the sites without sample application as a control (day 3; p < 0.05). Compared to petrolatum, AGCEs showed remarkably quick recovery (days 2,3; p < 0.05). Although AGCEs tended to reduce the dermal scores more than cholesteryl hydroxy stearate, the difference in the recovery effect was not significant. Figure 2 shows changes in the water-holding capacity of damaged skin. When left untreated, the water-holding capacity remained at a low level for three days. In contrast, application of any sample consistently induced recovery in the water-holding capacity. The water-holding capacity of stratum corneum treated with AGCE-202 was significantly greater than that with cholesteryl hydroxy stearate (days 1,2,3; p < 0.05) or petrolatum (day 3; p < 0.02). TEWL increased significantly in SLS-induced damaged skin (Figure 3). Compared to

7 LIPO-AMINO ACID CHOLESTERYL DERIVATIVES 357 Model A Model B Figure 4. Optical texture of Models A and B under cross polarization. I 0 e i (degree) 20 (degree) Model A Model B Figure 5. Small-angle X-ray diffraction patterns of Model A and Model B. untreated sites, the sites treated with sample exhibited recovery in TEWL. Recovery of TEWL in skin treated with AGCE-301 was significantly greater than with petrolatum (day 1; p < 0.05). No significant difference was observed in TEWL recovery between AGCEs and cholesteryl hydroxy stearate. CHARACTERIZATION OF STRATUM CORNEUM LIPID MODEL When water was added and the heating and cooling process was repeated several times,

8 358 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS 4 1 o mean_+s.e o days after application = blank -- Model A o Model B [] Petrolatum Figure 6. Dermal scores following application of stratum corneum lipid model. model A (the model containing ceramide) exhibited the formation of a lameliar structure, demonstrated by the optical texture under cross-polarization shown in Figure 4. Under the same conditions, model B with AGCE also showed the same optical texture, indicating that AGCEs have the potential to form a lameliar structure. The small-angle X-ray diffraction spectra for model A showed a pronounced peak at 59 fl., corresponding to the double-layer spacing, and a hollow peak around 5 fi- for lateral spacing (Figure 5). This is a typical pattern for lipid layers with bimolecular lameliar structures. Model B showed a similar spectrum, expect that the double-layer spacing occurred at 63 fi-. Thus, it was confirmed that the formation of lipid bilayers in models A and B mimicked the natural intercellular lipid layers in the stratum corneum. RECOVERY EFFECT OF STRATUM CORNEUM LIPID MODEL FOR DAMAGED SKIN Damaged skin treated with model B recovered significantly better in visual appearance compared with skin treated with petrolatum (day 3; p < 0.05). No significant differences were observed between model A and model B with respecto the recovery of visual appearance (Figures 6, 7). The visual appearance of damaged skin treated with models

9 LIPO-AMINO ACID CIIOLESTERYL DERIVATIVES 359 Petrolatum Model A Model B Control Figure 7. Visual appearance of damaged skin treated with Models A and B (day 7). A and B recovered from "well-defined erythema" to "barely perceptible erythema" within three days. Models A and B induced a significant increase in water-holding capacity in damaged skin compared with petrolatum (day 3; p < 0.05). No significant differences were observed between models A and B with respecto recovery of waterholding capacity or TEWL (Figures 8, 9). A significant decrease in TEWL was observed for models A and B when compared with the no-treatment condition. DISCUSSION EFFECT OF CHOLESTERYL DERIVATIVES ON DAMAGED SKIN Damaged skin shows a marked decrease in water-holding capacity in the stratum corneum accompanied by considerable and selective loss of intercellular lipids such as ceramide, cholesterol, cholesterol esters, and polar lipids. In contrast, a similar significant decrease in water-holding capacity could not be induced by a loss of lipids such as wax esters, squalene, or triglycerides (8). The present study evaluated the possibility of using cholesteryl derivatives to promote the recovery effect in damaged skin, and whether lipo-amino acid cholesteryl derivatives (AGCEs) could be used as a substitute for ceramide. The results showed that AGCEs are more effective than cholesteryl hydroxy stearate or petrolatum in promoting the recovery of water-holding capacity, as shown in Figures 2, 3, and 4. Occlusive agents such as petrolatum increase the water content in the stratum corneum simply by forming an occlusive film that traps beneath it the water already present in the skin (2). The ability

10 360 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS ' 10' O mean+s.e.!!!! ß i days after application = blank Model A o Model B [] Petrolatum Figure 8. Water-holding capacity following application of stratum comeurn lipid models. of petrolatum to promote recovery in damaged skin is thought to be due to this occlusiveness. Cholesteryl ester showed better recovery effect upon visual and instrumental assessment than petrolatum. As reported before, cholesteryl esters spread on a cellophane film showed water permeability, and the recovery effect for this class of molecule can be attributed to the emollient effect combined with water in the stratum corneum rather than simple occlusion. AGCE, which has a higher water-holding capacity and water permeability, showed better recovery effect than cholesteryl hydroxy stearate. These results indicate that cholesterol esters applied on damaged skin may be incorporated into the lipid component in the stratum corneum to reconstruct damaged lipid layers. CHARACTERIZATION AND EFFECT OF STRATUM CORNEUM LIPID MODEL AGCEs are derivatives of an amino acid (glutamic acid) bearing an amide group and having structural resemblance to ceramide. Ceramides have been reported to be the main component in stratum corneum lipids that form the lameliar structure. The results in Figure 5 suggesthat stratum corneum lipid models A (ceramide) and B (AGCE sub-

11 LIPO-AMINO ACID CHOLESTERYL DERIVATIVES 361 2O 10 mean+s.e. i i i i days after application = blank -- Model A o Model B []-- Petrolatum Figure 9. TEWL following application of stratum corneum lipid models. stituted for ceramide) both form a lameliar structure similar to that in the stratum corneum. EFFECT OF MODEL STRATUM CORNEUM LIPIDS ON DAMAGED SKIN In the present study, we attempted to elucidate the recovery effect in damaged skin by applying a stratum corneum lipid model containing AGCE. As shown in Figures 1 and 6, these models exhibited a similar degree of recovery compared to cholesteryl esters. These results suggest that AGCE can be easily incorporated into existing stratum corneum lipids and that the preconstituted lameliar structure used in the models is a useful vehicle in enhancing the recovery effect of AGCE. Models A (ceramide) and B (AGCE substituted for ceramide) produced virtually the same recovery effect in damaged skin. Thus, AGCE is thought to contribute to the formation of the lameliar structure in the same way as ceramide, and this structure promotes the recovery by holding water between the intercellular lipid bilayers. As mentioned above, AGCEs are used as a cosmetic ingredient substitute for ceramide, especially with regard to its use for formation of the lameliar structure. AGCE is a lipo-amino acid that is prepared from stratum corneum lipids (cholesterol, fatty acid) and amino acids (a natural moisturizing factor).

12 362 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS The properties of AGCEs are produced through the combined effects of the functionalities possessed by lipo-glutamic acid and cholesterol. It can be assumed that AGCEs play an essential role in the maintenance of water-holding capacity in the stratum corneum. Topics for further study include the interactions of AGCE and other lipid components in the stratum corneum, which will be discussed elsewhere, and the possibility of using AGCE as a substitute for ceramides. REFERENCES (1) I. H. Blank, Factors which influence the water content of the stratum corneum,j. Invest. DermatoL, 18, (1952). (2) H. Tagami, M. Ohi, K. Iwatsuki, Y. Kanamaru, M. Yamada, and B. Ichijo, Evaluation of the skin surface hydration in vivo by electrical measurement, J. Invest. Dermatol., 75, (1980). (3) G. Imokawa and M. Hattori, A possible function of structuralipids in the water holding properties of the stratum corneum, J. Invest. Dermatol., 84, (1985). (4) M. Takenouchi, H. Suzuki, Y. Okaya, M. Ohyama, T. Kaneko, and H. Tagami, Hydration characteristics of the stratum corneum derived from scaly skin, J. Jpn. Cosmet. Sci. Soc., 9, (1985). (5) G. Imokawa, S. Akasaki, and M. Hattori, Selective recovery of deranged water holding properties by stratum corneum lipids,j. Invest. Dermatol., 87, (1986). (6) W. Abraham, P. W. Wertz, and P.M. Elias, Fusion patterns of liposomes from stratum corneum lipids,j. Invest. Dermatol., 90, (1988). (7) S. Akasaki, Y. Minematsu, N. Yoshizuka, and G. Imokawa, The role of intercellular lipids in the water holding properties of the stratum corneum--recovery effect on experimentally induced dry skin,jpn. J. Dermatol., 98, (1988). (8) G. Imokawa and Naonobu Yoshizuka, Skin lipid film and its role in skin conditions, FragranceJ., 64, 84-89, (1984). (9) S. Freeman and H. Maibach, Study of irritant contact dermatitis produced by repeat patch test with sodium lauryl sulfate and assessed by visual methods, transepidermal water loss, and laser doppler velocimetry, J. Am. Acad. Dermatol., 19, (1988). (lo) P.J. Frosch and A.M. Kligman, The soap chamber test, J. Am. Acad. Dermatol., 1, (1979). G. Imokawa and S. Akasaki, Water-retaining function in the stratum comeurn and its recovery properties by synthetic pseudoceramides,j. Soc. Cosmet. Chem., 40, (1989). (]2) J. Pinnagoda, R. A. Tupker, T. Agner, and J. Serup, Guidelines for transepidermal water loss (TEWL) measurement, Contact Dermatitis, 22, (1990). (13) G. E. Nilsson, Measurement of water exchange through skin, Med. Biol. Eng. Cornput., 15, (1977). (]4) K. P. Wilhelm, C. Surber, and H. Maibach, Quantification of sodium lauryl sulfate irritant dermatitis in man, Arch. Dermatol. Res., 281, (1989). (15) K. P. Wilhelm and H. I. Maibach, Skin color reflectance measurement for objective quantification of erythema in human beings, J. Am. Acad. Dermatol., 21, (1989). (]6) L. C. Froebe, F. A. Simon, H. O. L. Rhein, J. Mattai, R. H. Caganand, and S. E. Friberg, Prevention of stratum corneum lipid phase transitions in vivo, by glycerol,j. Soc. Cosmet. Chem., 41, (1990). (17) S. E. Friberg and D. W. Osborne, Small angle x-ray diffraction patterns of stratum corneum and a model structure for its lipids, J. Di p. Sci. Technol., 6, (1985).

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