The effect of two Terpenoids, Ursolic acid and Oleanolic acid on epidermal permeability barrier and simultaneously on dermal functions |
Lim Suk Won
(R & D Center of Skin Science & Cosmetics, ENPRANI Co., Ltd)
Jung Sung Won (R & D Center of Skin Science & Cosmetics, ENPRANI Co., Ltd) Ahn Sung Ku (Dept. of Dermatology Dermatology, Yonsei Univ. college of Medicine) Kim Bora (R & D Center of Skin Science & Cosmetics, ENPRANI Co., Ltd) Ryoo Hee Chang (R & D Center of Skin Science & Cosmetics, ENPRANI Co., Ltd) Lee Seung Hun (Dept. of Dermatology Dermatology, Yonsei Univ. college of Medicine) |
1 | Subbaramaiah K, Michaluart P, Sporn MB et al. Ursolic acid inhibits cyclooxygenase-2 transcription in human mammary epithelial cells. Cancer Res 2000; 60: 2399-2404 PUBMED |
2 | Kersten S, Desvergne B, Wahli W. Roles of PPAR in health and disease. Nature 2000; 405:421-424 DOI ScienceOn |
3 | River M, Safonova I, Lebrun P et al. Differential expression of peroxisome proliferator-activated receptor subtypes during the differentiation of keratinocytes. J Invest Dermatol 1998; 111: 1116-1121 DOI ScienceOn |
4 | Komuves LG, Hanley K, Lefebver AM et al. Stimulation of PPAR a promotes epidermal keratinocyte differentiation in vivo. J Invest Dermatol 2000; 115: 353-360 DOI ScienceOn |
5 | Keller H, Drayer C, Medin J et al. Fatty acids and retinoids control lipid metabolism through activation of peroxisome proliferator-activated receptor-retinoid X receptor heterodimers. Proc Natl Acad Sci 1993; 90: 2160-2164 DOI |
6 | Tang HQ, Hu J, Yang L et al. Terpenoids and flavonoids from Artemisia species. Planta Med 2000; 66: 391-393 DOI ScienceOn |
7 | Jeong TS, Hwang EI, Lee HB et al. Chitin synthase II inhibitory activity of ursolic acid, isolated from crataegus pinnatifida. Planta Med 1999; 65: 261-263 DOI ScienceOn |
8 | Marquina S, Maldonado N, Garduno-Ramirez ML et al. Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens. Phytochemistry 2001; 56: 93-97 DOI ScienceOn |
9 | Ma C, Nakamura N, Hattori M et al. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia. J Nat Prod 2000; 63: 238-242 DOI ScienceOn |
10 | Latha PG, Panikkar KR. Modulatory effects of ixora coccinea flower on cyclophosphamide-induced toxicity in mice. Phytother Res 1999; 13: 517-520 DOI ScienceOn |
11 | Lauthier F, Taillet L, Trouillas P et al. Ursolic acid triggers calcium-dependent apoptosis in human Daudi cells. Anticancer Drugs 2000; 11: 737-745 PUBMED |
12 |
Matsuura H, Adachi H, Smart RC et al. Correlation between expression of peroxisome proliferator-activated receptor |
13 | Kliwer SA, Umesono K, Noonan DJ et al. Convergence of 9-cis retinoid and peroxisome proliferator signaling pathways through heterodimer formation of their receptors. Nature 1992; 358: 771-774 DOI ScienceOn |
14 | Fuchs E. Epidermal differentiation: the bare essentials. J Cell Biol 1990; 111: 2807-2814 DOI |
15 |
Wang Y, Porter WW, Suh N et al. A synthetic triterpenoid, 2-cyano-3, 12-dioxooleana-1,9dien-28-oic acid (CDDO), is a ligand for the peroxisome proliferator-activated receptor |
16 | Kliewer SA, Sundseth SS. Jones SA et al. Fatty acids and eicosanoids regulate gene expression through direct interactions with peroxisome proliferator-activated receptors a and Proc Natl Acad Sci USA 1997; 94: 4318-4323 |
17 | Hanley K, Komuves LG, Bass NB et al. Fetal epidermal differentiation and barrier development in vivo is accelerated by nuclear hormone receptor activators. J Invest Dermatol 1999; 113: 788-795 DOI ScienceOn |
18 | Ponec M, Weerheim A, Kempenaar J et al. Retinoids and lipid changes in keratinocytes. Methods Enzymol 190:30-41 |
19 | Kashiwada Y, Nagao T, Hashimoto A et al. Anti-AIDS agents.38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives. J Nat Prod 2000; 63: 1619-1622 DOI ScienceOn |
20 | River M, Casiel I, Safonova I et al. Peroxisome proliferator activated receptor- enhances lipid metabolism in a skin equivalent model. J Invest Dermatol 2000; 114: 681-687 DOI ScienceOn |
21 | Rios MY, Gonzalez-Morales A, Villarreal ML. Sterols, triterpenes and biflavonoids of Viburnum jucundum and cytotoxic activity of ursolic acid. Planta Med 2001; 67: 683-684 DOI ScienceOn |
22 | Xu HE, Lambert MH, Montana VG et al. Structural determinants of ligand binding selectivity between the peroxisome proliferator-activated receptors. Proc Natl Acad Sci USA 1997; 94: 4318-4323 DOI |
23 | Ohigashi H, Takamura H, Koshimizu K et al. Search for possible antitumor promoters by inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation; ursolic acid and oleanolic acid from an anti-inflammatory Chinese medicinal plant, Glechoma hederaceae L. Cancer Lett 1986; 30(2): 143-51 DOI ScienceOn |
24 | Schoonjans K, Staels B, Auwerx J. Role of the peroxisome proliferator-activated receptor (PPAR) in mediating the effects of fibrates and fatty acids on gene expression. J Lipid Res 1996; 37: 907-925 PUBMED |
25 | Jeong HG. Inhibition of cytochrome P450 2E1 expression by oleanolic acid hepatoprotective effects against carbon tetrachloride-induced hepatic injury. Toxicol Lett 1999; 105: 215-222 DOI ScienceOn |
26 | Baricevic D, Sosa S, Della Loggia R et al. Topical anti-inflammatory activity of Salvia officinalis L. leaves: the relevance of ursolic acid. J Ethnopharmacol 2001; 75: 125-132 DOI ScienceOn |
27 | Huang MT, Ho CT, Wang ZY et al. Inhibition of skin tumorigenesis by rosemary and its constituents carnosol and ursolic acid. Cancer Res 1994; 154(3): 701-8 |
28 | Rogers J, Harding C, Mayo A et al. Stratum corneum lipids: the effects of ageing and the seasons. Arch Dermatol Res 1996; 288: 765-770 DOI |
29 |
Choi CY, You HJ, Jeong HG. Nitric oxide and tumor necrosis factor-a production by oleanolic acid via |
30 | Pinnagoda J, Tupker RA, Agner T ea al. Guidelines for transepidermal water loss (TEWL) measurement. A report from the Standardization Group of the European Society of Contact Dermatitis. Contact Dermatitis. 1990; 22: 164-178 DOI ScienceOn |
31 | Cha HJ, Park MT, Chung HY et al. Ursolic acid-induced down-regulation of MMP-9 gene is mediated through the nuclear translocation of glucocorticoid receptor in HT1080 human fibrosarcoma cells. Oncogene 1998; 16: 771-778 DOI |
32 | Landmann L. Epidermal permeability barrier: transformation of lamella-granule disks into intercellular sheets by membrane-fusion process, a freeze-fracture study. J Invest Dermatol 1986; 87: 202-209 DOI ScienceOn |
33 | Gendimenico GJ, Mezick JA. Pharmacological effects of retinoids on skin cells. Skin Pharmacol 1993; 6: 24-34 DOI |
34 | Downing DT. Lipid and protein structures in the permeability barrier of mammalian epidermis. J Lipid Res 1992; 33: 301-313 PUBMED |
35 | Ahn SK, Hwang SM, Jiang SJ et al. The changes of epidermal calcium gradient and transitional cells after prolonged occlusion followinq tape stripping in murine epidermis. J Invest Dermatol 1999; 113: 189-195 DOI ScienceOn |
36 | Giner-Larza EM, Manez S, Recio MC et al. Oleanolic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity. Eur J Pharmacol 2001; 428: 137-143 DOI ScienceOn |
37 | Assefa H, Nimrod A, Walker L et al. Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid. Bioorg Med Chem Lett 2001; 11: 1619-1623 DOI ScienceOn |
38 | Mahto SB, Sarkar SK, Poddar G. phytochemistry 1988; 7: 3037-3067 |
39 | Nishimori Y, Tsuruoka H, Matsumoto K et al. A new approach for the improvement of photoaged skin through collagen fiber bundle reconstruction mechanism. In: Proceedings of the 20th International Federation of Societies of Cosmetic Chemists Congress, Section O009, pp 1-21 |
40 | Yarosh DB, Both D, Brown D. Liposomal ursolic acid (merotaine) increases ceramides and collagen in human skin. Horm Res 2000; 54: 318-321 DOI ScienceOn |
41 | Lampe MA, Williams ML, Elias PM. Human epidermal lipids: Characterization and modulations during differentiation. J Lipid Res 1983; 24: 131-140 PUBMED |
42 | Steinert PM. The complexity and redundancy of epithelial barrier function. J Cell Biol 2000; 151: F5-F8 DOI PUBMED |
43 | Hollosy F, Idei M, Csorba G et al. Activation of caspase-3 protease during the process of ursolic acid and its derivative-induced apoptosis. Anticancer Res 2001; 21: 3485-3491 PUBMED |
44 | Muto Y, Ninomiya M, Fujiki H. Present status research on cancer chemoprevention in Japan. Japanese J. of Clinical Oncology 1990; 20: 219-224 |
45 | Ryu SY, Oak MH, Yoon SK et al. Anti-allergic and anti-inflammatory triterpenes from the herb of Prunella vulgaris. Planta Med 2000; 66: 358-360 DOI ScienceOn |
46 | Imokawa G, Akasaki S, Kawamata A et al. Water-retaining function in the stratum corneum and its recovery properties by synthetic pseudoceramide. J Soc Cosmet Chem 1989; 40: 273-285 |
47 | James AEK, Timothy DW and Gorden L. Inhibition of human leucocyte and porcine pancreatic elastase by homologues of bovine pancreatic truosin inhibitors. Biochemistry 1996; 35: 9090-9096 DOI ScienceOn |
48 | Choi EH, Ahn SK, Lee SH. The changes of stratum corneum interstices and calcium distribution of follicular epithelium of experimentally induced comedones (EIC) by oleic acid. Exp Dermatol 1997; 6: 29-35 DOI ScienceOn |
49 | Griffiths CEM, Voorhees JJ. Topical retinoic acid for photoaging: clinical response and underlying mechanisms. Skin Pharmacol 1993; 6: 70-77 DOI |
50 | Schurer NY, Elias PM. The biochemistry and function of stratum corneum lipids. In: Elias P(ed.) Skin Lipids, Advances in Lipid Res San Diego: Academic Press, 1991; 24: 27-56 |
51 | Saraswat B, Visen PK, Agarwal DP. Ursolic acid isolated from Eucalyptus tereticornis protects against ethanol toxicity in isolated rat hepatocytes. Phytother Res 2000; 14: 163-166 DOI ScienceOn |
52 | Tsukahara K. Moriwaki S, Fujimura T et al. Inhibitory effect of an extract of Sanguisorba officinalis L. on ultraviolet-B-Induced photodamage of rat skin. Biol Pharm Bull 2001; 24:998-1003 DOI ScienceOn |
53 |
Hanley K, Jiang Y, Crumrine D et al. Activators of the nuclear hormone receptors PPAR |
54 | Wertz PW, Downing DT. Epidermal lipids. In: Golsmith LA(ed.) Physiology, Biochemistry and Molecular Biology of the skin. New York: Oxford University Press, 1991; 205-236 |
55 | Komuves LG, Hanley K, Man MQ et al. Keratinocytes differentiation in hyperproliferative epidermis: topical application of PPAR a activators restores tissue homeostasis. J Invest Dermatol 2000; 115: 361-367 DOI ScienceOn |
56 | Alvarez ME, Maria AO, Saad JR. Diuretic activity of Fabiana patagonica in rats. Phytother Res 2002; 16: 71-73 PUBMED |
57 | Xu HE, Lambert MH, Montana VG et al. Molecular recognition of fatty acids by peroxisome proliferator-activated receptors. Mol Cell 1999; 3: 397-403 DOI ScienceOn |
58 | Both D, Goodzova K, Yarosh DB et al. Liposome-encapsulated ursolic acid increased ceramides and collagen in human skin cells. Arch Dermatol Res 2002; 293: 569-575 PUBMED |
59 | Hollosy F, Meszaros G, Bokonyi G et al. cytotoxic and protein tyrosine kinase inhibitory activity of ursolic acid in A431 human tumor cells. Anticancer Res 2000; 20: 4563-4570 PUBMED |
60 | Li J, Xu LZ, Zhu WP et al. Effects of ursolic acid and oleanolic acid on Jurkat lymphoma cell line in vitro. Zhongguo Aizheng Zazhi 1999; 9: 395-397 |
61 | Bolognia JL, Braverman IM, Rousseau ME et al. Skin changes in menopause. Maturitas 1989; 11:295-304 DOI |
62 | Tokuda, H., Ohigashi, H., Koshimizu, K et al. Inhibitory effects of ursolic and oleanolic acid on skin tumor promotion by 12-O-tetradecanoylphorbol-13-acetate. Cancer Letters 1986; 33:279-285 DOI ScienceOn |
63 | Grubauer G, Feingold KR, Elias PM. Transepidermal water loss: the signal for recovery of barrier structure and function. J Lipid Res 1989; 30: 323-333 PUBMED |
64 | Yim TK, Wu WK, Pak WF et al. Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice. Phytother Res 2001; 15: 589-592 DOI ScienceOn |
65 | Mangelsdorf DJ, Evans RM. The RXR heterodimers and orphan receptors. Cell 1995; 83:841-850 DOI ScienceOn |
66 | Martin-Cordero C, Reyes M, Ayuso MJ et al. Cytotoxic triterpenoids from Erica andevalensis. Z Naturforsch [C] 2001; 56: 45-48 PUBMED |
67 | Uitto J, Bernstein EF. Molecular mechanisms of cutaneous aging: connective tissue alterations in the dermis. J Invest Dermatol 1998; 3: 41-44 |
68 | Ko HH, Yen MH, Wu RR et al. Cytotoxic isoprenylated flavans of Broussonetia kazinoki. J Nat Prod 1999; 62: 164-166 DOI ScienceOn |
69 | Gottlicher M, Widmark E, Li Q et al. Fatty acids activate a chimera of the clofibric acid-activated receptor and the glucocorticoid receptor. Proc Natl Acad Sci USA 1992 15; 89: 4653-4657 DOI ScienceOn |
70 | Gottlicher M, Demoz A, Svensson D et al. Structural and metabolic requirements for activators of the peroxisome proliferator-activated receptor. Biochem Pharmacol 1993; 46: 2177-2184 DOI ScienceOn |
71 | Mukherjee R, Strasser J, Jow L et al. RXR agonists activate PPAR -inducible genes, lower triglycerides, and raise HDL levels in vivo. Arterioscler Thromb Vasc Biol 1998; 18: 272-276 PUBMED |
72 | Liu J Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 1995; 49: 57-68 |
73 | Ismaili H, Tortora S, Sosa S et al. Topical anti-inflammatory activity of Thymus willdenowii. J Pharm Pharmacol 2001; 53: 1645-1652 DOI ScienceOn |
74 | Elias PM and Menon GK. Structural and lipid biochemical correlates of the epidermal permeability barrier. Adv Lipid Res 1991; 24: 1-26 |
75 | Hanley K, Jiang Y, He SS et al. Keratinocyte differentiation is stimulated by activators of the nuclear hormone receptor peroxisome proliferator-activated receptor-a. J Invest Dermatol 1998; 110: 368-375 DOI ScienceOn |
76 | Yu K, Bayona W, Kallen CB et al. Differential activation of peroxisome proliferator-activated receptors by eicosanoids. J Biol Chem 1995; 270: 23975-23983 DOI ScienceOn |
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