Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells

Both, Dawn; Goodtzova, Karina; Yarosh, Daniel B.; Brown, David A.

doi:10.1007/s00403-001-0272-0

Cited by 52 publications

(44 citation statements)

References 27 publications

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“…As ursolic acid represents a promising chemical entity for the protection of human skin, in agreement with tests done by the cosmetic industry. 145,146 4.Structure similarity of ursolic acid 4.1.Induction of apoptosis in HeLa cells by 3β-hydroxyurs-12-en-27-oic acid 3-β-Hydroxy urs-12-en-27-oic acid (4), was structurally very similar to ursolic acid, with the only difference being the interchange of the COOH and Me group at C-14 and C-17.…”

Section: 3the Treatment Of Wrinkles With Ursolic Acid In Clinical mentioning

confidence: 99%

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

Sultana

2011

Journal of Enzyme Inhibition and Medicinal Chemistry

102

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Medicinal plants are becoming an important research area for novel and bioactive molecules for drug discovery. Novel therapeutic strategies and agents are urgently needed to treat different incurable diseases. Many plant derived active compounds are in human clinical trials. Currently ursolic acid is in human clinical trial for treating cancer, tumor, and skin wrinkles. This review includes the clinical use of ursolic acid in various diseases including anticancer, antitumor, and antiwrinkle chemotherapies, and the isolation and purification of this tritepernoid from various plants to update current knowledge on the rapid analysis of ursolic acid by using analytical methods. In addition, the chemical modifications of ursolic acid to make more effective and water soluble derivatives, previous and current information regarding, its natural and semisynthetic analogs, focusing on its anticancer, cytotoxic, antitumor, antioxidant, antiinflammatory, anti-HIV, acetyl cholinesterase, α-glucosidase, antimicrobial, and hepatoprotective activities, briefly discussion is attempted here for its research perspectives. This review article contains fourteen medicinally important ursolic acid derivatives and 351 references.

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Section: 3the Treatment Of Wrinkles With Ursolic Acid In Clinical mentioning

confidence: 99%

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

Sultana

2011

Journal of Enzyme Inhibition and Medicinal Chemistry

102

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“…To overcome this disadvantage, some alternatives have been proposed, including complexation with cyclodextrines (Li, 2009) and encapsulation in liposomes (Both et al, 2002); however none of these approaches have been evaluated for the enhancement of the trypanocidal activity. In previous studies, our group incorporated ursolic acid in solid dispersion formulations, which are mixtures of lipophilic drugs and hydrophilic carriers, resulting in improvement of drug solubility and dissolution profile as a consequence of decreased particle size, improved wettability and presence of drug in the more soluble molecular or amorphous state (Eloy et al, 2012a;Eloy, Marchetti, 2014;Vasconcelos, Sarmento, Costa, 2007).…”

Section: Introductionmentioning

confidence: 99%

Preparation, characterization and evaluation of the in vivo trypanocidal activity of ursolic acid-loaded solid dispersion with poloxamer 407 and sodium caprate

Eloy

Saraiva

Albuquerque

et al. 2015

Braz. J. Pharm. Sci.

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Ursolic acid is a promising candidate for treatment of Chagas disease; however it has low aqueous solubility and intestinal absorption, which are both limiting factors for bioavailability. Among the strategies to enhance the solubility and dissolution of lipophilic drugs, solid dispersions are growing in popularity. In this study, we employed a mixture of the surfactants poloxamer 407 with sodium caprate to produce a solid dispersion containing ursolic acid aimed at enhancing both drug dissolution and in vivo trypanocidal activity. Compared to the physical mixture, the solid dispersion presented higher bulk density and smaller particle size. Fourier Transform Infrared Spectroscopy results showed hydrogen bonding intermolecular interactions between drug and poloxamer 407. X-ray diffractometry experiments revealed the conversion of the drug from its crystalline form to a more soluble amorphous structure. Consequently, the solubility of ursolic acid in the solid dispersion was increased and the drug dissolved in a fast and complete manner. Taken together with the oral absorption-enhancing property of sodium caprate, these results explained the increase of the in vivo trypanocidal activity of ursolic acid in solid dispersion, which also proved to be safe by cytotoxicity evaluation using the LLC-MK2 cell line. O ácido ursólico é um candidato promissor para o tratamento da doença de Chagas, contudo este fármaco possui baixa solubilidade aquosa e limitada absorção intestinal, ambos os fatores limitantes da biodisponibilidade. Entre as estratégias para potencializar a solubilidade e a dissolução de fármacos lipofílicos, as dispersões sólidas estão crescendo em popularidade. Neste estudo, empregamos mistura dos tensoativos, poloxamer 407 e caprato de sódio, para produzir dispersão sólida contendo ácido ursólico, com o objetivo de aumentar tanto a dissolução do fármaco quanto a atividade tripanocida in vivo. Comparada à mistura física, a dispersão sólida apresentou maior densidade e menor tamanho de partícula. Os resultados da análise de espectroscopia no infravermelho com transformada de Fourier mostraram interações intermoleculares do tipo ligações de hidrogênio entre o fármaco e o poloxamer 407. Os experimentos de difratometria de raio-X revelaram a conversão do fármaco de sua forma cristalina para a forma amorfa, mais solúvel. Consequentemente, a solubilidade do ácido ursólico em dispersão sólida foi aumentada e o fármaco dissolveu-se de maneira mais rápida e completa. Em conjunto com as propriedades promotoras de absorção oral do caprato de sódio, estes resultados explicaram o aumento da atividade tripanocida in vivo do ácido ursólico em dispersão sólida, que também se provou segura após avaliação de citotoxicidade empregando a linhagem celular LLC-MK2.Unitermos: Ácido ursólico/atividade tripanocida. Doença de Chagas/tratamento. Tensoativos. Dispersões sólidas/dissolução. Poloxamer 407. Caproato de sódio.

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“…Several studies have shown that the levels of all major SC lipids, in particular CERs, decrease with increasing age [76,77]. Jin et al [78] reported that SC CERs decrease by approximately 10-15% per decade after the age of 20 years.…”

Section: Factors Affecting the Composition And Organization Of Sc Lipidsmentioning

confidence: 99%

Skin Diseases Associated with the Depletion of Stratum Corneum Lipids and Stratum Corneum Lipid Substitution Therapy

Sahle

Gebre‐Mariam²,

Dobner³

et al. 2014

Skin Pharmacol Physiol

170

164

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The skin is the largest organ of the body, whose main function is to protect the body against the loss of physiologically important components as well as harmful environmental insults. From the inside to the outside, the skin comprises three major structural layers: the hypodermis, the dermis and the epidermis. The epidermis contains four different sublayers, the stratum corneum (SC), stratum granulosum, stratum spinosum and stratum basale, where the barrier function of the skin mainly lies in the outermost layer of the epidermis, the SC. The SC contains corneocytes that are embedded in a lipid matrix existing in the form of lipid bilayers. The lipid bilayers are formed mainly from ceramides, free fatty acids and cholesterol, constitute the only continuous pathway across the SC and are responsible for the barrier function of the skin. However, the depletion or disturbance of SC lipids in the SC leads to a perturbation of the barrier function of the skin, and, conversely, several skin diseases such as psoriasis and atopic dermatitis are associated with the depletion of these SC lipids. Therefore, it is of paramount importance to understand the interrelationship between the depletion of SC lipids and skin diseases as well as factors that affect the composition and organization of SC lipids in order to assess the potential benefit of a direct replacement of the missing SC lipids as a means of treating affected, aged or diseased skin. i 2014 S. Karger AG, Basel

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Liposome-encapsulated ursolic acid increases ceramides and collagen in human skin cells

Cited by 52 publications

References 27 publications

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

Clinically useful anticancer, antitumor, and antiwrinkle agent, ursolic acid and related derivatives as medicinally important natural product

Preparation, characterization and evaluation of the in vivo trypanocidal activity of ursolic acid-loaded solid dispersion with poloxamer 407 and sodium caprate

Skin Diseases Associated with the Depletion of Stratum Corneum Lipids and Stratum Corneum Lipid Substitution Therapy

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