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Biological properties of Cistus species. 127 © Wydawnictwo UR 2018 http://www.ejcem.ur.edu.pl/en/ ISSN 2544-1361 (online); ISSN 2544-2406 European Journal of Clinical and Experimental Medicine doi: 10.15584/ejcem.2018.2.8 Eur J Clin Exp Med 2018; 16 (2): 127–132 REVIEW PAPER Agnieszka Stępień 1(ABDGF), David Aebisher 2(BDGF), Dorota Bartusik-Aebisher 3(BDGF) Biological properties of Cistus species 1 Centre for Innovative Research in Medical and Natural Sciences, Laboratory of Innovative Research in Dietetics Faculty of Medicine, University of Rzeszow, Rzeszów, Poland 2 Department of Human Immunology, Faculty of Medicine, University of Rzeszów, Poland 3 Department of Experimental and Clinical Pharmacology, Faculty of Medicine, University of Rzeszów, Poland ABSTRACT Aim. This paper presents a review of scientific studies analyzing the biological properties of different species of Cistus sp. Materials and methods. Forty papers that discuss the current research of Cistus sp. as phytotherapeutic agent were used for this discussion. Literature analysis. The results of scientific research indicate that extracts from various species of Cistus sp. exhibit antioxidant, antibacterial, antifungal, anti-inflammatory, antiviral, cytotoxic and anticancer properties. These properties give rise to the pos- sibility of using Cistus sp. as a therapeutic agent supporting many therapies. Keywords. biological properties, Cistus sp., medicinal plants Introduction cal activity which elicit healing properties. Phytochem- Cistus species (family Cistaceacea) are perennial, dicot- ical studies using chromatographic and spectroscopic yledonous flowering shrubs in white or pink depend- techniques have shown that Cistus is a source of active ing on the species. Naturally growing in Europe mainly bioactive compounds, mainly phenylpropanoids (flavo- in the Mediterranean region and in western Africa and noids, polyphenols) and terpenoids. Asia.1-3 These plants are capable of growing in difficult These compounds determine the medicinal proper- climatic and soil conditions.4,5 For many years, plants of ties of Cistus such as anti-inflammatory, antibacterial, the genus Cistus sp. were used in folk medicine mainly antifungal, antiviral, anti-allergic and strengthening the in Mediterranean regions as infusions, extracts and as a body’s resistance and an analgesic effect which allows resin Ladano in the treatment of many diseases. their use as therapeutic agents in a wide range of dis- Modern scientific research has focused on the iso- eases.6-19 lation and identification of compounds present in ex- This article presents the biological and pharmaco- tracts, and resins from various species of Cistus. Studies logical properties of various species of Cistus sp., with have also analyzed their biological and pharmacologi- Corresponding author: Agnieszka Ewa Stępień, e-mail: [email protected] Participation of co-authors: A – Author of the concept and objectives of paper; B – collection of data; C – implementation of re- search; D – elaborate, analysis and interpretation of data; E – statistical analysis; F – preparation of a manuscript; G – working out the literature; H – obtaining funds Received: 13.04.2018 | Accepted: 06.05.2018 Publication date: June 2018 Stępień A, Aebisher D, Bartusik-Aebisher D. Biological properties of “Cistus species”. Eur J Clin Exp Med. 2018;16(2):127–132. doi: 10.15584/ejcem.2018.2.8 128 European Journal of Clinical and Experimental Medicine 2018; 16 (2): 127–132 It was also confirmed that other Cistus species in- cluding Cistus incanus L., and Cistus monspeliensis L., contain numerous compounds with antioxidant po- tential, among others polyphenols and flavonoids.23,24 Their antioxidative capacity was also examined, due to the presence of phenols, flavonoids and tannins of the obtained ethanol, hexane and water extracts from the leaves of Cistus monspeliensis and Cistus salvifolius. The highest antioxidant activity was demonstrated by etha- nol extracts from both Cistus species. The research re- Fig. 1. Dried herb leaves Cistus incanus (photograph by sults indicate that the proper selection of the type of Agnieszka Ewa Stępień) solvent affects obtaining of an extract with a high con- tent of antioxidants. particular emphasis on Cistus creticus, Cistus creticus Research by Loizzo et al. (2013) indicated that the subspecies cretenicus L., Cistus creticus subspecies cre- essential oils of the species Cistus creticus, Cistus salv- ticus, Cistus creticus subspecies eriocephalus, Cistus in- ifolius, Cistus libanotis, Cistus monspeliensis and Cistus canus L., Cistus inacus, Cistus inacus subspecies creticus, villosus exhibit antioxidant properties.16 They indicat- Cistus inacus subspecies tauricus, Cistus monspeliensis L., ed that the greatest antioxidant properties have essential Cistus libanotis, Cistus villosus, Cistus villosus L., Cistus oils derived from Cistus monspeliensis and Cistus libano- monspeliensis, Cistus ladanifer, Cistus populifolius, Cis- tis. They also analyzed their acetylcholinesterase and tus salviifolius, Cistus parviflorus, and Cistus laurifolius. butyrylcholinesterase (BChE) inhibitory activity. Cistus Their antioxidant, antibacterial, antifungal, antiviral, cy- salvifolius species were characterized by the highest ac- totoxic and anti-cancer properties have been particular- tivity against AChE, while Cistus libanotis, Cistus creti- ly emphasized. cus, Cistus salvifolius had good inhibitory activity against Cistus sp. species are a rich source of natural com- BChE.There were 26 types of antioxidant present in the pounds with antioxidant properties, mainly flavonoids leaves and flower buds of Cistus salviifolius. The highest and polyphenols. The ability of antioxidants to capture concentration of phenols and flavonoids were record- toxic oxygen free radicals is very important. Oxygen re- ed in extracts from flower buds, while tanning agents active forms such as peroxides, superoxide, peroxy and and anthocyanins were found in leaf extracts. The ob- hydroxy radicals play an important role in oxidative tained results indicated that the leaf extract was charac- stress contributing to the development of many diseases terized by a higher inhibitory activity against the AChE including diabetes and Alzheimer’s disease. enzyme as compared to the extracts from flower buds. It was confirmed that the speciesCistus laurifoli- This activity is probably due to the higher content of an- us is characterized by antioxidant properties.20 In the thocyanins in the Cistus salviifolius leaf extract that may extract from leaves and small branches of Cistus lauri- have a significant effect on the inhibition of this enzyme. folius the presence of 16 bioactive compounds was de- The results of the above research work emphasize that termined by 1H and 13C NMR techniques and EI-MS extracts from the above Cistus species are a source of mass spectrometry. The following compounds from Cis- compounds with high antioxidant potential and can be tus laurifolius have shown the ability to capture free rad- used in therapy for many diseases caused by oxidative icals: 3-0-methyl quercetin (1), 3,7-0-dimethyl quercetin stress and may be helpful in the prevention and treat- (2), ellagic acid (8), quercetin 3-0-α-rhamnoside (10), ment of Alzheimer’s disease. 1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-α-L-rhamno- It has been determined that polyphenol compounds pyranoxypropyl)-2-methoxyphenoxy]-1,3-propanediol with antioxidant properties present in extracts also have (12), olivil 9-O-β-D-xyloside (13), berchemol 9-O-rham- antiviral properties. Activity against the influenza virus noside (14) and (7S,8R)-dihydrodehydrodiconiferyl al- from extracts derived from Cistus incanus spp. tauricus cohol 9’-O-α-L-rhamnoside (major isomer) (16).20 It was was found without negative side effects.13 observed that Cistus incanus and Cistus parviflorus both Researchers also point to the valuable antibacteri- show high activity of scavenging free toxic radicals.21 al and antifungal properties of Cistus species that result In subsequent studies, it was observed that the con- from their antioxidant activity, i.e. phenolic compounds.18 tent of antioxidant phenolic compounds in extracts of Antibacterial and antifungal properties of leaf extracts Cistus populifolius is higher than for Cistus ladanifer. of Cistus villosus L. (= incanus) and Cistus monspeliensis Also, analysis of the ability of extracts to inhibit the for- L. were determined against Gram-positive Staphylococ- mation of lipid peroxyl radicals confirmed that Cistus cus aureus and Gram-negative Pseudomonas aerugi- populifolius has higher antioxidant activity than Cistus nosa and the fungi Candida glabrata, Candida krusei ladanifer.22 and Aspergillus fumigatus. Extracts from Cistus villo- Biological properties of Cistus species. 129 sus showed higher activity than those from Cistus mon- coli, P. aeruginosa and C. albicana.25 Scientific research speliensis against Staphylococcus aureus and Candida indicates that the extracts of Cistus sp. can be potentially glabrata. However, Candida krusei and Aspergillus fumi- used as an adjuvant for the treatment of inflammation gatus were characterized as the most resistant among all caused by the undesirable effects of microorganisms. tested microorganisms for both extracts. The tests were Scientific research indicates and confirms the pres- carried out using chloramphenicol, amoxicillin and am- ence in many plants, including Cistus sp, of compounds photericin B as standard antibiotics for
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    UNIVERSIDADE DA BEIRA INTERIOR Ciências Preparação de Derivados Bioativos de Dammaranos Tiago Alexandre Pereira Abrantes Dissertação para obtenção do Grau de Mestre em Química Industrial (2º ciclo de estudos) Orientador: Professor Doutor Jesus Miguel Lopez Rodilla Co-orientador: Professor Doutor Pedro Miguel de Mendonça Rocha Covilhã, Outubro de 2014 ii Dedicatória Dedico este trabalho aos meus pais, à minha namorada, à família e aos meus amigos que foram determinantes para todo o meu sucesso académico. Em especial dedico este trabalho ao meu falecido avô que tanto me ensinou e serviu de fonte de inspiração. iii iv Agradecimentos Depois de tanto esforço e dedicação chega a altura emocionante em que se relembra todos os momentos passados, bem ou mal, no desenvolvimento deste Projeto e tanto há para agradecer a todos o que tornaram isto possível e estiveram la nas alturas mais necessárias, por isso aqui vai o meu obrigado… Em primeiro lugar agradecer ao Professor Doutor Jesus Rodilla, por toda a sua orientação científica e disponibilidade para ajuda deste Projeto sem o qual não seria possível a sua conclusão. Agradeço também ao Professor Doutor Pedro Rocha por todo o apoio e material disponibilizado e o incentivo em momentos menos positivos, que foram mais do que importantes para o término deste trabalho. Obrigado Tenho também agradecer a todos os colegas do Laboratório BR – Laboratório Ambiental e Alimentar Lda, à Doutora Celina, Diana, Estela e Rui por todas as horas despendidas para me ajudar e todos os momentos de convívio em tardes de muito trabalho. Agradeço também à Andreia pelos momentos de descompressão e convívio sem os quais não era capaz de passar.