See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/291136460 Bioactive Compounds of Aristotelia chilensis Stuntz and Their Pharmacological Effects Article in Current pharmaceutical biotechnology · January 2016 DOI: 10.2174/1389201017666160114095246 CITATIONS READS 6 503 8 authors, including: Armando Zarrelli Valeria Romanucci University of Naples Federico II University of Naples Federico II 103 PUBLICATIONS 1,445 CITATIONS 30 PUBLICATIONS 96 CITATIONS SEE PROFILE SEE PROFILE Annalisa Guaragna Giovanni Scapagnini University of Naples Federico II Università degli Studi del Molise 66 PUBLICATIONS 541 CITATIONS 128 PUBLICATIONS 5,625 CITATIONS SEE PROFILE SEE PROFILE Some of the authors of this publication are also working on these related projects: synthesis of new organocatalysts View project Gymnema sylvestre R. Br. View project All content following this page was uploaded by Armando Zarrelli on 20 April 2016. The user has requested enhancement of the downloaded file. Send Orders for Reprints to [email protected] Current Pharmaceutical Biotechnology, 2016, 17, 000-000 1 Bioactive Compounds of Aristotelia chilensis Stuntz and their Pharmacol- ogical Effects Valeria Romanucci1, Daniele D’Alonzo1, Annalisa Guaragna1, Cinzia Di Marino1, Sergio Davinelli2, 3 1 1* Giovanni Scapagnini , Giovanni Di Fabio and Armando Zarrelli 1Department of Chemical Sciences, University Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy; 2University of Molise, Department of Medicine and Health Science, 86100 Campobasso, Molise, Italy; 3Inter-University Consortium “SannioTech”, 82030 Apollosa, Benevento, Italy Abstract: Aristotelia chilensis ([Molina], Stuntz) a member of the family Eleocarpaceae, is a plant na- tive to Chile that is distributed in tropical and temperate Asia, Australia, the Pacific Area, and South America. The juice of its berries has important medicinal properties, as an astringent, tonic, and anti- A. Zarrelli diarrhoeal. Its many qualities make the maqui berry the undisputed sovereign of the family of so-called "superfruits", as well as a valuable tool to combat cellular inflammation of bones and joints. Recently, it is discovered that the leaves of the maqui berry have important antibacterial and antitumour activities. This review provides a comprehen- sive overview of the traditional use, phytochemistry, and biological activity of A. chilensis using information collected from scientific journals, books, and electronic searches. Anthocyanins, other flavonoids, alkaloids, cinnamic acid deriva- tives, benzoic acid derivatives, other bioactive molecules, and mineral elements are summarized. A broad range of activi- ties of plant extracts and fractions are presented, including antioxidant activity, inhibition of visible light-induced damage of photoreceptor cells, inhibition of α-glucosidase, inhibition of pancreatic lipase, anti-diabetic effects, anti-inflammatory effects, analgesic effects, anti-diabetes, effective prevention of atherosclerosis, promotion of hair growth, anti-photo age- ing of the skin, and inhibition of lipid peroxidation. Although some ethnobotanical uses have been supported in in vitro experiments, further studies of the individual compounds or chemical classes of compounds responsible for the pharma- cological effects and the mechanisms of action are necessary. In addition, the toxicity and the side effects from the use of A. chilensis, as well as clinical trials, require attention. Keywords: Aristotelia chilensis, functionals foods, traditional uses, phytochemical investigation, secondary metabolites, bio- logical activity. 1. INTRODUCTION The Mapuche Indians have medicinally used the maqui berry leaves, stems, fruits and wine for thousands of years. The maqui (Aristotelia chilensis), commonly known as maqui berry, clon, queldron, koelon or Chilean wineberry, is Traditionally, it is believed to heal wounds, relieve sore a delicious, dark red or purplish, sweet tasting, dry berry (it throats and act as an analgesic. Today, the maqui berry is resembles the elder, Sambucus nigra) of approximately 4-5 regarded as a “super fruit” due to its superior antioxidant mm in diameter, very similar to the blueberry, that ripens properties. from December to January [1]. The berries are rich in antho- cyanins (delphinidins and cyanidins), antioxidants responsi- 2. TAXONOMY, MORPHOLOGY AND DISTRIBU- ble for their purple coloration and, in all likelihood, for many TION of the medicinal properties attributed to it. For centuries, the The maqui belongs to the Eleocarpaceae family, with 10 therapeutic qualities of the maqui have been known to the genera and approximately 400 species. It is native to the Mapuche, indigenous people who have traditionally lived in Valdivian temperate rainforests of Chile and is distributed in the southern part of Chile. According to the conquistadors, tropical and temperate Asia, Australia, the Pacific Area, and the Mapuche warriors ate very little solid food and drank South America, but not Africa. It is found up to 2,500 m in both a fresh and a fermented beverage made from maqui elevation. It has white flowers and is a pioneer of deforested berry called “chicha”, which might have contributed to the or burned areas, growing in moist soil with plenty of humus. strength and stamina that the warriors exhibited. It grows on an evergreen bush that reaches approximately 3 to 4 metres high that flowers from September to December *Address correspondence to this author at the Department of Chemical [1]. The genus Aristotelia is so named in honour of the phi- Sciences, University Federico II, Complesso Universitario Monte S. Angelo, losopher Aristotle (384-323 BC). This plant was introduced Via Cintia 4, 80126 Napoli, Italy; Tel: +39-081-674472; Fax: +39-081- to the southeast of England in the 1700s and early 1900 to 674393; E-mail: [email protected] 1389-2010/16 $58.00+.00 © 2016 Bentham Science Publishers 2 Current Pharmaceutical Biotechnology, 2016, Vol. 17, No. 5 Romanucci et al. the United States (Seattle, Washington, California), where contain alkaloids that have a high antioxidant capacity. Their they call it "Chilean wineberry". It is grown in nurseries and use is in the preparation of infusions that fight irritation of then planted in acidic or slightly alkaline soils in the sun and the throat and that are analgesic and antipyretic. Recently, it shade. It can withstand temperatures to -10 °C. It propagates was discovered that the leaves of the maqui berry have im- by seed or cuttings. In Chile, industrial production does not portant antibacterial and antitumour activities. occur, and most of the berries are harvested from wild plants (90,000 kg per year). A mature plant produces 10 kg of fruit 4. PHYTOCHEMICAL INVESTIGATIONS every 7 years. The taxonomy of the plant is described in Table 1. Phytochemical screening of maqui extract (fruits or leaves) revealed the presence of anthocyanins, other flavon- oids, alkaloids, cinnamic acid derivates, benzoic acid deriva- Table 1. Taxonomy of A. chilensis. tives, other bioactive molecules, and mineral elements. Kingdom Plantae 4.1. Anthocyanins and Other Flavonoids Sub-kingdom Tracheobionta An increasing number of studies suggest that the con- sumption of fruits, vegetables, and beverages rich in pheno- Division Magnoliophyta (ex Angiospermae) lic antioxidants protects against cardiovascular disease. Ber- Class Magnoliopsida (ex Dicotyledones) ries and their derived products have shown a positive impact on several chronic conditions, including obesity, cancer, and Sub-class Dillenidae cardiovascular and neurodegenerative diseases. Their bio- logical properties have been largely attributed to high levels Order Malvales or Oxidales of various phenolic compounds, as well as to the interactive Sub-order Sterculiinae synergies between their natural phytochemical components. Like other fruits, berries contain high levels of various phe- Family Elaeocarpaceae nolic compounds. In the pulp or coat, the maqui berry con- Genus Aristotelia tains a particularly high concentration of anthocyanins and, to a lesser extent, other flavonoids. After different extraction Species chilensis and hydrolysis procedures, the isolation and purification of individual anthocyanins and flavonoids was performed by paper chromatography [2], open column chromatography 3. TRADITIONAL USE AND PROPERTIES [3], Sephadex LH-20, preparative, and reversed phase high- From the berries, a commercial product juice is obtained performance liquid chromatography (RP-HPLC) with diode with important medicinal properties, such as astringent, array detection (DAD) and mass spectrometry (ESIMS). tonic, and anti-diarrhoeal, and a natural dye from the antho- Total quantification was obtained using the colorimetric Fo- cyanin pigments of the red berries. Its many qualities make lin-Ciocalteu method [4-5], while their structure was deter- 1 13 the maqui berry the undisputed sovereign of the family of so- mined by UV, H-NMR and C-NMR spectra and by direct called "superfruits", and it is considered superior to goji, comparison with authentic samples. In particular, anthocyan- mirtili, cranberry, elderberry, blackcurrant and acai, as well ins are present as derivatives of delphinidin, malvidin, pe- as a valuable tool to combat cellular inflammation of bones tunidin, cyanidin, peonidin and their derivatives linked to and joints [1]. In Chile, the maqui berries are used to make different sugars (glucose, rhamnose,