Piper Species: a Comprehensive Review on Their Phytochemistry, Biological Activities and Applications
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Review Piper Species: A Comprehensive Review on Their Phytochemistry, Biological Activities and Applications Bahare Salehi 1, Zainul Amiruddin Zakaria 2, Rabin Gyawali 3, Salam A. Ibrahim 3, Jovana Rajkovic 4, Zabta Khan Shinwari 5, Tariq Khan 5, Javad Sharifi-Rad 6,*, Adem Ozleyen 7, Elif Turkdonmez 7, Marco Valussi 8,*, Tugba Boyunegmez Tumer 9,*, Lianet Monzote Fidalgo 10, Miquel Martorell 11,* and William N. Setzer 12,13,* 1 Student Research Committee, School of Medicine, Bam University of Medical Sciences, Bam 44340847, Iran; [email protected] 2 Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; [email protected] 3 Department of Food and Nutritional Sciences, North Carolina A&T State University, Greensboro, NC 27411, USA; [email protected] (R.G.); [email protected] (S.A.I.) 4 Institute of Pharmacology, Clinical Pharmacology and Toxicology, Medical Faculty, University of Belgrade, 11129 Belgrade, Serbia; [email protected] 5 Department of Biotechnology, Quaid-i-Azam University, Islamabad, 45320, Pakistan; [email protected] (Z.K.S.); [email protected] (T.K.) 6 Food Safety Research Center (salt), Semnan University of Medical Sciences, Semnan 35198-99951, Iran 7 Graduate Program of Biomolecular Sciences, Institute of Natural and Applied Sciences, Canakkale Onsekiz Mart University, 17020 Canakkale, Turkey; [email protected] (A.O.); [email protected] (E.T.) 8 European Herbal and Traditional Medicine Practitioners Association (EHTPA), 25 Lincoln Close, GL20 5TY Tewkesbury, UK 9 Department of Molecular Biology and Genetics, Faculty of Arts and Science, Canakkale Onsekiz Mart University, 17020 Canakkale, Turkey 10 Parasitology Department, Institute of Tropical Medicine “Pedro Kouri”, 10400 Havana, Cuba; [email protected] 11 Department of Nutrition and Dietetics, Faculty of Pharmacy, University of Concepcion, 4070386 Concepcion, VIII-Bio Bio Region, Chile 12 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA 13 Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA * Correspondence: [email protected] (J.S.-R.); [email protected] (M.V.); [email protected] (T.B.T.); [email protected] (M.M.); [email protected] (W.N.S.); Tel.: +98-21-8820-0104 (J.S.-R.); +39-04592517561 (M.V.); +90-2862180018 ext. 1844 (T.B.T.); +56-41-266-1671 (M.M.); +1-256-824-6519 (W.N.S.) Received: 13 March 2019; Accepted: 3 April 2019; Published: 7 April 2019 Abstract: Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. These plants are rich in essential oils, which can be found in their fruits, seeds, leaves, branches, roots and stems. Some Piper species have simple chemical profiles, while others, such as Piper nigrum, Piper betle, and Piper auritum, contain very diverse suites of secondary metabolites. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In addition, Piper species could be used as natural antioxidants and antimicrobial agents in food preservation. The phytochemicals and essential oils of Piper species have shown strong antioxidant activity, in comparison with synthetic antioxidants, and demonstrated antibacterial and antifungal activities against human pathogens. Moreover, Piper species possess therapeutic and preventive potential against several chronic disorders. Among the functional properties of Piper plants/extracts/active Molecules 2019, 24, 1364; doi:10.3390/molecules24071364 www.mdpi.com/journal/molecules Molecules 2019, 24, 1364 2 of 117 components the antiproliferative, anti-inflammatory, and neuropharmacological activities of the extracts and extract-derived bioactive constituents are thought to be key effects for the protection against chronic conditions, based on preclinical in vitro and in vivo studies, besides clinical studies. Habitats and cultivation of Piper species are also covered in this review. In this current work, available literature of chemical constituents of the essential oils Piper plants, their use in traditional medicine, their applications as a food preservative, their antiparasitic activities and other important biological activities are reviewed. Keywords: pepper; essential oil; antimicrobial; traditional medicine; anticancer; anti-inflammatory Table of Contents 1. Introduction ......................................................................................................................................6 2. Habitat and cultivation of Piper plants ...........................................................................................7 2.1. Habitat of Piper nigrum L. .........................................................................................................7 2.2. Cultivation of Piper nigrum L. ..................................................................................................8 3. Chemical constituents of the essential oils of Piper species ...........................................................9 3.1. Piper aduncum L. ...................................................................................................................... 11 3.2. Piper amalago L. ....................................................................................................................... 15 3.3. Piper betle L. ............................................................................................................................. 16 3.4. Piper cubeba Bojer .................................................................................................................... 18 3.5. Piper nigrum L. ........................................................................................................................ 20 3.6. Piper longum L. ........................................................................................................................ 24 3.7. Piper arboreum Aubl. ............................................................................................................... 24 3.8. Piper auritum Kunth ................................................................................................................ 26 3.9. Piper cernuum Vell. .................................................................................................................. 26 3.10. Piper dilatatum Rich. .............................................................................................................. 28 3.11. Piper gaudichaudianum Kunth ............................................................................................... 29 3.12. Piper hispidum Sw. (including references to the synonym Piper hispidinervum C.DC.) ..... 31 3.13. Piper guineense Schumach. & Thonn .................................................................................... 34 3.14. Piper marginatum Jacq. .......................................................................................................... 34 3.15. Piper umbellatum L. ................................................................................................................ 36 3.16. Piper tuberculatum Jacq. ......................................................................................................... 36 3.17. Other Piper species ................................................................................................................ 39 4. Traditional uses of Piper species ................................................................................................... 55 4.1. Piper abbreviatum Opiz ............................................................................................................ 55 Molecules 2019, 24, 1364 3 of 117 4.2. Piper aduncum L. ...................................................................................................................... 55 4.3. Piper boehmeriifolium (Wall. ex Miq.) C.DC. ........................................................................... 56 4.4. Piper sylvaticum Roxb. ............................................................................................................. 56 4.5. Piper capense L.f. ...................................................................................................................... 56 4.6. Piper cubeba L. .......................................................................................................................... 56 4.7. Piper gibbilimbum C.DC. .......................................................................................................... 56 4.8. Piper guineense Schum and Thonn ......................................................................................... 56 4.9. Piper longum L. (syn. P. latifolium Forst.; P. chaba Hunter) .................................................... 57 4.10. Piper nigrum L........................................................................................................................ 57 4.11. Piper cavalcantei Yunck. ......................................................................................................... 58 4.12. Piper marginatum Jacq. .......................................................................................................... 58 4.13. Piper umbellatum L. ...............................................................................................................