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Cytotoxic Activity of Alkaloids from the Fruits of Piper Nigrum

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Cytotoxic Activity of Alkaloids from the Fruits of Piper Nigrum See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/329269696 Cytotoxic Activity of Alkaloids from the Fruits of Piper nigrum Article in Natural product communications · November 2018 CITATIONS READS 0 85 1 author: Thao Quyen Cao Wonkwang University 16 PUBLICATIONS 21 CITATIONS SEE PROFILE All content following this page was uploaded by Thao Quyen Cao on 07 December 2018. The user has requested enhancement of the downloaded file. Volume 13. Issue 11. Pages 1419-1568. 2018 ISSN 1934-578X (printed); ISSN 1555-9475 (online) www.naturalproduct.us NPC Natural Product Communications EDITOR-IN-CHIEF HONORARY EDITOR DR. PAWAN K AGRAWAL PROFESSOR GERALD BLUNDEN Natural Product Inc. The School of Pharmacy & Biomedical Sciences, 7963, Anderson Park Lane, University of Portsmouth, Westerville, Ohio 43081, USA Portsmouth, PO1 2DT U.K. [email protected] [email protected] EDITORS ADVISORY BOARD PROFESSOR MAURIZIO BRUNO Department STEBICEF, Prof. Giovanni Appendino Prof. Niel A. Koorbanally University of Palermo, Viale delle Scienze, Novara, Italy Durban, South Africa Parco d’Orleans II - 90128 Palermo, Italy Prof. Chiaki Kuroda [email protected] Prof. Norbert Arnold Halle, Germany Tokyo, Japan PROFESSOR CARMEN MARTIN-CORDERO Department of Pharmacology, Faculty of Pharmacy, Prof. Yoshinori Asakawa Prof. Hartmut Laatsch Tokushima, Japan Gottingen, Germany University of Seville, Seville, Spain [email protected] Prof. Vassaya Bankova Prof. Marie Lacaille-Dubois PROFESSOR VLADIMIR I. KALININ Sofia, Bulgaria Dijon, France G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Prof. Roberto G. S. Berlinck Prof. Shoei-Sheng Lee Far Eastern Branch, Russian Academy of Sciences, São Carlos, Brazil Taipei, Taiwan Pr. 100-letya Vladivostoka 159, 690022, Vladivostok, Russian Federation Prof. Anna R. Bilia Prof. M. Soledade C. Pedras [email protected] Florence, Italy Saskatoon, Canada PROFESSOR YOSHIHIRO MIMAKI Prof. Geoffrey Cordell Prof. Luc Pieters School of Pharmacy, Chicago, IL, USA Antwerp, Belgium Tokyo University of Pharmacy and Life Sciences, Prof. Fatih Demirci Prof. Peter Proksch Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan Eskişehir, Turkey Düsseldorf, Germany [email protected] Prof. Phila Raharivelomanana PROFESSOR STEPHEN G. PYNE Prof. Francesco Epifano Chieti Scalo, Italy Tahiti, French Polynesia Department of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia Prof. Ana Cristina Figueiredo Prof. Stefano Serra [email protected] Lisbon, Portugal Milano, Italy PROFESSOR MANFRED G. REINECKE Prof. Cristina Gracia-Viguera Dr. Bikram Singh Department of Chemistry, Texas Christian University, Murcia, Spain Palampur, India Forts Worth, TX 76129, USA [email protected] Dr. Christopher Gray Prof. Marina Stefova Saint John, NB, Canada Skopj, Republic of Macodenia PROFESSOR WILLIAM N. SETZER Department of Chemistry, The University of Alabama in Huntsville, Prof. Dominique Guillaume Prof. Leandros A. Skaltsounis Huntsville, AL 35809, USA Reims, France Zografou, Greece [email protected] Prof. John L. Sorensen Prof. Duvvuru Gunasekar PROFESSOR PING-JYUN SUNG Tirupati, India Manitoba, Canada National Museum of Marine Biology and Aquarium Prof. Hisahiro Hagiwara Prof. Johannes van Staden Checheng, Pingtung 944 Niigata, Japan Scottsville, South Africa Taiwan [email protected] Prof. Judith Hohmann Prof. Valentin Stonik Szeged, Hungary Vladivostok, Russia PROFESSOR YASUHIRO TEZUKA Faculty of Pharmaceutical Sciences, Hokuriku University, Prof. Tsukasa Iwashina Prof. Winston F. Tinto Ho-3 Kanagawa-machi, Kanazawa 920-1181, Japan Tsukuba, Japan Barbados, West Indies [email protected] Prof. Leopold Jirovetz Prof. Sylvia Urban PROFESSOR DAVID E. THURSTON Vienna, Austria Melbourne, Australia Institute of Pharmaceutical Science Faculty of Life Sciences & Medicine Prof. Phan Van Kiem Prof. Karen Valant-Vetschera Hanoi, Vietnam Vienna, Austria King’s College London, Britannia House 7 Trinity Street, London SE1 1DB, UK [email protected] INFORMATION FOR AUTHORS Full details of how to submit a manuscript for publication in Natural Product Communications are given in Information for Authors on our Web site http://www.naturalproduct.us. Authors may reproduce/republish portions of their published contribution without seeking permission from NPC, provided that any such republication is accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. 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All issues are dispatched by airmail throughout the world, excluding the USA and Canada. 2018 NPC Natural Product Communications Vol. 13 No. 11 Cytotoxic Activity of Alkaloids from the Fruits of Piper nigrum 1467 - 1469 Quynh Mai Thi Ngo1, Thao Quyen Cao1, Le Son Hoang, Manh Tuan Ha, Mi Hee Woo and Byung Sun Min* College of Pharmacy, Daegu Catholic University, Gyeongbuk 38430, Republic of Korea 1These authors contributed equally to this work. [email protected] Received: July 27th, 2017; Accepted: September 3rd, 2018 Medicinal plants have been shown to have tremendous potential for the development of new drug molecules for various serious diseases. Piper nigrum L. (Piperaceae) is a well-known spice considered to be the “The King of Spices” among various spices. The phytochemicals isolated from P. nigrum L. are potent biological agents with anticancer properties. Our study was designed to evaluate the cytotoxic activities of chemical compounds from the dried fruits of P. nigrum L. Sixteen known compounds (1−16), including fifteen alkaloids, were isolated and identified. Compounds 10, 11, 12, 13, 14, and 15 exhibited cytotoxic activities against a human cervical cancer cell line, Hela, with IC50 values of 49.8, 40.4, 23.1, 22.1, 41.0, and 26.9 µM, respectively. Compounds 10, 12, and 15 exhibited cytotoxicities against a breast cancer cell line, MCF-7, with IC50 values of 36.9, 55.7, and 36.0 µM, respectively. Compounds 6, 12, 13, 14, 15, and 16 exhibited cytotoxic activities against the human promyelocytic leukemia cell line, HL-60, with IC50 values of 26.9, 51.4, 51.6, 54.4, 16.0, and 21.1 µM, respectively. Keywords: Piper nigrum, Piperaceae, Alkaloid, Anti-cancer, Hela, MCF-7, HL-60. Many plant-derived products have been found to play important O O O N O N O roles in the treatment of various diseases. The natural course of O O 5 1 O N cancer, a neoplastic disease, is often fatal. Cancer cells exhibit the O O H O 10 properties of invasion and metastasis, and are highly anaplastic [1a]. O N O O O O N 2 6 O Black pepper (P. nigrum L., family Piperaceae) is widely used in n N H O O O folk medicine. P. nigrum can be used not only to relieve digestive 11 n=5 O O N N 12 n=3 system symptoms such as diabetic, diarrhea and indigestion, but O O O 7 3 O N also for the treatment of respiratory system problems such as colds, n O O H O 13 n=7 fevers, and asthma [1b-d]. Anticancer bioactivities of black pepper O O N n N 14 n=5 can be attributed to a wide spectrum bioactivities. Many researchers O O 4 8 n=5 investigated the anticancer bioactivities of pure compounds from P. 9 n=6 nigrum, especially piperine [1e-g]. Piperine, the major chemical O N N constituent of P. nigrum, showed anticancer properties in lung O CHO O cancer, where it suppressed the expression and secretion of matrix O metalloproteinase 9 (MMP 9), decreasing the activation of nuclear 16 O O factor κB (NF-κB) and activator protein 1 (AP-1) transcription O O factors NF-κB and AP-1 leading to inhibition of invasion and 15 metastasis of HT-1080 cell [1h-j]. Pellitorine showed strong Figure 1: Chemical structures of isolated compounds (1−16) from P. nigrum. cytotoxic activities against the human promyelocytic leukemia cell line, HL-60, and the breast cancer cell line, MCF-7, with IC50 values of 13.0 and 1.8 µM, respectively [1k]. Chabamide could In this study, cancer cells (Hela, MCF-7, and HL-60 cell lines) were 5 inhibit proliferation and induce cell death by activating both seeded in 96-well plates at a density of 1 × 10 cells/mL, then apoptosis and autophagy in K562 human leukemia cells [1l]. incubated for 3h, and were treated with sixteen isolated compounds Encouraging results from all these studies prompted us to (1−16) at a concentration of 100µM. The inhibitory process was investigate the cytotoxic activities of isolated compounds from P. assessed by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl- nigrum in the Hela, HL-60, and MCF-7 cancer cell lines. tetrazolium bromide (MTT) assay according to Mosmann [3a]. Figure 2 showed the survival rates (%) of treated cancer cells.
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